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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, 08/01 - Wed, 22/01
JetBlue - Roundtrip, Economy
US$177
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Chicago, IL (CHI) Boston, MA (BOS)
Tue, 17/12 - Tue, 31/12
JetBlue - Roundtrip, Economy
US$184
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Chicago, IL (CHI) Los Angeles, CA (LAX)
Wed, 11/03 - Tue, 17/03
Alaska Airlines - Roundtrip, Economy
US$200
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Chicago, IL (CHI) Raleigh, NC (RDU)
Mon, 01/06 - Sat, 06/06
United Airlines - Roundtrip, Economy
US$228
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Chicago, IL (CHI) Buffalo, NY (BUF)
Fri, 03/01 - Fri, 17/01
JetBlue - Roundtrip, Economy
US$262
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Chicago, IL (CHI) Toronto, CA (YTO)
Wed, 22/01 - Sat, 01/02
Air Canada - Roundtrip, Economy
US$274
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Chicago, IL (CHI) Miami, FL (MIA)
Wed, 11/12 - Fri, 13/12
United Airlines - Roundtrip, Economy
US$283
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Chicago, IL (CHI) Seattle, WA (SEA)
Tue, 07/01 - Tue, 21/01
JetBlue - Roundtrip, Economy
US$343
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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.