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Cheap flights from Calgary to Chicago from C$ 176

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 27/11. 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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Find the cheapest flights from Calgary to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:30 a.m. - 5:19 p.m.YYC-MDW
9h 49m1 stop
Delta Logo
11:48 a.m. - 9:06 p.m.MDW-YYC
10h 18m1 stop
C$ 311Delta
Find Deal
Wed, 24 Dec - Wed, 31 Dec
Delta Logo
6:30 a.m. - 5:19 p.m.YYC-MDW
9h 49m1 stop
Delta Logo
6:00 a.m. - 9:06 p.m.MDW-YYC
16h 06m2 stops
C$ 360Delta
Find Deal
Wed, 24 Dec - Tue, 30 Dec
Multiple Airlines Logo
7:30 a.m. - 10:12 p.m.YYC-MDW
13h 42m2 stops
Multiple Airlines Logo
6:00 a.m. - 7:09 p.m.MDW-YYC
14h 09m1 stop
C$ 375Multiple Airlines
Find Deal
Thu, 4 Dec - Sat, 6 Dec
Delta Logo
6:35 a.m. - 1:10 p.m.YYC-MDW
5h 35m1 stop
Delta Logo
9:59 a.m. - 7:15 p.m.MDW-YYC
10h 16m2 stops
C$ 399Delta
Find Deal
Wed, 10 Dec - Wed, 17 Dec
Delta Logo
12:30 a.m. - 12:34 p.m.YYC-MDW
11h 04m2 stops
Delta Logo
9:59 a.m. - 7:15 p.m.MDW-YYC
10h 16m2 stops
C$ 414Delta
Find Deal
Tue, 9 Dec - Wed, 17 Dec
Delta Logo
6:35 a.m. - 1:10 p.m.YYC-MDW
5h 35m1 stop
Delta Logo
10:49 a.m. - 7:09 p.m.MDW-YYC
9h 20m1 stop
C$ 460Delta
Find Deal
Wed, 10 Dec - Wed, 17 Dec
Multiple Airlines Logo
8:55 a.m. - 6:08 p.m.YYC-MDW
8h 13m1 stop
Multiple Airlines Logo
6:00 a.m. - 7:09 p.m.MDW-YYC
14h 09m1 stop
C$ 470Multiple Airlines
Find Deal
Thu, 4 Dec - Sat, 6 Dec
WestJet Logo
6:35 a.m. - 6:18 p.m.YYC-MDW
10h 43m1 stop
WestJet Logo
10:36 a.m. - 9:02 p.m.MDW-YYC
11h 26m2 stops
C$ 820WestJet
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Thu, 11 Dec - Mon, 15 Dec
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$ 821WestJet
Find Deal
Thu, 11 Dec - Mon, 15 Dec
Porter Airlines Logo
8:20 a.m. - 10:05 a.m.YYC-MDW
24h 45m2 stops
Porter Airlines Logo
4:15 p.m. - 9:35 p.m.MDW-YYC
30h 20m2 stops
C$ 869Porter Airlines
Find Deal
Thu, 4 Dec - Sun, 7 Dec

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
24 Dec
YYC6:30 a.m.Calgary
9h 49m
1 stop
MDW5:19 p.m.Chicago Midway
30 Dec
MDW11:48 a.m.Chicago Midway
10h 18m
1 stop
YYC9:06 p.m.Calgary
C$ 311
Find similar
Delta
24 Dec
YYC6:30 a.m.Calgary
9h 49m
1 stop
MDW5:19 p.m.Chicago Midway
30 Dec
MDW6:00 a.m.Chicago Midway
16h 06m
2 stops
YYC9:06 p.m.Calgary
C$ 360
Find similar
Delta
1 Nov
YYC6:45 a.m.Calgary
5h 23m
1 stop
MDW1:08 p.m.Chicago Midway
8 Nov
MDW10:35 a.m.Chicago Midway
13h 27m
2 stops
YYC11:02 p.m.Calgary
C$ 374
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
10h 43m
1 stop
MDW6:18 p.m.Chicago Midway
15 Dec
MDW10:36 a.m.Chicago Midway
11h 26m
2 stops
YYC9:02 p.m.Calgary
C$ 820
Find similar
WestJet
11 Dec
YYC7:00 a.m.Calgary
10h 18m
2 stops
MDW6:18 p.m.Chicago Midway
15 Dec
MDW10:49 a.m.Chicago Midway
11h 13m
2 stops
YYC9:02 p.m.Calgary
C$ 821
Find similar
WestJet
11 Dec
YYC7:00 a.m.Calgary
10h 18m
2 stops
MDW6:18 p.m.Chicago Midway
15 Dec
MDW10:49 a.m.Chicago Midway
11h 13m
2 stops
YYC9:02 p.m.Calgary
C$ 838
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 27 October 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

Wed 24/12

6:30 a.m.-5:19 p.m.

1 stop9h 49m

Chicago Midway

Wed 31/12

11:48 a.m.-9:06 p.m.

1 stop10h 18m

C$ 311

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 24/12

6:30 a.m.-5:19 p.m.

1 stop9h 49m

Chicago Midway

Tue 30/12

6:00 a.m.-9:06 p.m.

2 stops16h 06m

C$ 360

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 4/12

7:30 a.m.-10:12 p.m.

2 stops13h 42m

Chicago Midway

Sat 6/12

6:00 a.m.-7:09 p.m.

1 stop14h 09m

C$ 375

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 10/12

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

1 stop5h 35m

Chicago Midway

Wed 17/12

9:59 a.m.-7:15 p.m.

2 stops10h 16m

C$ 399

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 9/12

12:30 a.m.-12:34 p.m.

2 stops11h 04m

Chicago Midway

Wed 17/12

9:59 a.m.-7:15 p.m.

2 stops10h 16m

C$ 414

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 10/12

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

1 stop5h 35m

Chicago Midway

Wed 17/12

10:49 a.m.-7:09 p.m.

1 stop9h 20m

C$ 460

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 4/12

8:55 a.m.-6:08 p.m.

1 stop8h 13m

Chicago Midway

Sat 6/12

6:00 a.m.-7:09 p.m.

1 stop14h 09m

C$ 470

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 11/12

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

1 stop10h 43m

Chicago Midway

Mon 15/12

10:36 a.m.-9:02 p.m.

2 stops11h 26m

C$ 820

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 11/12

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

2 stops10h 18m

Chicago Midway

Mon 15/12

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

2 stops11h 13m

C$ 821

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 4/12

8:20 a.m.-10:05 a.m.

2 stops24h 45m

Chicago Midway

Sun 7/12

4:15 p.m.-9:35 p.m.

2 stops30h 20m

C$ 869

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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