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Calgary Intl. Airport to Chicago Midway International Airport flight

Explore the cheapest one-way and round-trip flights from Calgary Intl. Airport to Chicago Midway International Airport over the next 90 days, with one-way fares from CAD 225 and round-trip from CAD 349. Based on Trip.com's latest 7-day flight data.

      • YYC 8:45 AM
        7h 54m
        1 stop
        MDW 4:39 PM
        Calgary - Chicago | Fri, Nov 27 | Delta Air Lines
        ORD 2:03 PM
        10h 14m
        1 stop
        YYC 12:17 AM
        Chicago - Calgary | Tue, Dec 1 | Delta Air Lines
        CAD 349 CAD 586
        40% off
        40% off
        CAD 586 CAD 349
      • YYC 8:45 AM
        8h 2m
        1 stop
        MDW 4:47 PM
        Calgary - Chicago | Mon, Nov 9 | Delta Air Lines
        ORD 2:03 PM
        10h 14m
        1 stop
        YYC 12:17 AM
        Chicago - Calgary | Mon, Nov 16 | Delta Air Lines
        CAD 351 CAD 586
        40% off
        40% off
        CAD 586 CAD 351
      • YYC 8:45 AM
        7h 54m
        1 stop
        MDW 4:39 PM
        Calgary - Chicago | Sat, Nov 28 | Delta Air Lines
        ORD 2:03 PM
        10h 14m
        1 stop
        YYC 12:17 AM
        Chicago - Calgary | Tue, Dec 1 | Delta Air Lines
        CAD 351 CAD 586
        40% off
        40% off
        CAD 586 CAD 351
      • YYC 7:45 AM
        8h 2m
        1 stop
        MDW 4:47 PM
        Calgary - Chicago | Tue, Oct 13 | Delta Air Lines
        ORD 2:03 PM
        10h 7m
        1 stop
        YYC 11:10 PM
        Chicago - Calgary | Mon, Oct 19 | Delta Air Lines
        CAD 351
        40% off
        CAD 586 CAD 351
      • YYC 8:45 AM
        7h 54m
        1 stop
        MDW 4:39 PM
        Calgary - Chicago | Mon, Nov 23 | Delta Air Lines
        ORD 2:03 PM
        10h 14m
        1 stop
        YYC 12:17 AM
        Chicago - Calgary | Sun, Nov 29 | Delta Air Lines
        CAD 351
        40% off
        CAD 586 CAD 351
      • YYC 7:45 AM
        8h 2m
        1 stop
        MDW 4:47 PM
        Calgary - Chicago | Fri, Nov 6 | Delta Air Lines
        ORD 4:00 PM
        8h 12m
        1 stop
        YYC 12:12 AM
        Chicago - Calgary | Fri, Nov 13 | Delta Air Lines
        CAD 351
        40% off
        CAD 586 CAD 351
      • YYC 7:45 AM
        8h 2m
        1 stop
        MDW 4:47 PM
        Calgary - Chicago | Thu, Nov 5 | Delta Air Lines
        ORD 2:03 PM
        10h 7m
        1 stop
        YYC 12:10 AM
        Chicago - Calgary | Thu, Nov 12 | Delta Air Lines
        CAD 351
        40% off
        CAD 586 CAD 351
      • YYC 7:45 AM
        8h 2m
        1 stop
        MDW 4:47 PM
        Calgary - Chicago | Tue, Oct 27 | Delta Air Lines
        ORD 2:03 PM
        10h 7m
        1 stop
        YYC 11:10 PM
        Chicago - Calgary | Tue, Nov 3 | Delta Air Lines
        CAD 354
        40% off
        CAD 586 CAD 354
      • YYC 8:45 AM
        7h 54m
        1 stop
        MDW 4:39 PM
        Calgary - Chicago | Fri, Nov 20 | Delta Air Lines
        MDW 12:30 PM
        9h 28m
        1 stop
        YYC 9:58 PM
        Chicago - Calgary | Fri, Nov 27 | Delta Air Lines
        CAD 354
        40% off
        CAD 586 CAD 354
      • YYC 8:45 AM
        7h 54m
        1 stop
        MDW 4:39 PM
        Calgary - Chicago | Tue, Nov 24 | Delta Air Lines
        ORD 1:55 PM
        10h 55m
        1 stop
        YYC 12:50 AM
        Chicago - Calgary | Sun, Nov 29 | Air Canada
        CAD 385
        34% off
        CAD 586 CAD 385
      • YYC 7:45 AM
        8h 2m
        1 stop
        MDW 4:47 PM
        Calgary - Chicago | Fri, Oct 30 | Delta Air Lines
        ORD 1:59 PM
        10h 13m
        1 stop
        YYC 11:12 PM
        Chicago - Calgary | Fri, Nov 6 | Delta Air Lines
        CAD 406
        31% off
        CAD 586 CAD 406
      • YYC 12:20 AM
        8h 43m
        1 stop
        MDW 10:03 AM
        Calgary - Chicago | Wed, Oct 21 | Delta Air Lines
        ORD 3:40 PM
        9h 7m
        1 stop
        YYC 11:47 PM
        Chicago - Calgary | Fri, Oct 23 | Air Canada
        CAD 410
        30% off
        CAD 586 CAD 410
      • YYC 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        Calgary - Chicago | Tue, Oct 6 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        YYC 4:00 PM
        Chicago - Calgary | Thu, Oct 8 | Normal Airline
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      • YYC 7:45 AM
        8h 2m
        1 stop
        MDW 4:47 PM
        Calgary - Chicago | Tue, Oct 27 | Delta Air Lines
        CAD 225 CAD 415
        46% off
        46% off
        CAD 415 CAD 225
      • YYC 7:45 AM
        9h 5m
        1 stop
        MDW 4:50 PM
        Calgary - Chicago | Fri, Nov 20 | Delta Air Lines
        CAD 225 CAD 415
        46% off
        46% off
        CAD 415 CAD 225
      • YYC 8:45 AM
        7h 54m
        1 stop
        MDW 4:39 PM
        Calgary - Chicago | Sat, Nov 28 | Delta Air Lines
        CAD 226 CAD 415
        46% off
        46% off
        CAD 415 CAD 226
      • YYC 1:25 AM
        8h 59m
        1 stop
        MDW 10:24 AM
        Calgary - Chicago | Wed, Nov 18 | Delta Air Lines
        CAD 271
        35% off
        CAD 415 CAD 271
      • YYC 11:00 AM
        6h 33m
        1 stop
        MDW 6:33 PM
        Calgary - Chicago | Thu, Oct 8 | Delta Air Lines
        CAD 274
        34% off
        CAD 415 CAD 274
      • YYC 7:45 AM
        9h 5m
        1 stop
        MDW 4:50 PM
        Calgary - Chicago | Fri, Nov 27 | Delta Air Lines
        CAD 274
        34% off
        CAD 415 CAD 274
      • YYC 7:45 AM
        8h 2m
        1 stop
        MDW 4:47 PM
        Calgary - Chicago | Mon, Oct 26 | Delta Air Lines
        CAD 280
        33% off
        CAD 415 CAD 280
      • YYC 6:35 AM
        6h 36m
        1 stop
        MDW 1:11 PM
        Calgary - Chicago | Sun, Nov 8 | Delta Air Lines
        CAD 283
        32% off
        CAD 415 CAD 283
      • YYC 6:35 AM
        5h 36m
        1 stop
        MDW 1:11 PM
        Calgary - Chicago | Mon, Nov 2 | Delta Air Lines
        CAD 283
        32% off
        CAD 415 CAD 283
      • YYC 8:45 AM
        7h 54m
        1 stop
        MDW 4:39 PM
        Calgary - Chicago | Tue, Nov 24 | Delta Air Lines
        CAD 288
        31% off
        CAD 415 CAD 288
      • YYC 12:30 AM
        8h 22m
        1 stop
        MDW 9:52 AM
        Calgary - Chicago | Tue, Nov 3 | Delta Air Lines
        CAD 289
        30% off
        CAD 415 CAD 289
      • YYC 8:55 AM
        11h 50m
        1 stop
        MDW 9:45 PM
        Calgary - Chicago | Fri, Nov 6 | Delta Air Lines
        CAD 290
        30% off
        CAD 415 CAD 290
      • YYC 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        Calgary - Chicago | Tue, Oct 6 | Normal Airline
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Displayed flight fares from Calgary Intl. Airport to Chicago Midway International Airport are based on average prices across airlines for the next 3 months, according to the latest Trip.com database.

Which airline offers the cheapest flights from Calgary Intl. Airport to Chicago Midway International Airport?

The cheapest airline flying from Calgary Intl. Airport to Chicago Midway International Airport is Delta Air Lines (from CAD 225) among 5 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Delta Air Lines
From CAD 225
WestJet
From CAD 294
Flair Airlines
From CAD 401
Apg Airlines
From CAD 410
Air Canada
From CAD 451

Find more flights and airlines

What is the flight schedule from Calgary Intl. Airport to Chicago Midway International Airport?

Check the schedule for flights from Calgary to Chicago and find the flight that best matches your travel plans.

Flight info.
Departure
Arrival
Weekly Schedule

  1. DL2492

    Calgary Intl. Airport

    6:35 AM

    YYC

    2h 41m

    Nonstop

    10:16 AM

    MSP

    S M T W T F S
    Search

  2. DL4714

    Minneapolis-Saint Paul International Airport

    3:00 PM

    MSP

    1h 50m

    Nonstop

    4:50 PM

    MDW

    S M T W T F S

  3. DL7192

    Calgary Intl. Airport

    7:00 AM

    YYC

    4h 25m

    Nonstop

    1:25 PM

    ATL

    S M T W T F S
    Search

  4. DL1728

    Hartsfield–Jackson Atlanta International Airport

    3:30 PM

    ATL

    1h 55m

    Nonstop

    4:25 PM

    MDW

    S M T W T F S

  5. DL6896

    Calgary Intl. Airport

    12:20 AM

    YYC

    4h 25m

    Nonstop

    6:45 AM

    ATL

    S M T W T F S
    Search

  6. DL1063

    Hartsfield–Jackson Atlanta International Airport

    8:55 AM

    ATL

    1h 54m

    Nonstop

    9:49 AM

    MDW

    S M T W T F S

  7. DL6896

    Calgary Intl. Airport

    12:20 AM

    YYC

    4h 25m

    Nonstop

    6:45 AM

    ATL

    S M T W T F S
    Search

  8. DL2417

    Hartsfield–Jackson Atlanta International Airport

    11:00 AM

    ATL

    1h 56m

    Nonstop

    11:56 AM

    MDW

    S M T W T - S

  9. WS1590

    Calgary Intl. Airport

    7:00 AM

    YYC

    4h 25m

    Nonstop

    1:25 PM

    ATL

    S M T W T F S
    Search

  10. F92291

    Hartsfield–Jackson Atlanta International Airport

    10:50 PM

    ATL

    1h 54m

    Nonstop

    11:44 PM

    MDW

    S - - W T F S
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About Calgary Intl. Airport and Chicago Midway International Airport

Learn about Calgary Intl. Airport (YYC) and Chicago Midway International Airport (MDW) — including location, terminals, transportation, and travel tips.

Flight distance 2,250.21 km
Cheapest one-way ticket price CAD 225
Cheapest return ticket price CAD 349

FAQs for Calgary Intl. Airport to Chicago Midway International Airport Flights

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
    • The distance from Chicago Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.
  • The closest airport to Chicago Midway International Airport (MDW) is O'Hare International Airport. The distance is around 25 km.
  • One-way flights from Calgary Intl. Airport to Chicago Midway International Airport currently start from CAD 225, and round-trip fares start from CAD 349. The current lowest fare is a Delta Air Lines flight departing on Tue, Oct 27; prices may vary depending on availability.
  • Based on Trip.com flight data for departures within the next 30 days with at most one stop, the average one-way price from Calgary Intl. Airport to Chicago Midway International Airport is CAD 547. Prices may vary depending on the departure date, airline, and availability.
  • Enter Calgary Intl. Airport and Chicago Midway International Airport, select your departure date and number of passengers, then compare flights by price, flight duration, and baggage allowance. Once you've chosen a fare, review the change and refund rules, fill in passenger details, and pay to receive your booking confirmation.

Popular Destinations

Note: Prices shown on this page are estimated lowest price and include all taxes and fees found in the last 24 hours.

Book with no extra fees

Prices displayed in this page are all-inclusive prices (incl. taxes, fuel surcharge, civil aviation development fund, etc) with all fees confirmed before payment. Fees for luggage, meals, WLAN, or other additional services are also included as shown in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page were updated within last 24 hours—even in real-time. The more popular the route, the more precise the data.

Change & Cancellation Policy

Trip.com displays flight cancellation and change policies for each flight ticket during the booking process, including fees and applicable conditions. Please check the following scenarios:
Voluntary cancellation/change:
To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy.
Cancellation/change due to a flight schedule change:
If the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.