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Cheap flights from Calgary to Chicago Midway Airport from C$ 192

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 4/6. 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
15 May — 22 May1
1 adult
Wed 15/5
Wed 22/5

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 10 May 2024.

Round-trip from

C$ 353
From Calgary to Chicago Midway
Search Deals

How far in advance should I book a flight from Calgary to Chicago Midway Airport?

To save on the cost of your flight from Calgary to Chicago Midway Airport, book at least 46 days before your planned departure. Booking around this time can save you about 105% on the cost of this flight compared to booking a flight leaving this week. We have found prices from C$ 456 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as C$ 832.

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 C$ 536 for the month, but tickets can be as low as C$ 295. Due to multiple factors, prepare for potentially higher prices in July.

When is the cheapest time to fly from Calgary to Chicago Midway Airport (YYC - MDW)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Calgary to Chicago Midway Airport as you normally would.

Cheap Delta flights from Calgary to Midway

Explore cheap flight options specifically provided by Delta for the route between Calgary and Midway. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 437,143 searches. Data last updated 10 May 2024.
Check out some of the cheapest Delta flights we've come across from Calgary to Chicago. Deals update often to give you more flight options matching your criteria
Sat 25/57:55 a.m.YYC - MDW
1 stop8h 00mDelta
Wed 29/58:45 a.m.MDW - YYC
2 stops13h 01mDelta
Deal found 9/5C$ 559
Sat 18/57:55 a.m.YYC - MDW
1 stop8h 00mDelta
Mon 27/59:46 a.m.MDW - YYC
2 stops14h 27mDelta
Deal found 9/5C$ 561
Sat 25/59:00 a.m.YYC - MDW
2 stops22h 51mDelta
Wed 29/59:32 a.m.MDW - YYC
2 stops12h 14mDelta
Deal found 9/5C$ 635
Wed 5/67:55 a.m.YYC - MDW
2 stops13h 06mDelta
Mon 10/610:41 a.m.MDW - YYC
1 stop10h 17mDelta
Deal found 8/5C$ 788
Wed 17/712:30 a.m.YYC - MDW
1 stop7h 44mDelta
Wed 24/79:33 a.m.MDW - YYC
1 stop9h 52mDelta
Deal found 8/5C$ 973
Wed 5/612:30 a.m.YYC - MDW
1 stop10h 22mDelta
Thu 13/612:45 p.m.MDW - YYC
1 stop8h 13mDelta
Deal found 9/5C$ 1,173
Sun 2/612:30 a.m.YYC - MDW
1 stop10h 22mDelta
Sat 8/610:41 a.m.MDW - YYC
1 stop10h 17mDelta
Deal found 8/5C$ 1,678
Tue 4/612:30 a.m.YYC - MDW
1 stop10h 22mDelta
Mon 10/62:24 p.m.MDW - YYC
1 stop7h 02mDelta
Deal found 8/5C$ 2,336

Cheap Porter Airlines flights from Calgary to Midway

Explore cheap flight options specifically provided by Porter Airlines for the route between Calgary and Midway. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 437,143 searches. Data last updated 10 May 2024.
To aid your search, here are some of the cheapest Porter Airlines flights we've found from Calgary to Chicago. If these deals don't fit your criteria, make sure to check back soon as new deals are always added.
Thu 13/69:30 a.m.YYC - MDW
2 stops11h 07mPorter Airlines
Mon 17/68:00 a.m.MDW - YYC
2 stops14h 44mPorter Airlines
Deal found 9/5C$ 698
Fri 7/69:30 a.m.YYC - MDW
2 stops11h 07mPorter Airlines
Fri 14/611:25 a.m.MDW - YYC
2 stops11h 44mPorter Airlines
Deal found 8/5C$ 902
Wed 5/69:30 a.m.YYC - MDW
2 stops11h 07mPorter Airlines
Sun 9/612:15 p.m.MDW - YYC
2 stops10h 54mPorter Airlines
Deal found 8/5C$ 1,012

Cheap Calgary to Midway flights in May & June 2024

Find cheap flight options from Calgary to Midway specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 437,143 searches. Prices were last updated on 10 May 2024.
These are some of the most attractive deals on flights from Calgary to Chicago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Tue 4/612:30 a.m.YYC - MDW
1 stop13h 04mMultiple Airlines
Tue 11/61:50 p.m.MDW - YYC
2 stops11h 53mMultiple Airlines
Deal found 8/5C$ 376
Mon 3/612:30 a.m.YYC - MDW
1 stop8h 27mMultiple Airlines
Tue 11/68:02 p.m.MDW - YYC
1 stop19h 37mMultiple Airlines
Deal found 8/5C$ 389
Mon 3/612:30 a.m.YYC - MDW
1 stop8h 27mMultiple Airlines
Tue 11/61:50 p.m.MDW - YYC
2 stops11h 53mMultiple Airlines
Deal found 8/5C$ 391
Tue 4/67:30 p.m.YYC - MDW
1 stop8h 10mMultiple Airlines
Tue 11/68:02 p.m.MDW - YYC
1 stop19h 37mMultiple Airlines
Deal found 8/5C$ 395
Tue 4/612:30 a.m.YYC - MDW
1 stop13h 04mMultiple Airlines
Wed 12/611:26 a.m.MDW - YYC
1 stop11h 39mMultiple Airlines
Deal found 8/5C$ 398
Mon 3/612:30 a.m.YYC - MDW
1 stop8h 27mMultiple Airlines
Wed 12/611:26 a.m.MDW - YYC
1 stop11h 39mMultiple Airlines
Deal found 8/5C$ 413
Sun 2/612:30 a.m.YYC - MDW
1 stop13h 11mMultiple Airlines
Tue 11/61:50 p.m.MDW - YYC
2 stops11h 53mMultiple Airlines
Deal found 8/5C$ 444
Sun 2/612:30 a.m.YYC - MDW
1 stop13h 11mMultiple Airlines
Wed 12/61:43 p.m.MDW - YYC
2 stops12h 00mMultiple Airlines
Deal found 8/5C$ 456
Thu 6/611:00 a.m.YYC - MDW
1 stop9h 45mMultiple Airlines
Tue 11/61:50 p.m.MDW - YYC
2 stops11h 53mMultiple Airlines
Deal found 8/5C$ 458

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 437,143 searches. Data last updated 10 May 2024.
These are some of the most attractive deals on flights from Calgary to Chicago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Tue 4/612:30 a.m.YYC - MDW
1 stop13h 04mMultiple Airlines
Tue 11/61:50 p.m.MDW - YYC
2 stops11h 53mMultiple Airlines
Deal found 8/5C$ 376
Mon 3/612:30 a.m.YYC - MDW
1 stop8h 27mMultiple Airlines
Tue 11/68:02 p.m.MDW - YYC
1 stop19h 37mMultiple Airlines
Deal found 8/5C$ 389
Mon 3/612:30 a.m.YYC - MDW
1 stop8h 27mMultiple Airlines
Tue 11/61:50 p.m.MDW - YYC
2 stops11h 53mMultiple Airlines
Deal found 8/5C$ 391
Tue 4/67:30 p.m.YYC - MDW
1 stop8h 10mMultiple Airlines
Tue 11/68:02 p.m.MDW - YYC
1 stop19h 37mMultiple Airlines
Deal found 8/5C$ 395
Tue 4/612:30 a.m.YYC - MDW
1 stop13h 04mMultiple Airlines
Wed 12/611:26 a.m.MDW - YYC
1 stop11h 39mMultiple Airlines
Deal found 8/5C$ 398
Mon 3/612:30 a.m.YYC - MDW
1 stop8h 27mMultiple Airlines
Wed 12/611:26 a.m.MDW - YYC
1 stop11h 39mMultiple Airlines
Deal found 8/5C$ 413
Sun 2/612:30 a.m.YYC - MDW
1 stop13h 11mMultiple Airlines
Tue 11/61:50 p.m.MDW - YYC
2 stops11h 53mMultiple Airlines
Deal found 8/5C$ 444
Sun 2/612:30 a.m.YYC - MDW
1 stop13h 11mMultiple Airlines
Wed 12/61:43 p.m.MDW - YYC
2 stops12h 00mMultiple Airlines
Deal found 8/5C$ 456
Thu 6/611:00 a.m.YYC - MDW
1 stop9h 45mMultiple Airlines
Tue 11/61:50 p.m.MDW - YYC
2 stops11h 53mMultiple Airlines
Deal found 8/5C$ 458

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 437,143 searches. Data last updated 10 May 2024.
Have a look at some of the last-minute flights available departing from Calgary to Chicago. To prevent any unwanted surprises, users should verify their flight info before booking.
Sat 18/57:55 a.m.YYC - MDW
1 stop8h 00mDelta
Mon 27/59:46 a.m.MDW - YYC
2 stops14h 27mDelta
Deal found 9/5C$ 561
Sat 18/57:30 p.m.YYC - MDW
1 stop9h 20mMultiple Airlines
Mon 27/55:11 a.m.MDW - YYC
1 stop12h 40mMultiple Airlines
Deal found 9/5C$ 626

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 437,143 searches. Data last updated 10 May 2024.
Users travelling one-way from Calgary to Chicago can select one of these great deals. Those seeking round-trip flights from Calgary to Chicago should utilize the search form at the top of the page.
Tue 4/67:55 a.m.YYC - MDW
1 stop9h 12mDelta
Deal found 9/5C$ 192
Wed 5/67:55 a.m.YYC - MDW
1 stop9h 12mDelta
Deal found 9/5C$ 207
Mon 3/67:00 a.m.YYC - MDW
1 stop21h 50mMultiple Airlines
Deal found 9/5C$ 212
Wed 5/67:55 a.m.YYC - MDW
1 stop9h 12mDelta
Deal found 9/5C$ 237
Wed 5/67:55 a.m.YYC - MDW
2 stops13h 06mDelta
Deal found 9/5C$ 244
Wed 5/67:55 a.m.YYC - MDW
2 stops13h 06mDelta
Deal found 9/5C$ 245
Tue 9/77:30 p.m.YYC - MDW
1 stop10h 03mMultiple Airlines
Deal found 9/5C$ 249
Sun 2/612:30 a.m.YYC - MDW
1 stop13h 11mMultiple Airlines
Deal found 9/5C$ 255
Mon 15/711:00 a.m.YYC - MDW
1 stop25h 20mMultiple Airlines
Deal found 9/5C$ 258

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 437,143 searches. Data last updated 10 May 2024.

Fly from

Any airport

Fly to

Any airport

Budget

C$ 376 - C$ 1,007

Route

Depart

Return

Price

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Tue 4/6

1 stop13h 04m

Chicago Midway

Tue 11/6

2 stops11h 53m

C$ 376

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Mon 3/6

1 stop8h 27m

Chicago Midway

Tue 11/6

1 stop19h 37m

C$ 389

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Mon 3/6

1 stop8h 27m

Chicago Midway

Tue 11/6

2 stops11h 53m

C$ 391

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Tue 4/6

1 stop8h 10m

Chicago Midway

Tue 11/6

1 stop19h 37m

C$ 395

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Tue 4/6

1 stop13h 04m

Chicago Midway

Wed 12/6

1 stop11h 39m

C$ 398

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Mon 3/6

1 stop8h 27m

Chicago Midway

Wed 12/6

1 stop11h 39m

C$ 413

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Sat 25/5

1 stop8h 00m

Chicago Midway

Wed 29/5

2 stops13h 01m

C$ 559

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Thu 13/6

2 stops11h 07m

Chicago Midway

Mon 17/6

2 stops14h 44m

C$ 698

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Fri 25/10

2 stops12h 01m

Chicago Midway

Tue 29/10

2 stops13h 14m

C$ 1,007

Flights are sorted by cheapest first

Deals found on 8/5

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

Average price of flights to Midway by month

Plan your trip from Calgary to Midway by taking into account the cheapest months to travel. The average price of a one-way flight from Calgary to Midway is currently C$ 233 while a round-trip flight costs C$ 514. Price data was last updated on 5 May 2024.

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

-5 - 23 °C

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 10 May 2024.
To help decide which airline to fly from Calgary to Chicago, see what other customers have to say about Delta and Porter Airlines. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
10,768 reviews
Check prices

Boarding

8.2

Comfort

7.9

Crew

8.6

Entertainment

8.0

Food

7.4

Overall

8.0

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
10,768 reviews
Delta
8.0
Very good
10,768 reviews
Check prices

Boarding

8.2

Comfort

7.9

Crew

8.6

Entertainment

8.0

Food

7.4

Overall

8.0

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
7.6
Good
2,940 reviews
Delta
8.0
Very good
10,768 reviews
Check prices

Boarding

8.2

Comfort

7.9

Crew

8.6

Entertainment

8.0

Food

7.4

Overall

8.0

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
7.4
Good
424 reviews
Delta
8.0
Very good
10,768 reviews
Check prices

Boarding

8.2

Comfort

7.9

Crew

8.6

Entertainment

8.0

Food

7.4

Overall

8.0

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?

    Calgary (YYC), located 9.3 km from the city centre, is the airport you fly out of when you book flights from Calgary to Chicago Midway. 0 airlines have flights from Calgary to Chicago Midway on a regular basis. Booking flights from Calgary to Chicago Midway should not be difficult; the airport handles an average of 0 outbound flights to Chicago Midway per day.

  • Can I find flights from Calgary to Chicago Midway Airport for under C$ 400 on Cheapflights?

    Yes, there are multiple flights from Calgary to Chicago Midway Airport for under C$ 400. The cheapest flight booked recently is on Multiple Airlines for just C$ 376, but on average you can expect to pay C$ 456.

  • Are there last-minute flights available from Calgary to Chicago Midway Airport for under C$ 600?

    There are currently 2+ open flights from Calgary to Chicago Midway Airport within the next 7 days for less than C$ 600.

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

    Cheapflights users have booked flights from Calgary to Chicago Midway Airport round-trip from C$ 559.

  • What are the cheapest airlines to fly from Calgary to Chicago Midway Airport one-way?

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as C$ 192. However, be on the lookout for offers from Porter Airlines and WestJet, as they are both options that can get you from Calgary to Chicago Midway Airport for a low price.

  • What does YYC to MDW mean?

    This is defined as Calgary Airport (YYC) and Chicago Midway Airport (MDW). Codes like Chicago Midway Airport are often used to just call airports uniquely.

  • 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 9/5.

See more FAQs

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Calgary to Midway?

Deals for Calgary to Midway flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Calgary to Midway?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Midway from Calgary.

Can Cheapflights find flights from Calgary to Midway with no change fees?

Yes, we can. To see specific flights from Calgary to Midway with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Calgary to Midway become cheaper?

Yes, Cheapflights offers price alerts on Calgary to Midway flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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