Instead of starting a new thread, I'll ride on Pawrestler's coat tails. I'm spending a day in Chicago and a day in Madison/Milwaukee before the PSU/Wisconsin season opener in September. I'm seeing a Cubs game Thursday night but will have all day Thursday in Chicago before the game. I would welcome any and all recommendations for both towns, please.
Chicago:
Frontera Grill -- the restaurant that made Rick Bayless famous, and he has not coasted on his reputation. If you have to rearrange the rest of the day to eat there, do it. It's amazing.
If possible, go to Buddy Guy's Legends. Yes, THAT Buddy Guy, and he does occasionally drop in to play. He's in his 80s and still brings it. (Even if he doesn't appear, it's a great blues bar.)
Tourists go to Giordano's (Chicago-style pizza, near Willis Tower or on Navy Pier); Billy Goat Tavern (Belushi skit + greasy double-cheeseburgers, near Navy Pier); or the hot dog cart outside the Field Museum (seriously). There's also a good Russian restaurant a block from the Art Institute.
With only one day, do an architecture bus or boat tour, plus the Field Museum or Art Institute. Willis Tower is OK but you need to be there when it opens, or else wait and wait and wait. Navy Pier is an overrated tourist trap (though the museum at the end is pretty good if you're already there).
It sounds as though you're driving between Chicago and Milwaukee. The map says 90 minutes. It's more like 3.5 hrs -- Chicago traffic right there with NYC, DC, LA, and San Francisco. Waiting out traffic is yet another good reason to go to Buddy Guy's.
If you're flying in/out of the Chicago airports, be prepared for some horrific third-world driving patterns like driving the wrong way down busy streets (especially around Midway).
Illinois has very expensive toll roads, but uses the same EZ Pass as PA. Bring your transponder, just be sure to register your rental car on the EZ Pass website before hitting any toll roads.
Milwaukee:
- Safe House -- spy-themed bar. Really fun place, go for drinks, recommend eating elsewhere. Bonus: a block from the Bronze Fonz statue (!).
- Three Brothers -- Serbian. James Beard award winner. Bonus: building is on the National Register of Historic Places -- former Schlitz Brewery.
Do not miss the Harley Davidson Museum.
The Basilica is also worth a visit if time allows.
If you're just looking to kill time, drive from downtown along Lake Michigan, northbound, as far as you care to go. Milwaukee has a reputation as a gritty industrial town, but this is a pretty coastline.