Whenever I visit a decent sized city, I check for a Hotel Indigo. Chicago has one, and I highly recommend it.

I've never stayed in am Indigo I didn't love.

>Chicago

First, you have to answer these two questions.

1. Are you white?
2. Are you a woman?

If you answered yes to #1, you're going to die. If you answered to #2, you're going to be raped before you die.

Enjoy your trip.

>>1117016
>I've never been outside of my small mid-western hick town: the post

As for OP, what exactly is it that you are interested in? You can start off at the cultural center in the loop (I think it's pretty close to the art institute) and start your trip there with some info.

>>1117005
check out the palmer house hilton, or that wyndham on the river. i always wanted to stay there for the view its got, never have.

second city is a goode idea. the official architecture tour is great as well. it takes u up each branch of the river and to the lake. if you want to do something with a view, check our the signature room at the 95th in the hancock building. its expensive, but get a seat by a window. do some research on the food whereever you stay, theres a shitload of places around.

>>1117005
second city is a great idea! the chicago improv scene is equal to or even better than NYC and LA, so you can't go wrong with any improv venue.

>>1117016
You can fuck right off

Groupon usually has a good deal on Chicago hotels. I stayed at one recently just about 3 blocks from Union Station called Club Quarters Chicago that was relatively inexpensive and right in the center of the Loop. I would recommend finding a place in that neighborhood or in the Magnificent Mile as it puts you right in the middle of everything.

I write for Second City every now and then so of course I would recommend seeing a show there. You generally can't go wrong with a good sketch show at Second City though there are a few other amateur theaters like iO that are worth checking out.

Since you say you got baseball tickets I assume you're talking North-Side around Wrigleyville (because fuck the White Sox) and I would recommend making a day of just drinking/eating at the bars around the stadium. Wrigley on game day is a great deal of fun.

Use the L for transportation. There's no point in renting a car in Chicago.

>>1117725
Oh by the way the two greatest Chicago tourist destinations I've been to are the Field Museum and the Art Institute. The Art Institute is probably the finest art museum I've ever been in. The Shedd Aquarium is a great aquarium but it's not worth the same price as the Field in my opinion. The Planetarium is a waste of time. The Museum of Science and Industry is also worth a visit too imo but if you can't squeeze it in then don't worry about it