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Cheap flights from Calgary to Chicago from C$ 184

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 8/12. 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.
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$ 338Multiple Airlines
Find Deal
Fri, 5 Dec - Fri, 12 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$ 340Multiple Airlines
Find Deal
Fri, 5 Dec - Fri, 12 Dec
Delta Logo
8:55 a.m. - 9:45 p.m.YYC-MDW
11h 50m1 stop
Delta Logo
1:05 p.m. - 8:00 p.m.MDW-YYC
7h 55m1 stop
C$ 421Delta
Find Deal
Sat, 18 Apr - Tue, 28 Apr
Multiple Airlines Logo
4:30 p.m. - 10:05 a.m.YYC-MDW
16h 35m1 stop
Multiple Airlines Logo
11:00 a.m. - 12:05 a.m.MDW-YYC
14h 05m1 stop
C$ 475Multiple Airlines
Find Deal
Thu, 9 Apr - Sun, 12 Apr
Delta Logo
8:55 a.m. - 9:45 p.m.YYC-MDW
11h 50m1 stop
Delta Logo
10:35 a.m. - 7:09 p.m.MDW-YYC
9h 34m1 stop
C$ 482Delta
Find Deal
Sat, 18 Apr - Sat, 25 Apr
Multiple Airlines Logo
12:15 a.m. - 3:20 p.m.YYC-MDW
14h 05m1 stop
Multiple Airlines Logo
11:00 a.m. - 12:05 a.m.MDW-YYC
14h 05m1 stop
C$ 506Multiple Airlines
Find Deal
Wed, 8 Apr - Sun, 12 Apr
Delta Logo
8:55 a.m. - 9:45 p.m.YYC-MDW
11h 50m1 stop
Delta Logo
10:35 a.m. - 8:00 p.m.MDW-YYC
10h 25m1 stop
C$ 528Delta
Find Deal
Mon, 20 Apr - Tue, 28 Apr
WestJet Logo
6:35 a.m. - 1:10 p.m.YYC-MDW
5h 35m1 stop
WestJet Logo
10:49 a.m. - 9:02 p.m.MDW-YYC
11h 13m2 stops
C$ 822WestJet
Find Deal
Thu, 11 Dec - Mon, 15 Dec
WestJet Logo
6:35 a.m. - 6:18 p.m.YYC-MDW
10h 43m1 stop
WestJet Logo
10:49 a.m. - 9:02 p.m.MDW-YYC
11h 13m2 stops
C$ 837WestJet
Find Deal
Thu, 11 Dec - Mon, 15 Dec
WestJet Logo
6:35 a.m. - 1:10 p.m.YYC-MDW
5h 35m1 stop
WestJet Logo
10:49 a.m. - 9:02 p.m.MDW-YYC
11h 13m2 stops
C$ 840WestJet
Find Deal
Thu, 11 Dec - Mon, 15 Dec

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
18 Apr
YYC8:55 a.m.Calgary
11h 50m
1 stop
MDW9:45 p.m.Chicago Midway
28 Apr
MDW1:05 p.m.Chicago Midway
7h 55m
1 stop
YYC8:00 p.m.Calgary
C$ 421
Find similar
Delta
18 Apr
YYC8:55 a.m.Calgary
11h 50m
1 stop
MDW9:45 p.m.Chicago Midway
25 Apr
MDW10:35 a.m.Chicago Midway
9h 34m
1 stop
YYC7:09 p.m.Calgary
C$ 482
Find similar
Delta
20 Apr
YYC8:55 a.m.Calgary
11h 50m
1 stop
MDW9:45 p.m.Chicago Midway
28 Apr
MDW10:35 a.m.Chicago Midway
10h 25m
1 stop
YYC8:00 p.m.Calgary
C$ 528
Find similar

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
11 Dec
YYC6:35 a.m.Calgary
5h 35m
1 stop
MDW1:10 p.m.Chicago Midway
15 Dec
MDW10:49 a.m.Chicago Midway
11h 13m
2 stops
YYC9:02 p.m.Calgary
C$ 822
Find similar
WestJet
11 Dec
YYC6:35 a.m.Calgary
10h 43m
1 stop
MDW6:18 p.m.Chicago Midway
15 Dec
MDW10:49 a.m.Chicago Midway
11h 13m
2 stops
YYC9:02 p.m.Calgary
C$ 837
Find similar
WestJet
11 Dec
YYC6:35 a.m.Calgary
5h 35m
1 stop
MDW1:10 p.m.Chicago Midway
15 Dec
MDW10:49 a.m.Chicago Midway
11h 13m
2 stops
YYC9:02 p.m.Calgary
C$ 840
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 10 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

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$ 338

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$ 340

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 18/4

8:55 a.m.-9:45 p.m.

1 stop11h 50m

Chicago Midway

Tue 28/4

1:05 p.m.-8:00 p.m.

1 stop7h 55m

C$ 421

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 9/4

4:30 p.m.-10:05 a.m.

1 stop16h 35m

Chicago Midway

Sun 12/4

11:00 a.m.-12:05 a.m.

1 stop14h 05m

C$ 475

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 18/4

8:55 a.m.-9:45 p.m.

1 stop11h 50m

Chicago Midway

Sat 25/4

10:35 a.m.-7:09 p.m.

1 stop9h 34m

C$ 482

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 8/4

12:15 a.m.-3:20 p.m.

1 stop14h 05m

Chicago Midway

Sun 12/4

11:00 a.m.-12:05 a.m.

1 stop14h 05m

C$ 506

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 20/4

8:55 a.m.-9:45 p.m.

1 stop11h 50m

Chicago Midway

Tue 28/4

10:35 a.m.-8:00 p.m.

1 stop10h 25m

C$ 528

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 11/12

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

1 stop5h 35m

Chicago Midway

Mon 15/12

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

2 stops11h 13m

C$ 822

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 11/12

6:35 a.m.-6:18 p.m.

1 stop10h 43m

Chicago Midway

Mon 15/12

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

2 stops11h 13m

C$ 837

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 11/12

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

1 stop5h 35m

Chicago Midway

Mon 15/12

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

2 stops11h 13m

C$ 840

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 35m.

  • 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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