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.

Home at last! | May 09 07'

by Bird a 31 year old female from Chicago, on vacation in Chicago

Hi everyone. I’m home. I’ve been reflecting a lot on my trip and the present. Thought I would add one final entry to close this chapter of my journ... Continue reading »
CHI-TOWN!!!!!!!! | Apr 11 08'

by summertime a traveling as a couple from New York City, on vacation in Chicago

"WHAT’S TO NAVIGATE WHEN ITS I-80 for 700+ MILES?!"

WE MADE IT!!! 13 hours door to door from Strong Island to Chi-town baby!! The drive was pretty drab, the highlight in scenery being a rogue Dunki... Continue reading »
Chicago ROCKS! | Mar 15 04'

by Frank D a 27 year old male, on vacation in Chicago

First of all, in case anybody doesn't know, City Passes are great things (see http://www.citypass.com). They are these incredible little pass... Continue reading »
the windy city | Apr 30 05'

by Horizon or Bust a 25 year old female, on vacation in Chicago

"My favorite part is the techno dancing with the strobe lights and toilet paper"

Our day trip to Chicago started early in the morning with a 4 and a half hour drive from Muncie to Chicago. Once arriving we got lunch at Subway... Continue reading »
Chicago | Sep 23 06'

by Jon & Hannah a 25 year old traveling as a couple from Letchworth, on vacation in Chicago

I think there can be no worse feeling than waiting for a train with heavy bags in the middle of the night, only to see a train approach an hour lat... Continue reading »
Time with family | Jun 08 07'

by WorldExplorer a traveling as a couple from New York City, on vacation in Chicago

June 9-June 11, 2007My entire family drove to Chicago on June 9 to spend a few days at my sister Libby’s apartment before John and I left on our t... Continue reading »
Ohhh nooo...it's over, Chicago | May 11 08'

by whichwayisnorth a 34 year old traveling as a couple from Chicago, on vacation in Chicago

Photo's are online but for our adventures you will have to wait until Anna finishes her book. Hopefully by Christmas. Continue reading »
Ooo Aaah Fireworks | Jul 03 08'

by AdamsMainer a female traveling as a family, on vacation in Chicago

"Fountains, Dresses and Revolving Doors oh my!"

We took a stroll down Magnificent Mile. The one thing I noticed about Chicago - it is very very clean. At least downtown. We went... Continue reading »
espelho | Sep 19 09'

by maycongp a male from Curitiba, on vacation in Chicago

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First Day in Chicago | Jun 27 08'

by iamwandering a female traveling as a family from Houghton, on vacation in Chicago

So here we are in the middle of Chicago with absolutely no clue as to where anything is or where we are - so we wandered the streets. We... Continue reading »