| Have never been and know nothing about the city. He just "wants to see it." We will be driving as part of a college trip but beyond that I have no plans, no ideas what we should do and no clue where to stay. Help! |
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Watch Ferris Buehler's Day Off...that should give you some ideas.
Stay near Michigan Ave and walk around. There's a Hyatt, Sheraton, intercontinental, Fairmont. Go to Navy Pier, ride the ginormous Ferris wheel. There's a big aquarium and science center. Take a selfie by the bean. Sears Tower (it's called something else now). Eat deep dish pizza. Go to a baseball game. That's pretty much it. |
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Things To Do: Art Institute, Millennium Park, Walking along Michigan Ave, Architectural Boat Tour, Wrigley Field, Skydeck, eat deep dish (Lou Malnatti's or Pequods)
To Stay: Palmer House is great, or AirBnB in Lincoln Park would be a good way to have a local experience. |
| A teen might like the improv/comedy stuff-- Second City, Improv Olympic. There's always lots of off-Broadway type shows as well. Maybe some kind of blues thing -- House of Blues, etc. |
Museum of Science & Industry Aquarium Art Museum Sears Tower/Hancock Building Wendella Boat Tour Duck Boat Tour on the Lake Rent a bike and bike up the path along Michigan Ave Lincoln Park Zoo is really fun walk downtown and visit the shops / cross the bridges |
| Water taxi easier/cheaper and less touristy than Duck Boat tour. |
| Great advice above. Definitely stay in a hotel within close walking distance of Michigan Ave and the waterfront (pier). Gotta eat deep dish pizza while there-- look them up in advance. |