10 Touristy And Totally Uncool Things To Do When Visiting Chicago

A crowd of people watching a person do a trick on a skateboard

I’ve been living in Chicago for about 9 years now – I like it here, but there are things I hate. I go to Michigan Avenue to watch people, so I can intentionally get annoyed. It’s one of my favorite past times.

Getting trampled by 45-year-old dads wearing cargo shorts and Crocs as they run from the Disney Store into Garrett Popcorn – don’t love it.

Here are some really touristy (uncool) things you can do when visiting Chicago. Dig a little deeper when visiting, folks.

10. Waiting in line for Garrett Popcorn.

It’s fucking popcorn, people. With cheese powder. Is it good? Fuck yeah it is. I don’t do lines for popped corn.

A kitchen with a sink and a toaster oven

9. Taking a photo under the Cubs marquee sign.

The younger you are, the more acceptable it is to do this. Take a photo of your drunk friend puking on his lap in the Bleachers, or of the scoreboard, for your Instagram. Go ahead, fine.

A kitchen with a sink and a toaster oven

8. The Sears Tower Skydeck.

I refuse to call it W-i-l-l-i-s. Sure it’s kinda cool, but I hate heights and my palms are sweaty even typing this thinking about this thing.

7. Taking a selfie at The Bean.

Royal Rumble with 65 suburban teenagers. For a shiny bean selfie?

A black coffee maker on a counter

6. The Cheesecake Factory.

What the FUCK are you doing? One of the best food cities in America and you’re eating at T.G.I. McFunsters? I don’t care about its location, you walk a few blocks and eat at a real restaurant, not one that looks like the set of Alice in Wonderland.

A kitchen with a sink and a toaster oven

5. Segway Tours.

Why would you do that (13 goobers pictured)? I can’t even look at this photo without getting upset.

A kitchen with a sink and a toaster oven

4. Portillo’s.

I like the cheese fries, but there are much better, less touristy, places for this type of food. You’re uncomfortably surrounded by the Rock N’ Roll McDonald’s, Rainforest Cafe, and the Hard Rock Cafe for a reason.

For an Italian Beef, Mr. Beef or Al’s.

There’s 6 dozen places that do hot dogs better. RIP Hot Doug’s…

3. Navy Pier.

It’s like experiencing New York City by eating at Bubba Gump Shrimp in Times Square. Same shit. Oh wait, there’s a Bubba Gump at Navy Pier…

2. Going to She-Nannigan’s or the Hangge Uppe.

If you want to meet a bachelorette party full of 37-year-olds from Schaumburg, go to She-Nannigan’s.

If you want to give yourself a heat stroke and E.coli head to the Hangge Uppe basement.

1. Taste Of Chicago.

I used to go to this before I moved to the city, now, you can’t pay me to get near it.

How many sweat-soaked turkey leg eating Neanderthals can bump into your face before you stab yourself in the eye with a plastic fork? That’s the real question.

A kitchen with a sink and a toaster oven

A beer bottle on a dock



A beer bottle on a dock