Travel with Air Canada from Winnipeg to Chicago (YWG - ORD) from CAD 443*

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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 Winnipeg and Chicago - our lowest fares in cash

Aug 2026
FromCAD 561*
One way/Economy
Sep 2026
FromCAD 443*
One way/Economy
Oct 2026
FromCAD 476*
One way/Economy
cmp-daily-histogram-bars-legend-min-price-aria-label CAD 475
cmp-daily-histogram-bars-legend-max-price-aria-label CAD 878
Displaying fares for August-2026
  • YWG–ORD, Aug 06, 2026: From CAD 867
    06

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    AUG

  • YWG–ORD, Aug 07, 2026: From CAD 867
    07

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  • YWG–ORD, Aug 08, 2026: From CAD 777
    08

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  • YWG–ORD, Aug 09, 2026: From CAD 878
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  • YWG–ORD, Aug 10, 2026: From CAD 839
    10

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  • YWG–ORD, Aug 11, 2026: From CAD 777
    11

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  • YWG–ORD, Aug 12, 2026: From CAD 699
    12

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  • YWG–ORD, Aug 13, 2026: From CAD 688
    13

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  • YWG–ORD, Aug 14, 2026: From CAD 688
    14

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  • YWG–ORD, Aug 15, 2026: From CAD 688
    15

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  • YWG–ORD, Aug 16, 2026: From CAD 688
    16

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  • YWG–ORD, Aug 17, 2026: From CAD 688
    17

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  • YWG–ORD, Aug 18, 2026: From CAD 688
    18

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  • YWG–ORD, Aug 19, 2026: From CAD 610
    19

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  • YWG–ORD, Aug 20, 2026: From CAD 607
    20

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  • YWG–ORD, Aug 21, 2026: From CAD 599
    21

    Fr

  • YWG–ORD, Aug 22, 2026: From CAD 607
    22

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  • YWG–ORD, Aug 23, 2026: From CAD 599
    23

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  • YWG–ORD, Aug 24, 2026: From CAD 610
    24

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  • YWG–ORD, Aug 25, 2026: From CAD 599
    25

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  • YWG–ORD, Aug 26, 2026: From CAD 568
    26

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  • YWG–ORD, Aug 27, 2026: From CAD 561
    27

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  • YWG–ORD, Aug 28, 2026: From CAD 561
    28

    Fr

  • YWG–ORD, Aug 29, 2026: From CAD 568
    29

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  • YWG–ORD, Aug 30, 2026: From CAD 568
    30

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  • YWG–ORD, Aug 31, 2026: From CAD 561
    31

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  • YWG–ORD, Sep 01, 2026: From CAD 475
    01

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    SEP

  • YWG–ORD, Sep 02, 2026: From CAD 475
    02

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  • YWG–ORD, Sep 03, 2026: From CAD 475
    03

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  • YWG–ORD, Sep 04, 2026: From CAD 475
    04

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  • YWG–ORD, Sep 05, 2026: From CAD 475
    05

    Sa

    • RangeCAD 475-CAD 878

    *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 Winnipeg (YWG) to Chicago (ORD) | Air Canada

    Flights between Winnipeg and Chicago - our lowest fares in points

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    Flights between Winnipeg and Chicago - our lowest fares in points
    From
    To
    Fare Type
    Departure
    Price
    Winnipeg (YWG)Chicago (ORD)One-way
    /
    Economy    		 Sep 16, 2026

    From

    20,000 pts
    + CAD 335

    Viewed: 22 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.

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