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Cheap flights from Calgary to Chicago from C$ 179

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Calgary to Chicago departing on 6/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:35 a.m. - 1:10 p.m.YYC-MDW
5h 35m1 stop
Delta Logo
1:50 p.m. - 8:57 p.m.MDW-YYC
8h 07m1 stop
C$ 311Delta
Find Deal
Tue, 2 Dec - Tue, 9 Dec
Multiple Airlines Logo
9:45 p.m. - 1:59 p.m.YYC-MDW
15h 14m2 stops
Multiple Airlines Logo
6:15 a.m. - 7:09 p.m.MDW-YYC
13h 54m1 stop
C$ 322Multiple Airlines
Find Deal
Fri, 5 Dec - Fri, 12 Dec
Delta Logo
12:30 a.m. - 11:52 a.m.YYC-MDW
10h 22m1 stop
Delta Logo
9:29 a.m. - 8:57 p.m.MDW-YYC
12h 28m2 stops
C$ 387Delta
Find Deal
Thu, 13 Nov - Sat, 6 Dec
Delta Logo
12:30 a.m. - 11:52 a.m.YYC-MDW
10h 22m1 stop
Delta Logo
1:50 p.m. - 8:57 p.m.MDW-YYC
8h 07m1 stop
C$ 388Delta
Find Deal
Thu, 13 Nov - Sat, 6 Dec
Delta Logo
6:35 a.m. - 1:10 p.m.YYC-MDW
5h 35m1 stop
Delta Logo
9:34 a.m. - 8:56 p.m.MDW-YYC
12h 22m2 stops
C$ 399Delta
Find Deal
Tue, 16 Dec - Sun, 11 Jan
Delta Logo
12:30 a.m. - 9:54 a.m.YYC-MDW
8h 24m1 stop
Delta Logo
1:50 p.m. - 11:13 p.m.MDW-YYC
10h 23m2 stops
C$ 403Delta
Find Deal
Mon, 1 Dec - Tue, 9 Dec
Multiple Airlines Logo
6:30 p.m. - 6:18 p.m.YYC-MDW
22h 48m2 stops
Multiple Airlines Logo
9:59 a.m. - 12:05 a.m.MDW-YYC
15h 06m2 stops
C$ 679Multiple Airlines
Find Deal
Tue, 2 Dec - Tue, 9 Dec
WestJet Logo
12:30 a.m. - 9:52 a.m.YYC-MDW
8h 22m1 stop
WestJet Logo
9:41 a.m. - 9:02 p.m.MDW-YYC
12h 21m2 stops
C$ 836WestJet
Find Deal
Mon, 24 Nov - Fri, 28 Nov
WestJet Logo
7:00 a.m. - 6:18 p.m.YYC-MDW
10h 18m2 stops
WestJet Logo
10:49 a.m. - 9:02 p.m.MDW-YYC
11h 13m2 stops
C$ 839WestJet
Find Deal
Mon, 8 Dec - Thu, 11 Dec
WestJet Logo
7:00 a.m. - 6:18 p.m.YYC-MDW
10h 18m2 stops
WestJet Logo
10:49 a.m. - 11:32 p.m.MDW-YYC
13h 43m2 stops
C$ 842WestJet
Find Deal
Mon, 8 Dec - Thu, 11 Dec

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
2 Dec
YYC6:35 a.m.Calgary
5h 35m
1 stop
MDW1:10 p.m.Chicago Midway
9 Dec
MDW1:50 p.m.Chicago Midway
8h 07m
1 stop
YYC8:57 p.m.Calgary
C$ 311
Find similar
Delta
13 Nov
YYC12:30 a.m.Calgary
10h 22m
1 stop
MDW11:52 a.m.Chicago Midway
6 Dec
MDW9:29 a.m.Chicago Midway
12h 28m
2 stops
YYC8:57 p.m.Calgary
C$ 387
Find similar
Delta
13 Nov
YYC12:30 a.m.Calgary
10h 22m
1 stop
MDW11:52 a.m.Chicago Midway
6 Dec
MDW1:50 p.m.Chicago Midway
8h 07m
1 stop
YYC8:57 p.m.Calgary
C$ 388
Find similar

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
24 Nov
YYC12:30 a.m.Calgary
8h 22m
1 stop
MDW9:52 a.m.Chicago Midway
28 Nov
MDW9:41 a.m.Chicago Midway
12h 21m
2 stops
YYC9:02 p.m.Calgary
C$ 836
Find similar
WestJet
8 Dec
YYC7:00 a.m.Calgary
10h 18m
2 stops
MDW6:18 p.m.Chicago Midway
11 Dec
MDW10:49 a.m.Chicago Midway
11h 13m
2 stops
YYC9:02 p.m.Calgary
C$ 839
Find similar
WestJet
8 Dec
YYC7:00 a.m.Calgary
10h 18m
2 stops
MDW6:18 p.m.Chicago Midway
11 Dec
MDW10:49 a.m.Chicago Midway
13h 43m
2 stops
YYC11:32 p.m.Calgary
C$ 842
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Calgary to Chicago Midway Airport 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 3 November 2025.
Use the filters below to find and compare flights from Calgary to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 2/12

6:35 a.m.-1:10 p.m.

1 stop5h 35m

Chicago Midway

Tue 9/12

1:50 p.m.-8:57 p.m.

1 stop8h 07m

C$ 311

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 5/12

9:45 p.m.-1:59 p.m.

2 stops15h 14m

Chicago Midway

Fri 12/12

6:15 a.m.-7:09 p.m.

1 stop13h 54m

C$ 322

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 13/11

12:30 a.m.-11:52 a.m.

1 stop10h 22m

Chicago Midway

Sat 6/12

9:29 a.m.-8:57 p.m.

2 stops12h 28m

C$ 387

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 13/11

12:30 a.m.-11:52 a.m.

1 stop10h 22m

Chicago Midway

Sat 6/12

1:50 p.m.-8:57 p.m.

1 stop8h 07m

C$ 388

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 16/12

6:35 a.m.-1:10 p.m.

1 stop5h 35m

Chicago Midway

Sun 11/1

9:34 a.m.-8:56 p.m.

2 stops12h 22m

C$ 399

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 1/12

12:30 a.m.-9:54 a.m.

1 stop8h 24m

Chicago Midway

Tue 9/12

1:50 p.m.-11:13 p.m.

2 stops10h 23m

C$ 403

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 2/12

6:30 p.m.-6:18 p.m.

2 stops22h 48m

Chicago Midway

Tue 9/12

9:59 a.m.-12:05 a.m.

2 stops15h 06m

C$ 679

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 24/11

12:30 a.m.-9:52 a.m.

1 stop8h 22m

Chicago Midway

Fri 28/11

9:41 a.m.-9:02 p.m.

2 stops12h 21m

C$ 836

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 8/12

7:00 a.m.-6:18 p.m.

2 stops10h 18m

Chicago Midway

Thu 11/12

10:49 a.m.-9:02 p.m.

2 stops11h 13m

C$ 839

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 8/12

7:00 a.m.-6:18 p.m.

2 stops10h 18m

Chicago Midway

Thu 11/12

10:49 a.m.-11:32 p.m.

2 stops13h 43m

C$ 842

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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

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

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

You could potentially save up to 21% on your flight if you consider stops on a Calgary to Chicago Midway Airport flight.

When to book flights from Calgary to Chicago Midway Airport

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

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

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

Direct flights

None
There are no direct flights from Calgary to Chicago Midway Airport. There are no popular flight routes from Calgary to Chicago Midway Airport.
Search flight deals

  • How far is Calgary to Chicago Midway by plane?

    The straight-line distance from Calgary to Chicago Midway is 2247.1 km. In terms of flight time, this usually takes a little over 5h 32m.

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

    Prices for flights from Calgary Airport to Chicago Midway Airport are refreshed on a daily basis.

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

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

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Munster
Hammond
Merrillville

Why use momondo?

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

It is quick and easy to find Calgary to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Yes. momondo enables you to select and highlight flights to Chicago from Calgary with this policy.

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

momondo provides multiple filters to help you find the best flight to Chicago from Calgary. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Price alerts on flights to Chicago from Calgary are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago Midway Airport 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.
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