Find flights
Deals
Insights
When to book
FAQs & Tips

YYC - MDW

$139 Find cheap flights from Calgary to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Calgary to Midway departing on 10/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sat 6/29
Sat 7/6

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Calgary to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Calgary to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 42,686,544 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Calgary to Midway (YYC-MDW)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Calgary to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
11:00 am - 11:47 amYYC-MDW
23h 47m1 stop
5:55 am - 4:47 pmMDW-YYC
11h 52m1 stop
$271
Find Deal
Fri, Jun 21 - Wed, Jun 26
12:30 am - 4:51 pmYYC-MDW
15h 21m1 stop
5:55 am - 4:47 pmMDW-YYC
11h 52m1 stop
$302
Find Deal
Wed, Jun 19 - Wed, Jun 26
11:00 am - 9:45 pmYYC-MDW
9h 45m1 stop
7:05 am - 4:47 pmMDW-YYC
10h 42m1 stop
$318
Find Deal
Thu, Jul 4 - Sat, Jul 6
12:30 am - 2:34 pmYYC-MDW
13h 04m1 stop
5:55 am - 4:47 pmMDW-YYC
11h 52m1 stop
$324
Find Deal
Tue, Jun 11 - Wed, Jun 19
6:50 am - 6:05 pmYYC-MDW
10h 15m1 stop
11:59 am - 11:21 pmMDW-YYC
12h 22m2 stops
$490Delta
Find Deal
Tue, Nov 5 - Sun, Nov 10
10:00 am - 9:46 pmYYC-MDW
10h 46m1 stop
10:28 am - 7:59 pmMDW-YYC
10h 31m1 stop
$515WestJet
Find Deal
Wed, Aug 14 - Wed, Aug 21
6:45 am - 1:43 pmYYC-MDW
5h 58m1 stop
10:28 am - 12:40 amMDW-YYC
15h 12m2 stops
$517WestJet
Find Deal
Tue, Aug 13 - Wed, Aug 21
7:35 am - 9:37 pmYYC-MDW
13h 02m2 stops
8:00 am - 9:05 pmMDW-YYC
14h 05m2 stops
$542Porter Airlines
Find Deal
Fri, Jun 14 - Mon, Jun 17
9:30 am - 9:37 pmYYC-MDW
11h 07m2 stops
8:00 am - 9:44 pmMDW-YYC
14h 44m2 stops
$563Porter Airlines
Find Deal
Tue, Jul 23 - Fri, Jul 26
6:50 am - 5:03 pmYYC-MDW
9h 13m2 stops
11:59 am - 11:21 pmMDW-YYC
12h 22m2 stops
$575Delta
Find Deal
Tue, Nov 5 - Sun, Nov 10

Flights from Calgary to Midway - Travel Insights & Trends

Get data-powered insights and trends into flights from Calgary to Midway to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Calgary to Chicago Midway Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the past 3 days, the cheapest one-way tickets to Chicago Midway Airport from Calgary were found on Delta ($139) and Porter Airlines ($260), and the lowest round-trip tickets were found on Delta ($490) and WestJet ($515).

Good to know

Cheapest flight

$139
Flight from Calgary to Chicago Midway Airport

When to book flights from Calgary to Midway

Are your dates flexible? Find out the best times to travel from Calgary to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Calgary to Chicago Midway Airport flights

  • What is the cheapest flight from Calgary to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Calgary to Chicago Midway Airport was $139 for a one-way ticket and $271 for a round-trip.

  • Do I need a passport to fly between Calgary and Chicago Midway Airport?

    Yes, you’ll need a passport to travel to Chicago Midway Airport from Calgary.

  • Which aircraft models fly most regularly from Calgary to Chicago Midway Airport?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Calgary to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Calgary and Chicago Midway Airport.

  • How does KAYAK find such low prices on flights from Calgary to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Calgary to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Calgary to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Calgary is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Calgary to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Calgary with another airline. Booking your flights between Calgary and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Calgary to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Calgary up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Book cheap flights from Calgary to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Calgary to Chicago found on KAYAK in the last 72 hours.
10/5Sat
1 stopDelta
10h 15mYYC-MDW
$139
6/12Wed
1 stop
23h 08mYYC-MDW
$145
6/11Tue
1 stop
13h 04mYYC-MDW
$149
6/4Tue
1 stopDelta
9h 12mYYC-MDW
$153
6/5Wed
1 stopDelta
9h 12mYYC-MDW
$154
6/4Tue
2 stops
31h 30mYYC-MDW
$164
6/19Wed
2 stopsPorter Airlines
13h 02mYYC-MDW
$260
7/27Sat
2 stopsWestJet
10h 56mYYC-MDW
$277
8/27Tue
1 stopWestJet
10h 14mYYC-MDW
$282
6/16Sun
2 stopsPorter Airlines
13h 02mYYC-MDW
$284

Search by stops

Search by airline

Search by price

Calgary - Chicago Midway Airport Flights

Departure:

Calgary (YYC)Canada

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Calgary

Cabin classes:

Browse origins:

Browse destinations: