Travel with Air Canada from Calgary to Chicago (YYC - ORD) from CAD 228*

Promotion code

*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 Calgary and Chicago - our lowest fares in cash

Aug 2026
FromCAD 329*
One way/Economy
Sep 2026
FromCAD 233*
One way/Economy
Oct 2026
FromCAD 235*
One way/Economy
cmp-daily-histogram-bars-legend-min-price-aria-label CAD 233
cmp-daily-histogram-bars-legend-max-price-aria-label CAD 650
Displaying fares for August-2026
  • YYC–ORD, Aug 31, 2026: From CAD 329
    31

    Mo

    AUG

  • YYC–ORD, Sep 01, 2026: From CAD 299
    01

    Tu

  • YYC–ORD, Sep 02, 2026: From CAD 329
    02

    We

  • YYC–ORD, Sep 03, 2026: From CAD 336
    03

    Th

  • YYC–ORD, Sep 04, 2026: From CAD 298
    04

    Fr

  • YYC–ORD, Sep 05, 2026: From CAD 305
    05

    Sa

  • YYC–ORD, Sep 06, 2026: From CAD 650
    06

    Su

  • YYC–ORD, Sep 07, 2026: From CAD 452
    07

    Mo

  • YYC–ORD, Sep 08, 2026: From CAD 336
    08

    Tu

  • YYC–ORD, Sep 09, 2026: From CAD 305
    09

    We

  • YYC–ORD, Sep 10, 2026: From CAD 336
    10

    Th

  • YYC–ORD, Sep 11, 2026: From CAD 336
    11

    Fr

  • YYC–ORD, Sep 12, 2026: From CAD 336
    12

    Sa

  • YYC–ORD, Sep 13, 2026: From CAD 457
    13

    Su

  • YYC–ORD, Sep 14, 2026: From CAD 427
    14

    Mo

  • YYC–ORD, Sep 15, 2026: From CAD 265
    15

    Tu

  • YYC–ORD, Sep 16, 2026: From CAD 296
    16

    We

  • YYC–ORD, Sep 17, 2026: From CAD 296
    17

    Th

  • YYC–ORD, Sep 18, 2026: From CAD 296
    18

    Fr

  • YYC–ORD, Sep 19, 2026: From CAD 427
    19

    Sa

  • YYC–ORD, Sep 20, 2026: From CAD 534
    20

    Su

  • YYC–ORD, Sep 21, 2026: From CAD 469
    21

    Mo

  • YYC–ORD, Sep 22, 2026: From CAD 264
    22

    Tu

  • YYC–ORD, Sep 23, 2026: From CAD 257
    23

    We

  • YYC–ORD, Sep 24, 2026: From CAD 396
    24

    Th

  • YYC–ORD, Sep 25, 2026: From CAD 396
    25

    Fr

  • YYC–ORD, Sep 26, 2026: From CAD 390
    26

    Sa

  • YYC–ORD, Sep 27, 2026: From CAD 438
    27

    Su

  • YYC–ORD, Sep 28, 2026: From CAD 264
    28

    Mo

  • YYC–ORD, Sep 29, 2026: From CAD 264
    29

    Tu

  • YYC–ORD, Sep 30, 2026: From CAD 233
    30

    We

    • RangeCAD 233-CAD 650

    *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 Calgary (YYC) to Chicago (ORD) | Air Canada

    Flights between Calgary and Chicago - our lowest fares in points

    pts
    keyboard_arrow_down
    Flights between Calgary and Chicago - our lowest fares in points
    From
    To
    Fare Type
    Departure
    Price
    Calgary (YYC)Chicago (ORD)One-way
    /
    Economy    		 Oct 13, 2026

    From

    22,600 pts
    + CAD 260

    Viewed: 1 day ago

    Calgary (YYC)Chicago (ORD)One-way
    /
    Economy    		 Nov 11, 2026

    From

    48,800 pts
    + CAD 630

    Viewed: 1 day ago

    Calgary (YYC)Chicago (ORD)One-way
    /
    Economy    		 Jul 26, 2027

    From

    17,600 pts
    + CAD 130

    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 Calgary to Chicago