Has Everything Gone Cashless And Over-Reliant On Tech? (2025)

I’m feeling old. While tech savvy, I am beginning to feel the emotional confusion of the elderly people I know who tell me that the world seems to be passing them by now. Case in point: Just came back from a fun trip to Chicago where it seems every venue we encountered had gone cashless and tech-centric.

And while I understand the trend, it comes with its share of problems. It started to hit me when I went to buy some three-day Chicago Transit Authority train passes. The vending machine had no problem accepting my credit card, but it did have an issue in giving me our tickets. It just failed that part of the transaction. Which put me on the phone with a CTA representative for 30 minutes, in an attempt to get refunded. The rep finally transferred me over to a different department, which accidentally disconnected me before we actually spoke. That resulted in another 15 minutes on the phone with the right person who admitted her attempt at a refund may or may not work.

Next day we decided to go to the Cubs game. Because we suspected it would be a sellout for opening weekend – turns out it was – we opted to buy tickets on the MLB Ballpark app that I’ve used before. The app offers seat previews, but we subsequently noticed it somehow forgot to include the view-obstructing pole in our sight line. And by the way, it charged 34 percent extra on top of the ticket prices for the so-called convenience of using this service.

Stopped in for a pre-game drink at a local bar. Ordered and drank, then flagged down the waiter to pay up. When he saw me reach for cash, he said “Oh, did I not mention we are card only?” I told him he did not, but that was okay, and I paid by credit card. That was the first restaurant of many over the week in which the server brought a handheld card processor to pay the bill – with suggested tips starting at 25 percent. And by the way, all of the tip suggestions are based on the price of the meal plus tax. So really it’s more like 28 percent. While they usually give you three tip options – in our home area it’s typically 15, 18 and 20 percent – these were 25, 28 and 30 percent. Since when is entitlement like that okay? At the Cubs game itself, of course, we found nowhere inside Wrigley Field that would let fans pay cash for snacks. Everything is cashless.

Then we went to a board game restaurant for dinner. Again, cashless. Except at this place you had to download the menu to your phone and enter your credit card information – before you could even order food and drinks. Typically as you probably know, you don’t pay for food until after you eat. So it just struck me as odd and presumptuous.

We took a mob and crime bus tour the last day, which we loved. And as we left, the guide asked for tips by advertising her Venmo account. Par for the course. And for the times we live in.

On another night, we ducked into what looked like an upscale restaurant. After being shown to a table, the hostess directed us to the two iPads on our table. There we ordered our food, without ever interacting with an employee. Finally, one person came over to verify our order and officially place it. The only other time we interacted with anyone was getting our water refilled, our food dropped off at the table, and to collect my credit card. That of course led to a spirited conversation at our table of if we would rather have a real person checking in to see if we needed anything. For the record, I prefer the latter.

Of the many restaurants we visited all week, only one was cash only. And I applaud the owners for doing that. It was a pretty nice neighborhood restaurant in Lincoln Park. They even warn you it’s cash only with signs on the door, and again when they seat you. And after all of the credit card only places we found over the week, this approach – which should be the norm, in my opinion – stuck out as odd that they need to warn customers so many times. Maybe I just acclimated and desensitized over the week.

I certainly hope we can still use cash in the future. My daughter has accused me before of looking like an old woman fumbling through a coin purse for cash. But I just don’t want to be surprised with a high credit card bill at the end of every month. Would much rather use cash. I realize it’s probably safer just paying for things with a card or Apple Pay. But I’m old school. And just not ready to – pun intended – change with the times.