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Find the best flight to Chicago

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Great deals to Chicago

We’ve searched 100s of deals recently found by travellers.*
Columbus, OH (CMH) Chicago, IL (CHI)
Thu, 19/09 - Sat, 21/09
United Airlines - Roundtrip, Economy
US$169
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San Diego, CA (SAN) Chicago, IL (CHI)
Tue, 24/09 - Tue, 08/10
Alaska Airlines - Roundtrip, Economy
US$247
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New York City, NY (NYC) Chicago, IL (CHI)
Sat, 24/08 - Wed, 28/08
United Airlines - Roundtrip, Economy
US$251
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Boston, MA (BOS) Chicago, IL (CHI)
Sat, 27/07 - Tue, 30/07
United Airlines - Roundtrip, Economy
US$258
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Calgary, CA (YYC) Chicago, IL (CHI)
Tue, 06/08 - Tue, 20/08
Air Canada - Roundtrip, Economy
US$309
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Omaha, NE (OMA) Chicago, IL (CHI)
Fri, 19/07 - Sun, 21/07
United Airlines - Roundtrip, Economy
US$310
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San Francisco, CA (SFO) Chicago, IL (CHI)
Wed, 18/09 - Tue, 24/09
American Airlines - Roundtrip, Economy
US$341
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Houston, TX (HOU) Chicago, IL (CHI)
Wed, 10/07 - Sun, 14/07
United Airlines - Roundtrip, Economy
US$382
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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.
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Flight stats for Chicago - did you know?

  • Chicago is 14 km from Midway Airport (Chicago, IL).
  • Midway Airport (Chicago, IL)
    • Right now, 10 airlines operate out of Midway Airport.
    • Midway Airport offers nonstop flights to 68 cities.
    • Every week, at least 1,630 domestic flights and 75 international flights depart from Midway Airport.
  • Chicago is 25 km from O'Hare Intl Airport (Chicago, IL).
  • O'Hare Intl Airport (Chicago, IL)
    • Right now, 76 airlines operate out of O'Hare Intl Airport.
    • O'Hare Intl Airport offers nonstop flights to 218 cities.
    • Every week, at least 21,253 domestic flights and 2,008 international flights depart from O'Hare Intl Airport.
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