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Cheap Flights from Toronto to Chicago from C$288.59

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

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

Fri, 16 Nov - Mon, 19 Nov
YYZ
Toronto
to
ORD
Chicago
C$288.59

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just found

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Fri, 16 Nov - Mon, 19 Nov
YYZ
Toronto
to
ORD
Chicago
C$288.61

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just found

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Thu, 13 Dec - Thu, 13 Dec
YYZ
Toronto
to
ORD
Chicago
C$288.86

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found 9 hours ago

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Wed, 5 Dec - Sat, 8 Dec
YYZ
Toronto
to
ORD
Chicago
C$289.26

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found 1 day ago

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Fri, 2 Nov - Tue, 6 Nov
YYZ
Toronto
to
ORD
Chicago
C$294.17

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found 7 hours ago

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Mon, 29 Oct - Tue, 6 Nov
YYZ
Toronto
to
ORD
Chicago
C$294.52

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found 4 days ago

Open YYZ to ORD flights search result page
Sat, 10 Nov - Wed, 14 Nov
YYZ
Toronto
to
ORD
Chicago
C$296.09

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found 20 hours ago

Open YYZ to ORD flights search result page
Thu, 11 Oct - Sat, 13 Oct
YYZ
Toronto
to
ORD
Chicago
C$296.55

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found 1 day ago

Open YYZ to ORD flights search result page
Mon, 29 Oct - Mon, 29 Oct
YYZ
Toronto
to
ORD
Chicago
C$299.36

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found 8 hours ago

Open YYZ to ORD flights search result page
Thu, 13 Dec - Thu, 13 Dec
YYZ
Toronto
to
ORD
Chicago
C$300.41

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found 9 hours ago

Open YYZ to ORD flights search result page
Mon, 29 Oct - Tue, 6 Nov
YYZ
Toronto
to
ORD
Chicago
C$302.99

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found 4 days ago

Open YYZ to ORD flights search result page
Tue, 16 Oct - Sat, 20 Oct
YYZ
Toronto
to
ORD
Chicago
C$304.61

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found 2 hours ago

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Fri, 2 Nov - Sun, 4 Nov
YYZ
Toronto
to
ORD
Chicago
C$305.66

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found 6 hours ago

Open YYZ to ORD flights search result page
Tue, 16 Oct - Sat, 20 Oct
YYZ
Toronto
to
ORD
Chicago
C$306.61

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found 2 hours ago

Open YYZ to ORD flights search result page
Fri, 16 Nov - Mon, 19 Nov
YYZ
Toronto
to
ORD
Chicago
C$307.65

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just found

Open YYZ to ORD flights search result page
Thu, 11 Oct - Sat, 13 Oct
YYZ
Toronto
to
ORD
Chicago
C$309.28

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found 1 day ago

Open YYZ to ORD flights search result page
Tue, 16 Oct - Sat, 20 Oct
YYZ
Toronto
to
ORD
Chicago
C$309.86

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found 2 hours ago

Open YYZ to ORD flights search result page
Thu, 11 Oct - Fri, 12 Oct
YYZ
Toronto
to
ORD
Chicago
C$310.91

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found 16 hours ago

Open YYZ to ORD flights search result page
Wed, 3 Oct - Mon, 15 Oct
YYZ
Toronto
to
ORD
Chicago
C$311.50

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found 3 days ago

Open YYZ to ORD flights search result page
Tue, 16 Oct - Tue, 16 Oct
YYZ
Toronto
to
ORD
Chicago
C$374.96

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found 14 hours ago

Open YYZ to ORD flights search result page

Hotels by Airports near

See all 328 properties in O'Hare Intl.
Hilton Chicago O'Hare Airport C$140
See details
 
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

Ohare International Airport, Chicago
     
    4.0
    of 5, from 3,396 reviews
    4.0 out of 5.0

    The only hotel on airport property, the Hilton Chicago O'Hare Airport is located 2 miles from the Donald E. Stephens Convention Center and the Rosemont Theatre, and 18 miles from downtown Chicago.

    Edward Hotel Chicago C$128
    See details
     
    Edward Hotel Chicago

    Edward Hotel Chicago

    6600 N. Mannheim Rd, Rosemont
       
      4.0
      of 5, from 2,052 reviews
      3.0 out of 5.0

      Situated near the airport, this hotel is 0.4 mi (0.6 km) from Allstate Arena and within 3 mi (5 km) of Rivers Casino and Donald E. Stephens Convention Center. Rosemont Theatre and MB Financial Park at Rosemont are also within 3 mi (5 km). Rosemont O'Hare Transfer Station is 11 minutes by foot.

      Four Points by Sheraton Chicago O'Hare Airport C$127
      See details
       
      Four Points by Sheraton Chicago O'Hare Airport

      Four Points by Sheraton Chicago O'Hare Airport

      10249 Irving Park Road, Schiller Park
         
        3.7
        of 5, from 3,308 reviews
        3.0 out of 5.0

        This smoke-free hotel is 1.5 miles (2.4 kilometers) from O'Hare International Airport, the Donald E. Stephens Convention Center, the Rosemont Theatre, and a transit station with access to downtown Chicago.

        Crowne Plaza Hotel Chicago O'Hare C$139
        See details
         
        Crowne Plaza Hotel Chicago O'Hare

        Crowne Plaza Hotel Chicago O'Hare

        5440 N River Rd, Rosemont
           
          4.1
          of 5, from 1,746 reviews
          3.5 out of 5.0

          Situated near the airport, this hotel is within a 5-minute walk of Rosemont Theatre and Donald E. Stephens Convention Center. Fashion Outlets of Chicago and MB Financial Park at Rosemont are also within 10 minutes. Rosemont Station is 14 minutes by foot and Rosemont Station is 13 minutes.

          Wyndham Chicago O'Hare C$157
          See details
           
          Wyndham Chicago O'Hare

          Wyndham Chicago O'Hare

          1450 E Touhy Ave, Des Plaines
             
            4.0
            of 5, from 2,040 reviews
            3.0 out of 5.0

            Complimentary shuttle service whisks guests arriving from O'Hare International to Wyndham Chicago O'Hare, a mere 2 miles away; concert-goers and hockey fans can stroll a block down to Allstate Arena.

            Best Western At O'Hare C$121
            See details
             
            Best Western At O'Hare

            Best Western At O'Hare

            10300 W Higgins Road, Rosemont
               
              3.9
              of 5, from 810 reviews
              3.0 out of 5.0

              This hotel is 4 blocks from Allstate Arena (DePaul Blue Demons; Chicago Wolves) and 2 miles from O'Hare Airport; complimentary 24-hour shuttle service is provided.

              O'Hare Inn & Suites C$82
              See details
               
              O'Hare Inn & Suites

              O'Hare Inn & Suites

              4101 Mannheim Rd, Schiller Park
                 
                2.9
                of 5, from 2,290 reviews
                2.0 out of 5.0

                Situated in Schiller Park, this hotel is within 3 mi (5 km) of Fashion Outlets of Chicago, Rosemont Theatre, and MB Financial Park at Rosemont. Donald E. Stephens Convention Center is 2.7 mi (4.4 km) away. Franklin Park Mannheim Station is 17 minutes by foot and Schiller Park Station is 29 minutes.

                Hyatt Place Chicago/O'Hare Airport C$188
                See details
                 
                Hyatt Place Chicago/O'Hare Airport

                Hyatt Place Chicago/O'Hare Airport

                6810 Mannheim Rd, Rosemont
                   
                  4.5
                  of 5, from 1,402 reviews
                  3.0 out of 5.0

                  Situated in Rosemont, this golf hotel is within 1 mi (2 km) of Allstate Arena and Lake Park. Rivers Casino and Donald E. Stephens Convention Center are also within 3 mi (5 km). Rosemont O'Hare Transfer Station is 13 minutes by foot.

                  See all 328 properties in O'Hare Intl.

                  Chicago

                  MDW-Midway Intl.

                  C$288.86

                  Top Routes from Toronto

                  Top Routes to Chicago

                  Toronto to Chicago Flights

                  Ready for an adventure? Thought so! Prepare to see the sights when you book your trip from Toronto to Chicago with Expedia.ca. Whether you’re visiting for business or pleasure, we know how important it is to bring home travel stories. Maybe your tales will include the best dinner of your life, or the weirdest street art you saw in the city, or the concert that turned you into a fan of a new band. Whatever it is, your new favourite anecdote is right around the corner. Book your trip from YYZ to ORD and begin your journey!

                  Getting a cheap deal on your trip sets the tone for the perfect holiday. And with Expedia.ca, you know you can travel from Toronto to Chicago on the cheap, with enough money left over for a stellar time in the city. That could mean more tours with the kids, more concerts with the spouse, more dessert amongst co-workers, or even front row seats to a sports game if you’re travelling solo. It’s your holiday! Make it great.

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