Imagining a Cashless Chicago

If it were up to my generation, cold hard cash would be a thing of the past. It just so happens summertime is always the hardest for us anti-cash types; between the farmers markets, festivals and pedicab rides home, it ain’t easy living cash free.

Whenever I find myself on the wrong side of a cash only situation, I can’t help but return to the idea that mobile payment services like Square and PayPal Here would eliminate such headaches. From the festival goer thirsty for a cold Goose Island beer to the grumpy hot dog saleslady who misses out on sale after sale because she can’t accept card, this tiny technology could really make a difference.

Someday, we’ll all accept credit cards. Until then, Chicago, here’s a good place to start our quest to become plastic-friendly city.

farmer's market1. Farmer’s market vendors

This past weekend I sought out the one unhealthy item at Logan Square Farmer’s Market – the sausage booth. The product? Delicious. But the friendly vendors were in a fluster about making change for big bills. “Do you have any smaller bills?” she asked of my ten dollar bill. No pocketful of ones here, unfortunately.


summer festival

2. Summer festivals

Here we’ve got the same scenario as above. Come summertime, Chicagoans flood into summer festivals by the thousands. RibFest, BurgerFest, Taste of Chicago, Old Town Art Fair, Lollapalooza – you name it. All of these vendors are selling items pined after by the masses, but without cash, everyone’s out of luck. And with hot summer temperatures, we don’t need one more minor inconvenience ($4 ATM fee?!) to tick us off.

hot dog, hot dog stands, food trucks

3. Hot dog stands

As a food truck fiend, I’ve found that this new wave of mobile eateries is pretty darn tech friendly. Food trucks embrace social media as a means of survival, and the vast¬†majority are equipped with mobile payment devices. It’s the old school hot dog vendors that are steadfastly cash only establishments. And come on, how is a Chicagoan supposed to make it through a summer without hot dogs?

babysitter, the babysitter's club

4. Babysitters

I am by no means in the market for babysitting services, but back in college, it was the easiest (and most enjoyable) route to quick cash. The problem was, after a night on the town mom and dad often strolled home with empty pockets. “Can we just get you next time?” they’d ask. Instead of going home¬†empty handed, babysitters should take the problem into their own hands, coming equipped with mobile payment services.

pedicab, Chicago5. Pedicabs

True city dwellers know that pedicabs are the fun alternative to a late night cab ride home. One weekend, after being dropped off by a friendly cyclist, my friends and I dug deep in our pockets, quickly realizing that between the three of us we couldn’t pull the cash to pay our fare. Next time, hopefully we can charge it rather than tipping our driver by covering his bar tab. Because that just doesn’t seem safe, right?


An international crisis? Perhaps not. But I think Chicago’s hearts and minds (and stomachs) could really benefit from a step into the plastic-friendly universe.