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Ultimate Chicago Bucket List: Must-See Attractions & Hidden Gems

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I absolutely loved my trip to Chicago, and you will too! Whether you're a first-time visitor or a seasoned local, this curated list of Chicago’s top attractions and off-the-beaten-path spots will help you experience the Windy City like never before. ...
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Sights

If you love architecture, this is a must! Along with the art, the river, and all the fun places to go and experiences to have, this city is a treasure! 

 
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Hands down, this was one of my favorite things to do during my visit. First up, the building is beautiful, so if you love architecture, then this is a goldmine. But the most fun thing about it is the artifacts from around the world embedded into the ...
Tribune Tower
 
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AKA "The Bean" is a fun photo opportunity for all ages. Unfortunately, when I was there, it was closed due to construction, but it still looked great from afar! A must-see!
Cloud Gate
 
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The Chicago Theater might be the most beautiful theater I have ever seen! Tip: If you do see a show here, get inside as early as you can and don't forget to look up and around at the gorgeous architecture.
The Chicago Theatre
 
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Tip: Go near St. Patrick's Day if you can, because that's when they dye the river green! That's what we did, and it was great. Around the river is very walkable, and there are also boat tours that you can take to look around the Windy City.
Welcome to the Chicago Riverwalk
 
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If you love Soarin' in Disney, then you'll love this! It's a 9-minute tour that takes you high above the city to see things from a new perspective. Lots of fun for all!
Flyover
 
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So much fun to spend an afternoon! Has everything for all ages, from shops, eats, and even a Ferris wheel! A must-do, definitely!
Navy Pier
 
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I ran out of time to visit the butterfly House but next time…🦋😀
The Butterfly House at Navy Pier
 
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Being an artist, this was fantastic! I had so much fun talking to a young artist whose work was being featured when I was there. This is located inside the Family Pavilion at Navy Pier.
Women's Live Artist Studio
 
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A beautiful, award-winning display you must see!
Fireworks at Navy Pier
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A beautiful place to unwind and relax!
Polk Bros Park
 
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I did not visit this because I didn't have any small ones with me but I hear great things about it!
Chicago Children's Museum
 
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Something for everyone to enjoy!
Pier Park Rides
 
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Awesome place to visit and will be loved by all!
Amazing Chicago's Funhouse Maze
 
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You won't be fearing rainy days on your visit with this indoor golf and soccer!
Fairways Indoor Golf & Play, Navy Pier | Indoor Soccer Simulator | Navy Pier ...
 
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I missed this unfortunately, but it's on my list for next time!
Puttery Chicago | Play a Round. Stay for the Night.

Eats

I am still dreaming about the food I ate in Chicago. The deep-dish pizza, the Chicago dogs and I could never forget the popcorn, yes, I said popcorn. Chicago is teeming with great eats with something for everyone.  

 
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Best pizza I have ever had! I'm still having dreams of this authentic Chicago pizza!
Lou Malnati's Pizzeria
 
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Okay, so when someone suggested buying this popcorn when I go to Chicago, I thought, okay, but how good could it actually be? Well, it was freaking delicious! I don't know exactly what they do to this unbelievable treat, but it's magical! You have to...
Garrett Popcorn Shops
 
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I had to get a Chicago dog and it was so delicious! But here's a tip, this place is very popular and fills up fast for seating, so it might be wise to go enjoy a hot dog on an off-time. So well worth it!
Chicago's Dog House