When Square announced Bitcoin Square in October of last year, I was hopeful. When I learned how easy it would be to enable, I grew optimistic. I then heard from people who got a chance to use it in the United States, and I became euphoric. However, signing up merchants to enable the feature seemed difficult, and awkward at best. In March 2026, when Square shared its plans to bring this feature as a default to all of it's merchants, I was ecstatic. This July, I finally got the chance to travel to the States to see for myself.

Finding places that take Bitcoin is difficult. I do not have access to the Cash App merchant map, and my understanding is that only those merchants that specifically opted into the Bitcoin trial are listed here. Only a subset of these merchants made it to BTCMap, and while BTCMap volunteers are diligent in adding merchants by request from Square, they will rarely remove a merchant if they move, shut down or stop accepting Bitcoin. My best strategy is to just walk around and rely on the profile of likely Square merchants: Small independent self-service delis, breweries, coffee shops and boutiques with high margins. At these places, I can usually see what checkout terminals they are using from the outside or the door, and I quickly learn how to distinguish them from their doppelgänger toast point of sale.

🛞Detroit: My trip begins in Detroit. A friend recommends a chicken sandwich place by the Eastern Market. It's Saturday, and the market is sprawled and busy. The chicken place however is closed, and I find only one other place with a Square terminal nearby. Bitcoin does not show up as an option on the top left of the screen, and the friendly clerk shows me that it can't be found in the 'Other' options either, although there is a Cash app QR code on the front. I head back to downtown, which looks like a terrible war destroyed most of it seventy years ago, and the city couldn't be rebuilt due to catastrophic collectivist economic policies. I find another place with two Square terminals, an old one and a new one, but neither has the option available, and they also don't have a Cash App option. Finally, at a soft serve ice cream shop with a long line, I peek over the shoulder of somebody paying and notice multiple fingerprints on the top left corner of the screen. I queue and indeed find the Bitcoin option. I have trouble scanning the QR code as the sun shines directly on it, and as I finally succeed and dispatch the payment, the clerk resets the payment screen in an attempt to help me. My payment is rejected, and only as we try a second time I succeed. I held up the line a bit and made the clerk a bit nervous, but I'm glad it worked in the end.

🚆There was one site around 2022 that sold train tickets for Bitcoin, Future Travel. It shut down, and I claim to be the very last person on earth to ever buy a train ticket over Lightning, hopefully not forever. You can however buy Amtrak gift cards on Bitrefill relatively painlessly, and that's what I do for my trip to Chicago.

⛩️My first day in Chicago takes me to Chinatown, where a big festival is held. There are dozens of small merchants, and three of them have handheld Square terminals. We cannot find the Bitcoin option on any of them. I also cannot find a simple merchant advertising their Cash App tag. In the area are lots of small shops selling food, crafts and souvenirs, but nobody seems to have a Square Terminal.

🥽The Riverwalk is probably the best thing to happen to Chicago in the past ten years. I find eight Square merchants in the area, and they all seem to have the latest handheld and tabletop devices, but I can only pay with Bitcoin at two of them. On both screens the Bitcoin and dollar symbols are seen on the top left of the screen. I can tap the ₿ and am then prompted to enter a tipping amount before I'm shown the QR code. I overheard somewhere that this flow would also support "tapping" the NFC antenna to retrieve the Bolt11 invoice, but that does not seem to be true.

🍔There aren't as many Steak & Shake locations in Chicago as there used to be, but there is still one within reach. The experience is absolutely fantastic. There is a special Bitcoin burger on the menu, and paying with Lightning is seamless. The burger is branded with a big ₿, and it tastes quite good, especially for the price (18,584 satoshis plus a 3 satoshi routing fee). There is a claw machine in the room, and I'm sure I could easily Lightningfy that, too.

🏝️Downtown Chicago isn't very lively, not even during the week. I expect my best shot at finding some Square merchants to go to the food courts. The first food court exclusively uses Toast terminals, the second is closed entirely, and the third, at the Willis Tower, seems modern but empty and has one ice cream shop using Square. However, Bitcoin is not available. Around the entire downtown area I can only find five places with Square terminals, including one with a self-service kiosk hooked to a Square handheld device, but Bitcoin isn't available at any of them.

🎩North of the city I find a milk tea place, but the restaurant that I originally come up here for is unexpectedly closed. The donut shop that I found on BTCMap is gone entirely, but there is a soft serve ice cream place nearby where I am lucky to pay with sats. My biggest surprise was Nancy's, a deep dish pizza place where Bitcoin payments were enabled. They had also set a 3% surcharge for card payments, and that charge did not apply to Lightning payments. In this area I also encounter my first real Square self-checkout terminal, which sadly cannot handle Bitcoin payments.

🍸The Chicago Bitcoin Collective is a newly established social and co-working space in a quiet neighborhood around Portage Park about half way to the airport. Even if you're just visiting Chicago for a short trip and are interested in meeting Bitcoiners, joining for a single month is very much worth the $25 membership fee. They are preparing to launch a restaurant downstairs, Fork & Coin. This restaurant is also using a Square terminal, including a small handheld device with the form factor of a smart phone. I'm told they have to opt into Bitcoin payments through the admin panel, and I quickly notice how the UI is not as polished, as the device asks for a tip twice, before and after selecting the Bitcoin payment option. A few blocks away there is a Mexican restaurant "Migos Fine Foods." They also have a self-service kiosk connected to a handheld Square terminal that does not take Bitcoin, but I succeed at the counter.

🪙There are a few Bitcoin ATMs around town, according to CoinATMRadar, but I only find one, a two-way operated by Rockitcoin. It requires me to register with a phone number to just show me the rate (a transparent 14% premium over the market rate to sell BTC), and requires me to scan a U.S. driver's license. I also check out a Coinstar machine, but it seems their Bitcoin integration is gone.

All together I found 24 Square merchants on my trip, 7 of which had Bitcoin payments enabled on their devices. Whenever I saw the ₿ symbol at the top left of the screen, payments were a breeze. I made nine payments, all of which went through within a few seconds, for between a 0.015 and 0.025% routing fee, virtually free. Square deserves a lot of praise for the solution they have come up with, even if it is not available at all locations. I wish Square could manage the data of their merchants on OpenStreetMaps better, which BTCMaps is based on. This would be a benefit to all their merchants, not just Bitcoin, and could even give them a small competitive advantage over competitors, as many Square merchants weren't found on OpenStreetMaps at all, or only with outdated opening hours or contact information.

It takes some imagination to see how all of this is supposed to come together. All Cash App users can supposedly pay the Lightning invoices shown on Square Terminals, but they have little incentive to do so, and more importantly, they likely don't know this option exists.

I'm personally strongly of the opinion that Lightning would be better branding than Bitcoin in this case. After all, Lightning is a payment protocol, and Bitcoin is a currency. We don't advertise which currencies we accept (you generally don't see "We accept USD" stickers in the U.S.), but rather what payment methods we process ("Cash and card accepted here"). Similarly, businesses would advertise "Lightning payments accepted here," and a Cash App user and Square merchant both holding U.S. dollars in their account would have no confusion over why they are going through a separate currency they both might not want. Additionally, I think Lightning has great branding, wonderful symbols that cannot be patented, it's easily translatable into all languages and doesn't carry awkward connotations.

I hope that we are going to see more businesses joining Square, upgrading their devices or opting into Lightning payments. I hope Cash App users learn they can pay from their app directly, rather than going through their cards, and I hope they financially benefit from paying with Lightning over card. Eventually Lightning will succeed over stable coins and card networks because it is an open system, that competitors like Toast and Venmo can freely integrate into their systems.

Chicago Hot Dog by the Riverwalk, ethically sourced with sats:

Self-serve kiosk at Steak & Shake:

The Bitcoin special:

The icon on the top left indicates that Lightning payments are an option. The card fee does not apply to Lightning payments.

After clicking on the Bitsoin symbol, the screen will show your amount in sats and the invoice as a QR code. You cannot (yet?) tap to retrieve the Bolt11 invoice.

Eat like your health care is free:

A Square-branded display showing all accepted payment methods.