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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$155 and round-trip from US$297. Based on Trip.com's latest 7-day flight data.

    • YYC 07:45
      8h 2m
      1 stop
      MDW 16:47
      Calgary - Chicago | Tue, Oct 27 | Delta Air Lines
      ORD 14:03
      10h 7m
      1 stop
      YYC 23:10
      Chicago - Calgary | Thu, Oct 29 | Delta Air Lines
      US$297 US$402
      26% off
      26% off
      US$402 US$297
    • YYC 08:45
      8h 5m
      1 stop
      MDW 16:50
      Calgary - Chicago | Tue, Dec 1 | Delta Air Lines
      ORD 14:04
      10h 17m
      1 stop
      YYC 00:21
      Chicago - Calgary | Thu, Dec 3 | Delta Air Lines
      US$342 US$402
      15% off
      15% off
      US$402 US$342
    • YYC 08:45
      7h 54m
      1 stop
      MDW 16:39
      Calgary - Chicago | Tue, Nov 24 | Delta Air Lines
      MDW 12:39
      9h 28m
      1 stop
      YYC 22:07
      Chicago - Calgary | Tue, Dec 1 | Delta Air Lines
      US$354 US$402
      12% off
      12% off
      US$402 US$354
    • YYC 08:45
      7h 54m
      1 stop
      MDW 16:39
      Calgary - Chicago | Sat, Nov 21 | Delta Air Lines
      MDW 12:30
      9h 28m
      1 stop
      YYC 21:58
      Chicago - Calgary | Sat, Nov 28 | Delta Air Lines
      US$354
      12% off
      US$402 US$354
    • YYC 08:45
      7h 54m
      1 stop
      MDW 16:39
      Calgary - Chicago | Thu, Nov 19 | Delta Air Lines
      ORD 14:03
      10h 14m
      1 stop
      YYC 00:17
      Chicago - Calgary | Sun, Nov 22 | Delta Air Lines
      US$354
      12% off
      US$402 US$354
    • YYC 08:45
      7h 54m
      1 stop
      MDW 16:39
      Calgary - Chicago | Thu, Nov 12 | Delta Air Lines
      ORD 14:03
      10h 14m
      1 stop
      YYC 00:17
      Chicago - Calgary | Tue, Nov 17 | Delta Air Lines
      US$354
      12% off
      US$402 US$354
    • YYC 08:45
      7h 54m
      1 stop
      MDW 16:39
      Calgary - Chicago | Wed, Nov 11 | Delta Air Lines
      ORD 14:03
      10h 14m
      1 stop
      YYC 00:17
      Chicago - Calgary | Tue, Nov 17 | Delta Air Lines
      US$354
      12% off
      US$402 US$354
    • YYC 08:45
      7h 54m
      1 stop
      MDW 16:39
      Calgary - Chicago | Tue, Nov 17 | Delta Air Lines
      ORD 14:03
      10h 14m
      1 stop
      YYC 00:17
      Chicago - Calgary | Sun, Nov 22 | Delta Air Lines
      US$354
      12% off
      US$402 US$354
    • YYC 08:45
      8h 5m
      1 stop
      MDW 16:50
      Calgary - Chicago | Thu, Dec 10 | Delta Air Lines
      ORD 14:04
      10h 17m
      1 stop
      YYC 00:21
      Chicago - Calgary | Tue, Dec 15 | Delta Air Lines
      US$354
      12% off
      US$402 US$354
    • YYC 13:00
      17h 25m
      1 stop
      CHI 14:00
      Calgary - Chicago | Tue, Oct 27 | Normal Airline
      CHI 15:00
      6h
      Direct
      YYC 16:00
      Chicago - Calgary | Thu, Oct 29 | Normal Airline
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    • Cheapest
      YYC 08:45
      8h 2m
      1 stop
      MDW 16:47
      Calgary - Chicago | Tue, Nov 3 | Delta Air Lines
      US$155 US$204
      24% off
      24% off
      US$204 US$155
    • YYC 07:35
      9h 4m
      1 stop
      MDW 16:39
      Calgary - Chicago | Sat, Dec 5 | Delta Air Lines
      US$158 US$204
      23% off
      23% off
      US$204 US$158
    • YYC 08:45
      7h 54m
      1 stop
      MDW 16:39
      Calgary - Chicago | Sun, Nov 22 | Delta Air Lines
      US$160 US$204
      22% off
      22% off
      US$204 US$160
    • YYC 08:45
      8h 5m
      1 stop
      MDW 16:50
      Calgary - Chicago | Tue, Dec 8 | Delta Air Lines
      US$168
      18% off
      US$204 US$168
    • YYC 08:45
      8h 5m
      1 stop
      MDW 16:50
      Calgary - Chicago | Sat, Dec 12 | Delta Air Lines
      US$168
      18% off
      US$204 US$168
    • YYC 08:45
      8h 5m
      1 stop
      MDW 16:50
      Calgary - Chicago | Mon, Dec 14 | Delta Air Lines
      US$168
      18% off
      US$204 US$168
    • YYC 07:45
      8h 2m
      1 stop
      MDW 16:47
      Calgary - Chicago | Fri, Oct 30 | Delta Air Lines
      US$173
      15% off
      US$204 US$173
    • YYC 07:45
      9h 5m
      1 stop
      MDW 16:50
      Calgary - Chicago | Wed, Nov 11 | Delta Air Lines
      US$174
      15% off
      US$204 US$174
    • YYC 08:45
      7h 54m
      1 stop
      MDW 16:39
      Calgary - Chicago | Mon, Nov 23 | Delta Air Lines
      US$175
      14% off
      US$204 US$175
    • YYC 13:00
      17h 25m
      1 stop
      CHI 14:00
      Calgary - Chicago | Tue, Oct 27 | Normal Airline
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    • YYC 08:45
      7h 54m
      1 stop
      MDW 16:39
      Calgary - Chicago | Sun, Nov 22 | Delta Air Lines
      US$160 US$204
      22% off
      22% off
      US$204 US$160
    • YYC 08:45
      7h 54m
      1 stop
      MDW 16:39
      Calgary - Chicago | Mon, Nov 23 | Delta Air Lines
      US$175 US$204
      14% off
      14% off
      US$204 US$175
    • YYC 08:45
      8h 2m
      1 stop
      MDW 16:47
      Calgary - Chicago | Tue, Nov 3 | Delta Air Lines
      US$155 US$204
      24% off
      24% off
      US$204 US$155
    • YYC 07:45
      8h 2m
      1 stop
      MDW 16:47
      Calgary - Chicago | Fri, Oct 30 | Delta Air Lines
      US$173
      15% off
      US$204 US$173
    • YYC 08:45
      8h 5m
      1 stop
      MDW 16:50
      Calgary - Chicago | Tue, Dec 8 | Delta Air Lines
      US$168
      18% off
      US$204 US$168
    • YYC 08:45
      8h 5m
      1 stop
      MDW 16:50
      Calgary - Chicago | Sat, Dec 12 | Delta Air Lines
      US$168
      18% off
      US$204 US$168
    • YYC 08:45
      8h 5m
      1 stop
      MDW 16:50
      Calgary - Chicago | Mon, Dec 14 | Delta Air Lines
      US$168
      18% off
      US$204 US$168
    • YYC 08:45
      8h 5m
      1 stop
      MDW 16:50
      Calgary - Chicago | Fri, Dec 4 | Delta Air Lines
      US$176
      14% off
      US$204 US$176
    • YYC 08:45
      8h 5m
      1 stop
      MDW 16:50
      Calgary - Chicago | Fri, Dec 11 | Delta Air Lines
      US$181
      11% off
      US$204 US$181
    • YYC 13:00
      17h 25m
      1 stop
      CHI 14:00
      Calgary - Chicago | Tue, Oct 27 | Normal Airline
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Displayed flight fares from Calgary to Chicago 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 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$155) among 2 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Delta Air Lines
From US$155
WestJet
From US$234

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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

    07:45

    YYC

    2h 44m

    Direct

    11:29

    MSP

    S M T W T F S
    Search

  2. DL4714

    Minneapolis-Saint Paul International Airport

    15:08

    MSP

    1h 39m

    Direct

    16:47

    MDW

    S M T W T F S

  3. DL6896

    Calgary International Airport

    00:20

    YYC

    4h 25m

    Direct

    06:45

    ATL

    - - - - T F -
    Search

  4. DL1063

    Hartsfield–Jackson Atlanta International Airport

    09:10

    ATL

    1h 53m

    Direct

    10:03

    MDW

    S M T W T F S

  5. DL6896

    Calgary International Airport

    00:20

    YYC

    4h 25m

    Direct

    06:45

    ATL

    - - - - T F -
    Search

  6. DL2417

    Hartsfield–Jackson Atlanta International Airport

    11:00

    ATL

    1h 56m

    Direct

    11:56

    MDW

    S M T W T - -

  7. WS1992

    Calgary International Airport

    00:25

    YYC

    4h 20m

    Direct

    06:45

    ATL

    S M T W T F S
    Search

  8. F92779

    Hartsfield–Jackson Atlanta International Airport

    16:44

    ATL

    2h 1m

    Direct

    17:45

    MDW

    - M T 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$155
Cheapest return ticket price US$297

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$155, and round-trip fares start from US$297. The current lowest fare is a Delta Air Lines flight departing on Tue, Nov 3; 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$478. 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.