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Midway

$147+ Cheap flights from Calgary (YYC) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — MDW
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheap flight deals from Calgary to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Calgary (YYC) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 3, 2025.

Round-trip from

$254
(Delta)

One-way from

$147
(Delta)

Popular in

December

Cheapest in

April

Average price

$349
From Calgary to Chicago Midway
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One-way flight from Calgary to Chicago Midway
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Highest demand for flights based on searches. 22% potential increase in price ($83 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Calgary to Midway

Cheapest flights from Calgary to Midway
Explore the most affordable flight options available from Calgary to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.

This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/307:55 amYYC - MDW
2 stops8h 42mDelta
Mon 9/19:30 amMDW - YYC
2 stops12h 13mDelta
Deal found 7/2$254
This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/248:55 amYYC - MDW
1 stop10h 59mMultiple Airlines
Mon 8/256:31 pmMDW - YYC
1 stop21h 15mMultiple Airlines
Deal found 7/1$299

Cheapflights Fare Finder

Customize your flight search to find flights from Calgary to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 3, 2025.
Use the filters below to find and compare flights from Calgary to Chicago Midway Airport that are best for you.

Fly from

Calgary

Fly to

Midway

Route

Depart

Return

Price

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 8/30

7:55 am-5:37 pm

2 stops8h 42m

Chicago Midway

Mon 9/1

9:30 am-8:43 pm

2 stops12h 13m

$254

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 7/24

8:55 am-8:54 pm

1 stop10h 59m

Chicago Midway

Mon 8/25

6:31 pm-2:46 pm

1 stop21h 15m

$299

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 8/24

6:40 am-1:03 pm

1 stop5h 23m

$147

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 9/11

7:00 am-11:20 pm

2 stops15h 20m

$150

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 8/9

4:35 pm-8:45 am

1 stop15h 10m

$215

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Best time to book a flight from Calgary to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Calgary with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated July 3, 2025.
Read reviews from past customers who have flown Porter Airlines and Delta from Calgary to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
298 reviews

Overall

8.0

Crew

8.7

Entertainment

7.0

Boarding

8.2

Food

7.7

Comfort

8.1

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
298 reviews
Porter Airlines
8.0
Very good
298 reviews

Overall

8.0

Crew

8.7

Entertainment

7.0

Boarding

8.2

Food

7.7

Comfort

8.1

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,982 reviews
Porter Airlines
8.0
Very good
298 reviews

Overall

8.0

Crew

8.7

Entertainment

7.0

Boarding

8.2

Food

7.7

Comfort

8.1

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

Related info for your journey

Find useful and relevant information for your journey from Calgary to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Calgary to Chicago Midway?

    For a flight from Calgary to Chicago Midway, you will be flying from Calgary. Calgary (YYC) is just 5.8 mi from the center of the city. Calgary is the only Calgary airport and it handles 0 outbound flights to Chicago Midway per day. 0 airlines have flights to Chicago Midway from Calgary on a regular basis.

  • What is the cheapest airline to fly from Calgary to Chicago Midway Airport round-trip?

    Our cheapest airline available from Calgary to Chicago Midway Airport is Delta. Our recent data shows that you can find tickets from as low as $254 on this airline.

  • Can I find deals for flights from Calgary to Midway that include hotel bookings?

    Yes. In addition to deals on Calgary to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Calgary to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Calgary to Midway.

  • Can I find deals for business class flights from Calgary to Midway?

    Yes. Cheapflights offers flight deals from Calgary to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, April is the cheapest month in which you can book a flight from Calgary to Chicago Midway Airport (average of $160). Flying from Calgary to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Calgary?

Book flights to Calgary if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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