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Cheap flights from Calgary to Chicago Midway Airport from C$ 221

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 27/1. 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
1:26 p.m. - 8:53 p.m.MDW-YYC
8h 27m1 stop
C$ 309Delta
Find Deal
Sat, 25 Jan - Mon, 27 Jan
6:35 a.m. - 6:14 p.m.YYC-MDW
10h 39m2 stops
9:34 a.m. - 8:53 p.m.MDW-YYC
12h 19m2 stops
C$ 358Delta
Find Deal
Fri, 24 Jan - Sun, 26 Jan
12:30 a.m. - 11:59 a.m.YYC-MDW
10h 29m1 stop
9:34 a.m. - 8:53 p.m.MDW-YYC
12h 19m2 stops
C$ 385Delta
Find Deal
Thu, 23 Jan - Sun, 26 Jan
6:35 a.m. - 5:47 p.m.YYC-MDW
10h 12m1 stop
9:34 a.m. - 10:30 p.m.MDW-YYC
13h 56m2 stops
C$ 392Delta
Find Deal
Tue, 7 Jan - Fri, 17 Jan
12:30 a.m. - 11:54 a.m.YYC-MDW
10h 24m1 stop
12:43 p.m. - 10:55 p.m.MDW-YYC
11h 12m1 stop
C$ 419
Find Deal
Thu, 23 Jan - Sun, 26 Jan
8:00 a.m. - 12:13 a.m.YYC-MDW
15h 13m2 stops
1:30 p.m. - 12:22 a.m.MDW-YYC
11h 52m1 stop
C$ 566
Find Deal
Thu, 12 Dec - Sun, 15 Dec
6:35 a.m. - 12:46 p.m.YYC-MDW
5h 11m1 stop
1:26 p.m. - 8:53 p.m.MDW-YYC
8h 27m1 stop
C$ 697WestJet
Find Deal
Thu, 9 Jan - Mon, 13 Jan
6:35 a.m. - 12:46 p.m.YYC-MDW
5h 11m1 stop
10:19 a.m. - 7:08 p.m.MDW-YYC
9h 49m2 stops
C$ 702WestJet
Find Deal
Thu, 9 Jan - Mon, 13 Jan
4:25 p.m. - 4:40 p.m.YYC-MDW
23h 15m1 stop
5:35 p.m. - 11:43 a.m.MDW-YYC
19h 08m1 stop
C$ 938Porter Airlines
Find Deal
Wed, 25 Dec - Thu, 2 Jan
12:50 p.m. - 11:10 a.m.YYC-MDW
21h 20m1 stop
11:15 a.m. - 11:43 a.m.MDW-YYC
25h 28m1 stop
C$ 940Porter Airlines
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Thu, 5 Dec - Sun, 8 Dec
8:00 a.m. - 8:12 p.m.YYC-MDW
11h 12m1 stop
C$ 221
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Mon, 27 Jan
8:00 p.m. - 4:16 p.m.YYC-MDW
19h 16m2 stops
C$ 225
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Mon, 20 Jan
8:00 a.m. - 12:17 a.m.YYC-MDW
15h 17m2 stops
C$ 233
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Mon, 27 Jan
7:10 p.m. - 8:14 p.m.YYC-MDW
24h 04m1 stop
C$ 240
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Thu, 5 Dec
6:35 a.m. - 5:47 p.m.YYC-MDW
10h 12m1 stop
C$ 268Delta
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Mon, 3 Mar
6:35 a.m. - 5:47 p.m.YYC-MDW
10h 12m1 stop
C$ 300Delta
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Sat, 15 Feb
7:00 a.m. - 9:46 p.m.YYC-MDW
13h 46m2 stops
C$ 370Delta
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Fri, 29 Nov
7:00 a.m. - 5:11 p.m.YYC-MDW
9h 11m1 stop
C$ 376WestJet
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Wed, 25 Dec
11:30 p.m. - 5:47 p.m.YYC-MDW
17h 17m2 stops
C$ 440WestJet
Find Deal
Mon, 3 Mar
7:00 a.m. - 6:32 p.m.YYC-MDW
10h 32m1 stop
C$ 447WestJet
Find Deal
Wed, 4 Dec
7:00 a.m. - 6:32 p.m.YYC-MDW
10h 32m1 stop
7:17 p.m. - 1:50 p.m.MDW-YYC
19h 33m1 stop
C$ 1,490WestJet
Find Deal
Fri, 22 Nov - Mon, 25 Nov

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
25 Jan
YYC6:35 a.m.Calgary
10h 12m
1 stop
MDW5:47 p.m.Chicago Midway
27 Jan
MDW1:26 p.m.Chicago Midway
8h 27m
1 stop
YYC8:53 p.m.Calgary
Delta
24 Jan
YYC6:35 a.m.Calgary
10h 39m
2 stops
MDW6:14 p.m.Chicago Midway
26 Jan
MDW9:34 a.m.Chicago Midway
12h 19m
2 stops
YYC8:53 p.m.Calgary
Delta
23 Jan
YYC12:30 a.m.Calgary
10h 29m
1 stop
MDW11:59 a.m.Chicago Midway
26 Jan
MDW9:34 a.m.Chicago Midway
12h 19m
2 stops
YYC8:53 p.m.Calgary

WestJet flights from Calgary to Chicago Midway Airport

Our best WestJet deals on Calgary to Chicago Midway Airport flight tickets
WestJet
9 Jan
YYC6:35 a.m.Calgary
5h 11m
1 stop
MDW12:46 p.m.Chicago Midway
13 Jan
MDW1:26 p.m.Chicago Midway
8h 27m
1 stop
YYC8:53 p.m.Calgary
WestJet
9 Jan
YYC6:35 a.m.Calgary
5h 11m
1 stop
MDW12:46 p.m.Chicago Midway
13 Jan
MDW10:19 a.m.Chicago Midway
9h 49m
2 stops
YYC7:08 p.m.Calgary
WestJet
13 Feb
YYC9:45 p.m.Calgary
11h 27m
2 stops
MDW10:12 a.m.Chicago Midway
19 Feb
MDW12:44 p.m.Chicago Midway
8h 20m
1 stop
YYC8:04 p.m.Calgary

See travel insights to Chicago from

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

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Our most recent data shows that the best time of day to fly to Chicago Midway Airport is at noon. Flights from Calgary to Chicago Midway Airport during this time can be as low as C$ 0. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the morning when prices are around C$ 807.

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

You could potentially save up to 1% 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 11m

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$ 309.
The fastest flight from Calgary to Chicago Midway Airport takes 5h 11m
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 11m.

  • 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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