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Chicago Hotel + Air Packages

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Chicago
Build your own Chicago vacation package
Want to book a vacation to Chicago? Whether you're off for a romantic vacation, family trip, or an all-inclusive holiday, Chicago vacation packages on TripAdvisor make planning your trip simple and affordable.
Find the perfect vacation package for Chicago on TripAdvisor by comparing Chicago hotel and flight prices. Travelers like you have written 105,730 reviews and posted 19,897 candid photos for Chicago hotels. Book your Chicago vacation today!
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Four Seasons Hotel Chicago
Four Seasons Hotel Chicago
I had the opportunity to stay at the Four Seasons Chicago a week ago and I was thoroughly impressed from the moment I wanted into the door. Then I walked into my upgraded and was...
1. Find your perfect hotel
2. Find the right flight
Build your luxury package
The Langham, Chicago
The Langham, Chicago
I don't know where to begin... After a disappointing stay at the Trump the night before me and my money check-out of there and walked across the street to The Langham…one of the...
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2. Find the right flight
Build your budget package
Thompson Chicago
Thompson Chicago
My boyfriend and I just returned from a phenomenal weekend at the Thompson Chicago. The check- in process was prompt and the receptionist was extremely courteous. We were upgraded...
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2. Find the right flight
Cheap Flights to Chicago
All Seattle to Chicago (SEA-CHI) fares found by travelers in the past 72 hours*
May
$284 round trip
Jun
$324 round trip
Jul
$352 round trip
†  Prices are based on round trip travel with returns between 1-21 days after departure. These are the best fares found by travelers who searched TripAdvisor and a select group of our fare search partners in the past 72 hours. Ticket prices and seat availability change rapidly and cannot be guaranteed.