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Cheap flights from Calgary to Chicago from C$ 192

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 31/1. 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. - 1:09 p.m.YYC-MDW
5h 39m1 stop
Delta Logo
1:49 p.m. - 8:54 p.m.MDW-YYC
8h 05m1 stop
C$ 312Delta
Find Deal
Wed, 14 Jan - Sun, 18 Jan
Multiple Airlines Logo
12:30 a.m. - 12:05 p.m.YYC-MDW
10h 35m1 stop
Multiple Airlines Logo
5:01 p.m. - 7:09 p.m.MDW-YYC
27h 08m1 stop
C$ 336Multiple Airlines
Find Deal
Tue, 20 Jan - Sun, 25 Jan
Delta Logo
6:35 a.m. - 6:06 p.m.YYC-MDW
10h 31m2 stops
Delta Logo
1:50 p.m. - 8:57 p.m.MDW-YYC
8h 07m1 stop
C$ 343Delta
Find Deal
Sat, 6 Dec - Tue, 16 Dec
Multiple Airlines Logo
9:45 p.m. - 11:45 a.m.YYC-MDW
13h 00m2 stops
Multiple Airlines Logo
5:01 p.m. - 7:09 p.m.MDW-YYC
27h 08m1 stop
C$ 347Multiple Airlines
Find Deal
Wed, 21 Jan - Sun, 25 Jan
Multiple Airlines Logo
12:30 a.m. - 10:31 a.m.YYC-MDW
9h 01m1 stop
Multiple Airlines Logo
8:19 p.m. - 12:20 p.m.MDW-YYC
17h 01m1 stop
C$ 350Multiple Airlines
Find Deal
Tue, 13 Jan - Sun, 18 Jan
Multiple Airlines Logo
12:30 a.m. - 12:05 p.m.YYC-MDW
10h 35m1 stop
Multiple Airlines Logo
6:20 a.m. - 5:30 p.m.MDW-YYC
12h 10m2 stops
C$ 358Multiple Airlines
Find Deal
Tue, 20 Jan - Sun, 25 Jan
Multiple Airlines Logo
7:30 a.m. - 11:47 p.m.YYC-MDW
15h 17m1 stop
Multiple Airlines Logo
4:19 p.m. - 9:51 p.m.MDW-YYC
30h 32m1 stop
C$ 364Multiple Airlines
Find Deal
Fri, 16 Jan - Mon, 19 Jan
Delta Logo
6:30 a.m. - 5:34 p.m.YYC-MDW
10h 04m2 stops
Delta Logo
9:32 a.m. - 8:54 p.m.MDW-YYC
12h 22m2 stops
C$ 365Delta
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Wed, 14 Jan - Sun, 18 Jan
Multiple Airlines Logo
7:30 a.m. - 10:19 p.m.YYC-MDW
13h 49m2 stops
Multiple Airlines Logo
4:19 p.m. - 9:51 p.m.MDW-YYC
30h 32m1 stop
C$ 384Multiple Airlines
Find Deal
Fri, 16 Jan - Mon, 19 Jan
Multiple Airlines Logo
12:30 a.m. - 10:19 p.m.YYC-MDW
20h 49m1 stop
Multiple Airlines Logo
12:57 p.m. - 10:52 p.m.MDW-YYC
10h 55m1 stop
C$ 389Multiple Airlines
Find Deal
Thu, 15 Jan - Mon, 19 Jan

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
14 Jan
YYC7:40 a.m.Calgary
9h 52m
2 stops
MDW6:32 p.m.Chicago Midway
18 Jan
MDW1:49 p.m.Chicago Midway
8h 05m
1 stop
YYC8:54 p.m.Calgary
C$ 312
Find similar
Delta
6 Dec
YYC6:35 a.m.Calgary
10h 31m
2 stops
MDW6:06 p.m.Chicago Midway
16 Dec
MDW1:50 p.m.Chicago Midway
8h 07m
1 stop
YYC8:57 p.m.Calgary
C$ 343
Find similar
Delta
14 Jan
YYC6:30 a.m.Calgary
10h 04m
2 stops
MDW5:34 p.m.Chicago Midway
18 Jan
MDW9:32 a.m.Chicago Midway
12h 22m
2 stops
YYC8:54 p.m.Calgary
C$ 365
Find similar

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
16 Jan
YYC9:00 a.m.Calgary
25h 05m
2 stops
MDW11:05 a.m.Chicago Midway
19 Jan
MDW10:46 a.m.Chicago Midway
30h 14m
2 stops
YYC4:00 p.m.Calgary
C$ 664
Find similar
WestJet
21 Jan
YYC5:15 p.m.Calgary
18h 54m
2 stops
MDW1:09 p.m.Chicago Midway
25 Jan
MDW7:16 p.m.Chicago Midway
30h 28m
3 stops
YYC12:44 a.m.Calgary
C$ 707
Find similar
WestJet
16 Jan
YYC6:30 p.m.Calgary
15h 35m
2 stops
MDW11:05 a.m.Chicago Midway
19 Jan
MDW1:49 p.m.Chicago Midway
25h 11m
3 stops
YYC2:00 p.m.Calgary
C$ 752
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 25 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

Wed 14/1

6:30 a.m.-1:09 p.m.

1 stop5h 39m

Chicago Midway

Sun 18/1

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

1 stop8h 05m

C$ 312

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 20/1

12:30 a.m.-12:05 p.m.

1 stop10h 35m

Chicago Midway

Sun 25/1

5:01 p.m.-7:09 p.m.

1 stop27h 08m

C$ 336

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 6/12

6:35 a.m.-6:06 p.m.

2 stops10h 31m

Chicago Midway

Tue 16/12

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

1 stop8h 07m

C$ 343

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 21/1

9:45 p.m.-11:45 a.m.

2 stops13h 00m

Chicago Midway

Sun 25/1

5:01 p.m.-7:09 p.m.

1 stop27h 08m

C$ 347

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 13/1

12:30 a.m.-10:31 a.m.

1 stop9h 01m

Chicago Midway

Sun 18/1

8:19 p.m.-12:20 p.m.

1 stop17h 01m

C$ 350

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 20/1

12:30 a.m.-12:05 p.m.

1 stop10h 35m

Chicago Midway

Sun 25/1

6:20 a.m.-5:30 p.m.

2 stops12h 10m

C$ 358

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 16/1

7:30 a.m.-11:47 p.m.

1 stop15h 17m

Chicago Midway

Mon 19/1

4:19 p.m.-9:51 p.m.

1 stop30h 32m

C$ 364

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 14/1

6:30 a.m.-5:34 p.m.

2 stops10h 04m

Chicago Midway

Sun 18/1

9:32 a.m.-8:54 p.m.

2 stops12h 22m

C$ 365

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 16/1

7:30 a.m.-10:19 p.m.

2 stops13h 49m

Chicago Midway

Mon 19/1

4:19 p.m.-9:51 p.m.

1 stop30h 32m

C$ 384

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 15/1

12:30 a.m.-10:19 p.m.

1 stop20h 49m

Chicago Midway

Mon 19/1

12:57 p.m.-10:52 p.m.

1 stop10h 55m

C$ 389

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

Fastest flight time

5h 38m

Direct flights

None
The fastest flight from Calgary to Chicago Midway Airport takes 5h 38m
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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