Welcome to the Windy City! Chicago is the major Midwest hub — and the third largest city in the country — with 2.9 million people in the city proper and about 9 million more in the metro area. It’s a melting pot, packed with different cultures bringing their traditions like delicious food from every corner of the globe and great global-influenced shopping.

We’re also known worldwide for our favorite quirks: Chicago-style hot dogs, Chicago stuffed pizza, and weather that can span all four seasons in the space of an hour. (And no, the wind isn’t the reason Chicago is called the Windy City — it’s actually a thinly veiled reference to our crooked politicians blowing hot air when they speak.) It’s a mecca rising up on the shore of Lake Michigan, one you have to see to believe.

If you’re visiting Chicago, there are some things you absolutely can’t miss — whether it’s strolling through a great city park, standing on glass far above the city, catching a game, or grabbing dinner and a show. These are some of the best spots to see in the city from our travelstoke app.

1. The Skydeck

 Skydeck ChicagoChicago, United StatesThe Skydeck in Chicago was pretty cool, pre-buy tickets and get there early, it gets packed with tourists wanting to take this same exact photo 😜

2. Millennium Park

 Millennium ParkChicago, United StatesGreat Chicago park with the famous “silver bean” which makes for fun fotos. I think it’s called Cloud Gate. Awesome art installation.

3. Soldier Field

 Soldier FieldChicago, United StatesWhat a blast! 🏈 Love me some preseason NFL🏈 #football #chicago #chicagosports

4. Grant Park

 Grant ParkChicago, United StatesSummer dancing in the park! #dancing #livemusic

5. Wrigley Field

 Wrigley FieldChicago, United StatesHelmet Nachos & Chicago Cubs Baseball. 🏆 #usa

6. Schubas Tavern

 Schubas TavernChicago, United StatesFamous Chicago live music venue. Great sounding live room with an intimate vibe, old school bar in front, and great food from the kitchen. Perfect spot to grab some food, catch a show, and have a few drinks. #casual #food #livemusic

7. Lou Malnati’s Pizzeria

 Lou Malnati’s PizzeriaChicago, United StatesSausage deep dish. A Chicago classic and arguably one of the best. #cheap-eats #classic

8. The Signature Room

 The Signature Room at the 95th®Chicago, United StatesThe Signature Room is a must-see! The views of the city from the lounge and from the bathroom are pretty awesome!


Find some of these spots on our travelstoke map: