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Calgary International Airport to Chicago Midway International Airport flight

Explore the cheapest one-way and round-trip flights from Calgary International Airport to Chicago Midway International Airport over the next 90 days, with one-way fares from US$153 and round-trip from US$246. Based on Trip.com's latest 7-day flight data.

      • YYC 08:45
        7h 54m
        1 stop
        MDW 16:39
        Calgary - Chicago | Mon, Nov 30 | Delta Air Lines
        ORD 14:03
        10h 14m
        1 stop
        YYC 00:17
        Chicago - Calgary | Fri, Dec 4 | Delta Air Lines
        US$246 US$413
        40% off
        40% off
        US$413 US$246
      • YYC 08:45
        8h 2m
        1 stop
        MDW 16:47
        Calgary - Chicago | Thu, Nov 12 | Delta Air Lines
        ORD 14:03
        10h 14m
        1 stop
        YYC 00:17
        Chicago - Calgary | Thu, Nov 19 | Delta Air Lines
        US$247 US$413
        40% off
        40% off
        US$413 US$247
      • YYC 08:45
        7h 54m
        1 stop
        MDW 16:39
        Calgary - Chicago | Tue, Dec 1 | Delta Air Lines
        ORD 14:03
        10h 14m
        1 stop
        YYC 00:17
        Chicago - Calgary | Fri, Dec 4 | Delta Air Lines
        US$247 US$413
        40% off
        40% off
        US$413 US$247
      • YYC 07:45
        8h 2m
        1 stop
        MDW 16:47
        Calgary - Chicago | Fri, Oct 16 | Delta Air Lines
        ORD 14:03
        10h 7m
        1 stop
        YYC 23:10
        Chicago - Calgary | Thu, Oct 22 | Delta Air Lines
        US$247
        40% off
        US$413 US$247
      • YYC 08:45
        7h 54m
        1 stop
        MDW 16:39
        Calgary - Chicago | Thu, Nov 26 | Delta Air Lines
        ORD 14:03
        10h 14m
        1 stop
        YYC 00:17
        Chicago - Calgary | Wed, Dec 2 | Delta Air Lines
        US$247
        40% off
        US$413 US$247
      • YYC 07:45
        8h 2m
        1 stop
        MDW 16:47
        Calgary - Chicago | Mon, Nov 9 | Delta Air Lines
        ORD 16:00
        8h 12m
        1 stop
        YYC 00:12
        Chicago - Calgary | Mon, Nov 16 | Delta Air Lines
        US$247
        40% off
        US$413 US$247
      • YYC 07:45
        8h 2m
        1 stop
        MDW 16:47
        Calgary - Chicago | Sun, Nov 8 | Delta Air Lines
        ORD 14:03
        10h 7m
        1 stop
        YYC 00:10
        Chicago - Calgary | Sun, Nov 15 | Delta Air Lines
        US$247
        40% off
        US$413 US$247
      • YYC 07:45
        8h 2m
        1 stop
        MDW 16:47
        Calgary - Chicago | Fri, Oct 30 | Delta Air Lines
        ORD 14:03
        10h 7m
        1 stop
        YYC 23:10
        Chicago - Calgary | Fri, Nov 6 | Delta Air Lines
        US$249
        40% off
        US$413 US$249
      • YYC 08:45
        7h 54m
        1 stop
        MDW 16:39
        Calgary - Chicago | Mon, Nov 23 | Delta Air Lines
        MDW 12:30
        9h 28m
        1 stop
        YYC 21:58
        Chicago - Calgary | Mon, Nov 30 | Delta Air Lines
        US$249
        40% off
        US$413 US$249
      • YYC 08:45
        7h 54m
        1 stop
        MDW 16:39
        Calgary - Chicago | Fri, Nov 27 | Delta Air Lines
        ORD 13:55
        10h 55m
        1 stop
        YYC 00:50
        Chicago - Calgary | Wed, Dec 2 | Air Canada
        US$271
        34% off
        US$413 US$271
      • YYC 07:45
        8h 2m
        1 stop
        MDW 16:47
        Calgary - Chicago | Mon, Nov 2 | Delta Air Lines
        ORD 13:59
        10h 13m
        1 stop
        YYC 23:12
        Chicago - Calgary | Mon, Nov 9 | Delta Air Lines
        US$286
        31% off
        US$413 US$286
      • YYC 00:20
        8h 43m
        1 stop
        MDW 10:03
        Calgary - Chicago | Sat, Oct 24 | Delta Air Lines
        ORD 15:40
        9h 7m
        1 stop
        YYC 23:47
        Chicago - Calgary | Mon, Oct 26 | Air Canada
        US$289
        30% off
        US$413 US$289
      • YYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        Calgary - Chicago | Tue, Oct 6 | Normal Airline
        CHI 15:00
        6h
        Direct
        YYC 16:00
        Chicago - Calgary | Thu, Oct 8 | Normal Airline
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      • YYC 08:45
        7h 54m
        1 stop
        MDW 16:39
        Calgary - Chicago | Sat, Nov 21 | Delta Air Lines
        US$153 US$273
        44% off
        44% off
        US$273 US$153
      • YYC 08:45
        8h 2m
        1 stop
        MDW 16:47
        Calgary - Chicago | Tue, Nov 3 | Delta Air Lines
        US$154 US$273
        44% off
        44% off
        US$273 US$154
      • YYC 07:45
        8h 2m
        1 stop
        MDW 16:47
        Calgary - Chicago | Wed, Oct 21 | Delta Air Lines
        US$158 US$273
        42% off
        42% off
        US$273 US$158
      • YYC 08:45
        7h 54m
        1 stop
        MDW 16:39
        Calgary - Chicago | Sun, Nov 22 | Delta Air Lines
        US$159
        42% off
        US$273 US$159
      • YYC 08:45
        7h 54m
        1 stop
        MDW 16:39
        Calgary - Chicago | Sat, Nov 14 | Delta Air Lines
        US$159
        42% off
        US$273 US$159
      • YYC 07:45
        8h 2m
        1 stop
        MDW 16:47
        Calgary - Chicago | Sat, Oct 31 | Delta Air Lines
        US$168
        38% off
        US$273 US$168
      • YYC 07:45
        8h 2m
        1 stop
        MDW 16:47
        Calgary - Chicago | Tue, Oct 27 | Delta Air Lines
        US$172
        37% off
        US$273 US$172
      • YYC 07:45
        8h 2m
        1 stop
        MDW 16:47
        Calgary - Chicago | Fri, Oct 30 | Delta Air Lines
        US$172
        37% off
        US$273 US$172
      • YYC 07:45
        9h 5m
        1 stop
        MDW 16:50
        Calgary - Chicago | Wed, Nov 11 | Delta Air Lines
        US$173
        37% off
        US$273 US$173
      • YYC 00:20
        9h 17m
        1 stop
        MDW 10:37
        Calgary - Chicago | Sat, Oct 24 | Delta Air Lines
        US$186
        32% off
        US$273 US$186
      • YYC 08:45
        8h 5m
        1 stop
        MDW 16:50
        Calgary - Chicago | Wed, Dec 2 | Delta Air Lines
        US$188
        31% off
        US$273 US$188
      • YYC 01:25
        8h 59m
        1 stop
        MDW 10:24
        Calgary - Chicago | Thu, Nov 12 | Delta Air Lines
        US$191
        30% off
        US$273 US$191
      • YYC 13:00
        17h 25m
        1 stop
        CHI 14:00
        Calgary - Chicago | Tue, Oct 6 | Normal Airline
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Displayed flight fares from Calgary International Airport to Chicago Midway International Airport are based on average prices across airlines for the next 3 months according to the latest Trip.com data.

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

The cheapest airline flying from Calgary International Airport to Chicago Midway International Airport is Delta Air Lines (from US$158) among 5 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Delta Air Lines
From US$158
WestJet
From US$229
Flair Airlines
From US$243
Apg Airlines
From US$255
Air Canada
From US$264

Find more flights and airlines

What is the flight schedule from Calgary International 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 International Airport

    06:35

    YYC

    2h 41m

    Direct

    10:16

    MSP

    S M T W T F S
    Search

  2. DL4714

    Minneapolis-Saint Paul International Airport

    15:00

    MSP

    1h 50m

    Direct

    16:50

    MDW

    S M T W T F S

  3. DL7192

    Calgary International Airport

    07:00

    YYC

    4h 25m

    Direct

    13:25

    ATL

    S M T W T F S
    Search

  4. DL1728

    Hartsfield–Jackson Atlanta International Airport

    15:30

    ATL

    1h 55m

    Direct

    16:25

    MDW

    S M T W T F S

  5. DL6896

    Calgary International Airport

    00:20

    YYC

    4h 25m

    Direct

    06:45

    ATL

    S M T W T F S
    Search

  6. DL1063

    Hartsfield–Jackson Atlanta International Airport

    08:55

    ATL

    1h 54m

    Direct

    09:49

    MDW

    S M T W T F S

  7. DL6896

    Calgary International Airport

    00:20

    YYC

    4h 25m

    Direct

    06:45

    ATL

    S M T W T F S
    Search

  8. DL2417

    Hartsfield–Jackson Atlanta International Airport

    11:00

    ATL

    1h 56m

    Direct

    11:56

    MDW

    S M T W T - S

  9. WS1590

    Calgary International Airport

    07:00

    YYC

    4h 25m

    Direct

    13:25

    ATL

    S M T W T F S
    Search

  10. F92291

    Hartsfield–Jackson Atlanta International Airport

    22:50

    ATL

    1h 54m

    Direct

    23:44

    MDW

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

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

Flight distance 2,250.21km
Cheapest one-way ticket price US$153
Cheapest return ticket price US$246

FAQs for Calgary International 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 25km, by taxi about 40 minutes.
    • The distance from Chicago Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
  • The closest airport to Chicago Midway International Airport (MDW) is O'Hare International Airport. The distance is around 25km.
  • One-way flights from Calgary International Airport to Chicago Midway International Airport currently start from US$153, and round-trip fares start from US$246. The current lowest fare is a Delta Air Lines flight departing on Sat, Nov 21; 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 International Airport to Chicago Midway International Airport is US$385. Prices may vary depending on the departure date, airline, and availability.
  • Enter Calgary International 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.

Find Cheap Flights with Trip.com

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

Book with no extra fees

Prices displayed on this page are all-inclusive (including taxes, fuel surcharges, civil aviation development fund, etc.), with all fees confirmed before payment. Fees for luggage, meals, Wi-Fi, 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 have been updated within the last 24 hours—sometimes even in real time. The more popular the route, the more accurate the data.

Change & Cancellation Policy

Trip.com shows the cancellation and change policies for each flight ticket during the booking process, including any fees and applicable conditions. Please check the following scenarios:
Voluntary cancellation/change:
To request a change or cancellation, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and flight segment, and submit your request. Please note that additional charges may apply according to the airline's ticket policy.
Cancellation/change due to a flight schedule change:
If the flight schedule has changed 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 visit the customer support pages.