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.

Fly Out Day | Sep 19 08'

by Jet Set Mari a female from Sacramento, on vacation in Chicago

"1am Alaska time"

Long Long day folks. Up at 5am chicago time (that's 1am Alaska time) and flying for 10 hours (not including preparation, transfers, and driving). B... Continue reading »
Here at Rods house | Sep 17 08'

by TonyCampiti a 40 year old male from Indianapolis, on vacation in Chicago

"Read Dislaimer in this entry!!!"

At Rods house finishing up last minute planning and packing...Did some last minute shopping, etc...Also, testing and learning all about this darn b... Continue reading »
Stayed with Ingrid and family, whilst we visited our old haunts | Oct 08 08'

by Niall and Brigid a male traveling as a couple from Dublin, on vacation in Chicago

"it was fondue-licious"

We had great craic staying with Ingrid and Gio and the kids in Chicago for a few days. It´s where me and Brigid met 7 years ago, so it was great to... Continue reading »
Airport Stop | Aug 26 07'

by BIRCHY a 27 year old male from Boston, on vacation in Chicago

Good flight from Boston to Chicago and all going well... but as ever as flight problems from Chicago...thankfully I was the first to see that the b... Continue reading »
Chicago! | Jul 28 07'

by KarenandBrad a traveling as a couple from Seal Beach, on vacation in Chicago

At 3:00am, I woke up and couldn’t sleep anymore. We stopped in Cleveland, where I was born. The train stop, which is a major one, is right next t... Continue reading »
Caught in Chicago | Oct 12 07'

by tassiebutlers a 39 year old male traveling as a couple from Blackmans Bay, on vacation in Chicago

"Caught in Chicago"

Waiting in Winnipeg:Caught in Chicago:Patient in Phoenix:Automatons in Anchorage:The journey we were hoping would never occur has started in the wa... Continue reading »
First time on a Harley | Sep 07 06'

by Kim Chris and Bert a female traveling as a family from London, on vacation in Chicago

First time on a Harley today. With a motorbike refresher course completed on Tuesday (thanks to Mik @ Advantage in Wimbledon), I am going from... Continue reading »
Mandala´s 30th Birthday | Jul 09 06'

by Mandala a 32 year old female from Trinidad, on vacation in Chicago

Charlie Trotters was the reason for our trip to Chicago, and it was absolutely amazing. We stayed at the Crown Plaza, and slept until 2 every... Continue reading »
Day Ten - Trondheim to USA | Jun 25 07'

by Kathleen H a female traveling as a family, on vacation in Chicago

We need to be on the bus by 9:15 for our transfer to the Trondheim hotel. We have our final breakfast buffet and say goodbye to the folks hea... Continue reading »
19 days and counting... | May 07 08'

by Kara & Nicki a female traveling as a couple from Chicago, on vacation in Chicago

Well hello! We are less than three weeks away from our departure and getting more and more excited! We are about 80% ready I would say. Stay tuned... Continue reading »