MDW - YYC

$100 Find Cheap Flights from Chicago Midway Airport to Calgary

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Calgary departing on 9/30. 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
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Calgary

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Calgary, 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 Chicago to Calgary, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

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

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

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

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Calgary (MDW-YYC)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Calgary 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Calgary

Tue, Sep 30 - Fri, Oct 3
Delta Logo
1:43 pm - 8:42 pmMDW-YYC
7h 59m1 stop
Delta Logo
6:40 am - 5:35 pmYYC-MDW
9h 55m1 stop
$251Delta
Find Deal
Wed, Oct 15 - Tue, Oct 21
Multiple Airlines Logo
8:05 am - 12:44 amMDW-YYC
17h 39m2 stops
Multiple Airlines Logo
12:30 am - 1:38 pmYYC-MDW
12h 08m1 stop
$256Multiple Airlines
Find Deal
Sat, Nov 8 - Sat, Nov 15
Delta Logo
1:06 pm - 11:02 pmMDW-YYC
10h 56m2 stops
Delta Logo
6:20 am - 1:07 pmYYC-MDW
5h 47m1 stop
$261Delta
Find Deal
Sat, Nov 8 - Sat, Nov 15
Delta Logo
9:20 am - 1:54 pmMDW-YYC
5h 34m1 stop
Delta Logo
6:20 am - 1:07 pmYYC-MDW
5h 47m1 stop
$262Delta
Find Deal
Sat, Nov 8 - Sat, Nov 15
Delta Logo
11:10 am - 11:02 pmMDW-YYC
12h 52m2 stops
Delta Logo
6:20 am - 6:08 pmYYC-MDW
10h 48m2 stops
$266Delta
Find Deal
Sat, Nov 8 - Sat, Nov 15
Delta Logo
3:00 pm - 8:47 pmMDW-YYC
6h 47m1 stop
Delta Logo
6:20 am - 6:08 pmYYC-MDW
10h 48m2 stops
$271Delta
Find Deal
Thu, Nov 6 - Sun, Nov 9
Multiple Airlines Logo
1:37 pm - 11:44 amMDW-YYC
23h 07m1 stop
Multiple Airlines Logo
8:15 pm - 6:39 pmYYC-MDW
21h 24m2 stops
$277Multiple Airlines
Find Deal
Mon, Oct 20 - Tue, Oct 28
Multiple Airlines Logo
10:56 pm - 12:12 pmMDW-YYC
14h 16m1 stop
Multiple Airlines Logo
8:55 am - 12:41 pmYYC-MDW
26h 46m1 stop
$283Multiple Airlines
Find Deal
Mon, Sep 29 - Thu, Oct 2
Delta Logo
9:20 am - 1:32 pmMDW-YYC
5h 12m1 stop
Delta Logo
6:40 am - 5:35 pmYYC-MDW
9h 55m1 stop
$289Delta
Find Deal
Sat, Oct 4 - Tue, Oct 7
Multiple Airlines Logo
6:15 am - 8:00 pmMDW-YYC
14h 45m1 stop
Multiple Airlines Logo
9:00 am - 1:38 pmYYC-MDW
27h 38m2 stops
$291Multiple Airlines
Find Deal

Everything you should know

Cheapest round-trip
$251
Delta
Tue 9/30Fri 10/3
MDW - YYC • 1 stop
Cheapest one-way
$100
Delta
Tue 9/30
MDW - YYC • 1 stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Calgary!
Booking Insights

KAYAK's insights & trends for Midway to Calgary flights

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

What is the most popular layover airport when flying from Chicago Midway Airport to Calgary?

Percentage of 1-stop round-trip flights from Chicago Midway Airport to Calgary chosen by KAYAK users via each layover airport in the last 12 months (only includes trips with the same layover airport on both legs).

Detroit (DTW) is the top choice – 50% of KAYAK users who clicked on 1-stop flights from Chicago Midway Airport to Calgary picked an itinerary connecting there.

What is the cheapest layover airport when flying from Chicago Midway Airport to Calgary?

Average round-trip price for 1-stop flights from Chicago Midway Airport to Calgary clicked by KAYAK users in the last 12 months (only includes trips with the same layover airport on both legs).

Flights via Detroit (DTW) offer the most affordable fares, with an average round-trip price of $566.

Which layover airport offers the shortest total travel time from Chicago Midway Airport to Calgary?

Shortest average total travel time for 1-stop one-way flights from Chicago Midway Airport to Calgary via different layover airports, based on KAYAK user data from the last 12 months.

Consider flying via Minneapolis (MSP) for the shortest journey. The average one-way travel time for flights connecting there is 5h 34m.

Which layover airport has the quickest connection when flying from Chicago Midway Airport to Calgary?

Average layover duration at different layover airports for 1-stop one-way flights from Chicago Midway Airport to Calgary, based on KAYAK user data from the last 12 months.

If you prefer a quick connection, Minneapolis (MSP) often has the shortest layovers from Chicago Midway Airport to Calgary, with an average of 1h 01m.

Find deals

Good to know

Cheapest flight$100
Flight from Chicago Midway Airport to Calgary

When to book flights from Midway to Calgary

Are your dates flexible? Find out the best times to travel from Midway to Calgary 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 Chicago Midway Airport to Calgary flights

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Calgary was $100 for a one-way ticket and $251 for a round-trip.

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

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

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

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

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

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

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

    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 Chicago Midway Airport to Calgary.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Calgary from Chicago Midway Airport 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 Chicago Midway Airport to Calgary?

    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 Calgary with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and YYC 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 Chicago Midway Airport to Calgary?

    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 Calgary from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Everything you need to know for your flight from Midway to Calgary

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Calgary (YYC)

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.