Chicago Trips

Plan a trip to Chicago with insights from Real Travelers like you. Browse top rated travel blogs and get ideas on things to see and do. Price compare flights, hotels and packages, and find great deals to get you there.

Seeing the Chicago sights | May 29 09'

by Jenica a 35 year old female traveling as a couple from San Francisco, on vacation in Chicago

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Two of my best friends live in one of my favorite cities so we went to visit them... more later Continue reading »
Chicago | Sep 08 07'

by Philip63 a real traveler from Stepaside, on vacation in Chicago

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Chicago | Sep 14 05'

by Philip63 a real traveler from Stepaside, on vacation in Chicago

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The Gift and The Curse | Jun 18 09'

by zachiss a 25 year old from Des Moines, on vacation in Chicago

"A bit of closure..."

In five months of traveling I have met so many amazing people from so many different countries. For posterity’s sake, a sampli... Continue reading »
Bare Naked Ladies Highlight | Jun 30 09'

by xcountryTVNC a 40 year old female traveling as a family from Lancaster, on vacation in Chicago

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We had a wakeup call for 5:30 this morning so we could make it to Chicago at a half decent hour. We had breakfast at the hotel and took off. The ca... Continue reading »
Day 23: Whirlwind Tour of the Windy City | Jun 25 09'

by Megan & Sam See America a 25 year old female traveling as a couple from San Luis Obispo, on vacation in Chicago

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If you read about how we felt upon nearing Gettysburg, we ended up getting the same feeling when an hour out from Chicago. After so many nights of... Continue reading »
Seeing the Fam | Oct 23 03'

by mooreje1 a real traveler, on vacation in Chicago

We left Rockford, drove thru Chicago and headed up to Kalamazoo, MI. Uncle Ed, Aunt Phyllis, Larry, Sue, Tad and Tova great... Continue reading »
Last Day of Work for Jen | Jul 30 02'

by mesch a real traveler, on vacation in Chicago

Well tomorrow is my last day of work. Although I am excited about the trip, I feel a little sadness saying goodbye to my co-workers and custom... Continue reading »
Our Packing Experience! | Oct 01 02'

by Goodonya a traveling as a couple from Chicago, on vacation in Chicago

Well, after about 5 hours, we have finished packing for 8 months... Yes, it's all in 1 big backpack and 1 small backpack for each of us! (Granted,... Continue reading »
Home, at Last! | Mar 11 02'

by flyboy35 a real traveler, on vacation in Chicago

The airplane landed at about 7pm, and taxied to the international terminal. I got out and went to immigration, had no trouble there. Then I... Continue reading »