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Exploring Chicago with Foursquare: An Unexpectedly Amazing Experience

(UPDATE: Thanks to everyone reading about my Foursquare journey through Chicago. Please feel free to follow me on Twitter at @chicagocarless, or subscribe to my blog or other social media presences via the neat little icons in my right sidebar!)

Until the past week, I didn’t give Foursquare much though. A GPS game you play with your smart phone, requiring that you “check-in” at businesses and landmarks around your city to earn points and “badges”? What am I, a boy scout? Nothing but a marketing gimmick, I assumed. And it is–business owners often offer discounts to Foursquare users who have checked-in often enough at their establishments to become “mayors.” But now I know it’s also a lot more. For one, it’s really addictive. For two, it’s fun. But most of all, it may be the most effective interactive tourism marketing tool ever.

My new friend, Uptown Boy, introduced me to the GPS game when his use of it got us in trouble at a concert last week. Since then, I’ve spent my time learning that almost every business, bridge, transit station, and most likely bird’s nest in Chicago has a Foursquare listing. First I didn’t see the point of it. Then to my surprise I became the “mayor” of a local park–and my competitive edge instantly decided that all bets were off. As I quickly became hooked on the game, I also tried to learn the etiquette of it–especially since your check-ins can be automatically posted to your other social media accounts. (And my Twitter followers don’t necessarily need or want to know every time I go to Jewel.)

But aside from the fun of the competition and maybe an occasional dollar appetizer or free drink at a local hoodie, I didn’t see much real worth of Foursquare for its users. It’s an insidiously addicting way for commercial interests to collect marketing-research data. But as far as offering anything of real depth to users? I didn’t get it.

And then Uptown Boy put me in charge of picking an adventure for our upcoming Saturday afternoon date. After several hours of wracking my brain (we’ve already been to every museum in town), I came across Explore Chicago’s Foursquare page, and my competitive Scooby Doo ears immediately went, “Hruh?” The brainchild of the Chicago Office of Tourism (find the backstory on, the city’s official tourism arm offers three Foursquare badges that visitors can earn by checking in at locations across town that have historic and cultural importance in the Windy City:

  • A Celery Salt badge, for visiting famous Chicago hot dog stands;
  • A Chicago Blues badge, for visiting historic sites and clubs associated with the history of Chicago blues; and
  • An On Location badge, for checking in at places where scenes from famous Chicago movies were filmed.

Check-ins are required at any five locations chosen from a longer list of eligible destinations to earn each badge, so you get to tailor your own itinerary, and each location has one or more “tips” associated with it written by Explore Chicago staff.  (For a list of eligible destinations, follow the above links.) In addition, the On Location badge requires you to choose a specific movie category (The Blues Brothers, The Dark Knight, Ferris Bueller’s Day Off, High Fidelity, or the cringingly named “Chick Flicks in Chicago.”)

Having a full day to spend, we decided to go for all three badges, with Blues Brothers as our movie theme. We figured if nothing else we’d earn a few Foursquare badges our friends didn’t have while passing the time on a sunny day. We started at Wrigley Field at 11 a.m. and ended at Muskie’s burger stand back in Lakeview at 7:30 p.m., eight-and-a-half hours later.  The day took us as far south as 47th Street (9.5 miles from our starting point at Wrigley), required 13 separate ‘L’ or bus journeys on the CTA, and a pit stop at a coffee shop to recharge our phones before we were done.

As it turned out, actually earning the badges was anti-climactic, though I did earn mine on the day. (Uptown Boy didn’t earn On Location until the next day for lack of following Explore Chicago before his first check-in at Wrigley.) No, our big surprise was how much we learned and how many unexpected surprises happened along the way. In order:

  • At Wrigley Field (where we didn’t sample the hot dogs), having once lived in the neighborhood, I taught Uptown Boy how to elbow your way onto the Red Line on a game day;
  • At the Blues Brothers’ fictional Ray’s Music Store on the corner of 47th and Prairie, Uptown Boy told me he’d never ventured this far south on the Green Line–and the Blues Brothers mural around the corner blew us both away;
  • Neither one of us knew that the long-gone Illinois Central depot was once known as the “Black Ellis Island,” and our walk to its remaining stone markers had us talking about how much has changed along Roosevelt Road in the past few years;
  • The decrepitude of the historic site of Vee-Jay Records at 14th and Michigan was sad, and made us both think about how precious our city’s architectural heritage is;
  • While checking in outside the locked Willie Dixon’s Blues Heaven Foundation at 21st and Michigan, former home of iconic Chess Records, an employee drove up and let us inside for an unexpected hour-long documentary and tour–at the same time  a woman from Indiana arrived to explore the history of a newly discovered relative–Willie Dixon, himself;
  • The location of the old Maxwell Street Market‘s nothing more than a student ghetto now–I’d been down that stretch of Halsted a hundred times and never knew that’s where it used to be–but Uptown and I both marveled at the Eastern European-inspired hot dogs from Jim’s Original around the corner on South Union as we scarfed down their grilled-onion goodness at the outdoor counter;
  • A need for another hot-dog check-in brought us back south to U.S. Cellular Field, where I’d never visited before–I tried to imagine how atmospheric Comiskey must have been (see how the Chicago Baseball Museum tells it) as I marveled at how ugly and uninspired “The Cell” is up close;
  • On the way back north, we watched a Chicago SWAT team spot check a Red Line train at Sox-35th and mused about racism and police mismanagement–but were brought back on track by a feisty little old black lady who regaled us with tales of the blues musicians she used to know, including none other than Muddy Waters;
  • At Daley Plaza for a Blues Brothers check-in, after seven years I finally climbed up the Picasso, but it being a Saturday, no one was visiting the Cook County Assessor’s Office (another potential On Location check-in location);
  • A check-in at the Blues Brothers location at Michigan and Lower Wacker nicely stood-in for the Assessor’s Office, and allowed me to drag Uptown into the Billy Goat Tavern–a friendly spot which I love but where he’d never been (apparently, for fear of venturing onto Lower Michigan thanks to a childhood viewing of Henry, Portrait of a Serial Killer!);
  • Walking into The Wiener’s Circle–and smelling the place–told us we’d never eat there;
  • The walk through drunken holiday hordes of Trixies and Chads in Lincoln Park as we headed to our last stop in Lakeview told us why we don’t live there;
  • And Muskie’s, when we finally got there, was closed, but I told Uptown all about the seasoned burgers–and how much I love Powell’s used bookstore just down the street.

As Uptown Boy and his graphical skills put it the next day, our journey looked like this:

Surprisingly for both of us, chasing the Explore Chicago Foursquare badges turned out really to be about traveling off the beaten path in Chicago, to experience the city and its people in unexpected ways. According to Explore Chicago, that was exactly their intention in creating the badges and selecting the destinations.

Uptown Boy and I both agreed the experience was an eye-opener. Besides being a lot of fun, we both learned interesting, at times amazing things about Chicago that we never knew before. Considering that he’s a lifelong resident of the region and I’ve been here almost eight years, that says a lot. Of course, we’re not alone. The Chicago badges have been pretty popular with locals since they debuted this year. I can only imagine how much fun it must be for a newbie Chicago visitor to go after them, or how much they find out about the Windy City that they might never otherwise have a chance to know.

I also wonder why other cities haven’t rolled out similar Foursquare badge hunts. The free-form tours seem to be a perfect, low-cost way for cities to engage visitors simply by leveraging the smart phones most of them carry around in their pockets and purses. After all, every city of any size anywhere has something cool to see somewhere.

And as our experience showed Uptown and me, the unexpected randomness that fills in the blanks between check-ins can be as fulfilling as the destinations, themselves.

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Mike Doyle

I’m an #OpenlyAutistic gay, Hispanic, urbanist, Disney World fan, New York native, politically independent, Jewish blogger in Chicago. I believe in social justice, big cities, and public transit. I write words and raise money for nonprofits. I’ve written this blog since 2005. And counting...

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