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Cheap flights from Calgary to Chicago Midway Airport from C$ 185

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 8/5. 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
29 Apr — 6 May1
1 adult
Mon 29/4
Mon 6/5

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 21 days before your planned departure. Booking around this time can save you about 49% on the cost of this flight compared to booking a flight leaving this week. We have found prices from C$ 624 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as C$ 831.

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

Our data shows that November tends to be the cheapest month to fly to Chicago Midway Airport from Calgary. Users have commonly found prices around C$ 603 for the month, but tickets can be as low as C$ 289. Due to multiple factors, prepare for potentially higher prices in December.

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 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 504,710 searches. Data last updated 24 April 2024.
Check out some of the cheapest Porter Airlines flights we've come across from Calgary to Chicago. Deals update often to give you more flight options matching your criteria
Fri 14/67:35 a.m.YYC - MDW
2 stops13h 02mPorter Airlines
Mon 17/65:15 p.m.MDW - YYC
2 stops19h 19mPorter Airlines
Deal found 23/4C$ 784
Wed 5/69:30 a.m.YYC - MDW
2 stops11h 07mPorter Airlines
Tue 11/68:00 a.m.MDW - YYC
2 stops14h 05mPorter Airlines
Deal found 23/4C$ 835

Cheap WestJet flights from Calgary to Midway

Explore cheap flight options specifically provided by WestJet 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 504,710 searches. Data last updated 24 April 2024.
To aid your search, here are some of the cheapest WestJet 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.
Fri 3/511:30 a.m.YYC - MDW
2 stops9h 01mWestJet
Tue 7/59:46 a.m.MDW - YYC
2 stops10h 29mWestJet
Deal found 23/4C$ 1,515
Wed 8/512:20 a.m.YYC - MDW
2 stops10h 32mWestJet
Sun 12/56:00 a.m.MDW - YYC
2 stops13h 03mWestJet
Deal found 23/4C$ 1,660
Fri 27/912:20 a.m.YYC - MDW
2 stops11h 51mWestJet
Fri 4/1010:11 a.m.MDW - YYC
2 stops13h 11mWestJet
Deal found 23/4C$ 1,694
Wed 29/57:00 a.m.YYC - MDW
2 stops10h 07mWestJet
Tue 11/610:41 a.m.MDW - YYC
2 stops12h 39mWestJet
Deal found 22/4C$ 2,053

Cheap Calgary to Midway flights in April & May 2024

Find cheap flight options from Calgary to Midway specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 504,710 searches. Prices were last updated on 24 April 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.
Wed 29/57:30 p.m.YYC - MDW
1 stop9h 20mMultiple Airlines
Tue 11/68:02 p.m.MDW - YYC
1 stop16h 56mMultiple Airlines
Deal found 22/4C$ 442
Wed 8/57:55 a.m.YYC - MDW
1 stop9h 12mDelta
Sat 11/511:59 a.m.MDW - YYC
1 stop9h 47mDelta
Deal found 23/4C$ 505
Tue 7/512:30 a.m.YYC - MDW
1 stop13h 09mMultiple Airlines
Mon 13/510:59 p.m.MDW - YYC
1 stop16h 40mMultiple Airlines
Deal found 23/4C$ 506
Tue 7/512:30 a.m.YYC - MDW
1 stop13h 09mMultiple Airlines
Sun 12/510:59 p.m.MDW - YYC
1 stop15h 21mMultiple Airlines
Deal found 24/4C$ 510
Tue 7/512:30 a.m.YYC - MDW
1 stop13h 09mMultiple Airlines
Sun 12/510:27 p.m.MDW - YYC
2 stops15h 53mMultiple Airlines
Deal found 23/4C$ 521
Tue 7/512:30 a.m.YYC - MDW
1 stop13h 09mMultiple Airlines
Sun 12/510:59 p.m.MDW - YYC
1 stop15h 21mMultiple Airlines
Deal found 23/4C$ 525
Tue 28/512:30 a.m.YYC - MDW
1 stop13h 11mMultiple Airlines
Tue 11/67:45 a.m.MDW - YYC
1 stop14h 51mMultiple Airlines
Deal found 22/4C$ 538
Thu 9/512:30 a.m.YYC - MDW
1 stop13h 09mMultiple Airlines
Mon 13/510:59 p.m.MDW - YYC
1 stop16h 40mMultiple Airlines
Deal found 23/4C$ 542
Thu 9/512:30 a.m.YYC - MDW
1 stop13h 09mMultiple Airlines
Sun 12/510:59 p.m.MDW - YYC
1 stop15h 21mMultiple Airlines
Deal found 23/4C$ 546

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 504,710 searches. Data last updated 24 April 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 20/812:30 a.m.YYC - MDW
1 stop10h 03mMultiple Airlines
Sun 25/810:00 a.m.MDW - YYC
1 stop10h 59mMultiple Airlines
Deal found 23/4C$ 434
Wed 29/57:30 p.m.YYC - MDW
1 stop9h 20mMultiple Airlines
Tue 11/68:02 p.m.MDW - YYC
1 stop16h 56mMultiple Airlines
Deal found 22/4C$ 442
Thu 5/912:30 a.m.YYC - MDW
1 stop9h 25mMultiple Airlines
Wed 11/910:00 a.m.MDW - YYC
1 stop11h 09mMultiple Airlines
Deal found 23/4C$ 446
Tue 4/612:30 a.m.YYC - MDW
1 stop13h 04mMultiple Airlines
Tue 11/61:42 p.m.MDW - YYC
2 stops11h 59mMultiple Airlines
Deal found 23/4C$ 464
Tue 6/86:50 p.m.YYC - MDW
1 stop14h 52mMultiple Airlines
Mon 12/811:32 a.m.MDW - YYC
1 stop11h 27mMultiple Airlines
Deal found 23/4C$ 501
Wed 8/57:55 a.m.YYC - MDW
1 stop9h 12mDelta
Sat 11/511:59 a.m.MDW - YYC
1 stop9h 47mDelta
Deal found 23/4C$ 505
Tue 7/512:30 a.m.YYC - MDW
1 stop13h 09mMultiple Airlines
Mon 13/510:59 p.m.MDW - YYC
1 stop16h 40mMultiple Airlines
Deal found 23/4C$ 506
Tue 7/512:30 a.m.YYC - MDW
1 stop13h 09mMultiple Airlines
Sun 12/510:59 p.m.MDW - YYC
1 stop15h 21mMultiple Airlines
Deal found 24/4C$ 510
Tue 7/512:30 a.m.YYC - MDW
1 stop13h 09mMultiple Airlines
Sun 12/510:27 p.m.MDW - YYC
2 stops15h 53mMultiple Airlines
Deal found 23/4C$ 521

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 504,710 searches. Data last updated 24 April 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.
Fri 3/511:30 a.m.YYC - MDW
2 stops9h 01mWestJet
Tue 7/59:46 a.m.MDW - YYC
2 stops10h 29mWestJet
Deal found 23/4C$ 1,515

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 504,710 searches. Data last updated 24 April 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.
Wed 8/57:55 a.m.YYC - MDW
1 stop9h 12mDelta
Deal found 23/4C$ 185
Tue 30/48:00 a.m.YYC - MDW
1 stop26h 36mMultiple Airlines
Deal found 23/4C$ 200
Tue 30/48:00 a.m.YYC - MDW
1 stop26h 36mMultiple Airlines
Deal found 23/4C$ 212
Tue 30/47:55 a.m.YYC - MDW
1 stop8h 25mDelta
Deal found 23/4C$ 227
Tue 30/46:25 a.m.YYC - MDW
2 stops8h 59mDelta
Deal found 23/4C$ 229
Mon 6/59:30 p.m.YYC - MDW
2 stops20h 45mMultiple Airlines
Deal found 23/4C$ 230
Tue 7/512:30 a.m.YYC - MDW
1 stop13h 09mMultiple Airlines
Deal found 23/4C$ 233
Mon 20/510:00 a.m.YYC - MDW
1 stop22h 57mMultiple Airlines
Deal found 22/4C$ 242
Mon 6/510:00 a.m.YYC - MDW
1 stop26h 53mMultiple Airlines
Deal found 23/4C$ 248

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 504,710 searches. Data last updated 24 April 2024.

Fly from

Any airport

Fly to

Any airport

Budget

C$ 442 - C$ 784

Route

Depart

Return

Price

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Wed 29/5

1 stop9h 20m

Chicago Midway

Tue 11/6

1 stop16h 56m

C$ 442

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Tue 4/6

1 stop13h 04m

Chicago Midway

Tue 11/6

2 stops11h 59m

C$ 464

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Tue 6/8

1 stop14h 52m

Chicago Midway

Mon 12/8

1 stop11h 27m

C$ 501

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Wed 8/5

1 stop9h 12m

Chicago Midway

Sat 11/5

1 stop9h 47m

C$ 505

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Tue 7/5

1 stop13h 09m

Chicago Midway

Mon 13/5

1 stop16h 40m

C$ 506

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Tue 7/5

1 stop13h 09m

Chicago Midway

Sun 12/5

2 stops15h 53m

C$ 521

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Wed 8/5

1 stop9h 12m

Chicago Midway

Sat 11/5

2 stops12h 14m

C$ 557

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Sat 11/5

2 stops12h 17m

Chicago Midway

Tue 14/5

2 stops16h 12m

C$ 631

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Fri 14/6

2 stops13h 02m

Chicago Midway

Mon 17/6

2 stops19h 19m

C$ 784

Flights are sorted by cheapest first

Deals found on 22/4

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

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 24 April 2024.
To help decide which airline to fly from Calgary to Chicago, see what other customers have to say about Porter Airlines, WestJet and Delta. 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
8.1
Very good
11,004 reviews
Check prices

Crew

8.6

Entertainment

8.0

Boarding

8.2

Overall

8.1

Food

7.5

Comfort

7.9

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

Delta
8.1
Very good
11,004 reviews
Delta
8.1
Very good
11,004 reviews
Check prices

Crew

8.6

Entertainment

8.0

Boarding

8.2

Overall

8.1

Food

7.5

Comfort

7.9

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

WestJet
7.5
Good
2,991 reviews
Delta
8.1
Very good
11,004 reviews
Check prices

Crew

8.6

Entertainment

8.0

Boarding

8.2

Overall

8.1

Food

7.5

Comfort

7.9

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

Porter Airlines
7.4
Good
438 reviews
Delta
8.1
Very good
11,004 reviews
Check prices

Crew

8.6

Entertainment

8.0

Boarding

8.2

Overall

8.1

Food

7.5

Comfort

7.9

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

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$ 500 on Cheapflights?

    Yes, there are multiple flights from Calgary to Chicago Midway Airport for under C$ 500. The cheapest flight booked recently is on Multiple Airlines for just C$ 442, but on average you can expect to pay C$ 557.

  • Are there last-minute flights available from Calgary to Chicago Midway Airport for under C$ 1,600?

    There are currently 1+ open flights from Calgary to Chicago Midway Airport within the next 7 days for less than C$ 1,600.

  • 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 24/4.

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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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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