On my air-mile accumulating trip to Brazil, I had 10-hour layover in Chicago. Initially I thought I would need to do some computer work during that time, but it turns out I managed to finish some things the day before, so I took the L into the city to take a look around. It was windy (naturally) but a balmy 3 degrees and sunny, so it was a good day to walk around.
Advice if you ever have a long layover in Chicago: take the Blue line to Washington. You will walk up to State street between Monroe and Washington. Walk 2-3 blocks to Michigan and enjoy the ‘magnificent mile’ of cool architecture, millennium park with all the public art, the lakeshore, and the Chicago Institute of Art. The Institute has some classic impressionists and lots of Americans: Warhol, Pollack, Wood, O’Keefe, etc.. It is worth a visit even if you hate art; they have a $1 bag check and great washrooms so it makes a nice starting place for a walkabout, and is close enough to the subway to swing by and get your bag on the way back to the airport.
Foods: working solely on intuition, I followed an ancient L track along van Buren and found an outstanding modern Isreali-style deli called Benjiyehuda. I had a bitchin’ falafel on rice with hot sauce and a buffet of 5-6 outstanding salads. I read the local free weekly while a Matisyahu concert played on a big screen tv. Keeping it real with everyone favourite hasidic reggae star! Later I felt like something sweet and stumbled upon the Magnolia Bakery; I got a piece of banana cream pie to eat at the airport.
Overall, Chicago was pretty cool and I would go back. Maybe it would be a bit prettier in the spring, but if you go for a museum winter is probably best. 🙂