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Cheap flights from Calgary to Chicago from C$ 221

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. - 4:47 p.m.YYC  Calgary-MDW Chicago Midway
9h 12m2 stops Salt Lake City Minneapolis St Paul
Delta Logo
1:27 p.m. - 1:10 a.m.MDW  Chicago Midway-YYC Calgary
11h 43m2 stops Detroit Metropolitan Wayne County Salt Lake City
C$ 363Delta
Sat, 31 Oct - Wed, 4 Nov
Delta Logo
8:45 a.m. - 3:39 p.m.YYC  Calgary-MDW Chicago Midway
6h 54m1 stop Minneapolis St Paul
Delta Logo
12:30 p.m. - 1:17 a.m.MDW  Chicago Midway-YYC Calgary
12h 47m2 stops Minneapolis St Paul Salt Lake City
C$ 383Delta
Sat, 14 Nov - Wed, 18 Nov
Delta Logo
7:25 a.m. - 5:04 p.m.YYC  Calgary-MDW Chicago Midway
9h 39m2 stops Salt Lake City Detroit Metropolitan Wayne County
Delta Logo
12:30 p.m. - 1:17 a.m.MDW  Chicago Midway-YYC Calgary
12h 47m2 stops Minneapolis St Paul Salt Lake City
C$ 383Delta
Sat, 14 Nov - Wed, 18 Nov
Delta Logo
8:45 a.m. - 3:39 p.m.YYC  Calgary-MDW Chicago Midway
6h 54m1 stop Minneapolis St Paul
Delta Logo
12:30 p.m. - 1:17 a.m.MDW  Chicago Midway-YYC Calgary
12h 47m2 stops Minneapolis St Paul Salt Lake City
C$ 384Delta
Tue, 17 Nov - Mon, 23 Nov
Delta Logo
7:25 a.m. - 3:39 p.m.YYC  Calgary-MDW Chicago Midway
8h 14m2 stops Salt Lake City Minneapolis St Paul
Delta Logo
12:30 p.m. - 1:17 a.m.MDW  Chicago Midway-YYC Calgary
12h 47m2 stops Minneapolis St Paul Salt Lake City
C$ 384Delta
Sat, 14 Nov - Mon, 23 Nov
Delta Logo
6:35 a.m. - 4:47 p.m.YYC  Calgary-MDW Chicago Midway
9h 12m2 stops Salt Lake City Minneapolis St Paul
Delta Logo
12:27 p.m. - 10:40 p.m.MDW  Chicago Midway-YYC Calgary
10h 13m1 stop Minneapolis St Paul
C$ 430Delta
Sat, 31 Oct - Wed, 4 Nov
Delta Logo
7:45 a.m. - 10:33 p.m.YYC  Calgary-MDW Chicago Midway
13h 48m2 stops Minneapolis St Paul Atlanta Hartsfield-Jackson
Delta Logo
12:30 p.m. - 1:17 a.m.MDW  Chicago Midway-YYC Calgary
12h 47m2 stops Minneapolis St Paul Salt Lake City
C$ 464Delta
Tue, 27 Oct - Tue, 10 Nov
Multiple Airlines Logo
8:45 a.m. - 5:47 p.m.YYC  Calgary-MDW Chicago Midway
8h 02m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:16 a.m. - 7:55 p.m.MDW  Chicago Midway-YYC Calgary
13h 39m1 stop Atlanta Hartsfield-Jackson
C$ 486Multiple Airlines
Sat, 31 Oct - Wed, 4 Nov
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. - 1:10 a.m.MDW  Chicago Midway-YYC Calgary
12h 43m2 stops Minneapolis St Paul Salt Lake City
C$ 489Delta
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
12:27 p.m. - 1:10 a.m.MDW  Chicago Midway-YYC Calgary
12h 43m2 stops Minneapolis St Paul Salt Lake City
C$ 500Delta
Thu, 29 Oct - Thu, 5 Nov

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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
31 Oct
YYC6:35 a.m.Calgary
9h 12m
2 stops
MDW4:47 p.m.Chicago Midway
4 Nov
MDW1:27 p.m.Chicago Midway
11h 43m
2 stops
YYC1:10 a.m.Calgary
C$ 363
Delta
14 Nov
YYC7:25 a.m.Calgary
9h 39m
2 stops
MDW5:04 p.m.Chicago Midway
18 Nov
MDW12:30 p.m.Chicago Midway
12h 47m
2 stops
YYC1:17 a.m.Calgary
C$ 383
Delta
14 Nov
YYC7:25 a.m.Calgary
8h 14m
2 stops
MDW3:39 p.m.Chicago Midway
23 Nov
MDW12:30 p.m.Chicago Midway
12h 47m
2 stops
YYC1:17 a.m.Calgary
C$ 384

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
14 Nov
YYC8:52 a.m.Calgary
6h 54m
1 stop
MDW3:46 p.m.Chicago Midway
23 Nov
MDW12:37 p.m.Chicago Midway
10h 28m
1 stop
YYC11:05 p.m.Calgary
C$ 564
WestJet
23 Sep
YYC11:00 a.m.Calgary
6h 33m
1 stop
MDW6:33 p.m.Chicago Midway
26 Sep
MDW9:59 a.m.Chicago Midway
11h 26m
2 stops
YYC8:25 p.m.Calgary
C$ 1,277
WestJet
16 Sep
YYC7:00 a.m.Calgary
10h 19m
2 stops
MDW6:19 p.m.Chicago Midway
22 Sep
MDW9:59 a.m.Chicago Midway
11h 26m
2 stops
YYC8:25 p.m.Calgary
C$ 1,281

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

Sat 31/10

6:35 a.m.-4:47 p.m.

2 stops9h 12m

Chicago Midway

Wed 4/11

1:27 p.m.-1:10 a.m.

2 stops11h 43m

C$ 363

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Sat 14/11

8:45 a.m.-3:39 p.m.

1 stop6h 54m

Chicago Midway

Wed 18/11

12:30 p.m.-1:17 a.m.

2 stops12h 47m

C$ 383

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Sat 14/11

7:25 a.m.-5:04 p.m.

2 stops9h 39m

Chicago Midway

Wed 18/11

12:30 p.m.-1:17 a.m.

2 stops12h 47m

C$ 383

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Tue 17/11

8:45 a.m.-3:39 p.m.

1 stop6h 54m

Chicago Midway

Mon 23/11

12:30 p.m.-1:17 a.m.

2 stops12h 47m

C$ 384

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Sat 14/11

7:25 a.m.-3:39 p.m.

2 stops8h 14m

Chicago Midway

Mon 23/11

12:30 p.m.-1:17 a.m.

2 stops12h 47m

C$ 384
Quickest round-trip

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Sat 31/10

6:35 a.m.-4:47 p.m.

2 stops9h 12m

Chicago Midway

Wed 4/11

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

1 stop10h 13m

C$ 430

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Tue 27/10

7:45 a.m.-10:33 p.m.

2 stops13h 48m

Chicago Midway

Tue 10/11

12:30 p.m.-1:17 a.m.

2 stops12h 47m

C$ 464

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Sat 31/10

8:45 a.m.-5:47 p.m.

1 stop8h 02m

Chicago Midway

Wed 4/11

6:16 a.m.-7:55 p.m.

1 stop13h 39m

C$ 486

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.-1:10 a.m.

2 stops12h 43m

C$ 489

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 29/10

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

1 stop10h 29m

Chicago Midway

Thu 5/11

12:27 p.m.-1:10 a.m.

2 stops12h 43m

C$ 500

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$ 221

Fastest flight time

5h 45m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Calgary in the past 72 hours is C$ 221. The best round-trip flight deal from Calgary to Chicago Midway Airport found on momondo in the last 72 hours is C$ 363.
The fastest flight from Calgary to Chicago Midway Airport takes 5h 45m
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 5h 45m.

  • 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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