Chicago is just a cool city. Since I've been there on multiple occasions and only for a couple days at a time, instead of a trip report, I thought I'd just make a small list of the reasons I like it. There's so much to do and see even just wandering around. It's the big city of the Midwest after all! In American terms, I'd tell people it's "not too far from me." Only a 6 hour drive! It's nothing! Also, you can find tickets from Cleveland for something like $15 on the Megabus. I love Megabus. Or, you can do a fun thing and fly from Cleveland, which means you land at exactly the same time you took off. If you think that's worth the extra $100. Probably not.
Boat (/drinking in the bar at the bottom of the boat) tour
Navy Pier
Everyone likes a good view of a skyline over the water.
Combine the views with the vendors selling you margaritas and elephant ears on the street, an indoor shopping center with a greenhouse, and a ferris wheel, and you've got a fun afternoon out where you can be a drunken kid again.
On one visit, we even got free entry to a swanky new rooftop bar where we had a perfect view for the public fireworks.
Millennium Park & the many other parks
Millennium Park is the famous one. You've got the Chicago Bean with its trippy vortex interior, a metallic amphitheater, and Crown Fountain with its giant faces.
But just wandering around the city, you'll find tons of other parks which are, at a minimum, very pretty.
Deep-dish pizza
If there's one thing I have learned from living abroad, it's that other cultures just have it wrong when it comes to pizza (and even parts of America... sorry New York). Pizza is not meant to be thin. I should not be able to finish an entire pizza by myself. Nope, nothing compares to deep-dish pizza. This is going to sound like blasphemy, but... I'm not even a huge fan of the thin pizzas in Italy.
Of course, Chicago is known for its deep-dish pizza. On my first trip to Chicago, one of my friends took us all to a famous Chicago pizzeria where we literally waited an hour for delicious, inches-thick pizzas. Worth it.
Pequod's
Shedd Aquarium
It's not like I've scoured the earth to rank aquariums or whatever, but this aquarium is the second best I've ever been to (I finally went to Atlanta and that beat it out). It is very large and very nice.
Along with fish, frogs, and eels, there are sea otters, penguins, sea lions, and even dolphins! But the coolest thing has to be the beluga whales. They were massive! They were all swimming vertically near the top of their tank and dancing to the music that was playing for them. Dancing! Dancing beluga whales, guys. Don't miss this aquarium.
Nightlife shows
My experiences in Chicago have led me to believe that something is happening literally every night in that city. My first time there, I saw my first Broadway show, Wicked. The second, I went to a hilarious and uncensored improv show. The third, my friends and I went into a club called Hydrate in the rainbow district, Belmont, and ended up walking into a full-on gay interpretation of Alice called Alex in Wonderland. It was amazing.
More recently, we saw the absolutely spectacular musical Six at the Chicago Shakespeare Theater on Navy Pier.
Speaking of Belmont, the brunches. One I've been to was at noon on a Sunday with club music blaring and drink specials for $3 mimosas and $4 bloody marys. There is no better way to wake up. Also, barhopping the rainbow district is just fun. Great, cocktail bars, fun clubs... do it.
Sidetrack in Boystown has a cloud bar
Another good brunch, not in Belmont, at The Dawson.
Other bars I've enjoyed were the Howl at the Moon dueling pianos bar, the rooftop bar at the Wit (where I stayed with my brother for his bachelor party), and Sluggers, a massive complex of dueling pianos, arcade, batting cages, and more.
Rooftop at the Wit
Riot Fest
Chicago also hosts the annual Riot Fest, a three day outdoor music festival that is mostly rock music. I went in 2021 and got to see so many amazing bands, including but not limited to Smashing Pumpkins, Dropkick Murphys, Slipknot, Simple Plan, Sublime, GWAR, Flaming Lips, and so much more. Absolutely worth the cost of admission (although catching the train back to the city afterwards is a gigantic pain in the ass).
Tip: Avoid the winter. I MEAN AVOID.
My second trip to Chicago happened to be in February- never again. I can't remember ever being so cold in my life. It was -10 outside with -27 degree wind chill. I remember shuffling through the city having to talk myself into each step because it was that. fucking. cold. In this photo, I am wearing a shirt, a jacket, a hoodie, a coat, a hat, and TWO pairs of pants. Guys, if you're doubling up on layers of pants, it is too damn cold to be outside.
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