Travel with Air Canada from Toronto to Chicago (YTO - ORD) from CAD 262*

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*Fares displayed have been collected within the last 48 hours and may no longer be available at the time of booking. Learn more about this offer. Additional baggage fees and charges for optional products and services may apply.

Flights between Toronto and Chicago - our lowest fares in cash

Oct 2026
FromCAD 269*
One way/Economy
Nov 2026
FromCAD 262*
One way/Economy
Dec 2026
FromCAD 269*
One way/Economy
cmp-daily-histogram-bars-legend-min-price-aria-label CAD 269
cmp-daily-histogram-bars-legend-max-price-aria-label CAD 560
Displaying fares for October-2026
  • YTZ–ORD, Oct 10, 2026: From CAD 523
    10

    Sa

    OCT

  • YTZ–ORD, Oct 11, 2026: From CAD 548
    11

    Su

  • YTZ–ORD, Oct 12, 2026: From CAD 552
    12

    Mo

  • YTZ–ORD, Oct 13, 2026: From CAD 520
    13

    Tu

  • YTZ–ORD, Oct 14, 2026: From CAD 515
    14

    We

  • YTZ–ORD, Oct 15, 2026: From CAD 548
    15

    Th

  • YTZ–ORD, Oct 16, 2026: From CAD 552
    16

    Fr

  • YYZ–ORD, Oct 17, 2026: From CAD 528
    17

    Sa

  • YYZ–ORD, Oct 18, 2026: From CAD 560
    18

    Su

  • YYZ–ORD, Oct 19, 2026: From CAD 560
    19

    Mo

  • YYZ–ORD, Oct 20, 2026: From CAD 528
    20

    Tu

  • YYZ–ORD, Oct 21, 2026: From CAD 528
    21

    We

  • YYZ–ORD, Oct 22, 2026: From CAD 554
    22

    Th

  • YYZ–ORD, Oct 23, 2026: From CAD 554
    23

    Fr

  • YYZ–ORD, Oct 24, 2026: From CAD 355
    24

    Sa

  • YYZ–ORD, Oct 25, 2026: From CAD 376
    25

    Su

  • YYZ–ORD, Oct 26, 2026: From CAD 434
    26

    Mo

  • YYZ–ORD, Oct 27, 2026: From CAD 355
    27

    Tu

  • YYZ–ORD, Oct 28, 2026: From CAD 355
    28

    We

  • YYZ–ORD, Oct 29, 2026: From CAD 376
    29

    Th

  • YYZ–ORD, Oct 30, 2026: From CAD 376
    30

    Fr

  • YYZ–ORD, Oct 31, 2026: From CAD 269
    31

    Sa

  • YYZ–ORD, Nov 01, 2026: From CAD 269
    01

    Su

    NOV

  • YYZ–ORD, Nov 02, 2026: From CAD 269
    02

    Mo

  • YYZ–ORD, Nov 03, 2026: From CAD 269
    03

    Tu

  • YYZ–ORD, Nov 04, 2026: From CAD 269
    04

    We

  • YYZ–ORD, Nov 05, 2026: From CAD 269
    05

    Th

  • YYZ–ORD, Nov 06, 2026: From CAD 269
    06

    Fr

  • YYZ–ORD, Nov 07, 2026: From CAD 269
    07

    Sa

  • YYZ–ORD, Nov 08, 2026: From CAD 269
    08

    Su

  • YYZ–ORD, Nov 09, 2026: From CAD 269
    09

    Mo

    • RangeCAD 269-CAD 560

    *Fares displayed have been collected within the last 48 hours and may no longer be available at the time of booking. Learn more about this offer. Additional baggage fees and charges for optional products and services may apply.

    Book flights from Toronto (YTO) to Chicago (ORD) | Air Canada

    Flights between Toronto and Chicago - our lowest fares in points

    pts
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    Flights between Toronto and Chicago - our lowest fares in points
    From
    To
    Fare Type
    Departure
    Price
    Toronto (YYZ)Chicago (ORD)One-way
    /
    Economy    		 Nov 11, 2026

    From

    9,513 pts
    + CAD 127

    Viewed: 1 day ago

    Toronto (YYZ)Chicago (ORD)One-way
    /
    Economy    		 Oct 30, 2026

    From

    10,000 pts
    + CAD 166

    Viewed: 15 hours ago

    Toronto (YYZ)Chicago (ORD)One-way
    /
    Economy    		 Oct 13, 2026

    From

    10,000 pts
    + CAD 166

    Viewed: 1 day ago

    Toronto (YYZ)Chicago (ORD)One-way
    /
    Economy    		 Oct 12, 2026

    From

    10,000 pts
    + CAD 166

    Viewed: 1 day ago

    Toronto (YYZ)Chicago (ORD)One-way
    /
    Economy    		 Oct 16, 2026

    From

    10,000 pts
    + CAD 166

    Viewed: 1 day ago

    Toronto (YYZ)Chicago (ORD)One-way
    /
    Economy    		 Oct 20, 2026

    From

    30,000 pts
    + CAD 458

    Viewed: 1 day ago

    Toronto (YYZ)Chicago (ORD)One-way
    /
    Economy    		 Oct 19, 2026

    From

    34,593 pts
    + CAD 482

    Viewed: 1 day ago

    Toronto (YYZ)Chicago (ORD)One-way
    /
    Economy    		 Nov 07, 2026

    From

    9,513 pts
    + CAD 127

    Viewed: 2 hours ago

    Toronto (YYZ)Chicago (ORD)One-way
    /
    Economy    		 Oct 15, 2026

    From

    10,000 pts
    + CAD 166

    Viewed: 6 hours ago

    Toronto (YYZ)Chicago (ORD)One-way
    /
    Economy    		 Nov 06, 2026

    From

    19,026 pts
    + CAD 253

    Viewed: 7 hours ago

    Toronto (YTZ)Chicago (ORD)One-way
    /
    Economy    		 Nov 16, 2026

    From

    23,062 pts
    + CAD 373

    Viewed: 1 day ago

    *Points displayed do not reflect preferred pricing for Aeroplan Elite Status Members and/or Aeroplan Credit Cardholders. Prices have been collected within the past 48 hrs and may no longer be available at time of booking. Learn more about this offer. Additional baggage fees and charges for optional products and services may apply.

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