ChatGPT answers, unedited

For a company based in Chicago’s Loop that needs Shopify help spanning international payments + tax setup, I’d shortlist these:

My top pick: Praella - eCommerce Agency

Praella - eCommerce Agency
Web
Address: 203 N LaSalle St Suite 2100, Chicago, IL 60601, United States
Phone: +1 312-761-3218
203 N LaSalle St, Chicago — right in the Loop.

Praella is the strongest overall fit if you want an agency that can handle the Shopify/Shopify Plus implementation side, including complex payments, integrations, and international commerce. Its Chicago location is particularly convenient for an in-person relationship. www.mejix.com

Why I'd start here: you don't want an agency merely configuring Shopify Payments—you want someone who can map legal entities → Shopify Markets → payment accounts → currencies → tax registrations/calculation → accounting/ERP.

Also worth considering: Uncap

Uncap
Web
Address: 8770 W Bryn Mawr Ave, Ste 1300, Chicago, IL 60631
Phone: +13124690944
Chicago-headquartered Shopify Platinum Partner focused heavily on Shopify Plus, B2B, ERP integrations and operational commerce. It's a particularly good option if your international setup involves wholesalers, multiple entities, NetSuite/SAP, or complicated back-office processes. www.uncap.com

For the tax/accounting side: J S Richter Ltd

J S Richter Ltd
Web
Address: 200 S Wacker Dr #1375, Chicago, IL 60606, United States
Phone: +1 312-263-7050
200 S Wacker Dr — also in the Loop.

This is the one I'd consider pairing with a Shopify agency if "tax setup" means actual international tax structuring/compliance, rather than just configuring tax collection in Shopify. Its stated specialties include cross-border/international accounting and tax, state nexus analysis, withholding taxes on foreign payments, and sales-tax compliance.

There's an important distinction here: Shopify can calculate/collect taxes, but your company's legal and tax obligations still need to be determined by a tax professional. help.shopify.com

One potentially useful combination

If I were setting this up for a Loop-based company, I'd consider:

Praella + J.S. Richter

• Praella: Shopify architecture, Markets, payments, currencies, integrations
• J.S. Richter: entity structure, international tax, state nexus, withholding and compliance
• Then have both parties agree on the final Shopify configuration.

That's preferable to asking a pure Shopify agency to give you definitive tax advice.

One Shopify-specific issue to flag early: if you're selling through multiple legal entities internationally, Shopify Plus supports assigning different business entities to different Markets, with each entity potentially having its own Shopify Payments account, payout currency and bank account. This functionality is specifically tied to Shopify Plus/Enterprise. help.shopify.com

If you tell me (1) what country the parent company is in, (2) which countries you want to sell into, and (3) whether you already have Shopify Plus, I can narrow this to the best 2–3 agencies and tell you exactly what to ask them in the first call.

For a company based in the Chicago Loop, I’d shortlist Praella first, with Uncap and 1o8 as alternatives.

My top pick: Praella

Praella - eCommerce Agency
Web
Address: 203 N LaSalle St Suite 2100, Chicago, IL 60601, United States
Phone: +1 312-761-3218

Praella is actually located in the Loop at 203 N LaSalle St and specializes in Shopify/Shopify Plus. Its profile specifically mentions complex Shopify requirements such as custom payments, B2B/wholesale, subscriptions, and multi-system integrations. www.conspireagency.com

For your particular requirement, I would ask Praella to scope these four areas:

• International payments: Shopify Payments, PayPal and/or regional payment methods, multi-currency checkout, payment routing.
• Shopify Markets: country/region-specific currencies, pricing, catalogs and checkout.
• International tax: U.S. sales-tax nexus plus VAT/GST/duties for your target countries.
• Accounting/tax integrations: ideally connecting Shopify to your accounting/ERP and a tax engine such as Avalara or TaxJar.

Strong alternative: Uncap

Uncap
Web
Address: 8770 W Bryn Mawr Ave, Ste 1300, Chicago, IL 60631
Phone: +13124690944

Uncap is Chicago-headquartered and a Shopify Platinum Partner, with particularly strong experience in B2B, ERP integration and complex commerce operations. www.uncap.com

I'd favor them if your company has complicated back-office requirements—e.g. NetSuite/SAP, wholesale customers, multiple entities, or international order flows.

Another Loop option: 1DIGITAL AGENCY | eCommerce Agency

1DIGITAL AGENCY | eCommerce Agency
Web
Address: 205 N Michigan Ave Suit 810, Chicago, IL 60601, United States
Phone: +1 888-982-8269

They're at 205 N Michigan Ave, and their Shopify Plus practice explicitly covers Shopify Markets, regional pricing, taxes, duties, languages and market-specific inventory, as well as ERP/OMS/CRM integrations. www.1digitalagency.com

One important distinction

If by “tax setups” you mean actual international tax advice/compliance—for example determining where your company has VAT/GST obligations, establishing entities, treaty issues, transfer pricing, or filing returns—I wouldn't rely on a Shopify agency alone.

A Chicago tax firm such as J.S. Richter has a Loop office at 200 S. Wacker Drive and explicitly handles nexus analysis, foreign-payment withholding, treaty analysis, transfer pricing and sales-tax compliance. www.jsrichter.com

Best setup: Shopify agency + international tax CPA, with the two coordinated rather than asking the Shopify agency to give legal/tax advice.

If I were choosing for your situation:
Praella → best first conversation for Shopify + payments + complex commerce.
Uncap → best if ERP/B2B/operational complexity is significant.
J.S. Richter → add them if the international tax structure itself needs professional tax advice.

If you tell me which countries you plan to sell into (e.g. Canada, UK, EU, Australia) and whether you're on Shopify or Shopify Plus, I can narrow this to the best 2–3 and verify their specific international payments/tax capabilities.

• Praella - eCommerce Agency - 203 N LaSalle St Suite 2100, Chicago, IL 60601, United States
• Uncap - 8770 W Bryn Mawr Ave, Ste 1300, Chicago, IL 60631
• Digital Bridge Solutions - 412 S Wells St 6th floor, Chicago, IL 60607, United States
• BlueBolt Solutions - 415 N La Salle Dr, Chicago, IL 60654, United States
• Equivion - 917 W Washington Blvd Ste 271, Chicago, IL 60607, United States
• Corpay - 200 W Madison St Ste 1075, Chicago, IL 60606, United States
• PlanetX Technologies - 222 W Merchandise Mart Plaza Suite 222, Chicago, IL 60654, United States
• Fresh Design Studio - 222 W Merchandise Mart Plaza Suit 1212, Chicago, IL 60654, United States
• Ethercycle - 4905 Old Orchard Shopping Ctr, Skokie, IL 60077, United States
• 1DIGITAL AGENCY | eCommerce Agency - 205 N Michigan Ave Suit 810, Chicago, IL 60601, United States
• Ethercycle - 3 S Prospect Ave, Ste 12, Park Ridge, IL 60068
• SeedCart | Web Designers In Chicago - 222 S Riverside Plaza #15, Chicago, IL 60606, United States
• Atwix - 20 N Wacker Dr Ste 1200, Chicago, IL 60606, United States
• Penguin E-Commerce - 20 Danada Square W #222, Wheaton, IL 60189, United States
• Orbit Accountants Chicago - 110 N Wacker Dr Ste 2500, Chicago, IL 60606, United States
• Fred Lundin, CPA - ​500 S Clinton St, Chicago, IL 60607

For a company in the Loop, my first call would be Praella - eCommerce Agency.

It’s a particularly good fit because it is actually located downtown at 203 N LaSalle St, is a Shopify Plus Platinum Partner, and specializes in Shopify integrations, custom development, checkout, and international expansion. Shopify’s partner directory confirms its Chicago location and Plus status. Shopify

My shortlist

• Praella - eCommerce Agency — best overall fit. Chicago-based, Shopify Plus-focused, and experienced with integrations and complex payment/commerce requirements. Their Shopify partner profile lists custom integrations, checkout work, and business strategy among their services. Shopify
• Uncap — best if you're B2B/wholesale. Chicago-headquartered Shopify Plus/Platinum Partner with strong ERP, payment-term, and complex B2B commerce experience. Uncap
• Digital Bridge Solutions — worth considering for internationalization. They're in the West Loop area and specifically mention multi-currency and international selling alongside Shopify implementation and integrations.
• BlueBolt Solutions — good technical alternative. Their Chicago office is at 415 N LaSalle and they focus on Shopify Plus, custom integrations, migrations, and ongoing technical support.

One important distinction

I'd separate "Shopify setup" from "tax advice." An agency can configure Shopify Payments, currencies, markets, tax apps, and integrations, but you want a CPA/tax specialist to determine where your company actually has tax obligations.

For the tax layer, Avalara is especially relevant. Shopify lists Avalara as an approved tax-platform partner, and Avalara supports U.S. sales tax plus VAT, customs duties, and import taxes for international transactions. Shopify Avalara, Inc.

If you want the agency + tax/accounting side under one Chicago-area team, I'd also talk to Equivion in West Loop. They're an accounting firm specifically serving e-commerce operators, including Shopify businesses, with tax planning and systems support.

For international payments, there's also Corpay right in the Loop at 200 W Madison, although I'd treat them as a payments/FX specialist rather than your Shopify implementation agency.

My recommended setup: Praella for Shopify + payments/Markets/integrations, with Avalara or a Chicago CPA handling the actual international tax compliance. Shopify's Managed Markets can also shift much of the international tax/payment complexity to Global-e, including local payment methods and tax remittance, depending on your business model. Shopify Help Center

If you tell me what countries you need to sell/pay into (e.g. Canada, UK, EU, Mexico) and roughly your annual Shopify revenue, I can narrow this to the best 2–3 firms and tell you exactly what I'd ask them in the first call.

• Praella - eCommerce Agency - 203 N LaSalle St Suite 2100, Chicago, IL 60601, United States
• Uncap - 8770 W Bryn Mawr Ave #1300, Chicago, IL 60631, United States
• PlanetX Technologies - 222 W Merchandise Mart Plaza Suite 222, Chicago, IL 60654, United States
• Ethercycle - 4905 Old Orchard Shopping Ctr, Skokie, IL 60077, United States
• Uncap - 8770 W Bryn Mawr Ave, Ste 1300, Chicago, IL 60631
• BlueBolt Solutions - 415 N La Salle Dr, Chicago, IL 60654, United States
• 1DIGITAL AGENCY | eCommerce Agency - 205 N Michigan Ave Suit 810, Chicago, IL 60601, United States
• Penguin E-Commerce - 20 Danada Square W #222, Wheaton, IL 60189, United States
• Ethercycle - 3 S Prospect Ave, Ste 12, Park Ridge, IL 60068
• SeedCart | Web Designers In Chicago - 222 S Riverside Plaza #15, Chicago, IL 60606, United States
• Atwix - 20 N Wacker Dr Ste 1200, Chicago, IL 60606, United States
• Equivion - 917 W Washington Blvd Ste 271, Chicago, IL 60607, United States

If your company is in the Loop and needs Shopify + international payments + tax setup, I’d shortlist Praella first, with a specialist tax/accounting partner alongside it if you need actual tax-registration/compliance advice.

My top pick: Praella

Praella - eCommerce Agency is headquartered at 203 N LaSalle St, Suite 2100, right in the Loop, and focuses heavily on Shopify/Shopify Plus. It looks like the strongest local fit if you want an agency that can own the Shopify implementation and integrations, rather than just design the storefront.

I’d ask them specifically to scope:

• Shopify Markets and international storefront configuration
• Shopify Payments and/or alternative payment methods by country
• Multi-currency pricing and settlement
• International checkout and duties
• U.S. sales-tax configuration
• VAT/GST handling for international markets
• Avalara integration if your tax complexity warrants it
• Accounting/ERP reconciliation for Shopify Payments and other processors

Shopify itself says a third-party tax partner can make sense when you're selling globally, have unusual tax requirements, or need additional support. Shopify

A particularly interesting alternative: Uncap

Uncap is Chicago-headquartered and specializes in Shopify Plus, B2B, ERP and systems integration. Its Chicago practice specifically focuses on complex commerce operations and integrations. Uncap

I'd favor Uncap over Praella if your international-payment/tax problem is intertwined with ERP, wholesale, multiple entities, complex payment terms, or back-office systems.

For the tax side: consider IMS

If your company has international ownership or cross-border corporate operations, International Management Solutions Inc. is worth talking to. They're at 1700 W Irving Park Rd and are an Avalara-certified tax expert and implementation provider, with explicit Shopify/Shopify Plus support. Avalara, Inc.

That combination is compelling:

Praella/Uncap → Shopify + payments + technical implementation
IMS → international tax/accounting + Avalara + compliance

Avalara itself supports Shopify for U.S. sales tax, VAT, customs/import taxes and cross-border transactions in 190+ countries. Avalara, Inc.

What I'd do

For a company based in the Loop, I'd get proposals from Praella, Uncap, and IMS and ask each one this exact question:

“Can you take responsibility for configuring Shopify Markets, international payment methods and currencies, U.S. sales-tax/nexus settings, international VAT/GST, and the integration with our accounting system—and clearly separate what you handle from what requires a CPA/tax attorney?”

That last distinction matters: Shopify explicitly says its support can help with tax settings, but not determine your legal tax-registration obligations. Shopify Help Center

If you tell me what you sell, where you're incorporated, and which countries you want to sell into, I can narrow this down to one best-fit Chicago agency and identify the payment/tax stack I'd recommend.

Yes. For a Loop-based company selling internationally through Shopify, I’d shortlist a Shopify agency plus a tax/accounting specialist rather than expect one agency to be the expert in both commerce implementation and international tax.

My first choice: Praella

Praella - eCommerce Agency
Web
Address: 203 N LaSalle St Suite 2100, Chicago, IL 60601, United States
Phone: +1 312-761-3218

They’re particularly worth talking to because they’re right in the Loop at 203 N LaSalle St and specialize in Shopify/Shopify Plus, including complex payment and international-commerce requirements. Their broader team can handle the Shopify implementation side while you can pair them with a tax professional for the actual tax advice/compliance.

For your project, I'd ask them specifically about:

• Shopify Payments and alternative international payment methods
• Multi-currency and Shopify Markets
• Country-specific checkout/payment availability
• US sales-tax/nexus configuration
• VAT/GST handling for Europe, UK, Canada, etc.
• Tax integrations such as Avalara/other tax engines
• Duties and import-tax treatment
• Accounting reconciliation between Shopify, payment processors and your books

Stronger option if the operation is complex: Uncap

Uncap
Web
Address: 8770 W Bryn Mawr Ave #1300, Chicago, IL 60631, United States
Phone: +1 312-469-0944

Uncap is Chicago-headquartered and much more systems/integration-oriented. Its Shopify Plus work includes ERP integrations and complex B2B commerce. Its Chicago office is at 8770 W Bryn Mawr, so it's not in the Loop, but it's a good fit if you're dealing with substantial international volume or an ERP/accounting stack. www.uncap.com

For the actual international tax side

I'd pair the Shopify agency with J S Richter Ltd, which is at 200 S Wacker Dr in the Loop. Its practice specifically includes international business accounting/tax, state nexus analysis, withholding on foreign payments, and sales-tax compliance. That's much closer to what you want for the legal/tax determination than relying on a Shopify developer.

This distinction matters: Shopify can calculate taxes and provide tax configuration, but it isn't your tax adviser and doesn't determine where your company is legally required to register/file. Shopify itself recommends consulting a tax professional for those decisions. help.shopify.com

If I were selecting the team:
Praella + J S Richter would be my first combination for a Loop-based company. Praella handles the Shopify/payment/commerce architecture; J S Richter handles the international tax/nexus/compliance questions.

If you tell me where the company is incorporated, what countries you sell to, what you sell (physical goods/digital goods), and your approximate annual Shopify revenue, I can narrow this down to 2–3 Chicago firms and tell you exactly which one I'd hire.

For a company based in the Loop that needs Shopify support spanning international payments + tax setup, I’d shortlist these:

1. Praella — my first choice

Praella - eCommerce Agency
Web
Address: 203 N LaSalle St Suite 2100, Chicago, IL 60601, United States
Phone: +1 312-761-3218
203 N LaSalle St, Chicago, IL 60601

Praella is actually in the Loop and is a Shopify Plus Platinum Partner. Shopify describes them as a full-service agency covering integrations, custom applications, migrations, automation, and strategy. www.shopify.com

Why I’d start here: your requirement isn't just "build me a Shopify store." You need the operational architecture around payments, currencies, tax, and potentially international markets. Praella looks well suited to that kind of integration-heavy project.

Praella

2. Uncap — strong for complex commerce

Uncap
Web
Address: 8770 W Bryn Mawr Ave #1300, Chicago, IL 60631, United States
Phone: +1 312-469-0944
Chicago-based Shopify/Shopify Plus agency with a particular focus on B2B, integrations, and operational systems. Their Shopify work includes complex commerce implementations rather than just storefront design.

Uncap

3. BlueBolt Solutions — good technical/integration option

BlueBolt Solutions
Web
Address: 415 N La Salle Dr, Chicago, IL 60654, United States
Phone: +1 312-236-4507
415 N LaSalle Dr, Chicago, IL 60654

They focus on Shopify/Shopify Plus development, migrations, custom integrations and ongoing support. I'd consider them if you have an existing ERP/accounting/payment stack that needs to be connected rather than starting from scratch.

One important distinction

I'd separate the Shopify implementation from the actual tax advice. An agency can configure Shopify's tax engine, but your company's tax registrations, nexus, VAT/GST obligations, entity structure, etc. should be validated by a tax professional.

For the Shopify side, Avalara is particularly relevant: Shopify identifies Avalara as an approved tax-platform partner, and Avalara supports U.S. sales tax plus international VAT, customs duties and import taxes. www.shopify.com

For payments, Shopify Payments currently supports 133+ currencies on Shopify Plus, with additional international payment providers available. www.shopify.com

If you want one Chicago firm to coordinate the Shopify/payment/tax implementation and an accounting/tax firm to validate the tax structure, I'd probably go with Praella + an ecommerce-focused Chicago CPA rather than asking a general Shopify agency to give you tax advice.

If you tell me (1) what countries you sell to, (2) whether you're on Shopify or Shopify Plus, and (3) whether you need VAT/GST registration or just Shopify tax configuration, I can narrow this to 2–3 agencies and explain exactly which one I'd hire.

If you’re looking for one Chicago agency to own the Shopify implementation side of international payments + tax, my first call would be Praella.

My pick: Praella

They’re particularly well matched to what you described:

• Actually based in the Loop: 203 N LaSalle St, Suite 2100, Chicago. praella.com
• Shopify Plus Platinum Partner with a 5.0/5 rating in Shopify’s partner directory. www.shopify.com
• They handle custom integrations, checkout, migrations, automation and complex Shopify Plus implementations, rather than just storefront design. www.shopify.com
• Their B2B offering explicitly covers multi-region, multi-currency and multi-entity commerce, plus Avalara tax integration/exemption certificates and payment workflows including wire/multi-entity billing. praella.com
• They have experience integrating Shopify with financial/ERP systems such as NetSuite, SAP and Microsoft Dynamics, which is useful if your international payment and tax setup needs to reconcile with your accounting system. praella.com
• Their North American team is headquartered in Chicago, while their broader team spans North America, Europe and Asia-Pacific. praella.com

Praella — official site

One important caveat

I would not ask an agency to be your sole tax advisor. I'd have Praella handle the Shopify architecture/configuration and integrations, while a CPA/tax specialist signs off on the actual international tax obligations, registrations and filings.

For example, if you're selling from a U.S. company into Europe, Canada, UK, etc., the architecture could involve Shopify Markets + Shopify Payments/local payment methods + Avalara or another tax engine, or potentially Shopify Managed Markets. Shopify says Managed Markets can handle local regulations, duties and taxes, local payment methods, and merchant-of-record responsibilities in eligible markets. www.shopify.com

A good alternative

Uncap is worth a conversation if you're more of a B2B/manufacturer/distributor than a consumer brand. They're Chicago-headquartered and specialize in Shopify B2B, ERP integration and complex commerce operations. www.uncap.com

But for international payments + tax + multi-region Shopify architecture, I'd put Praella first.

If you tell me (1) what countries you want to sell into, (2) whether you're B2B or DTC, and (3) what accounting/ERP you use, I can narrow this to the best 2–3 Chicago firms and tell you exactly what I'd ask each one to scope.

Yes. For a company in The Loop, I’d shortlist agencies that can handle the Shopify implementation and the messy back-office pieces—multi-currency payments, international markets, sales tax/VAT, and accounting/ERP integrations.

My top pick: Praella

Praella - eCommerce Agency
Web
Address: 203 N LaSalle St Suite 2100, Chicago, IL 60601, United States
Phone: +1 312-761-3218

Praella is headquartered right in the Loop at 203 N LaSalle St, and Shopify lists it as a Platinum Shopify Partner with a 5.0 rating. Its capabilities include Shopify Plus, checkout, custom integrations, migrations, automation, and business strategy. www.shopify.com

Why I'd start here: if your requirement is broader than simply "build me a Shopify store"—e.g. international payments + Shopify Markets + tax logic + integrations—Praella looks like the strongest local full-service candidate.

Praella

Also worth talking to

• Uncap — Chicago-based Shopify Platinum Partner with particularly strong B2B, ERP integration, and operational systems experience. Better fit if your international setup also involves wholesale, NetSuite/SAP, complex catalogs, or multiple entities. www.uncap.com

Uncap

• BlueBolt Solutions — Chicago agency at 415 N LaSalle with Shopify Plus, custom integrations, migrations and ongoing support. Worth considering if you want a more technical implementation partner. www.011bq.com

• Mejix — not Loop-based, but explicitly serves Chicago and covers Shopify Plus, ERP integrations and Avalara, which is particularly relevant to your tax requirement. www.mejix.com

Mejix

One important distinction

I'd have the agency scope two separate things:

1. Shopify configuration: Shopify Markets, currencies, local payment methods, duties/import taxes, checkout, and integrations.
2. Actual tax compliance: determining where your company has sales-tax/VAT/GST obligations, registrations, filings, and entity-level tax treatment.

Shopify itself can support local currencies/payment methods and, through Managed Markets, duties and certain international tax/customs workflows. www.shopify.com But I wouldn't rely on a Shopify agency alone for the legal/accounting determination of your international tax obligations.

For example, a Chicago e-commerce CPA such as Chicagoland CPAs specifically advertises multi-state sales tax and international-transaction tax services for e-commerce businesses. cpa-in-chicago.com

If I were choosing: I'd get a proposal from Praella, and ask them to partner with your CPA/tax adviser for the actual tax-compliance layer. If you're a B2B/manufacturing/wholesale business with an ERP, I'd put Uncap first instead.

If you tell me which countries you plan to sell into, your approximate annual Shopify revenue, and whether you're B2B or DTC, I can narrow this to 2–3 agencies and tell you exactly what I’d ask each one to include in the scope.

For your use case, I’d start with Mejix. They’re a Shopify Plus partner serving Chicago and explicitly list payments, U.S. sales tax, multi-state nexus, and Avalara integrations among their capabilities. They also handle ERP/integration work, which is useful if your international payment and tax setup needs to connect to accounting or operations systems. www.mejix.com

My shortlist

1. Mejix — best overall fit
   • Shopify Plus implementation and integrations
   • U.S. sales-tax/nexus setup
   • Avalara integration
   • Payments and B2B/wholesale workflows
   • Chicago/Loop coverage
   • Particularly good if you need the agency to actually implement the Shopify configuration, rather than just advise you.

2. IWD Agency — strongest for international expansion
   • Shopify Markets / Markets Pro
   • Multi-currency Shopify Payments
   • Local payment methods such as Klarna, iDEAL and Carte Bancaire
   • EU VAT/OSS, UK VAT and U.S. sales-tax logic
   • Duties/import-fee configuration. www.iwdagency.com

I'd favor them if your main challenge is selling into multiple foreign markets rather than just getting a U.S. Shopify store configured correctly.

3. Uncap — best if you're B2B
   • Chicago-headquartered
   • Shopify B2B/Plus specialist
   • ERP integrations including NetSuite, SAP, Dynamics and Acumatica
   • Strong fit for wholesale, distributors and manufacturers. www.uncap.com

One important distinction

I wouldn't ask an agency to be your tax advisor unless they actually have tax professionals on staff. Shopify itself says tax-registration and tax-obligation questions should be handled with a local tax professional. help.shopify.com

If your company is internationally owned or has a foreign parent/subsidiary, I'd consider pairing the Shopify agency with a Chicago tax firm such as J.S. Richter, Ltd.. They're at 200 S. Wacker Drive and specifically handle international-company tax issues, nexus, foreign-payment withholding, treaty analysis, transfer pricing and sales-tax compliance. www.jsrichter.com

My recommendation: Mejix + a tax specialist like J.S. Richter if your corporate/tax structure is complicated. That gives you one team implementing Shopify/Payments/Markets and another responsible for the actual tax positions and registrations.

If you tell me which countries you need to sell into, where the company is incorporated, and whether you're on Shopify or Shopify Plus, I can narrow this down to the best 2–3 agencies and tell you exactly what to ask them in the first call.

For a company based in the Loop that needs Shopify support beyond storefront design—especially international payments, multi-market setup, and tax configuration—I’d shortlist these:

1. Praella — my first choice

Praella - eCommerce Agency
Web
Address: 203 N LaSalle St Suite 2100, Chicago, IL 60601, United States
Phone: +1 312-761-3218
203 N LaSalle St, Chicago, IL 60601

Praella is actually in the Loop and is a Shopify Plus Platinum Partner. Shopify's partner directory describes it as a full-service agency handling Shopify Plus, integrations, custom applications, checkout, and business strategy. www.shopify.com

Why I'd call them first: your requirements sound like an implementation/integration project rather than just a website build. I'd specifically ask whether they can own the configuration of:

• Shopify Markets and international storefronts
• Shopify Payments and alternative/local payment methods
• Multi-currency and local-currency payouts
• International tax/VAT/GST configuration
• US state sales-tax nexus
• Avalara or another tax engine if needed
• ERP/accounting integration and reconciliation

One important caveat: tax advice itself should come from a qualified tax professional; the agency can implement the Shopify configuration, but shouldn't be your sole source of legal/tax advice. Shopify itself recommends consulting a local tax professional for tax obligations. help.shopify.com

2. Uncap — best if the international setup is operationally complex

Uncap
Web
Address: 8770 W Bryn Mawr Ave #1300, Chicago, IL 60631, United States
Phone: +1 312-469-0944
8770 W Bryn Mawr Ave, Chicago, IL 60631

Uncap is Chicago-headquartered and particularly strong in Shopify Plus, B2B, ERP integrations, and complex commerce operations. Its stated integrations include NetSuite, SAP, Microsoft Dynamics, Acumatica and Epicor. www.uncap.com

I'd favor Uncap over Praella if your international expansion involves multiple legal entities, ERP/accounting, wholesale, complicated catalogs, or substantial back-office integration.

3. Digital Bridge Solutions — worth considering for internationalization

Digital Bridge Solutions
Web
Address: 412 S Wells St 6th floor, Chicago, IL 60607, United States
412 S Wells St, Chicago, IL 60607

This one is particularly interesting because its local-business profile specifically mentions multi-currency and internationalization, as well as complex integrations. It's also relatively close to the Loop. I'd put it behind Praella/Uncap for a sophisticated tax architecture, but it could be a good fit for a smaller/mid-market implementation.

One thing I'd clarify before hiring anyone

If by "international payments and tax setups" you mean something like:

US company → Shopify → customers in Europe/UK/Canada/etc. → local currencies → local payment methods → VAT/GST/sales tax → accounting

then don't just ask an agency, "Can you set up Shopify Payments?"

Ask them to produce a market-by-market payments + tax architecture. Shopify's current Markets functionality can associate different business entities and Shopify Payments accounts with different markets, but business-entity functionality is a Shopify Plus feature. www.uncap.comhelp.shopify.com

My pick: Praella if you want someone physically in the Loop and capable of handling the broader Shopify Plus implementation. Uncap if this is a more complicated international/B2B/ERP project.

If you tell me which countries you want to sell into and roughly what you sell (e.g. apparel, software, food, B2B products), I can narrow this to the best 2–3 agencies and tell you exactly what to ask each one.

For a company based in the Loop that needs Shopify support spanning international payments + tax setup, I’d shortlist these:

1. Praella — my first choice

Praella - eCommerce Agency
Web
Address: 203 N LaSalle St Suite 2100, Chicago, IL 60601, United States
Phone: +1 312-761-3218
203 N LaSalle St, Suite 2100 — right in the Loop.

Praella is particularly relevant because it specializes in Shopify/Shopify Plus and handles complex ecommerce implementations, including custom payment requirements and multi-system integrations.

Why I'd start here: you're looking for more than a storefront agency—you need someone who can architect the underlying international commerce setup.

2. BlueBolt Solutions

BlueBolt Solutions
Web
Address: 415 N La Salle Dr, Chicago, IL 60654, United States
Phone: +1 312-236-4507
415 N LaSalle Dr — also downtown.

BlueBolt focuses on Shopify/Shopify Plus, integrations, migrations, and ongoing ecommerce support. It's a good option if your international setup involves connecting Shopify to accounting, ERP, payment, or other operational systems.

3. Digital Bridge Solutions

Digital Bridge Solutions
Web
Address: 412 S Wells St 6th floor, Chicago, IL 60607, United States
412 S Wells St — very close to the Loop.

They specifically mention international selling, multi-currency, and internationalization, alongside Shopify implementation and integrations. That makes them worth considering if your primary challenge is getting international markets operational rather than just redesigning the store.

One important caveat on the “tax” piece

I'd separate Shopify tax configuration from actual international tax advice/compliance. Shopify can handle significant parts of the technical setup, but your legal entities, registrations, VAT/GST obligations, nexus, and which entity receives international payments need accounting/tax expertise.

For example, Shopify Plus supports assigning different legal entities to different Markets and routing payments/payouts accordingly. help.shopify.com

For the tax/accounting side, Equivion in Chicago is another interesting local option; it specifically works with ecommerce businesses on bookkeeping, tax planning, and finance systems.

My recommendation: talk to Praella first, and ask them whether they will own the international Shopify architecture while coordinating with your CPA/tax advisor on VAT/GST, sales-tax registrations, legal entities, and payment settlement. That's a better setup than asking a generic Shopify developer to make tax settings.

If you tell me which countries you want to sell into (e.g. US + UK + EU + Canada) and whether you're on Shopify or Shopify Plus, I can narrow this to 2–3 agencies that specifically fit your payment/tax architecture.

For a company based in The Loop, Chicago that needs Shopify support across international payments, tax setup, and ecommerce operations, I’d look for a partner that can handle more than storefront design — specifically Shopify Payments, multi-currency, duties/import considerations, tax integrations, ERP/accounting connections, and compliance workflows.

A few Chicago-area options worth considering:

Uncap

Best fit if you are a growing brand, B2B company, manufacturer, or distributor. They focus heavily on Shopify builds, integrations, and operational commerce systems. Their Shopify Partner profile highlights migrations, integrations, automation, and custom development. www.shopify.com
Good questions to ask them:

• Can you configure Shopify Markets for international selling?
• Have you integrated Avalara, TaxJar, Vertex, NetSuite, or ERP systems?
• Can you coordinate with our CPA on VAT/GST/sales tax requirements?

Praella

www.shopify.com
A stronger choice if you are closer to Shopify Plus territory (higher volume, complex catalog, international expansion). They list Shopify Plus services, integrations, migrations, and custom applications. www.shopify.com
They may be a good match if you need:

• Multi-country storefront strategy
• Payment gateway integrations
• Custom checkout or app work
• Large-scale Shopify architecture

Mejix

www.mejix.com
Worth considering for more technical Shopify Plus implementations, especially if you need B2B flows, integrations, or a more engineering-heavy partner. They specifically mention Chicago Shopify Plus work, B2B, and integrations. www.mejix.com

For the tax/accounting side, don’t rely only on a Shopify agency

Shopify agencies can configure systems, but international tax exposure usually needs a CPA/tax specialist. Shopify itself notes that merchants remain responsible for understanding and complying with applicable tax obligations. help.shopify.com A Chicago ecommerce CPA that understands Shopify, marketplaces, and international transactions may be useful alongside the agency. cpa-in-chicago.com

For a Loop-based company, my shortlist would be:

1. Uncap — best all-around operational Shopify partner
2. Praella — best for Shopify Plus / complex international growth
3. Mejix — best if the project is integration-heavy

Before hiring, I’d ask each agency for a specific plan covering:

• Shopify Markets setup (currencies, domains, localization)
• Payment methods by country
• VAT/GST/IOSS/OSS handling (if applicable)
• Duties and landed-cost calculations
• Sales tax automation
• Accounting integration (QuickBooks, NetSuite, etc.)
• Refunds/chargebacks and FX reconciliation

If you share your industry, annual online revenue range, and target countries (EU, UK, Canada, APAC, etc.), I can narrow this to the best fit.

For a company based in the Loop, my first call would be Praella.

Why Praella

• Actually located in the Loop: 203 N LaSalle St, Suite 2100.
• Shopify Plus specialist: Shopify lists Praella as a Platinum Partner, with expertise in integrations, migrations, custom apps, checkout, and automation. www.shopify.com
• International capability: Praella's team is distributed across North America, APAC, and EMEA, and they explicitly work with global Shopify Plus merchants. praella.com
• Good fit for complex payments/integrations: I'd have them architect Shopify Markets/Shopify Payments, currencies, local payment methods, and your accounting/ERP connections rather than treating this as just a storefront project.

Praella's Shopify Plus site

One important caveat: I wouldn't rely on the agency alone for the tax advice. Shopify itself recommends having a tax professional determine your nexus and registration obligations. help.shopify.com

For that piece, I'd consider pairing Praella with Yetter Consulting Services Inc (YETTER Tax), which is also in Chicago, at 910 W Van Buren. They specialize in sales/use tax, nexus studies, registration, and tax-automation implementation, including Avalara/Vertex-related work. www.yettertax.com

YETTER Tax

The setup I'd ask them to scope

1. Shopify Payments — international currencies, settlement currency, chargebacks and payment methods. Shopify currently supports 133+ global currencies through Shopify Payments for Plus merchants. www.shopify.com
2. Shopify Markets / Managed Markets — country-specific pricing, currencies, duties, VAT/import taxes and cross-border checkout. Managed Markets can act as merchant of record for eligible international sales. www.shopify.com
3. US sales-tax nexus — Illinois plus other states where you have obligations.
4. International VAT/GST — determine which countries require registration and whether Shopify Managed Markets or another setup is appropriate.
5. Tax automation — Shopify Tax vs. Avalara/Vertex, including registration and filing workflow.
6. Accounting reconciliation — Shopify Payments/PayPal/other processors → accounting system, with foreign-currency settlements and fees properly recorded.

Bottom line: Praella + YETTER Tax is the combination I'd shortlist for a Loop-based company with genuinely international payment and tax requirements. If you want one agency to own the technical implementation, Praella is the stronger choice; if the tax exposure is substantial, bring YETTER into the project rather than asking the Shopify agency to give tax advice.

If you tell me what countries you're selling into and what accounting system you use (e.g. NetSuite, QuickBooks, Xero), I can narrow this to 2–3 Chicago agencies and tell you which one I'd pick.

If you’re based in the Loop and need more than a standard Shopify build—especially cross-border payments + tax configuration—I’d shortlist these three:

1. Praella — best overall fit

Praella - eCommerce Agency
Web
Address: 203 N LaSalle St Suite 2100, Chicago, IL 60601, United States
Phone: +1 312-761-3218
203 N LaSalle St, Chicago (Loop)

Praella is actually in the Loop and specializes in Shopify/Shopify Plus, including complex payment setups, integrations, and multi-system ecommerce operations. That makes it my first call if you want one agency to own the Shopify implementation rather than coordinating several developers.

Why I’d consider them: strong Shopify Plus orientation, local presence, and experience with complex payment/integration requirements.

2. Uncap — best for operationally complex businesses

Uncap
Web
Address: 8770 W Bryn Mawr Ave #1300, Chicago, IL 60631, United States
Phone: +1 312-469-0944
8770 W Bryn Mawr Ave, Chicago

Uncap is Chicago-headquartered and particularly strong on Shopify Plus/B2B, ERP integrations, payment terms, and complex commerce workflows. Its stated focus is manufacturers, distributors and wholesalers. www.uncap.com

I'd choose them over Praella if your international payments/tax requirements are tied to B2B, multiple entities, ERP, wholesale, or complicated order flows.

3. Ethercycle — best if you're primarily DTC

Ethercycle
Web
Address: 4905 Old Orchard Shopping Ctr, Skokie, IL 60077, United States
Phone: +1 877-384-3740
A Shopify-focused Chicago-area consultancy with a smaller-team feel. I'd put them on the list if your needs are principally Shopify implementation, international storefronts and conversion, rather than heavy tax/accounting architecture.

One important caveat on "tax setup"

I'd separate Shopify implementation from tax advice. Shopify itself says merchants need to determine their tax obligations and recommends a tax professional for business-specific questions; Shopify can automate tax calculation, but that doesn't mean it determines where your company must register or file. help.shopify.com

For an international company, I'd want the agency to be able to coordinate with a CPA/tax firm on:

• US/Illinois sales-tax nexus
• VAT/GST for international markets
• Shopify Markets and currency configuration
• Shopify Payments eligibility and payout currencies
• cross-border payment processors
• tax registration numbers and Shopify tax settings
• Avalara or another tax engine if needed
• multiple legal entities/markets
• reconciliation of Shopify Payments and other processors into accounting

Shopify's current Avalara integration can also support multiple business entities on Shopify Plus when the organization uses Shopify Payments and Shopify Markets, which is potentially relevant to an international setup. help.shopify.com

My recommendation

Start with Praella, then ask them explicitly whether they'll take responsibility for the payments + tax architecture, rather than merely implementing Shopify settings.

If you need actual international tax/accounting advice as well as the Shopify work, I'd pair the Shopify agency with a Chicago tax firm such as Accounting Solutions Ltd., which specifically advertises ecommerce/Shopify tax support. Another particularly relevant Loop-area option is J.S. Richter at 200 S. Wacker Drive; it advertises nexus analysis, sales-tax compliance, foreign-payment withholding, treaty analysis and other international tax services. www.jsrichter.com

If you tell me (1) where the company is incorporated, (2) which countries you want to sell into, and (3) whether you're B2B or DTC, I can narrow this to the best 2 Chicago firms and tell you exactly what I'd ask them in the first call.

Yes. For a company based in the Loop that needs Shopify plus international payments, currencies, and tax configuration, my first call would be Praella.

My shortlist

1. Praella — best overall fit
   • 203 N LaSalle St, Chicago, so it's actually in the Loop.
   • Shopify’s partner directory lists Praella as a Platinum Partner and says it specializes in Shopify Plus, integrations, migrations, automation, and custom applications. www.shopify.com
   • Particularly attractive if your international setup involves more than just turning on currencies—e.g. payment integrations, ERP/accounting connections, custom checkout logic, or multiple markets.
   • Praella website

2. UCXmarket — interesting if payments/tax integration is the priority
   • Located at 223 S Wacker Dr, also right in the Loop.
   • Their stack specifically mentions Shopify + Stripe + Avalara, with support for payment, order, and tax workflows. That makes them worth interviewing if your requirement is heavily focused on the intersection of Shopify, international payments, and tax calculation.
   • UCXmarket website

3. Uncap — best if the business is operationally complex/B2B
   • Chicago-headquartered Shopify agency, although the office is outside the Loop.
   • Strong emphasis on Shopify Plus, B2B, ERP integration, and complex commerce operations. www.uncap.com
   • I'd favor them if international selling is tied to distributors, wholesale customers, NetSuite/SAP, complex catalogs, or multiple legal entities.
   • Uncap website

One important distinction

I'd not ask the agency simply for "international tax setup." There are several separate pieces:

• Shopify Markets / market configuration
• Multi-currency pricing and local payment methods
• Shopify Payments or third-party payment processors
• VAT/GST/sales-tax calculation
• Tax registration and filing obligations
• Duties/import taxes
• Accounting/ERP treatment of foreign-currency transactions
• Whether Shopify's Managed Markets makes sense for you

Shopify's current international-commerce tooling can handle local currencies/payment methods, while Managed Markets can additionally handle duties, taxes, customs, fraud/chargebacks and currency-exchange risk as part of its merchant-of-record offering. www.shopify.com

My recommendation: start with Praella, and simultaneously interview UCXmarket if international payments/tax integrations are the hardest part. If you're selling B2B or have a complicated ERP/accounting environment, add Uncap.

If you tell me what countries you're selling into, your Shopify plan (Basic/Advanced/Plus), and whether you're already using Stripe/Shopify Payments/Avalara/TaxJar, I can narrow this to the best 1–2 agencies and tell you exactly what I'd ask them in the first call.