Planning a trip to Chicago with a friend. He’s never been and wants to visit—I’ve been once for work and didn’t care for it so much. We’ll be there for two nights and plan to just stay in the downtown area. Any recs on what to do/see/eat? Just looking for something relaxing. Don’t care so much for sports. Love good food and sights. We’ll be going in June.

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You have to go on the Chicago Architecture Center boat tour. Seriously, absolutely cannot let your friend miss the chance to do that. Weather in June will be great for it too.

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I’m a Chicago kid but live on the West Coast now. This is what I recommend to EVERYBODY going to Chicago the first time. They’re the best way to see the city, especially with great weather like June should (hopefully) be.

The pier and neighboring park is nice, nothing revolutionary but it’s right on the water and nice to just walk around. The blue angels do shows there occasionally and that’s worth watching if you can, too! Seems touristy, definitely, but that’s what I’d do.
LOADS of good restaurants.

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Chicago architecture boat tour for sure. Chicago’s museums are really excellent - pick the one that fits your vibe (personal favorite is science & industry, but art institute, field museum, and shedd aquarium are great). Check if there’s a concert in the park at millennium when you’re there. Not sure where you’re from, but Chicago beaches are genuinely nice - it’s no ocean, but if you’re not from a coast then you should hit the lake (oak street beach is busy but accessible if you’re downtown). I would skip navy pier unless you’re really into the touristy thing.

Chicago’s food scene is insane. Happy to give more specific recs if you share price point and/or any guidance on cuisine - but plan to venture out of downtown. Tons of great food in West Loop in particular.

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Frontera Grill
Lou Malnati's is my fave pizza but loads of options.
Boat tour?

Navy Pier and walk around downtown chicago. The bean is a popular picture stop.

Boat architecture tour

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