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Cheap flights from Calgary to Chicago from C$ 243

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Calgary to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:35 a.m. - 1:20 p.m.YYC  Calgary-MDW Chicago Midway
5h 45m1 stop Minneapolis St Paul
Delta Logo
2:00 p.m. - 8:42 p.m.MDW  Chicago Midway-YYC Calgary
7h 42m1 stop Minneapolis St Paul
C$ 412Delta
Tue, 22 Sep - Tue, 29 Sep
Delta Logo
12:25 a.m. - 11:54 a.m.YYC  Calgary-MDW Chicago Midway
10h 29m1 stop Atlanta Hartsfield-Jackson
Delta Logo
12:27 p.m. - 10:40 p.m.MDW  Chicago Midway-YYC Calgary
10h 13m1 stop Minneapolis St Paul
C$ 492Delta
Thu, 29 Oct - Mon, 2 Nov
Delta Logo
12:25 a.m. - 11:54 a.m.YYC  Calgary-MDW Chicago Midway
10h 29m1 stop Atlanta Hartsfield-Jackson
Delta Logo
10:01 a.m. - 1:10 a.m.MDW  Chicago Midway-YYC Calgary
15h 09m2 stops Minneapolis St Paul Salt Lake City
C$ 492Delta
Thu, 29 Oct - Mon, 2 Nov
Delta Logo
12:25 a.m. - 12:47 p.m.YYC  Calgary-MDW Chicago Midway
11h 22m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
10:01 a.m. - 1:10 a.m.MDW  Chicago Midway-YYC Calgary
15h 09m2 stops Minneapolis St Paul Salt Lake City
C$ 492Delta
Thu, 29 Oct - Mon, 2 Nov
Delta Logo
12:25 a.m. - 10:03 a.m.YYC  Calgary-MDW Chicago Midway
8h 38m1 stop Atlanta Hartsfield-Jackson
Delta Logo
12:27 p.m. - 10:40 p.m.MDW  Chicago Midway-YYC Calgary
10h 13m1 stop Minneapolis St Paul
C$ 495Delta
Thu, 29 Oct - Mon, 2 Nov
Delta Logo
12:25 a.m. - 12:47 p.m.YYC  Calgary-MDW Chicago Midway
11h 22m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
12:27 p.m. - 10:40 p.m.MDW  Chicago Midway-YYC Calgary
10h 13m1 stop Minneapolis St Paul
C$ 495Delta
Thu, 29 Oct - Mon, 2 Nov
Delta Logo
12:25 a.m. - 12:47 p.m.YYC  Calgary-MDW Chicago Midway
11h 22m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
10:01 a.m. - 1:10 a.m.MDW  Chicago Midway-YYC Calgary
15h 09m2 stops Minneapolis St Paul Salt Lake City
C$ 495Delta
Thu, 29 Oct - Mon, 2 Nov
Multiple Airlines Logo
9:00 p.m. - 5:51 p.m.YYC  Calgary-MDW Chicago Midway
19h 51m2 stops Vancouver Intl Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:25 a.m. - 5:10 p.m.MDW  Chicago Midway-YYC Calgary
11h 45m1 stop Atlanta Hartsfield-Jackson
C$ 498Multiple Airlines
Thu, 10 Sep - Sat, 12 Sep
Multiple Airlines Logo
7:00 a.m. - 11:44 p.m.YYC  Calgary-MDW Chicago Midway
15h 44m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:25 a.m. - 5:10 p.m.MDW  Chicago Midway-YYC Calgary
11h 45m1 stop Atlanta Hartsfield-Jackson
C$ 513Multiple Airlines
Thu, 10 Sep - Sat, 12 Sep
Multiple Airlines Logo
7:00 a.m. - 5:51 p.m.YYC  Calgary-MDW Chicago Midway
9h 51m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:25 a.m. - 5:10 p.m.MDW  Chicago Midway-YYC Calgary
11h 45m1 stop Atlanta Hartsfield-Jackson
C$ 544Multiple Airlines
Fri, 11 Sep - Sat, 12 Sep

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Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
22 Sep
YYC6:35 a.m.Calgary
5h 45m
1 stop
MDW1:20 p.m.Chicago Midway
29 Sep
MDW2:00 p.m.Chicago Midway
7h 42m
1 stop
YYC8:42 p.m.Calgary
C$ 412
Delta
29 Oct
YYC12:25 a.m.Calgary
10h 29m
1 stop
MDW11:54 a.m.Chicago Midway
2 Nov
MDW12:27 p.m.Chicago Midway
10h 13m
1 stop
YYC10:40 p.m.Calgary
C$ 492
Delta
29 Oct
YYC12:25 a.m.Calgary
11h 22m
2 stops
MDW12:47 p.m.Chicago Midway
2 Nov
MDW10:01 a.m.Chicago Midway
15h 09m
2 stops
YYC1:10 a.m.Calgary
C$ 495

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
21 Oct
YYC7:50 a.m.Calgary
8h 02m
1 stop
MDW4:52 p.m.Chicago Midway
24 Oct
MDW12:32 p.m.Chicago Midway
9h 13m
1 stop
YYC8:45 p.m.Calgary
C$ 570
WestJet
21 Oct
YYC7:50 a.m.Calgary
8h 02m
1 stop
MDW4:52 p.m.Chicago Midway
24 Oct
MDW12:32 p.m.Chicago Midway
9h 13m
1 stop
YYC8:45 p.m.Calgary
C$ 571
WestJet
9 Sep
YYC8:10 a.m.Calgary
9h 09m
2 stops
MDW6:19 p.m.Chicago Midway
12 Sep
MDW9:29 a.m.Chicago Midway
11h 46m
1 stop
YYC8:15 p.m.Calgary
C$ 1,234

momondo Fare Finder

 
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

Cheapest round-trip
Quickest round-trip

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Tue 22/9

6:35 a.m.-1:20 p.m.

1 stop5h 45m

Chicago Midway

Tue 29/9

2:00 p.m.-8:42 p.m.

1 stop7h 42m

C$ 412

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 29/10

12:25 a.m.-11:54 a.m.

1 stop10h 29m

Chicago Midway

Mon 2/11

12:27 p.m.-10:40 p.m.

1 stop10h 13m

C$ 492

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 29/10

12:25 a.m.-11:54 a.m.

1 stop10h 29m

Chicago Midway

Mon 2/11

10:01 a.m.-1:10 a.m.

2 stops15h 09m

C$ 492

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 29/10

12:25 a.m.-12:47 p.m.

2 stops11h 22m

Chicago Midway

Mon 2/11

10:01 a.m.-1:10 a.m.

2 stops15h 09m

C$ 492

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 29/10

12:25 a.m.-10:03 a.m.

1 stop8h 38m

Chicago Midway

Mon 2/11

12:27 p.m.-10:40 p.m.

1 stop10h 13m

C$ 495

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 29/10

12:25 a.m.-12:47 p.m.

2 stops11h 22m

Chicago Midway

Mon 2/11

12:27 p.m.-10:40 p.m.

1 stop10h 13m

C$ 495

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 29/10

12:25 a.m.-12:47 p.m.

2 stops11h 22m

Chicago Midway

Mon 2/11

10:01 a.m.-1:10 a.m.

2 stops15h 09m

C$ 495

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 10/9

9:00 p.m.-5:51 p.m.

2 stops19h 51m

Chicago Midway

Sat 12/9

6:25 a.m.-5:10 p.m.

1 stop11h 45m

C$ 498

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 10/9

7:00 a.m.-11:44 p.m.

1 stop15h 44m

Chicago Midway

Sat 12/9

6:25 a.m.-5:10 p.m.

1 stop11h 45m

C$ 513

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Fri 11/9

7:00 a.m.-5:51 p.m.

1 stop9h 51m

Chicago Midway

Sat 12/9

6:25 a.m.-5:10 p.m.

1 stop11h 45m

C$ 544

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 34% 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

Best price found

C$ 243

Fastest flight time

6h 33m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Calgary in the past 72 hours is C$ 243. The best round-trip flight deal from Calgary to Chicago Midway Airport found on momondo in the last 72 hours is C$ 412.
The fastest flight from Calgary to Chicago Midway Airport takes 6h 33m
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

Frequently asked questions about flying from Calgary to Chicago Midway Airport

  • 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 6h 33m.

  • 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
Merrillville
Benton Harbor
Hammond
Munster
Valparaiso
Portage

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.

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