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Find the best flight from Chicago

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Great deals from Chicago

We’ve searched 100s of deals recently found by travellers.*
Chicago, IL (CHI) Buffalo, NY (BUF)
Tue, 15/10 - Fri, 18/10
United Airlines - Roundtrip, Economy
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Chicago, IL (CHI) New York City, NY (NYC)
Wed, 31/07 - Tue, 06/08
United Airlines - Roundtrip, Economy
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Chicago, IL (CHI) San Francisco, CA (SFO)
Thu, 29/08 - Sun, 01/09
Alaska Airlines - Roundtrip, Economy
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Chicago, IL (CHI) Los Angeles, CA (LAX)
Sun, 13/10 - Tue, 15/10
Sun Country Airlines - Roundtrip, Economy
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Chicago, IL (CHI) Orlando, FL (ORL)
Thu, 30/01 - Mon, 03/02
United Airlines - Roundtrip, Economy
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Chicago, IL (CHI) Providenciales, TC (PLS)
Sat, 05/10 - Fri, 11/10
American Airlines - Roundtrip, Economy
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Chicago, IL (CHI) London, GB (LON)
Sun, 18/08 - Tue, 27/08
Multiple Airlines - Roundtrip, Economy
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Chicago, IL (CHI) Miami, FL (MIA)
Fri, 04/10 - Mon, 07/10
United Airlines - Roundtrip, Economy
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*Prices are based on round trip travel with returns between 1-21 days after departure. These are the best fares found by travellers 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.