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Cheap flights from Calgary (YYC) to Midway (MDW) from $134

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 8/23. 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.
YYC — MDW
Jun 16 — Jun 231
From?
To?
Sun 6/16
Sun 6/23
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 June 11, 2024.

Round-trip from

$222

One-way from

$134
From Calgary to Chicago Midway
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One-way flight from Calgary to Chicago Midway
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How far in advance should I book a flight from Calgary to Chicago Midway Airport?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 46 days in advance, which can save you up to 91% on flights from Calgary to Chicago Midway Airport compared to booking the week you need them. Waiting 46 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $333. For sooner than that we have options available in the next 3 days from $539.

What is the cheapest month to fly from Calgary to Chicago Midway Airport?

Our data shows that January tends to be the cheapest month to fly to Chicago Midway Airport from Calgary. Users have commonly found prices around $389 for the month, but tickets can be as low as $215. Due to multiple factors, prepare for potentially higher prices in July.

What is the cheapest time of day to fly from YYC to MDW?

When flying from Calgary to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap Calgary to Midway flights in June & July 2024

Find cheap flight options from Calgary to Midway specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,117,830 searches. Prices were last updated on June 11, 2024.
Check out some of the best flight deals from Calgary to Chicago in 2024. Check back in a little while for more flight options.
Thu 7/1111:00 amYYC - MDW
1 stop10h 00mMultiple Airlines
Mon 7/156:15 amMDW - YYC
1 stop11h 32mMultiple Airlines
Deal found 6/10$265
Fri 7/266:50 pmYYC - MDW
1 stop15h 23mMultiple Airlines
Sun 7/286:00 amMDW - YYC
1 stop11h 47mMultiple Airlines
Deal found 6/10$281
Fri 7/196:50 pmYYC - MDW
1 stop15h 23mMultiple Airlines
Tue 7/236:00 amMDW - YYC
1 stop11h 47mMultiple Airlines
Deal found 6/9$294
Sat 7/2011:00 amYYC - MDW
1 stop10h 00mMultiple Airlines
Tue 7/236:00 amMDW - YYC
1 stop11h 47mMultiple Airlines
Deal found 6/9$307
Fri 7/196:50 pmYYC - MDW
1 stop15h 23mMultiple Airlines
Mon 7/228:59 pmMDW - YYC
1 stop26h 03mMultiple Airlines
Deal found 6/10$308
Fri 7/262:00 pmYYC - MDW
2 stops14h 33mMultiple Airlines
Sun 7/286:00 amMDW - YYC
1 stop11h 47mMultiple Airlines
Deal found 6/10$316
Wed 7/107:30 pmYYC - MDW
1 stop9h 03mMultiple Airlines
Wed 7/1712:23 pmMDW - YYC
1 stop10h 36mMultiple Airlines
Deal found 6/10$319
Thu 7/112:00 pmYYC - MDW
2 stops13h 45mMultiple Airlines
Mon 7/156:15 amMDW - YYC
1 stop11h 32mMultiple Airlines
Deal found 6/10$342
Wed 6/197:30 pmYYC - MDW
1 stop8h 59mMultiple Airlines
Mon 6/245:55 amMDW - YYC
1 stop11h 52mMultiple Airlines
Deal found 6/11$346

Calgary to Midway 2024 flight deals

Discover exclusive flight deals for travel between Calgary and Midway in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,117,830 searches. Data last updated June 11, 2024.
Check out some of the best flight deals from Calgary to Chicago in 2024. Check back in a little while for more flight options.
Fri 10/256:50 amYYC - MDW
1 stop10h 15mDelta
Tue 10/2911:59 amMDW - YYC
1 stop9h 44mDelta
Deal found 6/10$257
Fri 10/256:50 amYYC - MDW
1 stop10h 15mDelta
Tue 10/2911:59 amMDW - YYC
2 stops12h 22mDelta
Deal found 6/11$258
Thu 7/1111:00 amYYC - MDW
1 stop10h 00mMultiple Airlines
Mon 7/156:15 amMDW - YYC
1 stop11h 32mMultiple Airlines
Deal found 6/10$265
Fri 7/266:50 pmYYC - MDW
1 stop15h 23mMultiple Airlines
Sun 7/286:00 amMDW - YYC
1 stop11h 47mMultiple Airlines
Deal found 6/10$281
Wed 9/1112:30 amYYC - MDW
1 stop9h 25mMultiple Airlines
Mon 9/1610:00 amMDW - YYC
1 stop11h 03mMultiple Airlines
Deal found 6/9$290
Fri 7/196:50 pmYYC - MDW
1 stop15h 23mMultiple Airlines
Tue 7/236:00 amMDW - YYC
1 stop11h 47mMultiple Airlines
Deal found 6/9$294
Sun 8/113:05 pmYYC - MDW
1 stop19h 23mMultiple Airlines
Fri 8/1611:32 amMDW - YYC
1 stop11h 27mMultiple Airlines
Deal found 6/10$305
Sat 7/2011:00 amYYC - MDW
1 stop10h 00mMultiple Airlines
Tue 7/236:00 amMDW - YYC
1 stop11h 47mMultiple Airlines
Deal found 6/9$307
Fri 7/196:50 pmYYC - MDW
1 stop15h 23mMultiple Airlines
Mon 7/228:59 pmMDW - YYC
1 stop26h 03mMultiple Airlines
Deal found 6/10$308

Calgary to Midway flights leaving soon

Find last-minute flight options from Calgary to Midway for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,117,830 searches. Data last updated June 11, 2024.
Check out these flights departing soon from Calgary to Chicago. Users should examine the flight details to ensure there are no surprises.
Wed 6/197:30 pmYYC - MDW
1 stop8h 59mMultiple Airlines
Mon 6/245:55 amMDW - YYC
1 stop11h 52mMultiple Airlines
Deal found 6/11$346
Wed 6/199:30 pmYYC - MDW
2 stops18h 21mMultiple Airlines
Mon 6/245:55 amMDW - YYC
1 stop11h 52mMultiple Airlines
Deal found 6/11$415
Thu 6/203:05 pmYYC - MDW
2 stops13h 09mMultiple Airlines
Fri 6/2111:26 amMDW - YYC
1 stop11h 33mMultiple Airlines
Deal found 6/11$516
Tue 6/1812:30 amYYC - MDW
1 stop13h 04mMultiple Airlines
Mon 6/245:55 amMDW - YYC
1 stop11h 52mMultiple Airlines
Deal found 6/11$545
Thu 6/206:50 pmYYC - MDW
1 stop14h 41mMultiple Airlines
Fri 6/218:58 pmMDW - YYC
1 stop15h 58mMultiple Airlines
Deal found 6/11$642
Tue 6/1812:30 amYYC - MDW
1 stop13h 04mMultiple Airlines
Mon 6/247:30 amMDW - YYC
2 stops15h 32mMultiple Airlines
Deal found 6/11$987
Wed 6/191:00 amYYC - MDW
2 stops15h 59mWestJet
Fri 6/212:24 pmMDW - YYC
1 stop7h 02mWestJet
Deal found 6/11$1,087
Fri 6/2112:30 amYYC - MDW
1 stop8h 21mWestJet
Mon 6/249:29 amMDW - YYC
1 stop5h 06mWestJet
Deal found 6/9$1,105
Thu 6/209:30 amYYC - MDW
2 stops11h 07mPorter Airlines
Fri 6/218:00 amMDW - YYC
2 stops14h 05mPorter Airlines
Deal found 6/11$1,114

One-way flights to Midway from Calgary

Search for one-way flight options from Calgary to Midway. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,117,830 searches. Data last updated June 11, 2024.
Some of the best available deals we've found on one-way flights from Calgary to Chicago. Those needing a return flight from Calgary to Chicago can use the search form above.
Fri 8/2311:00 amYYC - MDW
1 stop23h 52mMultiple Airlines
Deal found 6/11$134
Tue 7/911:00 amYYC - MDW
1 stop8h 50mMultiple Airlines
Deal found 6/10$141
Thu 7/1111:00 amYYC - MDW
1 stop10h 00mMultiple Airlines
Deal found 6/10$148
Fri 7/1211:00 amYYC - MDW
1 stop25h 03mMultiple Airlines
Deal found 6/10$153
Wed 8/146:50 pmYYC - MDW
1 stop14h 52mMultiple Airlines
Deal found 6/9$156
Tue 7/911:00 amYYC - MDW
1 stop8h 50mMultiple Airlines
Deal found 6/11$158
Fri 7/196:50 pmYYC - MDW
1 stop15h 23mMultiple Airlines
Deal found 6/10$167
Tue 7/1611:00 amYYC - MDW
1 stop8h 50mMultiple Airlines
Deal found 6/10$170
Tue 8/1312:30 amYYC - MDW
1 stop10h 03mMultiple Airlines
Deal found 6/9$174

Find flights from Calgary to Midway within your budget

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 3,117,830 searches. Data last updated June 11, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$257 - $491

Route

Depart

Return

Price

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Fri 10/25

1 stop10h 15m

Chicago Midway

Tue 10/29

1 stop9h 44m

$257

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Thu 7/11

1 stop10h 00m

Chicago Midway

Mon 7/15

1 stop11h 32m

$265

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Fri 7/26

1 stop15h 23m

Chicago Midway

Sun 7/28

1 stop11h 47m

$281

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Wed 9/11

1 stop9h 25m

Chicago Midway

Mon 9/16

1 stop11h 03m

$290

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Fri 7/19

1 stop15h 23m

Chicago Midway

Tue 7/23

1 stop11h 47m

$294

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Sun 8/11

1 stop19h 23m

Chicago Midway

Fri 8/16

1 stop11h 27m

$305

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Sat 7/20

1 stop10h 00m

Chicago Midway

Tue 7/23

1 stop11h 47m

$307

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Wed 7/10

2 stops11h 07m

Chicago Midway

Wed 7/17

2 stops19h 24m

$465

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Thu 8/22

1 stop10h 53m

Chicago Midway

Tue 8/27

1 stop10h 31m

$491

Flights are sorted by cheapest first

Deals found on 6/10

No data available for this route at this time. Please check back soon.

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.

Temperature and rainfall in Midway by month

Plan your trip to Midway by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

23 - 73.4 °F

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 11, 2024.
To help decide which airline to fly from Calgary to Chicago, see what other customers have to say about Porter Airlines, Delta and WestJet. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
10,277 reviews

Comfort

7.9

Entertainment

8.0

Crew

8.6

Overall

8.0

Food

7.4

Boarding

8.2

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Delta
8.0
Very good
10,277 reviews
Delta
8.0
Very good
10,277 reviews

Comfort

7.9

Entertainment

8.0

Crew

8.6

Overall

8.0

Food

7.4

Boarding

8.2

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Porter Airlines
7.5
Good
380 reviews
Delta
8.0
Very good
10,277 reviews

Comfort

7.9

Entertainment

8.0

Crew

8.6

Overall

8.0

Food

7.4

Boarding

8.2

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

WestJet
7.5
Good
2,842 reviews
Delta
8.0
Very good
10,277 reviews

Comfort

7.9

Entertainment

8.0

Crew

8.6

Overall

8.0

Food

7.4

Boarding

8.2

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

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.

  • Can I find flights from Calgary to Chicago Midway Airport for under $300 on Cheapflights?

    Yes, there are multiple flights from Calgary to Chicago Midway Airport for under $300. The cheapest flight booked recently is on Delta for just $257, but on average you can expect to pay $348.

  • Are there last-minute flights available from Calgary to Chicago Midway Airport for under $400?

    There are currently 11+ open flights from Calgary to Chicago Midway Airport within the next 7 days for less than $400.

  • What are the cheapest airlines flying 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 $257 on this airline. Additional options worth looking into are Porter Airlines and WestJet, starting at $465 and $491 round-trip.

  • What does YYC to MDW mean?

    YYC stands for Calgary Airport, while MDW stands for Chicago Midway Airport. These codes are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry.

  • Can I find deals for flights from Calgary to Midway that include extra baggage allowance?

    The amount of baggage you can bring on your Calgary to Midway flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Calgary to Midway with specific airlines?

    Yes, Cheapflights allows you to browse and filter Calgary to Midway flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Calgary to Midway that allow pets onboard?

    Many airlines flying from Calgary to Midway offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Calgary to Midway?

    Yes, you can often find last-minute deals on Calgary to Midway flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Calgary to Chicago Midway Airport flight deals updated?

    The Calgary to Chicago Midway Airport flight deals you see on this page were last updated on 6/11.

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

    Currently, December is the cheapest month in which you can book a flight from Calgary to Chicago Midway Airport (average of $141). Flying from Calgary to Chicago Midway Airport in July 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

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Search flights from Calgary to Midway by cabin class

Find flights from Calgary to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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