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Fantastic city architecturally, in particular don't miss the Chicago Tribune Tower. In a lot of ways I think it's a more "purely American" city in terms of style and feel than the more obvious example of New York, which is really rather European (well, Manhattan at least).

 

Also if you're into architecture, quite a lot of Frank Lloyd Wright in the suburbs, as I recall.

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I love photography, cultural experiences, beauty, good food, etc

 

I grew up there. Fantastic city. What time of year are you going? If the weather is nice hit Grant Park and Millennium Park. See the Millennium Bean in the park - makes for great photographs. Navy Pier is fun with lots to do. You can google to see if a festival is going on. During summer months there is one almost every weekend.

 

Take a cruise on Lake Michigan. Go on a horse drawn carriage ride at night along Lake Michigan - these are warmer weather adventures.

 

If you are going when it's cold then hit the museums. The Science and Industry Museum, Field Museum, Shedd Aqurium, and Adler Planetarium will keep you plenty busy.

 

For good food you have thousands of choices. If you like a certain ethnic food there is almost certainly a neighborhood that provides it. Chicago Style Pizza cannot be missed. Giordanos, Lou Malnatis, and Gino's East come to mind. But there are lots of other great ones too. Chinatown can be fun to explore.

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Ive been to Chicago many times, the best thing I did recently was take a bike tour of the city.. you can find it if you google Bobby's Bike Hike, its so worth it, you go with a large group and ride bikes right downtown. I went in August, thats a good time to go, also any time really between May-September is the best time to go. Also make sure you check out the pizza, Navy Pier, Michigan Avenue, Grant and Millinium Parks, Shedd is nice but really crowded, check out some local bars, they are great as well.

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I practically grew up there. Every summer when I was shipped off to stay with my grandparents, my grandma and I would take the commuter train into Chicago to go see my grandpa who had his offices in the Merchandise Mart. Loooooove Chicago.

 

I've been there in the winter plenty too. Yes, it gets really cold. It can go below -4 degrees F, but that's not average for the winter. More like about 20 degrees F or so? And plenty of snow most years. Lake Michigan is right there, so that moderates the weather a little bit compared with the rest of Illinois. You'll be fine.

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