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Cheap flights from Calgary to Chicago Midway Airport from $135

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 6/1. 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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0 bags

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Find the cheapest flights from Calgary to Chicago

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Calgary to Chicago.
 Logo
12:30 am - 9:33 amYYC-MDW
8h 03m1 stop
 Logo
9:34 am - 8:05 pmMDW-YYC
11h 31m1 stop
Fri, May 9 - Tue, May 13
 Logo
12:30 am - 9:33 amYYC-MDW
8h 03m1 stop
 Logo
9:34 am - 8:05 pmMDW-YYC
11h 31m1 stop
Fri, May 9 - Tue, May 13
 Logo
10:00 am - 11:54 pmYYC-MDW
12h 54m1 stop
 Logo
9:34 am - 8:05 pmMDW-YYC
11h 31m1 stop
Sun, May 11 - Tue, May 13
 Logo
10:00 am - 11:54 pmYYC-MDW
12h 54m1 stop
 Logo
9:34 am - 8:05 pmMDW-YYC
11h 31m1 stop
Sun, May 11 - Tue, May 13
Delta Logo
9:15 am - 4:21 pmYYC-MDW
6h 06m1 stop
Delta Logo
10:25 am - 8:05 pmMDW-YYC
10h 40m1 stop
$266Delta
Find Deal
Sat, May 10 - Tue, May 13
Delta Logo
6:45 am - 5:19 pmYYC-MDW
9h 34m1 stop
Delta Logo
12:48 pm - 8:05 pmMDW-YYC
8h 17m1 stop
$268Delta
Find Deal
Sat, May 3 - Fri, May 9
Porter Airlines Logo
7:10 am - 10:20 amYYC-MDW
26h 10m2 stops
Porter Airlines Logo
9:40 am - 10:30 pmMDW-YYC
13h 50m2 stops
$439Porter Airlines
Find Deal
Mon, Apr 28 - Fri, May 2
Porter Airlines Logo
7:00 am - 8:45 amYYC-MDW
24h 45m2 stops
Porter Airlines Logo
5:20 pm - 10:30 pmMDW-YYC
30h 10m2 stops
$560Porter Airlines
Find Deal
Sun, May 11 - Tue, May 13
WestJet Logo
12:30 am - 9:54 amYYC-MDW
8h 24m1 stop
WestJet Logo
12:41 pm - 8:00 pmMDW-YYC
8h 19m1 stop
$590WestJet
Find Deal
Fri, Jun 27 - Mon, Jun 30
WestJet Logo
10:00 am - 9:47 pmYYC-MDW
10h 47m1 stop
WestJet Logo
1:05 pm - 8:00 pmMDW-YYC
7h 55m1 stop
$595WestJet
Find Deal
Mon, Jul 14 - Thu, Jul 17

Porter Airlines flights from Calgary to Chicago Midway Airport

Our best Porter Airlines deals on Calgary to Chicago Midway Airport flight tickets
Porter Airlines
Apr 28
YYC7:10 amCalgary
26h 10m
2 stops
MDW10:20 amChicago Midway
May 2
MDW9:40 amChicago Midway
13h 50m
2 stops
YYC10:30 pmCalgary
Porter Airlines
May 11
YYC7:00 amCalgary
24h 45m
2 stops
MDW8:45 amChicago Midway
May 13
MDW5:20 pmChicago Midway
30h 10m
2 stops
YYC10:30 pmCalgary
Porter Airlines
May 26
YYC7:00 amCalgary
32h 24m
2 stops
MDW4:24 pmChicago Midway
May 28
MDW9:40 amChicago Midway
12h 35m
2 stops
YYC9:15 pmCalgary

Delta flights from Calgary to Chicago Midway Airport

Our best Delta deals on Calgary to Chicago Midway Airport flight tickets
Delta
May 10
YYC9:15 amCalgary
6h 06m
1 stop
MDW4:21 pmChicago Midway
May 13
MDW10:25 amChicago Midway
10h 40m
1 stop
YYC8:05 pmCalgary
Delta
May 3
YYC6:45 amCalgary
9h 34m
1 stop
MDW5:19 pmChicago Midway
May 9
MDW12:48 pmChicago Midway
8h 17m
1 stop
YYC8:05 pmCalgary
Delta
May 12
YYC12:30 amCalgary
10h 23m
1 stop
MDW11:53 amChicago Midway
May 19
MDW9:16 amChicago Midway
10h 12m
1 stop
YYC6:28 pmCalgary

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 airline that flies from Calgary to Chicago Midway?

Delta, Porter Airlines, and WestJet are the most popular carriers operating from Calgary to Chicago Midway

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

$135

Fastest flight time

5h 27m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Calgary in the past 72 hours is $135. The best round-trip flight deal from Calgary to Chicago Midway Airport found on momondo in the last 72 hours is $232.
The fastest flight from Calgary to Chicago Midway Airport takes 5h 27m
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?

    There are 1396.3 mi between Calgary and Chicago Midway. 5h 27m is a normal flight duration for this route.

  • 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 updated daily.

  • How old do you have to be to fly from Calgary Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check 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 required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.


Traveling to a place near Chicago?

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Why use momondo?

Why should I use momondo to find a flight deal from Calgary to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Calgary to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Calgary to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Calgary on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Calgary to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Calgary.

I’m not ready to book a flight from Calgary to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Calgary to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.


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