Toronto to Chicago IL Flights

  • Select Start Dateclose
  • Select End Dateclose
Best reviews in the industry (4.9/5)

From thousands of verified customers on Google, Facebook, and BBB

Potential for better fares than the airlines

Search all airlines at once, including combinations they don’t sell

Pay Monthly Option

Book now, pay in up to 12 monthly payments. Instant application.

Flights From Toronto To Chicago Recently Searched By Our Customers

  • From To Depart Return Price Airline
    Jul 07 Jul 09
    $350
    Mixed airline logo icon
    Jun 30 Jul 03
    $326
    Mixed airline logo icon
    Jun 05 Jun 09
    $381
    United Airlines airline logo icon
    Jun 19 Jun 26
    $302
    United Airlines airline logo icon
    Jul 21 Jul 23
    $354
    WestJet airline logo icon
    Sep 09 Sep 14
    $359
    Air Canada airline logo icon
    Jun 03 Jun 04
    $416
    American Airlines airline logo icon
    Jun 30 Jul 03
    $317
    United Airlines airline logo icon
    Jun 16 Jun 18
    $317
    United Airlines airline logo icon
  • From To Depart Return Price Airline
    Oct 06 Oct 08
    $434
    Air Canada airline logo icon
    Jun 09 Jun 18
    $301
    Mixed airline logo icon
    Jun 30 Jul 03
    $358
    United Airlines airline logo icon
    Oct 06 Oct 09
    $434
    Air Canada airline logo icon
    Jun 29 Jul 03
    $238
    WestJet airline logo icon
    Jul 30 Aug 04
    $348
    WestJet airline logo icon
    Jul 05 Jul 08
    $434
    American Airlines airline logo icon
    Jul 04 Jul 09
    $434
    Mixed airline logo icon
    Aug 17 Aug 20
    $329
    Air Canada airline logo icon
  • From To Depart Return Price Airline
    Jun 30 Jul 09
    $317
    United Airlines airline logo icon
    Jun 09 Jun 17
    $301
    Mixed airline logo icon
    Sep 28 Oct 01
    $358
    Air Canada airline logo icon
    Jun 02 Jun 03
    $302
    United Airlines airline logo icon
    Jun 01 Jun 02
    $302
    United Airlines airline logo icon
    May 31 Jun 01
    $302
    United Airlines airline logo icon
    May 30 May 31
    $412
    Mixed airline logo icon
    May 29 May 30
    $523
    Mixed airline logo icon
    Jul 05 Jul 09
    $434
    Air Canada airline logo icon

Cheap Flights to Chicago From

Chicago, IL, US - All Airports, United States (CHI) Pictures and Video - click to enlarge images or play videos

Photos and Videos

Send me a link to this page
X