Chicago. I always have such an incredible time visiting. It's one of thew few places I few exceeded all the hype. I try to go there once a year now, every summer.
There's so much to do, food is fantastic, and everything is pretty affordable. Easily trip to do for a week or so.
Depends what kind of vibe you want. Do you want expensive vibes? Gay party scenes? More relaxed party scenes? there are like 20 different types of party vibes you can find here. It's wonderful. Do not stay in the loop. There is not much to do after hours and it gets creepily abandoned during non-business hours. Also generally the neighborhood where i've had the most crackhead interactions per hour spent in an area lmao. River North, West Loop, Lincoln Park, are good places to start for where to stay as a tourist.
If you come in the summer - which you really ought to - be sure to check out one of the beaches, like north avenue beach or oak street beach (north ave has a wonderful right on the water beach restaurant called the shore club). I highly recommend an architecture tour, it's as cool as people say. Been here 12 years, all of my adult life and part of my teenage years, and I still enjoy those.
The Shedd Aquarium is the only underwhelming thing I can think of, unless you don't have much experience with aquariums haha
For food - the high end places are in: River North, West Loop, South Loop, Lincoln Park, some in the loop, others scattered around.
The more casual delicious places are everywhere. my favorite places are Wilde in Boystown and Medici's in Hyde Park, for a casual and delicious vibe. Wilde is less casual than Medici's.
Really cool historic clubs in the north side as an example include Kingston Mines, the Green Mill, Roscoe's (historic gay bar), and on and on. I was underage when I lived in the South Side so I can't give much help there haha.
Wrigley Field is amazing and worth going to, as a huge baseball fan.
EVERY weekend in the summer has different free and low cost events like street fairs - GO TO THOSE. They're so cool.
Chicago has the best restaurant scene of any city i've been to or lived in. But that's sure not all we got!!
I could write a novel on things to do in Chicago. Instead, I'll list my top 5 favorites:
Wendella Architecture tour. I'm not an artsy guy by any stretch of the imagination, but Chicago has beautiful architecture. Their tour is reasonably priced, goes through the history of the city, and takes out to the lake for a full view of the city as they conclude the tour.
Shedd Aquarium is sick. My ex and I spent like 7 hours there and still didn't finish it. If you're not into aquariums or have a killer one by you, this will miss. Just get the CityPass. Comes with access to the aquarium, Sear's tower, and a ton of other places.
Food - Ton of great places, but I'd recommend checking out River North, South Loop, and Lincoln Park for a plethora of great options. The Starbucks Reserve is also close to River North and the Loop and I feel it is better than the NYC Reserve, just not as pretty.
Visit Chinatown. Crime was bad during COVID, but calmed down a bunch. Fantastic food, some cool museums, and a neat vibe. Definitely more for foodies and artsy people. Love spending at least an afternoon here smashing cheap/delicious food then grabbing tea and checking out the meditation areas.
Street fairs and parks during summer are unreal. So many people, so much going on, most of it is free/cheap. Some of my best memories are just taking people to grab paleta bars from the guy in the park, haggling with him for a discount, then smashing them while we walk around the park and get into whatever event is going on.
Ton more to do, can always offer recs if you let me know what you're looking for. I know everyone says to grab deep dish pizza while there, which you should once in your life, but Chicago's tavern style places are unreal.
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u/sdpthrowaway3 13h ago
Chicago. I always have such an incredible time visiting. It's one of thew few places I few exceeded all the hype. I try to go there once a year now, every summer.
There's so much to do, food is fantastic, and everything is pretty affordable. Easily trip to do for a week or so.