Frank Lloyd Wright house and architetural walking tour in Oak Park--easy to get to on the train ("El").

Prairie Avenue houses (one of them is open for tours but with quite limited hours)

University of Chicago campus and Robe House (also a FLW house)

There is an architectual boat tour that's quite interesting.

I second the Maxwell Street Market idea for Sunday morning.

China Town--Totally touristy but still fun (a good evening activity).

Greek Town for eating--a number of excellent Greek restaurant, and a couple of inexpensive ones that are open all night

The street where all the Indian stores are (all I can think of is "Little India" but I think that's in Singapore!) is very interesting to walk along (and eat things there, too).

Chicago has GREAT transportation passes that are good for one, two, or three days for both buses and the El trains. If you come in through O'Hare, you can catch the blue train there and buy a pass right at the beginning of your trip, either from a vending machine (if they are working) or sometimes there is someone selling them from a table.

I forget the streetname too, but we sought this out about 5 years ago and it was totally worth it. We went because my wife was looking for some specific fabrics that were known to be available in that area, but we ended up thoroughly enjoying the food. We ate at a restaurant that had no liquor license - a "brown bag" place. Fantastic food...tiny mom & pop place about 1/2 block off the main drag. Conveniently located next to a liquor store that carried about a dozen Indian beer varieties.

Your hotel concierge should be able to give you directions, street names, restaurant/shop recommendations, and the nearest El stop. I'm sure Google can do the same...

I seem to recall it was a long walk from the El. We kept thinking "just another couple of blocks" for about a half-hour. We probably didn't cover more than 1-2 miles, but it seemed like forever with stoplights and such.

If you aren't up for the hike, just grab a cab. Unlike in a lot of cities, I've never gotten any 'tude from a Chicago cabbie for a short fare. At least not one cruising around on city streets...

Devon.

It's a lot of fun to drive several miles down Devon, from the lakefront to McCormick. It's like crossing multiple national borders without customs or TSA. There are stretches of Russian, Yemenite, Arabic, East Indian, Orthodox Jewish, Pakistani, and even a little Afghan and Italian, jammed together and occasionally overlapping.

The Cubs win?

Chicago has great architecture--and often, great examples of different architectural periods on the same block (especially downtown). The Chicago Architecture Foundation gives well-reviewed walking tours, as well as the boat tour on the Chicago River mentioned by an earlier poster. More information is here:

http://www.architecture.org/tours.aspx

For what it's worth, one can buy tour tickets online, but for the walking tours, I just went to their store and exhibit space on Michigan Avenue and got them the day of the tour, saving the ticketmaster fee. The middle of summer might be more hectic, including for the boat tour, but you might just call and see what's up. A great way to learn a bit about Chicago in just an hour or two, from a typically very well-informed docent.

Also, there are many books set in or about Chicago. Recently, "Devil in the White City," about the Columbian Exposition of 1892-3, was a hot seller in Chicago and elsewhere. Many of Chicago's leading lights were involved in it, and reading it before your trip might spark your memory as you see their names elsewhere in the City during the trip.

-Hayden

P.S. Go Cubbies!

I'm biased being from Chicago but I think you should try a good hot dog. I like Gold Coast, it's right nex to Harry Carey's restaurant and down the street from house of blues. Ask any train conductor and they'll lead you to where you need to go, have fun in my city!

FLY DELTA'S BIG JETS!

The art institute is a must. Wife and I went 12 times a year when we lived there. We typically spent 4-5 hours each time. Take your time it is amazing to see all those works of art. You can also find many galleries on side streets of Michigan Avenue - most were free to enter when I lived there years ago.

Go up to the signature lounge, 96th floor of Hancock Building, for a martini.

Definitely agree with previous post about food. Determine what ethnic food you love or would like to try and go from there. Since I've been away from Chicago for years now, the only site that comes to mind to get a headstart would be metromix.com.

Go to a cubs game, bleacher seat, if you can. Not interested in baseball - anytime before, during, and after a game in wrigleyville in 'most' bars is an interesting time.

I got a kick at just walking around the city. You feel like an ant in awe. I'd recommend the Mile, Gold Coast, Lincoln Park, and the lakefront. The lakefront is a prime area for jogging/walking, biking, and rollerblading.

If you want a laugh, try second city. They have great shows.

I'd stay on the mile or close to it. Peninsula, Drake, and the W are all good. Ride the l at least once.

Other things that are OK - navy pier to people watch, other musuems like shedd etc., tavern on rush friday early evening, and boat tours.