A Chicago Bucket List: 25 Things to Do In Chicago Beyond the Touristy Stuff

Happy birthday Chicago! You’re 175!

To celebrate, here’s a list of the 25 ultimate things to do that are ‘so Chicago’ (25 because I couldn’t think of  175. Deal with it).

I’m also not talking about the lame touristy ‘have deep dish pizza, ride the ferris wheel at Navy Pier, go to the top of the Sears Tower’ stuff either (although you ready should do that stuff). This list is legit and not for the faint of heart. A Chicago bucket list if you will, that can be taken on by couples, friends or just anyone angling to get to know the city better. Take on the list today, or save it for when you need an adventure.

Here it goes:

  1. Order a chocolate milkshake at The Weiner Circle. It’s $20 and totally not what you think. Helpful tip: AVOID THE CHEESE THEY USE FOR THE CHEESE FRIES. That stuff is just plain bad (not that you’re really going there for a gourmet meal).
  2. Jam all your friends in Bar Deville’s photo booth and go wild. Bonus tip: have a Moscow Mule. Best in the City.
  3. Hit up Neo. Try to blend in.
  4. Dance on the bar at McFadden’s (if you’re a girl). Yeah, totally cheesy. No one said this list wouldn’t be.
  5. Rock out at one of many summer festivals: Lollapalooza, Pitchfork, Northcoast to name a few.
  6. Andersonville’s Dinner Crawl. Best way to get to know the neighborhood and try out new spots for a low-cost. Bonus points if you do Salt AND Pepper. Don’t forget, Dessert Walk happens just a little later in the year.
  7. Play some old school video games at Galway Bay. The bar is stocked with classic systems like Sega and Nintendo (I’ll take anyone on Street Fighter). Extra tip: Have a Malort Shot! They sell more than any other bar in Chicago.
  8. Santa Speedo Run. It’s cold, it’s almost Christmas, you may or may not be young but you are fun so strap-on your best red (and skimpy outfit) and do the dash. Get drunk after!
  9. Watch a show from the boxed seats at House of Blues and feed the fishes. These are not real fishes this is metaphor for the people below and ‘food’ is dolla dolla bills ya’ll. They will love it, you will feel like a baller. It’s really a win-win.
  10. Shake a politician’s hand. It’s Chicago. These guys and girls are always out doing something. It’s pretty impossible not to.
  11. Do shots with Patrick Kane. Win or lose this guy loves to party. He’s often spotted around Chicago and you can be sure he won’t turn you down.
  12.  Attend a baseball game on the fourth of July. We have two teams in town. One of them is always in Chicago so one of them is always playing on the fourth. Very American and bonus America points if you catch the Sox (fireworks during homeruns and at the end!).
  13.  Bulls game from the 300-level. It’s not terrible. Crowd is always amped and more rowdy up there.
  14.  Buy tamales off the original tamale guy (red cooler). He sticks around the Wicker Park/Bucktown area and you can find his exact location by following him at @TamaleTracker.
  15.  Spot the CTA’s holiday train. Bonus points if you ride it.
  16.  Use the pedway! My best experience was during Chicago Shakespeare Theatre’s En Route, but since it’s no longer in production try Chicago Elevated’s pedway tour.
  17.  Take in one of Mark Bazer’s Interview Show. Not only does the location feel like you just stumbled upon one of Chicago’s best-kept secrets (The Hideout), the line-up is pretty sick. Past guests include Tavi Gevinson (The Style Rookie), Andrew Barber (Fake Shore Drive), Charlie Trotter and more.
  18.  Find a piece of free art by Patrick Skoff to decorate your home with. Free art does not equal shitty art. His artwork is fantastic and often Chicago-inspired.
  19.  Experience the city on bike. Take one of Bobby’s Bike Hike tours. Did the Lakefront Neighborhood Tour in 2006 and I still repeat the facts I learn and act like I’m super knowledgeable on chicago. Glad to see this place is alive and definitely gotta plug it now that my friend Mark is a manager there! Read his interview in TimeOut Chicago.
  20. Go paddle boarding at Montrose Beach. It feels like you’re away on vacation in Hawaii. Except you’re not. Pretend the high-rises are mountains.
  21.  Catch a free secret show. From Jennifer Hudson at Paris Club, to Maroon 5 at Union Station. These events happen all-year round, all over town and for every taste in music. Just gotta be at the right place at the right time.
  22.  Speaking of concerts. No better place to catch a show than on a warm night at Northerly Island. When the sun sets on the skyline and you’re rocking out to your favorite band of the moment you’ll definitely have a “Yes, this is my life and it rocks” moment.
  23.  Experience the awesomeness that is the Gay Pride parade.
  24.  Throw out a ceremonial first pitch. What! You haven’t already done this? Neither have I. BUT, I do see contests for this all the time. Fill-out enough of those contest forms and you’re bound to win.
  25. And the ultimate way to get to know Chicago? Run the marathon.

Feel free to throw any recs my way.

Filed under: Uncategorized

Tags: adult, adventure, chicago, fun, list, neat, to do


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  • wiener circle, the bulls, house of blues, lola, pitchfork, and attend a baseball game.... what is the title of this post again?

  • When do we get a 25 things to do beyond the Northside list?

  • Ah leave her alone. This is a great list that may include some "standard" activities, but also has some hidden gems. Have some better recommendations? Post 'em.

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    Gonna be my first time there, and im going to try the Tamale guy....i will be looking for Latinos :D

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  • fb_avatar

    Nice article. Here are the More things to do at Chicago.

  • Why do you go away? So that you can come back. So that you can see the place you came from with new eyes and extra colors. And the people there see you differently, too. Coming back to where you started is not the same as never leaving.

  • A pretty good list. I am heading to Chicago in a few weeks from L.A and will be checking a few of these things out so thank you. I've also found a few good things to see on www.hopolla.com, if you need some more inspiration. I find tripadviser to be full of boring tourist traps. I like reading blogs and smaller sites for travel tips.

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    Great list, I just moved to http://www.drhorton.com/Illinois/Chicago/Deerfield/Emerald-Deerfield-Premier-Homes and I love it, however, i have been looking for the best things to do here, I have family coming to visit that hasn't ever been here and I want them to have a great time, this is just what I needed. Thanks for taking the time to make a killer list.

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