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Cheap flights from Calgary to Chicago from C$ 288

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
7:25 a.m. - 4:39 p.m.YYC  Calgary-MDW Chicago Midway
9h 14m2 stops Salt Lake City Minneapolis St Paul
Delta Logo
12:30 p.m. - 12:19 a.m.MDW  Chicago Midway-YYC Calgary
11h 49m2 stops Minneapolis St Paul Salt Lake City
C$ 496Delta
Thu, 19 Nov - Sat, 21 Nov
Delta Logo
7:25 a.m. - 4:50 p.m.YYC  Calgary-MDW Chicago Midway
9h 25m2 stops Salt Lake City Minneapolis St Paul
Delta Logo
12:39 p.m. - 10:07 p.m.MDW  Chicago Midway-YYC Calgary
9h 28m1 stop Minneapolis St Paul
C$ 499Delta
Thu, 3 Dec - Wed, 9 Dec
Delta Logo
8:45 a.m. - 4:50 p.m.YYC  Calgary-MDW Chicago Midway
8h 05m1 stop Minneapolis St Paul
Delta Logo
12:39 p.m. - 12:21 a.m.MDW  Chicago Midway-YYC Calgary
11h 42m2 stops Minneapolis St Paul Salt Lake City
C$ 501Delta
Wed, 2 Dec - Tue, 8 Dec
Delta Logo
7:25 a.m. - 10:54 p.m.YYC  Calgary-MDW Chicago Midway
15h 29m2 stops Salt Lake City Atlanta Hartsfield-Jackson
Delta Logo
10:24 a.m. - 12:21 a.m.MDW  Chicago Midway-YYC Calgary
13h 57m2 stops Minneapolis St Paul Salt Lake City
C$ 523Delta
Thu, 3 Dec - Mon, 7 Dec
Delta Logo
8:45 a.m. - 4:50 p.m.YYC  Calgary-MDW Chicago Midway
8h 05m1 stop Minneapolis St Paul
Delta Logo
12:39 p.m. - 10:07 p.m.MDW  Chicago Midway-YYC Calgary
9h 28m1 stop Minneapolis St Paul
C$ 528Delta
Wed, 2 Dec - Wed, 9 Dec
Delta Logo
8:45 a.m. - 4:50 p.m.YYC  Calgary-MDW Chicago Midway
8h 05m1 stop Minneapolis St Paul
Delta Logo
10:24 a.m. - 12:21 a.m.MDW  Chicago Midway-YYC Calgary
13h 57m2 stops Minneapolis St Paul Salt Lake City
C$ 534Delta
Wed, 2 Dec - Fri, 4 Dec
Delta Logo
8:45 a.m. - 10:54 p.m.YYC  Calgary-MDW Chicago Midway
14h 09m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson
Delta Logo
12:39 p.m. - 12:21 a.m.MDW  Chicago Midway-YYC Calgary
11h 42m2 stops Minneapolis St Paul Salt Lake City
C$ 538Delta
Thu, 26 Nov - Wed, 2 Dec
Delta Logo
8:45 a.m. - 4:53 p.m.YYC  Calgary-MDW Chicago Midway
8h 08m1 stop Minneapolis St Paul
Delta Logo
12:44 p.m. - 10:01 p.m.MDW  Chicago Midway-YYC Calgary
9h 17m1 stop Minneapolis St Paul
C$ 548Delta
Thu, 21 Jan - Sun, 24 Jan
Delta Logo
8:45 a.m. - 4:53 p.m.YYC  Calgary-MDW Chicago Midway
8h 08m1 stop Minneapolis St Paul
Delta Logo
1:41 p.m. - 12:23 a.m.MDW  Chicago Midway-YYC Calgary
10h 42m2 stops Detroit Metropolitan Wayne County Salt Lake City
C$ 549Delta
Thu, 21 Jan - Sun, 24 Jan
Delta Logo
8:45 a.m. - 4:53 p.m.YYC  Calgary-MDW Chicago Midway
8h 08m1 stop Minneapolis St Paul
Delta Logo
12:44 p.m. - 10:01 p.m.MDW  Chicago Midway-YYC Calgary
9h 17m1 stop Minneapolis St Paul
C$ 551Delta
Thu, 21 Jan - Sun, 24 Jan

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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
19 Nov
YYC7:25 a.m.Calgary
9h 14m
2 stops
MDW4:39 p.m.Chicago Midway
21 Nov
MDW12:30 p.m.Chicago Midway
11h 49m
2 stops
YYC12:19 a.m.Calgary
C$ 496
Delta
3 Dec
YYC7:25 a.m.Calgary
9h 25m
2 stops
MDW4:50 p.m.Chicago Midway
9 Dec
MDW12:39 p.m.Chicago Midway
9h 28m
1 stop
YYC10:07 p.m.Calgary
C$ 499
Delta
2 Dec
YYC8:45 a.m.Calgary
8h 05m
1 stop
MDW4:50 p.m.Chicago Midway
8 Dec
MDW12:39 p.m.Chicago Midway
11h 42m
2 stops
YYC12:21 a.m.Calgary
C$ 501

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
20 Nov
YYC8:45 a.m.Calgary
7h 33m
1 stop
MDW4:18 p.m.Chicago Midway
22 Nov
MDW10:34 a.m.Chicago Midway
11h 56m
2 stops
YYC10:30 p.m.Calgary
C$ 1,112
WestJet
21 Nov
YYC8:45 a.m.Calgary
7h 54m
1 stop
MDW4:39 p.m.Chicago Midway
23 Nov
MDW9:30 a.m.Chicago Midway
16h 25m
2 stops
YYC1:55 a.m.Calgary
C$ 1,141
WestJet
11 Nov
YYC11:10 a.m.Calgary
29h 29m
2 stops
MDW4:39 p.m.Chicago Midway
18 Nov
MDW10:34 a.m.Chicago Midway
30h 01m
2 stops
YYC4:35 p.m.Calgary
C$ 1,189

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

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 19/11

7:25 a.m.-4:39 p.m.

2 stops9h 14m

Chicago Midway

Sat 21/11

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

2 stops11h 49m

C$ 496

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 3/12

7:25 a.m.-4:50 p.m.

2 stops9h 25m

Chicago Midway

Wed 9/12

12:39 p.m.-10:07 p.m.

1 stop9h 28m

C$ 499

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Wed 2/12

8:45 a.m.-4:50 p.m.

1 stop8h 05m

Chicago Midway

Tue 8/12

12:39 p.m.-12:21 a.m.

2 stops11h 42m

C$ 501

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 3/12

7:25 a.m.-10:54 p.m.

2 stops15h 29m

Chicago Midway

Mon 7/12

10:24 a.m.-12:21 a.m.

2 stops13h 57m

C$ 523

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Wed 2/12

8:45 a.m.-4:50 p.m.

1 stop8h 05m

Chicago Midway

Wed 9/12

12:39 p.m.-10:07 p.m.

1 stop9h 28m

C$ 528

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Wed 2/12

8:45 a.m.-4:50 p.m.

1 stop8h 05m

Chicago Midway

Fri 4/12

10:24 a.m.-12:21 a.m.

2 stops13h 57m

C$ 534

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 26/11

8:45 a.m.-10:54 p.m.

2 stops14h 09m

Chicago Midway

Wed 2/12

12:39 p.m.-12:21 a.m.

2 stops11h 42m

C$ 538
Quickest round-trip

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 21/1

8:45 a.m.-4:53 p.m.

1 stop8h 08m

Chicago Midway

Sun 24/1

12:44 p.m.-10:01 p.m.

1 stop9h 17m

C$ 548

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 21/1

8:45 a.m.-4:53 p.m.

1 stop8h 08m

Chicago Midway

Sun 24/1

1:41 p.m.-12:23 a.m.

2 stops10h 42m

C$ 549

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 21/1

8:45 a.m.-4:53 p.m.

1 stop8h 08m

Chicago Midway

Sun 24/1

12:44 p.m.-10:01 p.m.

1 stop9h 17m

C$ 551

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$ 288

Fastest flight time

6h 37m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Calgary in the past 72 hours is C$ 288. The best round-trip flight deal from Calgary to Chicago Midway Airport found on momondo in the last 72 hours is C$ 496.
The fastest flight from Calgary to Chicago Midway Airport takes 6h 37m
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 37m.

  • 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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