Beginning of main content

Cheap Flights from Toronto to Chicago from C$355

Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search over 1,000,000 properties worldwide and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more

No Expedia cancellation fee to change or cancel almost any hotel reservation.

Find cheap flights from Toronto (YTZ) to Chicago (ORD)

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed., 3 Jul. - Sun., 7 Jul.
YTZ
Toronto
to
ORD
Chicago
C$355

roundtrip

found 3 hours ago

Open YTZ to ORD flights search result page
Wed., 12 Jun. - Tue., 18 Jun.
YTZ
Toronto
to
ORD
Chicago
C$357

roundtrip

found 2 days ago

Open YTZ to ORD flights search result page
Fri., 7 Jun. - Tue., 11 Jun.
YTZ
Toronto
to
ORD
Chicago
C$359

roundtrip

found 19 hours ago

Open YTZ to ORD flights search result page
Thu., 22 Aug. - Sun., 25 Aug.
YTZ
Toronto
to
ORD
Chicago
C$381

roundtrip

found 20 hours ago

Open YTZ to ORD flights search result page
Wed., 17 Jul. - Sun., 21 Jul.
YTZ
Toronto
to
ORD
Chicago
C$382

roundtrip

found 6 hours ago

Open YTZ to ORD flights search result page
Wed., 17 Jul. - Sun., 21 Jul.
YTZ
Toronto
to
ORD
Chicago
C$388

roundtrip

found 20 hours ago

Open YTZ to ORD flights search result page
Wed., 3 Jul. - Sun., 7 Jul.
YTZ
Toronto
to
ORD
Chicago
C$390

roundtrip

found 3 hours ago

Open YTZ to ORD flights search result page
Sat., 8 Jun. - Tue., 11 Jun.
YTZ
Toronto
to
ORD
Chicago
C$394

roundtrip

found 9 hours ago

Open YTZ to ORD flights search result page
Thu., 8 Aug. - Sat., 17 Aug.
YTZ
Toronto
to
ORD
Chicago
C$407

roundtrip

found 21 hours ago

Open YTZ to ORD flights search result page
Sat., 10 Aug. - Sun., 11 Aug.
YTZ
Toronto
to
ORD
Chicago
C$408

roundtrip

found 3 days ago

Open YTZ to ORD flights search result page
Wed., 12 Jun. - Sat., 15 Jun.
YTZ
Toronto
to
ORD
Chicago
C$410

roundtrip

found 2 days ago

Open YTZ to ORD flights search result page
Wed., 3 Jul. - Sun., 7 Jul.
YTZ
Toronto
to
ORD
Chicago
C$413

roundtrip

found 3 hours ago

Open YTZ to ORD flights search result page
Fri., 26 Jul. - Sun., 28 Jul.
YTZ
Toronto
to
ORD
Chicago
C$414

roundtrip

found 20 hours ago

Open YTZ to ORD flights search result page
Wed., 17 Jul. - Sun., 21 Jul.
YTZ
Toronto
to
ORD
Chicago
C$416

roundtrip

found 6 hours ago

Open YTZ to ORD flights search result page
Wed., 17 Jul. - Sun., 21 Jul.
YTZ
Toronto
to
ORD
Chicago
C$421

roundtrip

found 20 hours ago

Open YTZ to ORD flights search result page
Thu., 19 Sep. - Sun., 22 Sep.
YTZ
Toronto
to
ORD
Chicago
C$422

roundtrip

found 1 day ago

Open YTZ to ORD flights search result page
Fri., 23 Aug. - Mon., 26 Aug.
YTZ
Toronto
to
ORD
Chicago
C$423

roundtrip

found 16 hours ago

Open YTZ to ORD flights search result page
Wed., 12 Jun. - Sat., 15 Jun.
YTZ
Toronto
to
ORD
Chicago
C$424

roundtrip

found 2 days ago

Open YTZ to ORD flights search result page
Thu., 13 Jun. - Sat., 15 Jun.
YTZ
Toronto
to
ORD
Chicago
C$425

roundtrip

found 4 hours ago

Open YTZ to ORD flights search result page
Thu., 8 Aug. - Sat., 17 Aug.
YTZ
Toronto
to
ORD
Chicago
C$434

roundtrip

found 21 hours ago

Open YTZ to ORD flights search result page
Thu., 22 Aug. - Sun., 25 Aug.
YTZ
Toronto
to
ORD
Chicago
C$439

roundtrip

found 20 hours ago

Open YTZ to ORD flights search result page
Fri., 9 Aug. - Mon., 12 Aug.
YTZ
Toronto
to
ORD
Chicago
C$441

roundtrip

found 2 days ago

Open YTZ to ORD flights search result page
Wed., 3 Jul. - Sun., 7 Jul.
YTZ
Toronto
to
ORD
Chicago
C$447

roundtrip

found 3 hours ago

Open YTZ to ORD flights search result page
Wed., 7 Aug. - Mon., 12 Aug.
YTZ
Toronto
to
ORD
Chicago
C$448

roundtrip

found 1 day ago

Open YTZ to ORD flights search result page
Thu., 26 Sep. - Sat., 28 Sep.
YTZ
Toronto
to
ORD
Chicago
C$449

roundtrip

found 2 days ago

Open YTZ to ORD flights search result page
Thu., 15 Aug. - Sun., 18 Aug.
YTZ
Toronto
to
ORD
Chicago
C$455

roundtrip

found 1 day ago

Open YTZ to ORD flights search result page
Thu., 29 Aug. - Mon., 2 Sep.
YTZ
Toronto
to
ORD
Chicago
C$457

roundtrip

found 8 hours ago

Open YTZ to ORD flights search result page
Wed., 26 Jun. - Mon., 1 Jul.
YTZ
Toronto
to
ORD
Chicago
C$462

roundtrip

found 22 hours ago

Open YTZ to ORD flights search result page
Sat., 15 Jun. - Tue., 18 Jun.
YTZ
Toronto
to
ORD
Chicago
C$463

roundtrip

found 2 hours ago

Open YTZ to ORD flights search result page
Wed., 3 Jul. - Sun., 7 Jul.
YTZ
Toronto
to
ORD
Chicago
C$464

roundtrip

found 3 hours ago

Open YTZ to ORD flights search result page
Thu., 8 Aug. - Sat., 17 Aug.
YTZ
Toronto
to
ORD
Chicago
C$465

roundtrip

found 21 hours ago

Open YTZ to ORD flights search result page
Wed., 7 Aug. - Mon., 19 Aug.
YTZ
Toronto
to
ORD
Chicago
C$466

roundtrip

found 13 hours ago

Open YTZ to ORD flights search result page
Thu., 26 Sep. - Sat., 28 Sep.
YTZ
Toronto
to
ORD
Chicago
C$471

roundtrip

found 2 days ago

Open YTZ to ORD flights search result page
Thu., 25 Jul. - Tue., 30 Jul.
YTZ
Toronto
to
ORD
Chicago
C$472

roundtrip

found 2 days ago

Open YTZ to ORD flights search result page
Thu., 25 Jul. - Mon., 29 Jul.
YTZ
Toronto
to
ORD
Chicago
C$474

roundtrip

found 8 hours ago

Open YTZ to ORD flights search result page
Fri., 9 Aug. - Mon., 12 Aug.
YTZ
Toronto
to
ORD
Chicago
C$475

roundtrip

found 2 days ago

Open YTZ to ORD flights search result page
Fri., 7 Jun. - Tue., 11 Jun.
YTZ
Toronto
to
ORD
Chicago
C$476

roundtrip

found 3 hours ago

Open YTZ to ORD flights search result page
Wed., 17 Jul. - Sun., 21 Jul.
YTZ
Toronto
to
ORD
Chicago
C$479

roundtrip

found 20 hours ago

Open YTZ to ORD flights search result page
Thu., 19 Sep. - Sun., 22 Sep.
YTZ
Toronto
to
ORD
Chicago
C$480

roundtrip

found 1 day ago

Open YTZ to ORD flights search result page
Thu., 8 Aug. - Sat., 17 Aug.
YTZ
Toronto
to
ORD
Chicago
C$481

roundtrip

found 21 hours ago

Open YTZ to ORD flights search result page

Toronto to Chicago route information

Origin Airport Billy Bishop Toronto City
Destination Airport O'Hare Intl.
Airlines Serving Air Canada
Flight Price C$355
Distance 713 km

Hotels by Airports near

See all 431 properties in O'Hare Intl.
Hilton Chicago O'Hare Airport C$174
Reviewed on 23 May 2019
See details
 
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

Ohare International Airport, Chicago, IL
     
    4.0 of 5
    4.0 out of 5.0

    Quick check in also after midnight. Very short time to get room due too tired day.

    Edward Hotel Chicago C$142
    Reviewed on 23 May 2019
    See details
     
    Edward Hotel Chicago

    Edward Hotel Chicago

    6600 N. Mannheim Rd, Rosemont, IL
       
      4.0 of 5
      3.0 out of 5.0

      The shuttle to the airport was awesome. Parking at the hotel was just outside. Great Hotel.

      Hyatt Place Chicago/O'Hare Airport C$168
      Reviewed on 21 May 2019
      See details
       
      Hyatt Place Chicago/O'Hare Airport

      Hyatt Place Chicago/O'Hare Airport

      6810 Mannheim Rd, Rosemont, IL
         
        4.4 of 5
        3.0 out of 5.0

        Great location and facility. Would definitely stay here again.

        Loews Chicago O'Hare Hotel C$160
        Reviewed on 21 May 2019
        See details
         
        Loews Chicago O'Hare Hotel

        Loews Chicago O'Hare Hotel

        5300 N River Rd, Rosemont, IL
           
          4.5 of 5
          4.5 out of 5.0

          Close proximity to the airport, and the convenience of it.

          Best Western At O'Hare C$134
          Reviewed on 21 May 2019
          See details
           
          Best Western At O'Hare

          Best Western At O'Hare

          10300 W Higgins Road, Rosemont, IL
             
            3.9 of 5
            3.0 out of 5.0

            Close to airport. Easy check in. Breakfast was great

            Crowne Plaza Hotel Chicago O'Hare C$146
            Reviewed on 20 May 2019
            See details
             
            Crowne Plaza Hotel Chicago O'Hare

            Crowne Plaza Hotel Chicago O'Hare

            5440 N River Rd, Rosemont, IL
               
              4.1 of 5
              3.5 out of 5.0

              On site restaurant. Good neighborhood. Rooms were nice.

              Wyndham Chicago O'Hare C$170
              Reviewed on 21 May 2019
              See details
               
              Wyndham Chicago O'Hare

              Wyndham Chicago O'Hare

              1450 E Touhy Ave, Des Plaines, IL
                 
                4.0 of 5
                3.0 out of 5.0

                Beautiful vintage(y) bar. Drinks and breakfast (when paid in advance) were very reasonable.

                Aloft Chicago O'Hare C$180
                Reviewed on 8 May 2019
                See details
                 
                Aloft Chicago O'Hare

                Aloft Chicago O'Hare

                9700 Balmoral Ave, Rosemont, IL
                   
                  4.2 of 5
                  3.0 out of 5.0

                  Location, location, location!!!!!! Great for concerts at Rosemont. Easy to get to and a easy walk to outlet mall. Clean and comfortable!

                  See all 431 properties in O'Hare Intl.

                  Hamilton

                  YHM-John C. Munro Hamilton Intl.

                  C$850.82

                  Toronto

                  YYZ-Pearson Intl.

                  C$292.79

                  Chicago

                  MDW-Midway Intl.

                  C$274.09

                  Top Routes from Toronto

                  Top Routes to Chicago