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5 Can’t-Miss Experiences in Chicago

Despite the fact that it was pretty much 40 degrees the entire time I was there (in May, no less), despite the fact that I ate my weight in cheese and my stomach hated me for it, and despite the fact that I spent most of my time working while I was there, Chicago charmed me. During breaks I got to explore downtown, and I added a few days onto the end of my trip to see even more of the city. Whether you’ve got one day, a weekend, or more, make sure to fit in these memorable experiences when you go to Chicago.

Cheese cheese and more cheese plz.

The pizza

Okay, no surprise here, but if you’re in Chicago you need to get your paws on a deep dish pizza. You have lots of picks, and I’m pretty sure a big ol’ cheese pie is good no matter what, but here are some of the popular places to get it:

  • Giordano’s—this is the pizza that my parents (who are from Chicago) always raved about and insisted we eat every time we visited Chicago.
  • Gino’s—one of the legends.
  • Lou Malnati’s—not “Illuminati’s” as I heard first heard it, but perhaps just as enlightening?
  • Pequod’s—a friend who lives in Chicago said this was his fave, and the guide on the Free Tours by Foot that I took told us this is the spot.

Pretty buildings, pretty bean.

The architecture

It had been over a decade since I’d last been in Chicago, and I definitely didn’t ever realize how beautiful the city is. As a total city gal, the architecture in Chicago truly made an impression on me. And as it turns out, architecture tours are a ~thing~, so book one for yourself—it offers a wonderful look into the history of the city! If the price of the Architecture River Tour makes you weep, then take the one from Free Tours by Foot (just remember to tip your guide!).

The view from 360 Chicago.

The views

Piggybacking on that, make sure you get somewhere off of ground level to take in the views. A lot of visitors think this will be Willis Tower (formerly Sears Tower) on their Skydeck, but the windows are situated so you’re looking west—rather than east towards the heart of the city. You’ll actually get a way better view in the John Hancock Observatory (now called 360 Chicago). For about $20, you get amazing views of the lake and the city, and I can attest that this is a wonderful sunset-viewing spot.

If you’re on an ultra budget, then get the same view (one floor up, actually) for free at the Signature Room Lounge. It’s a pretty swanky spot so drink prices are steep, but supposedly the best view of Chicago can be found from a window in the women’s bathroom!

A groovy exhibit in the Chicago Cultural Center.

The art

You will have no end to all of the museum options to visit in Chicago. I’m not personally much of a museum-goer when I travel, but I did get to explore the Chicago Design Museum (free) and the Chicago Cultural Center (also free) and both were definitely worth squeezing it in on a short lunch break. Sadly, I didn’t get to the Museum of Contemporary Photography, but I definitely will add that to my itinerary next trip. The Art Institute of Chicago would have been on my list if I’d had more time—it’s a pricier one, but a favorite amongst tourists and locals alike. Oh, and don’t forget Cloud Gate, AKA The Bean.

The neighborhoods

Public transit in Chicago will keep you well-connected to the vibrant neighborhoods that are just a short ride from the city center. I loved wandering around Logan Square which had adorable stores, a relaxing coffee shop, and a lovely park right in the middle of it. Other notable ‘hoods to visit include Irving Park (lots of outdoor space plus hip watering holes), Lincoln Park (home to a zoo, if that’s your thing), and Wicker Park (boutiques and cocktail bars).

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