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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 10/9. 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
6:40 a.m. - 1:03 p.m.YYC-MDW
5h 23m1 stop
Delta Logo
9:20 a.m. - 11:02 p.m.MDW-YYC
14h 42m2 stops
C$ 337Delta
Find Deal
Wed, 10 Sep - Sat, 13 Sep
Logo
10:00 a.m. - 11:17 p.m.YYC-MDW
12h 17m1 stop
Logo
6:20 a.m. - 8:00 p.m.MDW-YYC
14h 40m1 stop
C$ 468
Find Deal
Sat, 6 Sep - Mon, 8 Sep
Delta Logo
6:40 a.m. - 5:37 p.m.YYC-MDW
9h 57m1 stop
Delta Logo
1:43 p.m. - 8:43 p.m.MDW-YYC
8h 00m1 stop
C$ 481Delta
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Wed, 3 Sep - Tue, 9 Sep
Logo
12:30 a.m. - 4:00 p.m.YYC-MDW
14h 30m1 stop
Logo
6:20 a.m. - 8:00 p.m.MDW-YYC
14h 40m1 stop
C$ 515
Find Deal
Thu, 18 Sep - Sun, 21 Sep
Logo
12:30 a.m. - 3:58 p.m.YYC-MDW
14h 28m1 stop
Logo
6:20 a.m. - 8:00 p.m.MDW-YYC
14h 40m1 stop
C$ 516
Find Deal
Tue, 9 Sep - Mon, 15 Sep
Logo
7:35 p.m. - 9:23 a.m.YYC-MDW
12h 48m2 stops
Logo
6:20 a.m. - 8:00 p.m.MDW-YYC
14h 40m1 stop
C$ 527
Find Deal
Sat, 6 Sep - Mon, 8 Sep
Porter Airlines Logo
8:00 a.m. - 8:39 a.m.YYC-MDW
23h 39m2 stops
Porter Airlines Logo
9:35 a.m. - 10:28 p.m.MDW-YYC
13h 53m2 stops
C$ 590Porter Airlines
Find Deal
Sun, 14 Sep - Sun, 21 Sep
Porter Airlines Logo
8:20 a.m. - 10:05 a.m.YYC-MDW
24h 45m2 stops
Porter Airlines Logo
11:00 a.m. - 8:50 p.m.MDW-YYC
10h 50m2 stops
C$ 761Porter Airlines
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Thu, 20 Nov - Tue, 25 Nov
WestJet Logo
7:00 a.m. - 9:12 p.m.YYC-MDW
13h 12m2 stops
WestJet Logo
10:31 a.m. - 8:52 p.m.MDW-YYC
11h 21m2 stops
C$ 839WestJet
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Sat, 6 Sep - Mon, 8 Sep
WestJet Logo
12:30 a.m. - 9:36 a.m.YYC-MDW
8h 06m1 stop
WestJet Logo
10:31 a.m. - 8:52 p.m.MDW-YYC
11h 21m2 stops
C$ 843WestJet
Find Deal
Fri, 5 Sep - Mon, 8 Sep

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
6 Sep
YYC7:00 a.m.Calgary
13h 12m
2 stops
MDW9:12 p.m.Chicago Midway
8 Sep
MDW10:31 a.m.Chicago Midway
11h 21m
2 stops
YYC8:52 p.m.Calgary
C$ 839
Find similar
WestJet
5 Sep
YYC12:30 a.m.Calgary
8h 06m
1 stop
MDW9:36 a.m.Chicago Midway
8 Sep
MDW10:31 a.m.Chicago Midway
11h 21m
2 stops
YYC8:52 p.m.Calgary
C$ 843
Find similar
WestJet
11 Dec
YYC6:35 a.m.Calgary
10h 32m
1 stop
MDW6:07 p.m.Chicago Midway
15 Dec
MDW10:35 a.m.Chicago Midway
11h 27m
2 stops
YYC9:02 p.m.Calgary
C$ 859
Find similar

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
10 Sep
YYC6:40 a.m.Calgary
5h 23m
1 stop
MDW1:03 p.m.Chicago Midway
13 Sep
MDW9:20 a.m.Chicago Midway
14h 42m
2 stops
YYC11:02 p.m.Calgary
C$ 337
Find similar
Delta
3 Sep
YYC6:40 a.m.Calgary
9h 57m
1 stop
MDW5:37 p.m.Chicago Midway
9 Sep
MDW1:43 p.m.Chicago Midway
8h 00m
1 stop
YYC8:43 p.m.Calgary
C$ 481
Find similar
Delta
4 Sep
YYC6:40 a.m.Calgary
5h 23m
1 stop
MDW1:03 p.m.Chicago Midway
9 Sep
MDW1:43 p.m.Chicago Midway
8h 00m
1 stop
YYC8:43 p.m.Calgary
C$ 542
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 31 July 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 10/9

6:40 a.m.-1:03 p.m.

1 stop5h 23m

Chicago Midway

Sat 13/9

9:20 a.m.-11:02 p.m.

2 stops14h 42m

C$ 337

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 6/9

10:00 a.m.-11:17 p.m.

1 stop12h 17m

Chicago Midway

Mon 8/9

6:20 a.m.-8:00 p.m.

1 stop14h 40m

C$ 468

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 3/9

6:40 a.m.-5:37 p.m.

1 stop9h 57m

Chicago Midway

Tue 9/9

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

1 stop8h 00m

C$ 481

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 18/9

12:30 a.m.-4:00 p.m.

1 stop14h 30m

Chicago Midway

Sun 21/9

6:20 a.m.-8:00 p.m.

1 stop14h 40m

C$ 515

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 9/9

12:30 a.m.-3:58 p.m.

1 stop14h 28m

Chicago Midway

Mon 15/9

6:20 a.m.-8:00 p.m.

1 stop14h 40m

C$ 516

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 6/9

7:35 p.m.-9:23 a.m.

2 stops12h 48m

Chicago Midway

Mon 8/9

6:20 a.m.-8:00 p.m.

1 stop14h 40m

C$ 527

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 14/9

8:00 a.m.-8:39 a.m.

2 stops23h 39m

Chicago Midway

Sun 21/9

9:35 a.m.-10:28 p.m.

2 stops13h 53m

C$ 590

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 20/11

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

2 stops24h 45m

Chicago Midway

Tue 25/11

11:00 a.m.-8:50 p.m.

2 stops10h 50m

C$ 761

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 6/9

7:00 a.m.-9:12 p.m.

2 stops13h 12m

Chicago Midway

Mon 8/9

10:31 a.m.-8:52 p.m.

2 stops11h 21m

C$ 839

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 5/9

12:30 a.m.-9:36 a.m.

1 stop8h 06m

Chicago Midway

Mon 8/9

10:31 a.m.-8:52 p.m.

2 stops11h 21m

C$ 843

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

Best price found

C$ 192

Fastest flight time

5h 23m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Calgary in the past 72 hours is C$ 192. The best round-trip flight deal from Calgary to Chicago Midway Airport found on momondo in the last 72 hours is C$ 337.
The fastest flight from Calgary to Chicago Midway Airport takes 5h 23m
There are no direct flights from Calgary to Chicago Midway Airport. Popular non-direct route for this connection is Calgary Airport - 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
Hammond
Munster
Benton Harbor
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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