…what do I need to know?
The plan is for it to be probably 4 or 5 full days there. The main reason is because I’ve never been there and I want to see some improv shows up there. I’ll also be visiting a few museums. Any suggestions? Any ideas?
– IG
For better or for worse you may be there for The Taste of Chicago. I would avoid that mess. Get a Chicago style stuffed spinach pizza from Edwardo’s or Giordano’s. Others might suggest the plain old Chicago style pan pizza, but I don’t think it’s nearly as good. The Shedd Aquarium is quite good, and it’s right near the Atler Planetarium and the Field Museum of Natural History so you can make a good two days of it.
Avoid the Sears Tower, it is a long line for nothing really interesting. The John Hancock building is probably more interesting even if it isn’t that tall. You can get good boat tours depending on how much money your willing to spend. A good Cubs game at Wrigley Field would be fun.
Agreed. The Hancock is nearly as tall, and there’s a nice bar on an upper floor where you can relax, have a few drinks and listen to jazz, sometimes live. And it’s not even expensive.
They don’t call Chicago the Second City for nuthin’. Anything you’re looking for, you can find here. It’s not New York City, but nothing else is.
Go to a blues club and listen to music until 4 AM
Speaking of Second City, that is a comedy club you would regret missing. It is where a great many comedians got there start: John Belushi, Bill Murray, Dan Akroyd, George Wendt, Mike Meyers, Chris farley, Steve Carrell, Stephen Colbert… The point is if you go you are very likely to see a future star.
As for Blues Clubs I would recommend Momma Rosa’s, but don’t wander the neighborhood there. Buddy Guy’s Legends is also good, and in a safer neighborhood.
Second City and ImprovOlympic are the two main reasons I’m going. Chicago is the unofficial center of the improv comedy world, or at least it’s major birthplace. But so far, awesome advice guys!
– IG
The Signature Lounge is certainly not on the cheap side - martinis are a bit over 10 dollars if I am remembering correctly. (Or maybe that is cheap - I am a poor grad student, so everything seems expensive to me. 
) But the view is definitely worth it. Plus you don’t have to pay anything to get to the Lounge - you do have to pay something to go up to the observatory deck.
That means you definitely want to see Too Much Light Makes the Baby Go Blind while in town. It’s a really fun time!