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Cheap flights from Calgary to Chicago from C$ 186

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 12/10. 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

Delta Logo
6:45 a.m. - 1:08 p.m.YYC-MDW
5h 23m1 stop
Delta Logo
9:20 a.m. - 1:54 p.m.MDW-YYC
5h 34m1 stop
C$ 309Delta
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Sun, 26 Oct - Sat, 1 Nov
Multiple Airlines Logo
8:15 p.m. - 11:38 a.m.YYC-MDW
14h 23m2 stops
Multiple Airlines Logo
6:30 a.m. - 5:06 p.m.MDW-YYC
11h 36m1 stop
C$ 332Multiple Airlines
Find Deal
Mon, 10 Nov - Thu, 13 Nov
Multiple Airlines Logo
12:20 p.m. - 12:37 p.m.YYC-MDW
23h 17m1 stop
Multiple Airlines Logo
6:30 a.m. - 5:06 p.m.MDW-YYC
11h 36m1 stop
C$ 333Multiple Airlines
Find Deal
Thu, 30 Oct - Thu, 6 Nov
Delta Logo
6:45 a.m. - 5:43 p.m.YYC-MDW
9h 58m1 stop
Delta Logo
3:00 p.m. - 8:47 p.m.MDW-YYC
6h 47m1 stop
C$ 336Delta
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Sat, 11 Oct - Sat, 18 Oct
Delta Logo
6:40 a.m. - 5:35 p.m.YYC-MDW
9h 55m1 stop
Delta Logo
1:43 p.m. - 8:42 p.m.MDW-YYC
7h 59m1 stop
C$ 352Delta
Find Deal
Fri, 26 Sep - Mon, 29 Sep
Multiple Airlines Logo
12:30 a.m. - 11:38 a.m.YYC-MDW
10h 08m1 stop
Multiple Airlines Logo
6:15 a.m. - 7:09 p.m.MDW-YYC
13h 54m1 stop
C$ 354Multiple Airlines
Find Deal
Mon, 10 Nov - Fri, 14 Nov
Multiple Airlines Logo
12:30 a.m. - 11:38 a.m.YYC-MDW
10h 08m1 stop
Multiple Airlines Logo
6:15 a.m. - 5:30 p.m.MDW-YYC
12h 15m2 stops
C$ 355Multiple Airlines
Find Deal
Mon, 10 Nov - Fri, 14 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$ 779WestJet
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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
10:47 a.m. - 9:02 p.m.MDW-YYC
11h 15m2 stops
C$ 781WestJet
Find Deal
Mon, 10 Nov - Thu, 13 Nov
WestJet Logo
7:00 a.m. - 10:14 p.m.YYC-MDW
14h 14m2 stops
WestJet Logo
10:35 a.m. - 10:22 p.m.MDW-YYC
12h 47m2 stops
C$ 785WestJet
Find Deal
Sat, 11 Oct - Sat, 18 Oct

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
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$ 779
Find similar
WestJet
10 Nov
YYC7:00 a.m.Calgary
10h 18m
2 stops
MDW6:18 p.m.Chicago Midway
13 Nov
MDW10:47 a.m.Chicago Midway
11h 15m
2 stops
YYC9:02 p.m.Calgary
C$ 781
Find similar
WestJet
11 Oct
YYC7:00 a.m.Calgary
14h 14m
2 stops
MDW10:14 p.m.Chicago Midway
18 Oct
MDW10:35 a.m.Chicago Midway
12h 47m
2 stops
YYC10:22 p.m.Calgary
C$ 785
Find similar

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
26 Oct
YYC6:45 a.m.Calgary
5h 23m
1 stop
MDW1:08 p.m.Chicago Midway
1 Nov
MDW9:20 a.m.Chicago Midway
5h 34m
1 stop
YYC1:54 p.m.Calgary
C$ 309
Find similar
Delta
11 Oct
YYC6:45 a.m.Calgary
9h 58m
1 stop
MDW5:43 p.m.Chicago Midway
18 Oct
MDW3:00 p.m.Chicago Midway
6h 47m
1 stop
YYC8:47 p.m.Calgary
C$ 336
Find similar
Delta
26 Sep
YYC6:40 a.m.Calgary
9h 55m
1 stop
MDW5:35 p.m.Chicago Midway
29 Sep
MDW1:43 p.m.Chicago Midway
7h 59m
1 stop
YYC8:42 p.m.Calgary
C$ 352
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 16 September 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

Sun 26/10

6:45 a.m.-1:08 p.m.

1 stop5h 23m

Chicago Midway

Sat 1/11

9:20 a.m.-1:54 p.m.

1 stop5h 34m

C$ 309

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 10/11

8:15 p.m.-11:38 a.m.

2 stops14h 23m

Chicago Midway

Thu 13/11

6:30 a.m.-5:06 p.m.

1 stop11h 36m

C$ 332

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 30/10

12:20 p.m.-12:37 p.m.

1 stop23h 17m

Chicago Midway

Thu 6/11

6:30 a.m.-5:06 p.m.

1 stop11h 36m

C$ 333

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 11/10

6:45 a.m.-5:43 p.m.

1 stop9h 58m

Chicago Midway

Sat 18/10

3:00 p.m.-8:47 p.m.

1 stop6h 47m

C$ 336

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 26/9

6:40 a.m.-5:35 p.m.

1 stop9h 55m

Chicago Midway

Mon 29/9

1:43 p.m.-8:42 p.m.

1 stop7h 59m

C$ 352

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 10/11

12:30 a.m.-11:38 a.m.

1 stop10h 08m

Chicago Midway

Fri 14/11

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

1 stop13h 54m

C$ 354

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 10/11

12:30 a.m.-11:38 a.m.

1 stop10h 08m

Chicago Midway

Fri 14/11

6:15 a.m.-5:30 p.m.

2 stops12h 15m

C$ 355

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$ 779

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 10/11

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

2 stops10h 18m

Chicago Midway

Thu 13/11

10:47 a.m.-9:02 p.m.

2 stops11h 15m

C$ 781

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 11/10

7:00 a.m.-10:14 p.m.

2 stops14h 14m

Chicago Midway

Sat 18/10

10:35 a.m.-10:22 p.m.

2 stops12h 47m

C$ 785

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

What is the cheapest airline that flies from Calgary to Chicago Midway?

Delta, Porter Airlines, and WestJet are the most popular carriers operating from Calgary to Chicago Midway

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 23m.

  • 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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