What is cool to do in Chicago?

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The House of Blues is cool, and just around the corner from that is a wine bar called Bin 36, I suggest that. Also eating at the signature room of the John Hancock building is always fun. The Blue Man Group has a performance group there. If you're going to rent a car you can take a ride down LSD(lake shore drive). http://www.artic.edu/aic/, http://www.chicagoshakes.com/. I tend to have a lot of fun when I go to Chicago.
 
W

Wasabi Poptart

My friend who is living there now would tell you to make sure you see The Bean.
 
Depends what you're into, really. Plenty of sporting events, museums, sights, restaurants, food specialties, shopping, bars/clubs to check out in the downtown areas. If the weather's nice, there's plenty of places to even just walk along the lake shore, which is really picturesque.

As far as the main things:
- Sights: Willis (Sears) Tower, Millennium Park, Navy Pier, Wrigley Field
- Sports: Wrigley again, US Cellular field, United Center, Toyota Park (soccer)
- Museums: Field Museum of Natural History, Art Institute of Chicago, Shedd Aquarium, Adler Planetarium, Lincoln Park Zoo
- Food: Deep-dish pizza, Chicago-style hot dogs, italian beef sandwiches (yeah, the city isn't known for its healthy eating)
- Clubs/bars: House of Blues, Rush Street (the ultimate hipster area)
 
It's been a loooong time since I was there. Had an aunt that lived in a northern suburb for years until she moved about 6 years ago :(

Billy Goat Tavern - basis for the classic SNL "Cheeborger Cheeborger Pepsi!" sketch - 430 N Michigan near the Loop

Also - they have them elsewhere but this one just seemed right - Ed Debevic's - 640 N Wells between Erie & Ontario near the Hard Rock. Service with sass.

Other then that - yeah, see a game @ Wrigley even if you're not a baseball fan. Its been more about the party for years anyways. The museums - planetarium & aquarium are awesome. Science & Industry just didn't seem as cool as when I was younger + its a little out of the way.

There's a Six Flags in Gurnee, about 30-45 mins north on the expressway, along with a helluva big outlet mall.

Strangely though the best vacation I had was the last one I took to visit my aunt where I did nothing but drive around & watch movies @ the theater in Gurnee. But then again the visit before that I did the frantic dash around to all the attractions.
 
Field Museum was fantastic. Soldier Field was a little depressing up close. They pretty much stuffed the new stadium inside the old one.

And can anyone here look at the fountain in Grant Park without Love and Marriage creeping into their head? Not me.
 
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