Travel with Air Canada from Winnipeg to Chicago (YWG - ORD) from CAD 506*

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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

Nov 2026
FromCAD 605*
One way/Economy
Dec 2026
FromCAD 526*
One way/Economy
Jan 2027
FromCAD 520*
One way/Economy
cmp-daily-histogram-bars-legend-min-price-aria-label CAD 544
cmp-daily-histogram-bars-legend-max-price-aria-label CAD 1.8K
Displaying fares for November-2026
  • YWG–ORD, Nov 14, 2026: From CAD 1,498
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    NOV

  • YWG–ORD, Nov 15, 2026: From CAD 1,782
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  • YWG–ORD, Nov 16, 2026: From CAD 935
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  • YWG–ORD, Nov 17, 2026: From CAD 795
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  • YWG–ORD, Nov 18, 2026: From CAD 795
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  • YWG–ORD, Nov 19, 2026: From CAD 784
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  • YWG–ORD, Nov 20, 2026: From CAD 792
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  • YWG–ORD, Nov 21, 2026: From CAD 703
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  • YWG–ORD, Nov 22, 2026: From CAD 695
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  • YWG–ORD, Nov 23, 2026: From CAD 695
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  • YWG–ORD, Nov 24, 2026: From CAD 695
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  • YWG–ORD, Nov 25, 2026: From CAD 703
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  • YWG–ORD, Nov 26, 2026: From CAD 695
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  • YWG–ORD, Nov 27, 2026: From CAD 695
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  • YWG–ORD, Nov 28, 2026: From CAD 757
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  • YWG–ORD, Nov 29, 2026: From CAD 605
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  • YWG–ORD, Nov 30, 2026: From CAD 613
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  • YWG–ORD, Dec 01, 2026: From CAD 605
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    DEC

  • YWG–ORD, Dec 02, 2026: From CAD 605
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  • YWG–ORD, Dec 03, 2026: From CAD 605
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  • YWG–ORD, Dec 04, 2026: From CAD 605
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  • YWG–ORD, Dec 05, 2026: From CAD 568
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    Sa

  • YWG–ORD, Dec 06, 2026: From CAD 575
    06

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  • YWG–ORD, Dec 07, 2026: From CAD 595
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  • YWG–ORD, Dec 08, 2026: From CAD 544
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  • YWG–ORD, Dec 09, 2026: From CAD 544
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  • YWG–ORD, Dec 10, 2026: From CAD 544
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  • YWG–ORD, Dec 11, 2026: From CAD 544
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  • YWG–ORD, Dec 12, 2026: From CAD 595
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  • YWG–ORD, Dec 13, 2026: From CAD 544
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    Su

    • RangeCAD 544-CAD 1,782

    *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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