Mizzeaux and any other Chicago folks (Breakaway?)

Grant park is awesome
Museum of Science and Industry

I haven't stayed at Palmer House in a long time.

Will you have a car or are you training it?

Easy enough. I'm not a big fan of the loop area at night, it's really just offices and stuff, mostly busy during the day.

Since you're there for only a short time, I'd hit the tourist stuff. Get a meal at Ditkas on Oak St or Harry Caray's on (I Think) Kinzie St. Giordano's is my favorite Chicago style pizza, and the one on Rush Street is always good for a stop. Portillos has a few locations up in River North if you're looking for an Italian Beef or a Maxwell Street Polish. Again, all kind of touristy, but fun.

Art Institute is fun and close if you want to check out some priceless art, plus you can relive the scene in Faris Buelers Day Off. The River Architecture Tour is really good too, they'll take you up and down the Chicago river and show you all the cool skyscrapers and give you a rundown of the history of the area. Millennium Park is right across Michigan Ave from your place and is worth doing a walkthrough. I'm not sure if The Park Grill is still there, but they've got some decently priced food in Millennium Park.

If you want to get high, I suggest going to The John Hancock building instead of the Sears Tower, you can grab a bite to eat at the restaurant or a drink at the bar on the 95th or 96th floor.

If you want to take a cab to the Museum of Science and Industry, it's really cool. It's probably a $20 cab ride each way, but it's my favorite museum in the world.

Other than that, there's a lot of places to rent bicycles for a pretty small amount of money and ride up and down the lakeshore. Ride to the Shedd Aquarium/Adler Planetarium area and check out the view of the city from there.

Navy Pier is cool, especially if you take a ride on the little cruises they have out to the lake. I'm pretty sure they still do fireworks on the lake on Saturdays, and that's always fun. Honestly, I'd probably skip Navy Pier unless you're doing the cruise, though.

That's it for the real touristy/one day stuff. Chicago's really cool because of the neighborhoods, but they're not easy to find if you don't know what you want to do.

For the night time, I'd suggest going up to the area around the Magnificent Mile and checking out a few bars. The Loop as I remember it is pretty dead at night, like I mentioned before. The buses in that area are all really safe if you don't want to walk, but you can walk to pretty much all the places I've mentioned or jump in a cab for a few bucks.

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The River Architecture Tour is really good too, they'll take you up and down the Chicago river and show you all the cool skyscrapers and give you a rundown of the history of the area.

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This is a touristy favorite of mine.

Also, most people point to Mag Mile for shopping, but the real place to see for high-end shopping and restaurants is the Viagra Triangle. This is way less touristy and much better for people watching.

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the real place to see for high-end shopping and restaurants is the Viagra Triangle

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Yes, go hang out with the Trixies.