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.

Day 1: Taking Flight | Nov 06 09'

by Matt&MaryTill a real traveler from Chicago, on vacation in Chicago

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My kind of town..... | Oct 07 09'

by Mad Sal a female from Worthing, on vacation in Chicago

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I arrived in Chicago at 6pm after what felt like an insanely long flight but was in fact only 9 hours. I got pretty lucky as i moved seats so a fam... Continue reading »
espelho | Sep 19 09'

by maycongp a male from Curitiba, on vacation in Chicago

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centro Continue reading »
Train To Chicago | Sep 01 09'

by Gino Gallo a 46 year old male from Kenosha, on vacation in Chicago

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Day 2 Train to Chicago staying at Holiday Inn near O’Hare Airport for a early morning flight Continue reading »
Chicago, the Windy City! | Aug 17 09'

by James83 a 26 year old male from Dublin, on vacation in Chicago

"Its worth standing out on the glass ledge looking directly down from 103 stories up"

Chicago is a cool city. Its very modern with plenty of Skyscrapers, but also has Lake Michigan and some beaches. Its a bit more Eastern in culture,... Continue reading »
OMG! Nebraska and Indiana are like drive through Hell. | Jul 02 09'

by neverlong01 a 26 year old male from Annapolis, on vacation in Chicago

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Taste of Chicago, The L, The Bean, The Faces, Fun in the sun. 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 »
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 »
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 »