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Cheap flights from Calgary to Chicago from C$ 244

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 5/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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
6:45 a.m. - 3:57 p.m.YYC  Calgary-MDW Chicago Midway
8h 12m1 stop Minneapolis St Paul
Delta Logo
9:29 a.m. - 8:42 p.m.MDW  Chicago Midway-YYC Calgary
12h 13m2 stops Detroit Metropolitan Wayne County Minneapolis St Paul
C$ 382Delta
Sat, 5 Sep - Sat, 12 Sep
Delta Logo
8:45 a.m. - 3:39 p.m.YYC  Calgary-MDW Chicago Midway
6h 54m1 stop Minneapolis St Paul
Delta Logo
6:00 a.m. - 1:17 a.m.MDW  Chicago Midway-YYC Calgary
19h 17m2 stops Atlanta Hartsfield-Jackson Salt Lake City
C$ 395Delta
Mon, 14 Dec - Wed, 16 Dec
Delta Logo
8:45 a.m. - 3:22 p.m.YYC  Calgary-MDW Chicago Midway
6h 37m2 stops Minneapolis St Paul Detroit Metropolitan Wayne County
Delta Logo
10:35 a.m. - 1:13 a.m.MDW  Chicago Midway-YYC Calgary
14h 38m2 stops Atlanta Hartsfield-Jackson Salt Lake City
C$ 404Delta
Fri, 25 Dec - Sat, 9 Jan
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$ 442Delta
Sat, 14 Nov - Wed, 18 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$ 442Delta
Sat, 14 Nov - Wed, 18 Nov
Delta Logo
8:45 a.m. - 5:04 p.m.YYC  Calgary-MDW Chicago Midway
8h 19m2 stops Minneapolis St Paul Detroit Metropolitan Wayne County
Delta Logo
6:00 a.m. - 1:17 a.m.MDW  Chicago Midway-YYC Calgary
19h 17m2 stops Atlanta Hartsfield-Jackson Salt Lake City
C$ 449Delta
Mon, 14 Dec - Wed, 16 Dec
Delta Logo
8:45 a.m. - 3:39 p.m.YYC  Calgary-MDW Chicago Midway
6h 54m1 stop Minneapolis St Paul
Delta Logo
11:28 a.m. - 9:14 p.m.MDW  Chicago Midway-YYC Calgary
9h 46m1 stop Atlanta Hartsfield-Jackson
C$ 457Delta
Tue, 17 Nov - Thu, 19 Nov
Delta Logo
8:45 a.m. - 5:04 p.m.YYC  Calgary-MDW Chicago Midway
8h 19m2 stops Minneapolis St Paul Detroit Metropolitan Wayne County
Delta Logo
11:28 a.m. - 9:14 p.m.MDW  Chicago Midway-YYC Calgary
9h 46m1 stop Atlanta Hartsfield-Jackson
C$ 457Delta
Tue, 17 Nov - Thu, 19 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$ 468Delta
Fri, 13 Nov - Wed, 18 Nov
Delta Logo
12:30 a.m. - 12:47 p.m.YYC  Calgary-MDW Chicago Midway
11h 17m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
10:01 a.m. - 8:15 p.m.MDW  Chicago Midway-YYC Calgary
10h 14m2 stops Minneapolis St Paul Edmonton
C$ 473Delta
Thu, 29 Oct - Mon, 2 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
5 Sep
YYC6:45 a.m.Calgary
8h 12m
1 stop
MDW3:57 p.m.Chicago Midway
12 Sep
MDW9:29 a.m.Chicago Midway
12h 13m
2 stops
YYC8:42 p.m.Calgary
C$ 382
Delta
14 Dec
YYC8:45 a.m.Calgary
6h 54m
1 stop
MDW3:39 p.m.Chicago Midway
16 Dec
MDW6:00 a.m.Chicago Midway
19h 17m
2 stops
YYC1:17 a.m.Calgary
C$ 395
Delta
25 Dec
YYC8:45 a.m.Calgary
6h 37m
2 stops
MDW3:22 p.m.Chicago Midway
9 Jan
MDW10:35 a.m.Chicago Midway
14h 38m
2 stops
YYC1:13 a.m.Calgary
C$ 404

Porter Airlines flights from Calgary to Chicago Midway Airport

Our best Porter Airlines deals on Calgary to Chicago Midway Airport flight tickets
Porter Airlines
16 Sep
YYC7:05 a.m.Calgary
26h 55m
1 stop
MDW11:00 a.m.Chicago Midway
23 Sep
MDW11:45 a.m.Chicago Midway
10h 31m
1 stop
YYC9:16 p.m.Calgary
C$ 604
Porter Airlines
26 Aug
YYC12:00 p.m.Calgary
20h 45m
2 stops
MDW9:45 a.m.Chicago Midway
29 Aug
MDW10:20 a.m.Chicago Midway
13h 25m
2 stops
YYC10:45 p.m.Calgary
C$ 941
Porter Airlines
26 Aug
YYC7:00 a.m.Calgary
25h 45m
3 stops
MDW9:45 a.m.Chicago Midway
29 Aug
MDW10:20 a.m.Chicago Midway
13h 25m
2 stops
YYC10:45 p.m.Calgary
C$ 1,115

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 13 August 2026.
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 5/9

6:45 a.m.-3:57 p.m.

1 stop8h 12m

Chicago Midway

Sat 12/9

9:29 a.m.-8:42 p.m.

2 stops12h 13m

C$ 382

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Mon 14/12

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

1 stop6h 54m

Chicago Midway

Wed 16/12

6:00 a.m.-1:17 a.m.

2 stops19h 17m

C$ 395

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Fri 25/12

8:45 a.m.-3:22 p.m.

2 stops6h 37m

Chicago Midway

Sat 9/1

10:35 a.m.-1:13 a.m.

2 stops14h 38m

C$ 404

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$ 442

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Sat 14/11

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

2 stops8h 14m

Chicago Midway

Wed 18/11

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

2 stops12h 47m

C$ 442

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Mon 14/12

8:45 a.m.-5:04 p.m.

2 stops8h 19m

Chicago Midway

Wed 16/12

6:00 a.m.-1:17 a.m.

2 stops19h 17m

C$ 449
Quickest round-trip

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Tue 17/11

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

1 stop6h 54m

Chicago Midway

Thu 19/11

11:28 a.m.-9:14 p.m.

1 stop9h 46m

C$ 457

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Tue 17/11

8:45 a.m.-5:04 p.m.

2 stops8h 19m

Chicago Midway

Thu 19/11

11:28 a.m.-9:14 p.m.

1 stop9h 46m

C$ 457

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Fri 13/11

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$ 468

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 29/10

12:30 a.m.-12:47 p.m.

2 stops11h 17m

Chicago Midway

Mon 2/11

10:01 a.m.-8:15 p.m.

2 stops10h 14m

C$ 473

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

Fastest flight time

5h 25m

Direct flights

None
The fastest flight from Calgary to Chicago Midway Airport takes 5h 25m
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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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 25m.

  • 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
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.

An easier way to manage your Chicago Midway Airport trip

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