Chicago IS the Midwest, but it's a also a world-class, glamorous city! Everything revolves around the lake, and it's an extremely accessible and easy-to-navigate city. I have lived here for almost three years, and I love it. I love shopping on the Magnificent Mile, the Lincoln Park Zoo, the new Millennium Park, Navy Pier, Wrigley Field . . . you name it!
Quick Tips:
Check out metromix.com for what's happening -- it's a great website filled with entertainment, dining, shopping, nightlife, and much more.
Best Way To Get Around:
The CTA is really easy to figure out, and it will take you to most parts of the city . . . the good old "el."
But as far as downtown, you can walk everywhere if it's a nice day (bundle up if it's winter -- the wind off the lake coming through the skyscrapers can be nasty!).
Taxis, of course, are everywhere -- it's the pick of the lottery whether you'll have a good driver. Sometimes they're great, and sometimes they are a bit on the side of terrifying -- it's always a gamble! But you can count on being able to find one pretty much all the time, which is great.
If you're visiting Chicago, don't rent a car if you plan on being downtown the whole time. The hotels will charge you a fortune to park it, and you won't need it. If you're coming from the airport, cabs can get pricey ( to from either Midway or O'Hare, which can entirely depend on traffic). So take the el -- the Orange Line from Midway and the Blue Line from O'Hare will take you right into the Loop downtown, and you can either cab it or transfer from there.