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

Sep 2026
FromCAD 381*
One way/Economy
Oct 2026
FromCAD 198*
One way/Economy
Nov 2026
FromCAD 191*
One way/Economy
cmp-daily-histogram-bars-legend-min-price-aria-label CAD 198
cmp-daily-histogram-bars-legend-max-price-aria-label CAD 497
Displaying fares for September-2026
  • YYZ–ORD, Sep 19, 2026: From CAD 389
    19

    Sa

    SEP

  • YYZ–ORD, Sep 20, 2026: From CAD 439
    20

    Su

  • YTZ–ORD, Sep 21, 2026: From CAD 431
    21

    Mo

  • YTZ–ORD, Sep 22, 2026: From CAD 381
    22

    Tu

  • YTZ–ORD, Sep 23, 2026: From CAD 381
    23

    We

  • YTZ–ORD, Sep 24, 2026: From CAD 431
    24

    Th

  • YTZ–ORD, Sep 25, 2026: From CAD 431
    25

    Fr

  • YTZ–ORD, Sep 26, 2026: From CAD 381
    26

    Sa

  • YYZ–ORD, Sep 27, 2026: From CAD 439
    27

    Su

  • YYZ–ORD, Sep 28, 2026: From CAD 439
    28

    Mo

  • YTZ–ORD, Sep 29, 2026: From CAD 381
    29

    Tu

  • YTZ–ORD, Sep 30, 2026: From CAD 381
    30

    We

  • YTZ–ORD, Oct 01, 2026: From CAD 431
    01

    Th

    OCT

  • YTZ–ORD, Oct 02, 2026: From CAD 211
    02

    Fr

  • YYZ–ORD, Oct 03, 2026: From CAD 198
    03

    Sa

  • YYZ–ORD, Oct 04, 2026: From CAD 198
    04

    Su

  • YYZ–ORD, Oct 05, 2026: From CAD 256
    05

    Mo

  • YYZ–ORD, Oct 06, 2026: From CAD 198
    06

    Tu

  • YYZ–ORD, Oct 07, 2026: From CAD 198
    07

    We

  • YYZ–ORD, Oct 08, 2026: From CAD 256
    08

    Th

  • YYZ–ORD, Oct 09, 2026: From CAD 497
    09

    Fr

  • YYZ–ORD, Oct 10, 2026: From CAD 256
    10

    Sa

  • YYZ–ORD, Oct 11, 2026: From CAD 198
    11

    Su

  • YYZ–ORD, Oct 12, 2026: From CAD 198
    12

    Mo

  • YYZ–ORD, Oct 13, 2026: From CAD 198
    13

    Tu

  • YYZ–ORD, Oct 14, 2026: From CAD 198
    14

    We

  • YYZ–ORD, Oct 15, 2026: From CAD 198
    15

    Th

  • YYZ–ORD, Oct 16, 2026: From CAD 198
    16

    Fr

  • YTZ–ORD, Oct 17, 2026: From CAD 211
    17

    Sa

  • YYZ–ORD, Oct 18, 2026: From CAD 256
    18

    Su

    • RangeCAD 198-CAD 497

    *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    		 Dec 02, 2026

    From

    7,037 pts
    + CAD 125

    Viewed: 1 day ago

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

    From

    7,037 pts
    + CAD 125

    Viewed: 1 day ago

    Toronto (YYZ)Chicago (ORD)One-way
    /
    Economy    		 Sep 08, 2027

    From

    8,582 pts
    + CAD 125

    Viewed: 1 day ago

    Toronto (YYZ)Chicago (ORD)One-way
    /
    Economy    		 Oct 18, 2026

    From

    15,586 pts
    + CAD 172

    Viewed: 1 day ago

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

    From

    5,980 pts
    + CAD 125

    Viewed: 23 hours ago

    Toronto (YYZ)Chicago (ORD)One-way
    /
    Economy    		 Sep 26, 2026

    From

    6,918 pts
    + CAD 172

    Viewed: 4 hours ago

    Toronto (YYZ)Chicago (ORD)One-way
    /
    Economy    		 Sep 29, 2026

    From

    6,918 pts
    + CAD 172

    Viewed: 33 minutes ago

    Toronto (YYZ)Chicago (ORD)One-way
    /
    Economy    		 Sep 28, 2026

    From

    10,000 pts
    + CAD 164

    Viewed: 34 minutes ago

    Toronto (YTZ)Chicago (ORD)One-way
    /
    Economy    		 Oct 23, 2026

    From

    9,237 pts
    + CAD 163

    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.

    Explore all routes from Toronto to Chicago