Travel with Air Canada from Winnipeg to Chicago (YWG - ORD) from CAD 445*

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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 729*
One way/Economy
Sep 2026
FromCAD 445*
One way/Economy
Oct 2026
FromCAD 455*
One way/Economy
cmp-daily-histogram-bars-legend-min-price-aria-label CAD 445
cmp-daily-histogram-bars-legend-max-price-aria-label CAD 886
Displaying fares for August-2026
  • YWG–ORD, Aug 26, 2026: From CAD 881
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  • YWG–ORD, Aug 27, 2026: From CAD 881
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  • YWG–ORD, Aug 28, 2026: From CAD 886
    28

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  • YWG–ORD, Aug 29, 2026: From CAD 729
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  • YWG–ORD, Aug 30, 2026: From CAD 779
    30

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  • YWG–ORD, Aug 31, 2026: From CAD 779
    31

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  • YWG–ORD, Sep 01, 2026: From CAD 729
    01

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    SEP

  • YWG–ORD, Sep 02, 2026: From CAD 703
    02

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  • YWG–ORD, Sep 03, 2026: From CAD 703
    03

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  • YWG–ORD, Sep 04, 2026: From CAD 703
    04

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  • YWG–ORD, Sep 05, 2026: From CAD 703
    05

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  • YWG–ORD, Sep 06, 2026: From CAD 703
    06

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  • YWG–ORD, Sep 07, 2026: From CAD 703
    07

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  • YWG–ORD, Sep 08, 2026: From CAD 703
    08

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  • YWG–ORD, Sep 09, 2026: From CAD 593
    09

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  • YWG–ORD, Sep 10, 2026: From CAD 614
    10

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  • YWG–ORD, Sep 11, 2026: From CAD 614
    11

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  • YWG–ORD, Sep 12, 2026: From CAD 593
    12

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  • YWG–ORD, Sep 13, 2026: From CAD 614
    13

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  • YWG–ORD, Sep 14, 2026: From CAD 614
    14

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  • YWG–ORD, Sep 15, 2026: From CAD 593
    15

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  • YWG–ORD, Sep 16, 2026: From CAD 445
    16

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  • YWG–ORD, Sep 17, 2026: From CAD 445
    17

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  • YWG–ORD, Sep 18, 2026: From CAD 445
    18

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  • YWG–ORD, Sep 19, 2026: From CAD 445
    19

    Sa

  • YWG–ORD, Sep 20, 2026: From CAD 449
    20

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  • YWG–ORD, Sep 21, 2026: From CAD 546
    21

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  • YWG–ORD, Sep 22, 2026: From CAD 449
    22

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  • YWG–ORD, Sep 23, 2026: From CAD 449
    23

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  • YWG–ORD, Sep 24, 2026: From CAD 449
    24

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  • YWG–ORD, Sep 25, 2026: From CAD 541
    25

    Fr

    • RangeCAD 445-CAD 886

    *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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    *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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