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Cheap flights from Calgary to Chicago from C$ 170

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 12/12. 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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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$ 311Delta
Find Deal
Thu, 15 Jan - Tue, 20 Jan
Multiple Airlines Logo
7:30 a.m. - 11:44 p.m.YYC-MDW
15h 14m1 stop
Multiple Airlines Logo
9:13 a.m. - 7:09 p.m.MDW-YYC
10h 56m1 stop
C$ 328Multiple Airlines
Find Deal
Fri, 16 Jan - Sun, 18 Jan
Delta Logo
6:35 a.m. - 1:10 p.m.YYC-MDW
5h 35m1 stop
Delta Logo
11:48 a.m. - 11:15 p.m.MDW-YYC
12h 27m2 stops
C$ 338Delta
Find Deal
Wed, 17 Dec - Wed, 24 Dec
Multiple Airlines Logo
7:35 p.m. - 11:47 a.m.YYC-MDW
15h 12m1 stop
Multiple Airlines Logo
12:57 p.m. - 10:52 p.m.MDW-YYC
10h 55m1 stop
C$ 346Multiple Airlines
Find Deal
Thu, 15 Jan - Mon, 19 Jan
Multiple Airlines Logo
9:45 p.m. - 6:12 p.m.YYC-MDW
19h 27m2 stops
Multiple Airlines Logo
8:42 p.m. - 11:44 a.m.MDW-YYC
16h 02m1 stop
C$ 348Multiple Airlines
Find Deal
Sat, 13 Dec - Mon, 15 Dec
Delta Logo
6:35 a.m. - 6:00 p.m.YYC-MDW
10h 25m2 stops
Delta Logo
9:34 a.m. - 8:57 p.m.MDW-YYC
12h 23m2 stops
C$ 364Delta
Find Deal
Tue, 9 Dec - Tue, 16 Dec
Multiple Airlines Logo
8:55 a.m. - 11:25 p.m.YYC-MDW
13h 30m1 stop
Multiple Airlines Logo
12:50 p.m. - 12:05 a.m.MDW-YYC
12h 15m1 stop
C$ 366Multiple Airlines
Find Deal
Thu, 19 Feb - Sat, 21 Feb
Delta Logo
7:15 a.m. - 9:45 p.m.YYC-MDW
13h 30m2 stops
Delta Logo
10:35 a.m. - 11:06 p.m.MDW-YYC
13h 31m2 stops
C$ 384Delta
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Tue, 14 Apr - Thu, 16 Apr
Multiple Airlines Logo
8:55 a.m. - 10:13 p.m.YYC-MDW
12h 18m1 stop
Multiple Airlines Logo
9:13 a.m. - 7:09 p.m.MDW-YYC
10h 56m1 stop
C$ 387Multiple Airlines
Find Deal
Sat, 17 Jan - Sun, 18 Jan
Delta Logo
12:30 a.m. - 9:51 a.m.YYC-MDW
8h 21m1 stop
Delta Logo
9:20 a.m. - 11:06 p.m.MDW-YYC
14h 46m2 stops
C$ 394Delta
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Mon, 13 Apr - Thu, 16 Apr

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
17 Dec
YYC6:35 a.m.Calgary
5h 35m
1 stop
MDW1:10 p.m.Chicago Midway
24 Dec
MDW11:48 a.m.Chicago Midway
12h 27m
2 stops
YYC11:15 p.m.Calgary
C$ 338
Find similar
Delta
13 Apr
YYC12:30 a.m.Calgary
8h 21m
1 stop
MDW9:51 a.m.Chicago Midway
16 Apr
MDW9:20 a.m.Chicago Midway
14h 46m
2 stops
YYC11:06 p.m.Calgary
C$ 394
Find similar
Delta
14 Apr
YYC7:00 a.m.Calgary
10h 05m
2 stops
MDW6:05 p.m.Chicago Midway
16 Apr
MDW6:00 a.m.Chicago Midway
18h 06m
2 stops
YYC11:06 p.m.Calgary
C$ 395
Find similar

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
19 Feb
YYC6:30 p.m.Calgary
22h 15m
2 stops
MDW5:45 p.m.Chicago Midway
21 Feb
MDW9:50 a.m.Chicago Midway
24h 12m
2 stops
YYC9:02 a.m.Calgary
C$ 800
Find similar
WestJet
5 Mar
YYC6:30 a.m.Calgary
11h 07m
1 stop
MDW6:37 p.m.Chicago Midway
8 Mar
MDW10:35 a.m.Chicago Midway
11h 23m
2 stops
YYC8:58 p.m.Calgary
C$ 813
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 20 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

Thu 15/1

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

1 stop5h 39m

Chicago Midway

Tue 20/1

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

1 stop8h 05m

C$ 311

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 16/1

7:30 a.m.-11:44 p.m.

1 stop15h 14m

Chicago Midway

Sun 18/1

9:13 a.m.-7:09 p.m.

1 stop10h 56m

C$ 328

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 17/12

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

1 stop5h 35m

Chicago Midway

Wed 24/12

11:48 a.m.-11:15 p.m.

2 stops12h 27m

C$ 338

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 15/1

7:35 p.m.-11:47 a.m.

1 stop15h 12m

Chicago Midway

Mon 19/1

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

1 stop10h 55m

C$ 346

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 13/12

9:45 p.m.-6:12 p.m.

2 stops19h 27m

Chicago Midway

Mon 15/12

8:42 p.m.-11:44 a.m.

1 stop16h 02m

C$ 348

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 9/12

6:35 a.m.-6:00 p.m.

2 stops10h 25m

Chicago Midway

Tue 16/12

9:34 a.m.-8:57 p.m.

2 stops12h 23m

C$ 364

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 19/2

8:55 a.m.-11:25 p.m.

1 stop13h 30m

Chicago Midway

Sat 21/2

12:50 p.m.-12:05 a.m.

1 stop12h 15m

C$ 366

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 14/4

7:15 a.m.-9:45 p.m.

2 stops13h 30m

Chicago Midway

Thu 16/4

10:35 a.m.-11:06 p.m.

2 stops13h 31m

C$ 384

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 17/1

8:55 a.m.-10:13 p.m.

1 stop12h 18m

Chicago Midway

Sun 18/1

9:13 a.m.-7:09 p.m.

1 stop10h 56m

C$ 387

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 13/4

12:30 a.m.-9:51 a.m.

1 stop8h 21m

Chicago Midway

Thu 16/4

9:20 a.m.-11:06 p.m.

2 stops14h 46m

C$ 394

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.
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  • 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

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