Trip.com
>
Cheap Flights
>
United States
>
Illinois
>
Chicago
>
Calgary to Chicago flight
>
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 €138 and round-trip from €266. Based on Trip.com's latest 7-day flight data.

    • YYC 07:45
      8h 2m
      1 stop
      MDW 16:47
      Calgary - Chicago | Mon, Nov 2 | Delta Air Lines
      ORD 14:03
      10h 7m
      1 stop
      YYC 23:10
      Chicago - Calgary | Wed, Nov 4 | Delta Air Lines
      €266 €409
      35% off
      35% off
      €409 €266
    • YYC 00:20
      10h 34m
      1 stop
      MDW 11:54
      Calgary - Chicago | Wed, Oct 28 | Delta Air Lines
      ORD 15:40
      9h 7m
      1 stop
      YYC 23:47
      Chicago - Calgary | Fri, Oct 30 | Air Canada
      €266 €409
      35% off
      35% off
      €409 €266
    • 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 | Tue, Nov 3 | Delta Air Lines
      €300 €409
      27% off
      27% off
      €409 €300
    • YYC 08:45
      8h 5m
      1 stop
      MDW 16:50
      Calgary - Chicago | Fri, Dec 18 | Delta Air Lines
      ORD 14:04
      10h 17m
      1 stop
      YYC 00:21
      Chicago - Calgary | Tue, Dec 22 | Delta Air Lines
      €300
      27% off
      €409 €300
    • YYC 08:45
      8h 5m
      1 stop
      MDW 16:50
      Calgary - Chicago | Wed, Dec 16 | Delta Air Lines
      ORD 14:04
      10h 17m
      1 stop
      YYC 00:21
      Chicago - Calgary | Mon, Dec 21 | Delta Air Lines
      €300
      27% off
      €409 €300
    • YYC 07:45
      8h 2m
      1 stop
      MDW 16:47
      Calgary - Chicago | Fri, Nov 6 | Delta Air Lines
      ORD 06:20
      7h 15m
      1 stop
      YYC 13:35
      Chicago - Calgary | Fri, Nov 13 | Delta Air Lines
      €300
      27% off
      €409 €300
    • YYC 08:45
      7h 54m
      1 stop
      MDW 16:39
      Calgary - Chicago | Wed, Nov 25 | Delta Air Lines
      ORD 14:03
      10h 14m
      1 stop
      YYC 00:17
      Chicago - Calgary | Mon, Nov 30 | Delta Air Lines
      €301
      26% off
      €409 €301
    • YYC 08:45
      8h 2m
      1 stop
      MDW 16:47
      Calgary - Chicago | Sat, Nov 7 | Delta Air Lines
      ORD 15:30
      6h 10m
      1 stop
      YYC 21:40
      Chicago - Calgary | Fri, Nov 13 | Delta Air Lines
      €302
      26% off
      €409 €302
    • YYC 08:45
      8h 5m
      1 stop
      MDW 16:50
      Calgary - Chicago | Sat, Dec 12 | Delta Air Lines
      ORD 14:04
      10h 17m
      1 stop
      YYC 00:21
      Chicago - Calgary | Wed, Dec 16 | Delta Air Lines
      €302
      26% off
      €409 €302
    • YYC 13:00
      17h 25m
      1 stop
      CHI 14:00
      Calgary - Chicago | Mon, Oct 26 | Normal Airline
      CHI 15:00
      6h
      Direct
      YYC 16:00
      Chicago - Calgary | Wed, Oct 28 | Normal Airline
      Find more flights
      Find more flights
    • Cheapest
      YYC 08:45
      8h 2m
      1 stop
      MDW 16:47
      Calgary - Chicago | Tue, Nov 3 | Delta Air Lines
      €138 €215
      36% off
      36% off
      €215 €138
    • YYC 07:35
      9h 4m
      1 stop
      MDW 16:39
      Calgary - Chicago | Sat, Dec 5 | Delta Air Lines
      €141 €215
      34% off
      34% off
      €215 €141
    • YYC 08:45
      7h 54m
      1 stop
      MDW 16:39
      Calgary - Chicago | Sun, Nov 22 | Delta Air Lines
      €143 €215
      33% off
      33% off
      €215 €143
    • YYC 08:45
      7h 54m
      1 stop
      MDW 16:39
      Calgary - Chicago | Sat, Nov 14 | Delta Air Lines
      €143
      33% off
      €215 €143
    • YYC 08:45
      8h 5m
      1 stop
      MDW 16:50
      Calgary - Chicago | Tue, Dec 8 | Delta Air Lines
      €150
      30% off
      €215 €150
    • YYC 08:45
      8h 5m
      1 stop
      MDW 16:50
      Calgary - Chicago | Sat, Dec 12 | Delta Air Lines
      €150
      30% off
      €215 €150
    • YYC 08:45
      8h 5m
      1 stop
      MDW 16:50
      Calgary - Chicago | Mon, Dec 14 | Delta Air Lines
      €150
      30% off
      €215 €150
    • YYC 07:45
      8h 2m
      1 stop
      MDW 16:47
      Calgary - Chicago | Fri, Oct 30 | Delta Air Lines
      €155
      28% off
      €215 €155
    • YYC 07:45
      9h 5m
      1 stop
      MDW 16:50
      Calgary - Chicago | Wed, Nov 11 | Delta Air Lines
      €155
      28% off
      €215 €155
    • YYC 13:00
      17h 25m
      1 stop
      CHI 14:00
      Calgary - Chicago | Mon, Oct 26 | Normal Airline
      Find more flights
      Find more flights
    • YYC 08:45
      7h 54m
      1 stop
      MDW 16:39
      Calgary - Chicago | Sun, Nov 22 | Delta Air Lines
      €143 €215
      33% off
      33% off
      €215 €143
    • YYC 08:45
      7h 54m
      1 stop
      MDW 16:39
      Calgary - Chicago | Sat, Nov 14 | Delta Air Lines
      €143 €215
      33% off
      33% off
      €215 €143
    • YYC 08:45
      7h 54m
      1 stop
      MDW 16:39
      Calgary - Chicago | Mon, Nov 23 | Delta Air Lines
      €157 €215
      27% off
      27% off
      €215 €157
    • YYC 08:45
      8h 2m
      1 stop
      MDW 16:47
      Calgary - Chicago | Tue, Nov 3 | Delta Air Lines
      €138
      36% off
      €215 €138
    • YYC 07:45
      8h 2m
      1 stop
      MDW 16:47
      Calgary - Chicago | Fri, Oct 30 | Delta Air Lines
      €155
      28% off
      €215 €155
    • YYC 08:45
      8h 5m
      1 stop
      MDW 16:50
      Calgary - Chicago | Tue, Dec 8 | Delta Air Lines
      €150
      30% off
      €215 €150
    • YYC 08:45
      8h 5m
      1 stop
      MDW 16:50
      Calgary - Chicago | Sat, Dec 12 | Delta Air Lines
      €150
      30% off
      €215 €150
    • YYC 08:45
      8h 5m
      1 stop
      MDW 16:50
      Calgary - Chicago | Mon, Dec 14 | Delta Air Lines
      €150
      30% off
      €215 €150
    • YYC 08:45
      8h 5m
      1 stop
      MDW 16:50
      Calgary - Chicago | Fri, Dec 4 | Delta Air Lines
      €157
      27% off
      €215 €157
    • YYC 13:00
      17h 25m
      1 stop
      CHI 14:00
      Calgary - Chicago | Mon, Oct 26 | Normal Airline
      Find more flights
      Find more flights

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 €137) among 3 carriers operating this route. Based on Trip.com's latest 7-day flight data.

Delta Air Lines
From €137
WestJet
From €221
Air Canada
From €535

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

    08:45

    YYC

    2h 53m

    Direct

    11:38

    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 S
    Search

  4. DL1063

    Hartsfield–Jackson Atlanta International Airport

    08:55

    ATL

    1h 57m

    Direct

    09:52

    MDW

    S M T W T F S

  5. DL6896

    Calgary International Airport

    00:20

    YYC

    4h 25m

    Direct

    06:45

    ATL

    - - - - T F S
    Search

  6. DL2417

    Hartsfield–Jackson Atlanta International Airport

    11:00

    ATL

    1h 56m

    Direct

    11:56

    MDW

    S M T W T - S

  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
Find more flights and airlines

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 €138
Cheapest return ticket price €266

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 €138, and round-trip fares start from €266. 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 €427. 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 estimated lowest price 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 prices (incl. taxes, fuel surcharge, 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 were updated within the 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.