Travel with Air Canada from Toronto to Chicago (YTO - ORD) from CAD 191*

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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

Aug 2026
FromCAD 410*
One way/Economy
Sep 2026
FromCAD 191*
One way/Economy
Oct 2026
FromCAD 280*
One way/Economy
cmp-daily-histogram-bars-legend-min-price-aria-label CAD 191
cmp-daily-histogram-bars-legend-max-price-aria-label CAD 481
Displaying fares for August-2026
  • YTZ–ORD, Aug 30, 2026: From CAD 410
    30

    Su

    AUG

  • YTZ–ORD, Aug 31, 2026: From CAD 410
    31

    Mo

  • YTZ–ORD, Sep 01, 2026: From CAD 360
    01

    Tu

    SEP

  • YTZ–ORD, Sep 02, 2026: From CAD 360
    02

    We

  • YYZ–ORD, Sep 03, 2026: From CAD 423
    03

    Th

  • YTZ–ORD, Sep 04, 2026: From CAD 410
    04

    Fr

  • YTZ–ORD, Sep 05, 2026: From CAD 360
    05

    Sa

  • YTZ–ORD, Sep 06, 2026: From CAD 410
    06

    Su

  • YYZ–ORD, Sep 07, 2026: From CAD 423
    07

    Mo

  • YTZ–ORD, Sep 08, 2026: From CAD 360
    08

    Tu

  • YTZ–ORD, Sep 09, 2026: From CAD 360
    09

    We

  • YYZ–ORD, Sep 10, 2026: From CAD 423
    10

    Th

  • YYZ–ORD, Sep 11, 2026: From CAD 423
    11

    Fr

  • YYZ–ORD, Sep 12, 2026: From CAD 372
    12

    Sa

  • YYZ–ORD, Sep 13, 2026: From CAD 481
    13

    Su

  • YYZ–ORD, Sep 14, 2026: From CAD 359
    14

    Mo

  • YTZ–ORD, Sep 15, 2026: From CAD 268
    15

    Tu

  • YTZ–ORD, Sep 16, 2026: From CAD 268
    16

    We

  • YTZ–ORD, Sep 17, 2026: From CAD 289
    17

    Th

  • YTZ–ORD, Sep 18, 2026: From CAD 289
    18

    Fr

  • YTZ–ORD, Sep 19, 2026: From CAD 268
    19

    Sa

  • YTZ–ORD, Sep 20, 2026: From CAD 191
    20

    Su

  • YTZ–ORD, Sep 21, 2026: From CAD 191
    21

    Mo

  • YTZ–ORD, Sep 22, 2026: From CAD 191
    22

    Tu

  • YTZ–ORD, Sep 23, 2026: From CAD 191
    23

    We

  • YTZ–ORD, Sep 24, 2026: From CAD 191
    24

    Th

  • YTZ–ORD, Sep 25, 2026: From CAD 191
    25

    Fr

  • YTZ–ORD, Sep 26, 2026: From CAD 191
    26

    Sa

  • YYZ–ORD, Sep 27, 2026: From CAD 261
    27

    Su

  • YYZ–ORD, Sep 28, 2026: From CAD 352
    28

    Mo

  • YYZ–ORD, Sep 29, 2026: From CAD 203
    29

    Tu

    • RangeCAD 191-CAD 481

    *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    		 Oct 02, 2026

    From

    6,000 pts
    + CAD 171

    Viewed: 8 hours ago

    Toronto (YYZ)Chicago (ORD)One-way
    /
    Economy    		 Sep 05, 2026

    From

    6,000 pts
    + CAD 171

    Viewed: 8 hours ago

    Toronto (YYZ)Chicago (ORD)One-way
    /
    Economy    		 Sep 04, 2026

    From

    6,000 pts
    + CAD 171

    Viewed: 8 hours ago

    Toronto (YYZ)Chicago (ORD)One-way
    /
    Economy    		 Sep 01, 2026

    From

    6,000 pts
    + CAD 171

    Viewed: 7 hours ago

    Toronto (YYZ)Chicago (ORD)One-way
    /
    Economy    		 Sep 03, 2026

    From

    10,000 pts
    + CAD 164

    Viewed: 1 hour ago

    Toronto (YYZ)Chicago (ORD)One-way
    /
    Economy    		 Aug 31, 2026

    From

    10,000 pts
    + CAD 164

    Viewed: 4 hours 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.

    Explore all routes from Toronto to Chicago