What’s the best way to see Chicago’s famous architecture?

Honestly, nothing beats the architecture boat tour on the Chicago River. It’s a vibe, you get stories from the guides and a totally different perspective of the skyline. Running from April through fall, it’s a good idea to grab tickets early though, especially on weekends.

Are there any good places to walk or bike near downtown?

Absolutely. The Lakefront Trail is awesome for biking or walking and offers killer views of both the city and Lake Michigan. Also, the 606 Trail is a quieter, elevated greenway on the city’s northwest side,cool for a bike trip with less crowds.

Where’s a good spot to catch live music without the tourist crowds?

Check out The Empty Bottle in Ukrainian Village or on Sundays at Smart Bar in Lakeview. They’re locally loved spots where you catch emerging bands and authentic Chicago music vibes without the usual tourist swarm.

Is deep-dish pizza worth trying or is it overrated?

If you haven’t had it before, go for it. It’s an experience,heavy and cheesy and very different from thin crust. Giordano’s or Lou Malnati’s are classics, but if you want something a bit less touristy, try Pequod’s on the northwest side for a caramelized crust twist.

What’s a fun outdoor activity that’s less known for visitors?

If you get a chance, kayaking on the Chicago River is a blast and way less touristy than the boats. You can rent anytime in summer from spots like Urban Kayaks. It’s a cool way to see the city up close with a bit of a workout.

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Chicago Walk: Prohibition, Architecture & Hidden Gems

2 hours 30 minutes via GetYourGuide

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Chicago Prohibition and Architecture Walking Tour This guided walking tour in downtown Chicago suits history and architecture enthusiasts interested in the city's Prohibition era and iconic landmarks.

Page 2 - Things To Do in Chicago

Chicago Walk: Prohibition, Architecture & Hidden Gems

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