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Cheap flights from Calgary to Chicago from C$ 256

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
7:45 a.m. - 6:01 p.m.YYC  Calgary-MDW Chicago Midway
9h 16m2 stops Salt Lake City 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$ 433Delta
Tue, 1 Sep - Tue, 15 Sep
Delta Logo
7:00 a.m. - 4:47 p.m.YYC  Calgary-MDW Chicago Midway
8h 47m2 stops Edmonton Minneapolis St Paul
Delta Logo
12:27 p.m. - 12:44 a.m.MDW  Chicago Midway-YYC Calgary
13h 17m2 stops Minneapolis St Paul Vancouver Intl
C$ 521Delta
Sat, 17 Oct - Wed, 21 Oct
Delta Logo
11:00 a.m. - 6:00 p.m.YYC  Calgary-MDW Chicago Midway
6h 00m1 stop Detroit Metropolitan Wayne County
Delta Logo
1:27 p.m. - 8:15 p.m.MDW  Chicago Midway-YYC Calgary
7h 48m1 stop Detroit Metropolitan Wayne County
C$ 521Delta
Sat, 17 Oct - Wed, 21 Oct
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. - 10:35 p.m.MDW  Chicago Midway-YYC Calgary
12h 34m2 stops Minneapolis St Paul Edmonton
C$ 521Delta
Thu, 29 Oct - Mon, 2 Nov
Delta Logo
12:30 a.m. - 10:03 a.m.YYC  Calgary-MDW Chicago Midway
8h 33m1 stop Atlanta Hartsfield-Jackson
Delta Logo
10:01 a.m. - 8:15 p.m.MDW  Chicago Midway-YYC Calgary
10h 14m2 stops Minneapolis St Paul Edmonton
C$ 521Delta
Thu, 29 Oct - Mon, 2 Nov
Delta Logo
11:00 a.m. - 6:00 p.m.YYC  Calgary-MDW Chicago Midway
6h 00m1 stop Detroit Metropolitan Wayne County
Delta Logo
12:27 p.m. - 8:25 p.m.MDW  Chicago Midway-YYC Calgary
8h 58m2 stops Minneapolis St Paul Winnipeg
C$ 521Delta
Sat, 17 Oct - Wed, 21 Oct
WestJet Logo
6:50 a.m. - 1:15 p.m.YYC  Calgary-MDW Chicago Midway
5h 25m1 stop Minneapolis St Paul
WestJet Logo
2:05 p.m. - 8:47 p.m.MDW  Chicago Midway-YYC Calgary
7h 42m1 stop Minneapolis St Paul
C$ 528WestJet
Tue, 1 Sep - Tue, 15 Sep
Delta Logo
12:30 a.m. - 11:35 a.m.YYC  Calgary-MDW Chicago Midway
11h 05m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
9:30 a.m. - 8:30 p.m.MDW  Chicago Midway-YYC Calgary
11h 00m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl
C$ 533Delta
Thu, 12 Nov - Mon, 16 Nov
Delta Logo
12:30 a.m. - 11:05 a.m.YYC  Calgary-MDW Chicago Midway
10h 35m1 stop Atlanta Hartsfield-Jackson
Delta Logo
9:30 a.m. - 8:30 p.m.MDW  Chicago Midway-YYC Calgary
11h 00m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl
C$ 533Delta
Thu, 12 Nov - Mon, 16 Nov
Delta Logo
11:00 a.m. - 6:00 p.m.YYC  Calgary-MDW Chicago Midway
6h 00m1 stop Detroit Metropolitan Wayne County
Delta Logo
12:27 p.m. - 8:25 p.m.MDW  Chicago Midway-YYC Calgary
8h 58m2 stops Minneapolis St Paul Winnipeg
C$ 541Delta
Sat, 17 Oct - Wed, 21 Oct

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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
1 Sep
YYC7:45 a.m.Calgary
9h 16m
2 stops
MDW6:01 p.m.Chicago Midway
15 Sep
MDW2:00 p.m.Chicago Midway
7h 42m
1 stop
YYC8:42 p.m.Calgary
C$ 433
Delta
17 Oct
YYC7:00 a.m.Calgary
8h 47m
2 stops
MDW4:47 p.m.Chicago Midway
21 Oct
MDW12:27 p.m.Chicago Midway
13h 17m
2 stops
YYC12:44 a.m.Calgary
C$ 521
Delta
12 Nov
YYC12:30 a.m.Calgary
11h 05m
2 stops
MDW11:35 a.m.Chicago Midway
16 Nov
MDW9:30 a.m.Chicago Midway
11h 00m
2 stops
YYC8:30 p.m.Calgary
C$ 533

Porter Airlines flights from Calgary to Chicago Midway Airport

Our best Porter Airlines deals on Calgary to Chicago Midway Airport flight tickets
Porter Airlines
10 Sep
YYC4:40 p.m.Calgary
20h 55m
1 stop
MDW2:35 p.m.Chicago Midway
14 Sep
MDW11:45 a.m.Chicago Midway
11h 41m
2 stops
YYC10:26 p.m.Calgary
C$ 654
Porter Airlines
19 Aug
YYC12:00 p.m.Calgary
20h 45m
2 stops
MDW9:45 a.m.Chicago Midway
22 Aug
MDW10:20 a.m.Chicago Midway
13h 10m
2 stops
YYC10:30 p.m.Calgary
C$ 1,176
Porter Airlines
18 Aug
YYC12:00 p.m.Calgary
20h 45m
2 stops
MDW9:45 a.m.Chicago Midway
25 Aug
MDW3:15 p.m.Chicago Midway
26h 15m
2 stops
YYC4:30 p.m.Calgary
C$ 1,191

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 7 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

Tue 1/9

7:45 a.m.-6:01 p.m.

2 stops9h 16m

Chicago Midway

Tue 15/9

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

1 stop7h 42m

C$ 433

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Sat 17/10

7:00 a.m.-4:47 p.m.

2 stops8h 47m

Chicago Midway

Wed 21/10

12:27 p.m.-12:44 a.m.

2 stops13h 17m

C$ 521

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Sat 17/10

11:00 a.m.-6:00 p.m.

1 stop6h 00m

Chicago Midway

Wed 21/10

1:27 p.m.-8:15 p.m.

1 stop7h 48m

C$ 521

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.-10:35 p.m.

2 stops12h 34m

C$ 521

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 29/10

12:30 a.m.-10:03 a.m.

1 stop8h 33m

Chicago Midway

Mon 2/11

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

2 stops10h 14m

C$ 521

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Sat 17/10

11:00 a.m.-6:00 p.m.

1 stop6h 00m

Chicago Midway

Wed 21/10

12:27 p.m.-8:25 p.m.

2 stops8h 58m

C$ 521
Quickest round-trip

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Tue 1/9

6:50 a.m.-1:15 p.m.

1 stop5h 25m

Chicago Midway

Tue 15/9

2:05 p.m.-8:47 p.m.

1 stop7h 42m

C$ 528

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 12/11

12:30 a.m.-11:35 a.m.

2 stops11h 05m

Chicago Midway

Mon 16/11

9:30 a.m.-8:30 p.m.

2 stops11h 00m

C$ 533

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Thu 12/11

12:30 a.m.-11:05 a.m.

1 stop10h 35m

Chicago Midway

Mon 16/11

9:30 a.m.-8:30 p.m.

2 stops11h 00m

C$ 533

CalgaryChicago

YYC Calgary - MDW Chicago Midway

YYCMDW

Calgary

Sat 17/10

11:00 a.m.-6:00 p.m.

1 stop6h 00m

Chicago Midway

Wed 21/10

12:27 p.m.-8:25 p.m.

2 stops8h 58m

C$ 541

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

6h 00m

Direct flights

None
The fastest flight from Calgary to Chicago Midway Airport takes 6h 00m
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 6h 00m.

  • 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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