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Cheap flights from Calgary to Chicago Midway Airport from C$ 190

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 Midway Airport departing on 7/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Calgary to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Calgary to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Calgary to Chicago.

Cheap last-minute flights

Planning a quick getaway from Calgary to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Calgary to Chicago

Find recent round-trip train or bus tickets from Calgary to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
6:35 a.m. - 5:47 p.m.YYC-MDW
10h 12m1 stop
9:34 a.m. - 8:53 p.m.MDW-YYC
12h 19m2 stops
C$ 308Delta
Find Deal
Thu, 9 Jan - Sun, 12 Jan
6:35 a.m. - 5:47 p.m.YYC-MDW
10h 12m1 stop
9:34 a.m. - 8:53 p.m.MDW-YYC
12h 19m2 stops
C$ 351Delta
Find Deal
Mon, 27 Jan - Thu, 30 Jan
7:45 a.m. - 6:11 p.m.YYC-MDW
9h 26m1 stop
10:10 a.m. - 8:04 p.m.MDW-YYC
10h 54m1 stop
C$ 423Delta
Find Deal
Thu, 13 Feb - Wed, 19 Feb
12:20 p.m. - 10:45 p.m.YYC-MDW
9h 25m1 stop
6:17 p.m. - 3:16 p.m.MDW-YYC
21h 59m2 stops
C$ 450
Find Deal
Thu, 5 Dec - Mon, 9 Dec
12:30 a.m. - 5:12 p.m.YYC-MDW
15h 42m1 stop
12:55 p.m. - 9:36 p.m.MDW-YYC
9h 41m2 stops
C$ 548
Find Deal
Thu, 5 Dec - Sat, 7 Dec
6:00 a.m. - 6:32 p.m.YYC-MDW
11h 32m2 stops
10:38 a.m. - 11:16 p.m.MDW-YYC
13h 38m2 stops
C$ 568Delta
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Fri, 13 Dec - Sun, 15 Dec
4:25 p.m. - 10:20 a.m.YYC-MDW
16h 55m1 stop
12:55 p.m. - 9:36 p.m.MDW-YYC
9h 41m2 stops
C$ 605Porter Airlines
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Thu, 28 Nov - Sat, 7 Dec
7:10 a.m. - 10:20 a.m.YYC-MDW
26h 10m1 stop
11:15 a.m. - 3:28 p.m.MDW-YYC
29h 13m1 stop
C$ 651Porter Airlines
Find Deal
Thu, 28 Nov - Sun, 8 Dec
3:00 p.m. - 6:32 p.m.YYC-MDW
26h 32m1 stop
9:30 a.m. - 8:35 p.m.MDW-YYC
12h 05m1 stop
C$ 690WestJet
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Mon, 25 Nov - Fri, 29 Nov
9:45 p.m. - 9:32 a.m.YYC-MDW
10h 47m2 stops
9:30 a.m. - 7:08 p.m.MDW-YYC
10h 38m2 stops
C$ 708WestJet
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Mon, 25 Nov - Fri, 29 Nov
8:00 a.m. - 10:06 p.m.YYC-MDW
13h 06m2 stops
C$ 190Delta
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Sat, 7 Dec
7:00 a.m. - 6:32 p.m.YYC-MDW
10h 32m1 stop
C$ 191Delta
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Thu, 12 Dec
9:55 a.m. - 11:29 p.m.YYC-MDW
12h 34m1 stop
C$ 202
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Sat, 7 Dec
7:00 a.m. - 6:32 p.m.YYC-MDW
10h 32m2 stops
C$ 225Delta
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Thu, 12 Dec
7:10 p.m. - 10:45 p.m.YYC-MDW
26h 35m2 stops
C$ 232
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Wed, 4 Dec
7:45 a.m. - 6:11 p.m.YYC-MDW
9h 26m1 stop
C$ 271Delta
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Mon, 10 Mar
9:45 p.m. - 12:20 a.m.YYC-MDW
25h 35m3 stops
C$ 272
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Thu, 12 Dec
6:35 a.m. - 5:47 p.m.YYC-MDW
10h 12m1 stop
C$ 385WestJet
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Fri, 7 Feb
8:15 p.m. - 10:12 a.m.YYC-MDW
12h 57m2 stops
C$ 393WestJet
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Fri, 7 Feb
8:00 p.m. - 9:49 p.m.YYC-MDW
24h 49m2 stops
C$ 423WestJet
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Mon, 10 Mar
4:35 p.m. - 12:34 p.m.YYC-MDW
18h 59m1 stop
1:29 p.m. - 9:04 a.m.MDW-YYC
20h 35m2 stops
C$ 704
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Wed, 6 Nov - Thu, 14 Nov
4:35 p.m. - 12:34 p.m.YYC-MDW
18h 59m1 stop
12:00 p.m. - 9:45 p.m.MDW-YYC
10h 45m1 stop
C$ 809
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Wed, 6 Nov - Thu, 14 Nov
4:35 p.m. - 12:34 p.m.YYC-MDW
18h 59m1 stop
12:00 p.m. - 9:45 p.m.MDW-YYC
10h 45m1 stop
C$ 812
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Wed, 6 Nov - Thu, 14 Nov
4:35 p.m. - 12:34 p.m.YYC-MDW
18h 59m1 stop
12:00 p.m. - 9:45 p.m.MDW-YYC
10h 45m1 stop
C$ 823
Find Deal
Wed, 6 Nov - Thu, 14 Nov
9:55 a.m. - 9:59 a.m.YYC-MDW
23h 04m1 stop
9:30 a.m. - 9:46 p.m.MDW-YYC
13h 16m2 stops
C$ 1,192WestJet
Find Deal
Tue, 5 Nov - Thu, 14 Nov
9:55 a.m. - 9:59 a.m.YYC-MDW
23h 04m1 stop
9:30 a.m. - 9:46 p.m.MDW-YYC
13h 16m2 stops
C$ 1,194WestJet
Find Deal
Tue, 5 Nov - Thu, 14 Nov
6:45 a.m. - 9:38 p.m.YYC-MDW
13h 53m2 stops
9:31 a.m. - 8:35 p.m.MDW-YYC
12h 04m2 stops
C$ 1,219Delta
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Tue, 5 Nov - Thu, 14 Nov
7:10 a.m. - 10:20 a.m.YYC-MDW
26h 10m1 stop
11:15 a.m. - 3:28 p.m.MDW-YYC
29h 13m1 stop
C$ 1,268Porter Airlines
Find Deal
Tue, 5 Nov - Thu, 14 Nov
7:10 a.m. - 10:20 a.m.YYC-MDW
26h 10m1 stop
11:15 a.m. - 3:28 p.m.MDW-YYC
29h 13m1 stop
C$ 1,272Porter Airlines
Find Deal
Tue, 5 Nov - Wed, 13 Nov
6:45 a.m. - 9:38 p.m.YYC-MDW
13h 53m2 stops
9:31 a.m. - 8:35 p.m.MDW-YYC
12h 04m2 stops
C$ 1,324Delta
Find Deal
Tue, 5 Nov - Wed, 13 Nov

Porter Airlines flights from Calgary to Chicago Midway Airport

Our best Porter Airlines deals on Calgary to Chicago Midway Airport flight tickets
Porter Airlines
28 Nov
YYC4:25 p.m.Calgary
16h 55m
1 stop
MDW10:20 a.m.Chicago Midway
7 Dec
MDW12:55 p.m.Chicago Midway
9h 41m
2 stops
YYC9:36 p.m.Calgary
Porter Airlines
28 Nov
YYC7:10 a.m.Calgary
26h 10m
1 stop
MDW10:20 a.m.Chicago Midway
8 Dec
MDW11:15 a.m.Chicago Midway
29h 13m
1 stop
YYC3:28 p.m.Calgary
Porter Airlines
23 Nov
YYC12:55 p.m.Calgary
20h 25m
1 stop
MDW10:20 a.m.Chicago Midway
24 Nov
MDW5:35 p.m.Chicago Midway
22h 53m
1 stop
YYC3:28 p.m.Calgary

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
9 Jan
YYC6:35 a.m.Calgary
10h 12m
1 stop
MDW5:47 p.m.Chicago Midway
12 Jan
MDW9:34 a.m.Chicago Midway
12h 19m
2 stops
YYC8:53 p.m.Calgary
Delta
27 Jan
YYC6:35 a.m.Calgary
10h 12m
1 stop
MDW5:47 p.m.Chicago Midway
30 Jan
MDW9:34 a.m.Chicago Midway
12h 19m
2 stops
YYC8:53 p.m.Calgary
Delta
13 Feb
YYC7:45 a.m.Calgary
9h 26m
1 stop
MDW6:11 p.m.Chicago Midway
19 Feb
MDW10:10 a.m.Chicago Midway
10h 54m
1 stop
YYC8:04 p.m.Calgary

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

When is the cheapest time to fly from Calgary to Chicago Midway Airport?

Calgary to Chicago Midway Airport flights are currently only available in the morning

Can stopping save me money on Calgary to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Calgary to Chicago Midway Airport.

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$ 190

Fastest flight time

5h 35m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Calgary in the past 72 hours is C$ 190. The best round-trip flight deal from Calgary to Chicago Midway Airport found on momondo in the last 72 hours is C$ 308.
The fastest flight from Calgary to Chicago Midway Airport takes 5h 35m
There are no direct flights from Calgary to Chicago Midway Airport. Popular non-direct route for this connection is Calgary Airport - 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 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.


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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