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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) New York City, NY (NYC)
Wed, 11/09 - Thu, 19/09
American Airlines - Roundtrip, Economy
US$176
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Chicago, IL (CHI) Los Angeles, CA (LAX)
Mon, 27/01 - Fri, 31/01
Alaska Airlines - Roundtrip, Economy
US$182
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Chicago, IL (CHI) Minneapolis, MN (MSP)
Sun, 27/10 - Sat, 02/11
United Airlines - Roundtrip, Economy
US$187
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Chicago, IL (CHI) Boston, MA (BOS)
Tue, 24/12 - Fri, 03/01
United Airlines - Roundtrip, Economy
US$261
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Chicago, IL (CHI) Washington DC, DC (WAS)
Tue, 08/10 - Tue, 15/10
United Airlines - Roundtrip, Economy
US$270
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Chicago, IL (CHI) San Francisco, CA (SFO)
Sat, 19/10 - Wed, 23/10
Alaska Airlines - Roundtrip, Economy
US$276
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Chicago, IL (CHI) Orlando, FL (ORL)
Tue, 05/11 - Fri, 08/11
United Airlines - Roundtrip, Economy
US$282
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Chicago, IL (CHI) Raleigh, NC (RDU)
Sat, 28/09 - Mon, 30/09
United Airlines - Roundtrip, Economy
US$296
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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.