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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) Minneapolis, MN (MSP)
Sat, 03/08 - Mon, 05/08
Sun Country Airlines - Roundtrip, Economy
US$ 106
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Chicago, IL (CHI) New York City, NY (NYC)
Sun, 10/11 - Sat, 23/11
American Airlines - Roundtrip, Economy
US$ 164
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Chicago, IL (CHI) Orlando, FL (ORL)
Thu, 08/08 - Sun, 11/08
Frontier Airlines - Roundtrip, Economy
US$ 196
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Chicago, IL (CHI) Boston, MA (BOS)
Mon, 30/09 - Wed, 02/10
American Airlines - Roundtrip, Economy
US$ 222
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Chicago, IL (CHI) Guatemala City, GT (GUA)
Thu, 14/11 - Mon, 18/11
Copa Airlines - Roundtrip, Economy
US$ 229
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Chicago, IL (CHI) Toronto, CA (YTO)
Mon, 23/09 - Mon, 07/10
Porter Airlines - Roundtrip, Economy
US$ 234
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Chicago, IL (CHI) Detroit, MI (DTT)
Tue, 01/10 - Fri, 18/10
United Airlines - Roundtrip, Economy
US$ 257
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Chicago, IL (CHI) San Francisco, CA (SFO)
Tue, 13/08 - Sat, 17/08
Alaska Airlines - Roundtrip, Economy
US$ 276
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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.