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Re: Things To Do In Chicago?
Navy Pier, Museum of Science and Industry, Field Museum, any of the Rush Street bars, catch a Bears game, check out the music scene as there are a ton of clubs and theatres that have good live acts come through, there are usually a couple good Broadway shows as well. If you like The Beatles, I'd suggest checking out The Cavern Beat - they play all around Chicagoland.
Re: Things To Do In Chicago?
Brookfield Zoo is great, as Buzz alluded to. It's 5 minutes from my house. We have a membership and always are there.
So, I'd check out a show at the Metro, one of the famous clubs. Didn't Axl and Co. hang out there around UYI times and play the owner the record.
You also could do worse than checking out some comedy at IO or Second City. A lot of SNL members come from here.
Hell, if you're in town early enough, check into a Cubs game at Wrigley. Their last series is the first week. If nothing else, go to Wrigleyville and get drunk. You probably could do a insider Wrigley tour for a little bit of cash.
Take an evening dinner cruise on Lake Michigan. They leave from Navy Pier, which is a tourist trap but fun for killing time. Also, there are Chicago River architectural tours.
Have a drink at the Signature Room at the Hancock Center. It's on the 95th floor and has better views than the Sears Tower.
Go to the United Center for a preseason Bulls game and visit the Jordan statue outside Gate 4. I'm sure Bucket does everytime he's in town. The Bears probably have a home game while you're here.
Get a cheezborger no fries at the Billy Goat (from the famous SNL sketch). It's on Lower Michigan Ave., which is cool in itself. Eat soom Chicago-style brats at any hot dog stand; and authentic deep-dish pizza at Lou Malnati's or Gino's East.
Millennium Park is incredibly cool. Some really impressive architectural/art pieces there. It's on the lakefront. Park Grill is there and is supposed to be good.
Lincoln Park Zoo is free. Worth a trip, although Brookfield Zoo is better.
Visit Chinatown. During the day. Greektown for nice Greek food. Nothing else to do there.
Daley Plaza will have soom free Halloween activities. Mostly kid-related, but some not. You can do a haunted Chicago tour which takes you to the neighborhood where Public Enemies was filmed (John Dillenger was killed at the Biograph theater there.)
The new Riverwalk is nice.