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 7/2. 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 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
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41,299,237 searches in the past 7 days on KAYAK

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Flights Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Calgary to Midway

Tue, Sep 9 - Wed, Sep 17
Delta Logo
6:40 am - 5:37 pmYYC-MDW
9h 57m1 stop
Delta Logo
1:00 pm - 8:54 pmMDW-YYC
8h 54m2 stops
$240Delta
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Tue, Sep 9 - Tue, Sep 16
Delta Logo
6:40 am - 5:37 pmYYC-MDW
9h 57m1 stop
Delta Logo
9:30 am - 8:54 pmMDW-YYC
12h 24m2 stops
$256Delta
Find Deal
Sat, Sep 13 - Wed, Sep 17
Delta Logo
7:00 am - 6:07 pmYYC-MDW
10h 07m2 stops
Delta Logo
1:00 pm - 6:24 pmMDW-YYC
6h 24m1 stop
$265Delta
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Wed, Jul 23 - Tue, Jul 29
Delta Logo
6:45 am - 5:39 pmYYC-MDW
9h 54m1 stop
Delta Logo
1:09 pm - 8:50 pmMDW-YYC
8h 41m2 stops
$278Delta
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Fri, Jul 25 - Sat, Aug 2
Logo
12:30 am - 10:35 pmYYC-MDW
21h 05m1 stop
Logo
6:20 am - 12:44 amMDW-YYC
19h 24m2 stops
$348
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Tue, Jul 8 - Tue, Jul 15
Logo
11:55 pm - 4:24 pmYYC-MDW
15h 29m2 stops
Logo
11:39 am - 8:00 pmMDW-YYC
9h 21m1 stop
$377
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Mon, Jul 21 - Tue, Aug 5
Porter Airlines Logo
7:00 am - 4:24 pmYYC-MDW
32h 24m2 stops
Porter Airlines Logo
5:20 pm - 9:20 pmMDW-YYC
29h 00m2 stops
$460Porter Airlines
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Thu, Jul 17 - Sun, Jul 20
Porter Airlines Logo
11:55 pm - 4:24 pmYYC-MDW
15h 29m2 stops
Porter Airlines Logo
5:20 pm - 4:55 pmMDW-YYC
24h 35m2 stops
$520Porter Airlines
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Fri, Jul 25 - Sat, Aug 2
WestJet Logo
12:30 am - 9:42 pmYYC-MDW
20h 12m1 stop
WestJet Logo
12:43 pm - 10:15 pmMDW-YYC
10h 32m1 stop
$645WestJet
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Mon, Jul 21 - Tue, Jul 22
WestJet Logo
12:30 am - 9:45 amYYC-MDW
8h 15m1 stop
WestJet Logo
12:43 pm - 8:00 pmMDW-YYC
8h 17m1 stop
$653WestJet
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KAYAK's insights & trends for Calgary to Midway flights

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 round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Calgary to Chicago Midway Airport were found on Delta ($240) and Porter Airlines ($460).

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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 $240 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.

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

Information on your arrival and departure airports

Calgary (YYC)
Midway (MDW)

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