Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Chicago Midway Airport to Calgary from C$ 152

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Calgary departing on 6/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago Midway Airport to Calgary

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
1:49 p.m. - 8:54 p.m.
MDW
-
YYC
8h 05m
1 stop
Delta Logo
6:30 a.m. - 1:25 p.m.
YYC
-
MDW
5h 55m
1 stop
C$ 382Delta
Tue, 3 Mar - Tue, 10 Mar
Delta Logo
9:34 a.m. - 8:54 p.m.
MDW
-
YYC
12h 20m
2 stops
Delta Logo
6:30 a.m. - 1:25 p.m.
YYC
-
MDW
5h 55m
1 stop
C$ 394Delta
Tue, 3 Mar - Tue, 10 Mar
Delta Logo
9:34 a.m. - 8:54 p.m.
MDW
-
YYC
12h 20m
2 stops
Delta Logo
6:30 a.m. - 1:25 p.m.
YYC
-
MDW
5h 55m
1 stop
C$ 395Delta
Tue, 3 Mar - Tue, 10 Mar
Delta Logo
9:27 a.m. - 8:40 p.m.
MDW
-
YYC
12h 13m
2 stops
Delta Logo
6:45 a.m. - 5:56 p.m.
YYC
-
MDW
10h 11m
1 stop
C$ 408Delta
Sat, 2 May - Sat, 9 May
Delta Logo
1:49 p.m. - 8:54 p.m.
MDW
-
YYC
8h 05m
1 stop
Delta Logo
6:30 a.m. - 1:05 p.m.
YYC
-
MDW
5h 35m
1 stop
C$ 412Delta
Mon, 2 Mar - Thu, 5 Mar
Multiple Airlines Logo
6:00 a.m. - 5:10 p.m.
MDW
-
YYC
12h 10m
1 stop
Multiple Airlines Logo
8:00 p.m. - 7:31 p.m.
YYC
-
MDW
22h 31m
2 stops
C$ 424Multiple Airlines
Wed, 29 Apr - Mon, 4 May
Delta Logo
1:49 p.m. - 8:54 p.m.
MDW
-
YYC
8h 05m
1 stop
Delta Logo
6:30 a.m. - 1:05 p.m.
YYC
-
MDW
5h 35m
1 stop
C$ 426Delta
Mon, 2 Mar - Fri, 6 Mar
Multiple Airlines Logo
6:00 a.m. - 5:10 p.m.
MDW
-
YYC
12h 10m
1 stop
Multiple Airlines Logo
7:00 a.m. - 7:31 p.m.
YYC
-
MDW
11h 31m
1 stop
C$ 430Multiple Airlines
Wed, 6 May - Wed, 13 May
Delta Logo
9:27 a.m. - 8:40 p.m.
MDW
-
YYC
12h 13m
2 stops
Delta Logo
6:45 a.m. - 9:09 p.m.
YYC
-
MDW
13h 24m
2 stops
C$ 436Delta
Sat, 2 May - Sat, 9 May
Multiple Airlines Logo
6:00 a.m. - 5:10 p.m.
MDW
-
YYC
12h 10m
1 stop
Multiple Airlines Logo
12:50 a.m. - 4:50 p.m.
YYC
-
MDW
15h 00m
1 stop
C$ 445Multiple Airlines
Thu, 30 Apr - Sat, 2 May

Delta flights from Chicago Midway Airport to Calgary

Our best Delta deals on Chicago Midway Airport to Calgary flight tickets
Delta
3 Mar
MDW1:49 p.m.Chicago Midway
8h 05m
1 stop
YYC8:54 p.m.Calgary
10 Mar
YYC6:30 a.m.Calgary
5h 55m
1 stop
MDW1:25 p.m.Chicago Midway
C$ 382
Delta
3 Mar
MDW9:34 a.m.Chicago Midway
12h 20m
2 stops
YYC8:54 p.m.Calgary
10 Mar
YYC6:30 a.m.Calgary
5h 55m
1 stop
MDW1:25 p.m.Chicago Midway
C$ 394
Delta
3 Mar
MDW9:34 a.m.Chicago Midway
12h 20m
2 stops
YYC8:54 p.m.Calgary
10 Mar
YYC6:30 a.m.Calgary
5h 55m
1 stop
MDW1:25 p.m.Chicago Midway
C$ 395

WestJet flights from Chicago Midway Airport to Calgary

Our best WestJet deals on Chicago Midway Airport to Calgary flight tickets
WestJet
20 Feb
MDW9:34 a.m.Chicago Midway
16h 09m
2 stops
YYC12:43 a.m.Calgary
23 Feb
YYC5:15 p.m.Calgary
18h 31m
2 stops
MDW12:46 p.m.Chicago Midway
C$ 1,060
WestJet
13 Feb
MDW9:50 a.m.Chicago Midway
22h 58m
2 stops
YYC7:48 a.m.Calgary
16 Feb
YYC6:30 a.m.Calgary
26h 24m
2 stops
MDW9:54 a.m.Chicago Midway
C$ 1,237
WestJet
12 Feb
MDW9:50 a.m.Chicago Midway
10h 22m
2 stops
YYC7:12 p.m.Calgary
16 Feb
YYC7:00 a.m.Calgary
10h 40m
2 stops
MDW6:40 p.m.Chicago Midway
C$ 1,270

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Calgary that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 6 February 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Calgary that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 3/3

1:49 p.m.-8:54 p.m.

1 stop8h 05m

Calgary

Tue 10/3

6:30 a.m.-1:25 p.m.

1 stop5h 55m

C$ 382

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 3/3

9:34 a.m.-8:54 p.m.

2 stops12h 20m

Calgary

Tue 10/3

6:30 a.m.-1:25 p.m.

1 stop5h 55m

C$ 394

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 3/3

9:34 a.m.-8:54 p.m.

2 stops12h 20m

Calgary

Tue 10/3

6:30 a.m.-1:25 p.m.

1 stop5h 55m

C$ 395

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 2/5

9:27 a.m.-8:40 p.m.

2 stops12h 13m

Calgary

Sat 9/5

6:45 a.m.-5:56 p.m.

1 stop10h 11m

C$ 408

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Mon 2/3

1:49 p.m.-8:54 p.m.

1 stop8h 05m

Calgary

Thu 5/3

6:30 a.m.-1:05 p.m.

1 stop5h 35m

C$ 412

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 29/4

6:00 a.m.-5:10 p.m.

1 stop12h 10m

Calgary

Mon 4/5

8:00 p.m.-7:31 p.m.

2 stops22h 31m

C$ 424

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Mon 2/3

1:49 p.m.-8:54 p.m.

1 stop8h 05m

Calgary

Fri 6/3

6:30 a.m.-1:05 p.m.

1 stop5h 35m

C$ 426

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 6/5

6:00 a.m.-5:10 p.m.

1 stop12h 10m

Calgary

Wed 13/5

7:00 a.m.-7:31 p.m.

1 stop11h 31m

C$ 430

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 2/5

9:27 a.m.-8:40 p.m.

2 stops12h 13m

Calgary

Sat 9/5

6:45 a.m.-9:09 p.m.

2 stops13h 24m

C$ 436

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 30/4

6:00 a.m.-5:10 p.m.

1 stop12h 10m

Calgary

Sat 2/5

12:50 a.m.-4:50 p.m.

1 stop15h 00m

C$ 445

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Calgary from

How to get the cheapest flight ticket from Chicago Midway Airport to Calgary

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Calgary?

The cheapest day to depart on your flight to Calgary is on a Wednesday when prices can be found for as low as C$ 226. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 388.

What is the cheapest time of day to depart on your flight to Calgary?

Our data shows that the cheapest Chicago Midway Airport to Calgary flights are usually those with departure times in the evening. Our users have found flights to Calgary in the evening for as low as C$ 215. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are C$ 350 on average. Flights to Calgary from Chicago Midway Airport in the morning are generally more expensive because this time of day is more convenient for travellers’ schedules.

Can stopping save me money on Chicago Midway Airport to Calgary flights?

You could potentially save up to 62% on your flight if you consider stops on a Chicago Midway Airport to Calgary flight.

When to book flights from Chicago Midway Airport to Calgary

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Calgary according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Calgary (MDW to YYC) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Calgary

Fastest flight time

6h 25m

Direct flights

None
The fastest flight from Chicago Midway Airport to Calgary takes 6h 25m
There are no direct flights from Chicago Midway Airport to Calgary. There are no popular flight routes from Chicago Midway Airport to Calgary.
Search flight deals

  • How far is Chicago Midway to Calgary by plane?

    Chicago Midway and Calgary are 2247.1 km apart from one another. Flights usually cover this in 6h 25m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago Midway Airport to Calgary Airport?

    Prices for flights from Chicago Midway Airport to Calgary Airport were last updated today.

  • How old do you have to be to fly from Chicago Midway Airport to Calgary Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Calgary Airport.

  • What documentation or ID do you need to fly to Calgary Airport?

    The travel and health documents you'll need for your trip to Calgary Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Calgary Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Travelling to a place near Calgary?

Book flights to Calgary if you plan to visit one of these locations
Banff
Canmore
Lake Louise
Radium Hot Springs
Kananaskis
Drumheller
Airdrie

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Calgary?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Calgary from Chicago.

Can I find flights from Chicago to Calgary with flexible booking policies on momondo?

Flights from Chicago to Calgary with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Calgary?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Calgary.

I’m not ready to book a flight from Chicago to Calgary right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Calgary, momondo offers a useful price alert feature which will track prices for flights to Calgary from Chicago and alert you when they change.

An easier way to manage your Calgary trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sun 8/3
Sun 15/3
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Canada