Chicago? Any thoughts?
ihatewheat
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ah Chicago!!! summers are hot and humid and winters are icy and cold, and worse than the east coast, but it is a great city when the weather works out! i like to think of it as a nice cross between Boston and NYC. Good shopping, good food, fun nightlife, and also relatively close (like 3-5 hour drive) to other cities like Toronto, St. Louis, Cleveland, Indianapolis, Detroit, Columbus, and Cinncinati to name a few…
I was there is the summertime one long weekend and it was fabulous. I really like that the downtown hugs the lake with a nice big park as a buffer. Quite pretty. I had terrible thoughts though about how awful it must be the ride the heavy rail system (The L, I believe) during the winter–waiting in the bitter cold wind for a train to come can’t be pleasant.