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Cheap flights from Calgary to Chicago Midway Airport from C$ 194

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 11/5. 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
27 Apr — 4 May1
1 adult
Sat 27/4
Sat 4/5

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$ 627 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as C$ 834.

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$ 606 for the month, but tickets can be as low as C$ 290. 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 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 22 April 2024.
Check out some of the cheapest WestJet flights we've come across from Calgary to Chicago. Deals update often to give you more flight options matching your criteria
Fri 10/512:20 a.m.YYC - MDW
2 stops20h 41mWestJet
Tue 14/56:00 a.m.MDW - YYC
1 stop30h 21mWestJet
Deal found 20/4C$ 709
Sun 26/57:00 a.m.YYC - MDW
2 stops8h 55mWestJet
Wed 29/58:45 a.m.MDW - YYC
2 stops11h 30mWestJet
Deal found 21/4C$ 731
Sat 8/66:45 a.m.YYC - MDW
1 stop10h 45mWestJet
Tue 11/62:24 p.m.MDW - YYC
2 stops11h 17mWestJet
Deal found 21/4C$ 733
Fri 10/512:20 a.m.YYC - MDW
2 stops20h 41mWestJet
Tue 14/59:46 a.m.MDW - YYC
2 stops13h 34mWestJet
Deal found 20/4C$ 749
Fri 14/68:00 p.m.YYC - MDW
2 stops12h 51mWestJet
Mon 17/66:00 a.m.MDW - YYC
2 stops19h 40mWestJet
Deal found 21/4C$ 770
Fri 10/512:20 a.m.YYC - MDW
2 stops20h 41mWestJet
Tue 14/58:45 a.m.MDW - YYC
1 stop27h 36mWestJet
Deal found 21/4C$ 773
Wed 25/912:20 a.m.YYC - MDW
2 stops13h 36mWestJet
Wed 2/103:45 p.m.MDW - YYC
1 stop29h 18mWestJet
Deal found 21/4C$ 777
Fri 7/61:00 a.m.YYC - MDW
2 stops16h 30mWestJet
Tue 11/62:24 p.m.MDW - YYC
2 stops11h 17mWestJet
Deal found 21/4C$ 785
Sun 22/97:00 a.m.YYC - MDW
2 stops13h 44mWestJet
Thu 26/910:11 a.m.MDW - YYC
2 stops13h 11mWestJet
Deal found 21/4C$ 790

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 504,710 searches. Data last updated 22 April 2024.
To aid your search, here are some of the cheapest Delta 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 6/912:30 a.m.YYC - MDW
1 stop7h 42mDelta
Wed 11/91:05 p.m.MDW - YYC
1 stop7h 54mDelta
Deal found 21/4C$ 592
Sat 11/57:30 p.m.YYC - MDW
2 stops12h 17mDelta
Tue 14/59:32 a.m.MDW - YYC
1 stop9h 53mDelta
Deal found 21/4C$ 650
Sat 11/57:55 a.m.YYC - MDW
1 stop8h 00mDelta
Tue 14/59:32 a.m.MDW - YYC
1 stop9h 53mDelta
Deal found 21/4C$ 656
Sun 26/57:55 a.m.YYC - MDW
1 stop8h 00mDelta
Wed 29/59:32 a.m.MDW - YYC
1 stop9h 53mDelta
Deal found 21/4C$ 660
Sat 7/910:00 a.m.YYC - MDW
1 stop10h 47mDelta
Wed 11/91:05 p.m.MDW - YYC
1 stop7h 54mDelta
Deal found 21/4C$ 691
Wed 4/912:30 a.m.YYC - MDW
1 stop7h 42mDelta
Mon 9/99:20 a.m.MDW - YYC
2 stops9h 53mDelta
Deal found 21/4C$ 836
Wed 4/912:30 a.m.YYC - MDW
1 stop7h 42mDelta
Mon 9/92:00 p.m.MDW - YYC
1 stop7h 43mDelta
Deal found 21/4C$ 888
Wed 1/57:55 a.m.YYC - MDW
1 stop8h 25mDelta
Sun 5/511:20 a.m.MDW - YYC
1 stop10h 36mDelta
Deal found 22/4C$ 920
Thu 18/712:30 a.m.YYC - MDW
1 stop7h 44mDelta
Fri 26/71:05 p.m.MDW - YYC
1 stop7h 54mDelta
Deal found 21/4C$ 940

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 22 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 23/48:00 a.m.YYC - MDW
2 stops13h 05mMultiple Airlines
Tue 30/410:59 p.m.MDW - YYC
1 stop25h 11mMultiple Airlines
Deal found 20/4C$ 422
Sat 11/510:00 a.m.YYC - MDW
1 stop11h 09mMultiple Airlines
Tue 14/510:59 p.m.MDW - YYC
1 stop13h 59mMultiple Airlines
Deal found 21/4C$ 436
Sat 27/46:00 p.m.YYC - MDW
2 stops13h 31mMultiple Airlines
Tue 30/410:59 p.m.MDW - YYC
1 stop25h 11mMultiple Airlines
Deal found 20/4C$ 443
Thu 9/512:30 a.m.YYC - MDW
1 stop13h 09mMultiple Airlines
Tue 14/510:59 p.m.MDW - YYC
1 stop13h 59mMultiple Airlines
Deal found 21/4C$ 448
Thu 25/48:00 a.m.YYC - MDW
2 stops11h 29mMultiple Airlines
Tue 30/410:59 p.m.MDW - YYC
1 stop25h 11mMultiple Airlines
Deal found 20/4C$ 511
Tue 23/49:00 a.m.YYC - MDW
1 stop11h 44mMultiple Airlines
Tue 30/410:59 p.m.MDW - YYC
1 stop25h 11mMultiple Airlines
Deal found 20/4C$ 529
Fri 10/59:50 a.m.YYC - MDW
1 stop9h 24mMultiple Airlines
Tue 14/510:59 p.m.MDW - YYC
1 stop13h 59mMultiple Airlines
Deal found 21/4C$ 540
Tue 23/48:00 a.m.YYC - MDW
2 stops13h 05mMultiple Airlines
Mon 29/410:59 p.m.MDW - YYC
1 stop25h 11mMultiple Airlines
Deal found 20/4C$ 561
Sat 27/46:00 p.m.YYC - MDW
2 stops13h 31mMultiple Airlines
Mon 29/410:59 p.m.MDW - YYC
1 stop25h 11mMultiple Airlines
Deal found 20/4C$ 580

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 22 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 23/48:00 a.m.YYC - MDW
2 stops13h 05mMultiple Airlines
Tue 30/410:59 p.m.MDW - YYC
1 stop25h 11mMultiple Airlines
Deal found 20/4C$ 422
Sat 11/510:00 a.m.YYC - MDW
1 stop11h 09mMultiple Airlines
Tue 14/510:59 p.m.MDW - YYC
1 stop13h 59mMultiple Airlines
Deal found 21/4C$ 436
Sat 27/46:00 p.m.YYC - MDW
2 stops13h 31mMultiple Airlines
Tue 30/410:59 p.m.MDW - YYC
1 stop25h 11mMultiple Airlines
Deal found 20/4C$ 443
Thu 9/512:30 a.m.YYC - MDW
1 stop13h 09mMultiple Airlines
Tue 14/510:59 p.m.MDW - YYC
1 stop13h 59mMultiple Airlines
Deal found 21/4C$ 448
Thu 25/48:00 a.m.YYC - MDW
2 stops11h 29mMultiple Airlines
Tue 30/410:59 p.m.MDW - YYC
1 stop25h 11mMultiple Airlines
Deal found 20/4C$ 511
Tue 23/49:00 a.m.YYC - MDW
1 stop11h 44mMultiple Airlines
Tue 30/410:59 p.m.MDW - YYC
1 stop25h 11mMultiple Airlines
Deal found 20/4C$ 529
Fri 10/59:50 a.m.YYC - MDW
1 stop9h 24mMultiple Airlines
Tue 14/510:59 p.m.MDW - YYC
1 stop13h 59mMultiple Airlines
Deal found 21/4C$ 540
Tue 23/48:00 a.m.YYC - MDW
2 stops13h 05mMultiple Airlines
Mon 29/410:59 p.m.MDW - YYC
1 stop25h 11mMultiple Airlines
Deal found 20/4C$ 561
Thu 11/712:30 a.m.YYC - MDW
1 stop9h 25mMultiple Airlines
Tue 16/710:00 p.m.MDW - YYC
1 stop15h 15mMultiple Airlines
Deal found 21/4C$ 572

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 22 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.
Sat 27/46:00 p.m.YYC - MDW
2 stops13h 31mMultiple Airlines
Tue 30/410:59 p.m.MDW - YYC
1 stop25h 11mMultiple Airlines
Deal found 20/4C$ 443
Sat 27/46:00 p.m.YYC - MDW
2 stops13h 31mMultiple Airlines
Mon 29/410:59 p.m.MDW - YYC
1 stop25h 11mMultiple Airlines
Deal found 20/4C$ 580
Sat 27/46:00 p.m.YYC - MDW
2 stops13h 31mMultiple Airlines
Mon 29/410:59 p.m.MDW - YYC
1 stop25h 11mMultiple Airlines
Deal found 21/4C$ 584
Thu 2/512:30 a.m.YYC - MDW
1 stop13h 09mMultiple Airlines
Mon 6/510:59 p.m.MDW - YYC
1 stop13h 59mMultiple Airlines
Deal found 22/4C$ 605
Thu 2/512:30 a.m.YYC - MDW
1 stop13h 09mMultiple Airlines
Mon 6/58:00 a.m.MDW - YYC
2 stops14h 59mMultiple Airlines
Deal found 22/4C$ 767
Thu 2/512:30 a.m.YYC - MDW
1 stop13h 09mMultiple Airlines
Sun 5/55:03 p.m.MDW - YYC
1 stop19h 06mMultiple Airlines
Deal found 21/4C$ 788
Wed 1/57:55 a.m.YYC - MDW
1 stop8h 25mDelta
Sun 5/511:20 a.m.MDW - YYC
1 stop10h 36mDelta
Deal found 22/4C$ 920
Thu 2/512:30 a.m.YYC - MDW
1 stop13h 24mWestJet
Tue 7/59:46 a.m.MDW - YYC
1 stop12h 00mWestJet
Deal found 21/4C$ 936
Thu 2/512:30 a.m.YYC - MDW
1 stop13h 24mWestJet
Tue 7/59:46 a.m.MDW - YYC
2 stops13h 34mWestJet
Deal found 21/4C$ 939

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 22 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.
Sat 11/57:55 a.m.YYC - MDW
1 stop8h 00mDelta
Deal found 22/4C$ 194
Mon 13/57:00 a.m.YYC - MDW
1 stop27h 36mMultiple Airlines
Deal found 22/4C$ 212
Mon 3/67:00 a.m.YYC - MDW
1 stop21h 50mMultiple Airlines
Deal found 21/4C$ 220
Tue 30/47:55 a.m.YYC - MDW
1 stop8h 25mDelta
Deal found 21/4C$ 228
Wed 12/66:45 a.m.YYC - MDW
1 stop5h 59mDelta
Deal found 21/4C$ 230
Mon 3/68:00 p.m.YYC - MDW
2 stops24h 31mMultiple Airlines
Deal found 21/4C$ 241
Mon 13/57:00 a.m.YYC - MDW
2 stops24h 51mMultiple Airlines
Deal found 22/4C$ 245
Fri 31/57:00 a.m.YYC - MDW
1 stop21h 50mMultiple Airlines
Deal found 21/4C$ 250
Mon 20/512:30 a.m.YYC - MDW
1 stop8h 27mMultiple Airlines
Deal found 21/4C$ 252

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 22 April 2024.

Fly from

Any airport

Fly to

Any airport

Budget

C$ 436 - C$ 856

Route

Depart

Return

Price

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Sat 11/5

1 stop11h 09m

Chicago Midway

Tue 14/5

1 stop13h 59m

C$ 436

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Thu 9/5

1 stop13h 09m

Chicago Midway

Tue 14/5

1 stop13h 59m

C$ 448

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Fri 10/5

1 stop9h 24m

Chicago Midway

Tue 14/5

1 stop13h 59m

C$ 540

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Thu 11/7

1 stop9h 25m

Chicago Midway

Tue 16/7

1 stop15h 15m

C$ 572

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Fri 6/9

1 stop7h 42m

Chicago Midway

Wed 11/9

1 stop7h 54m

C$ 592

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Sat 11/5

2 stops12h 17m

Chicago Midway

Tue 14/5

1 stop9h 53m

C$ 650

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Sat 11/5

1 stop8h 00m

Chicago Midway

Tue 14/5

1 stop9h 53m

C$ 656

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Fri 10/5

2 stops20h 41m

Chicago Midway

Tue 14/5

1 stop30h 21m

C$ 709

CalgaryChicago Midway

YYC - MDW

YYCMDW

Calgary

Sun 19/5

2 stops11h 47m

Chicago Midway

Sun 26/5

2 stops14h 19m

C$ 856

Flights are sorted by cheapest first

Deals found on 21/4

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 22 April 2024.
To help decide which airline to fly from Calgary to Chicago, see what other customers have to say about 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.
8.1
Very good
11,042 reviews

Comfort

7.9

Food

7.5

Boarding

8.2

Crew

8.6

Overall

8.1

Entertainment

8.0

Reviews

1 / 10

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

8.1
Very good
11,042 reviews
8.1
Very good
11,042 reviews

Comfort

7.9

Food

7.5

Boarding

8.2

Crew

8.6

Overall

8.1

Entertainment

8.0

Reviews

1 / 10

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

7.5
Good
2,994 reviews
8.1
Very good
11,042 reviews

Comfort

7.9

Food

7.5

Boarding

8.2

Crew

8.6

Overall

8.1

Entertainment

8.0

Reviews

1 / 10

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

7.4
Good
440 reviews
8.1
Very good
11,042 reviews

Comfort

7.9

Food

7.5

Boarding

8.2

Crew

8.6

Overall

8.1

Entertainment

8.0

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$ 436, but on average you can expect to pay C$ 608.

  • Are there last-minute flights available from Calgary to Chicago Midway Airport for under C$ 500?

    There are currently 16+ open flights from Calgary to Chicago Midway Airport within the next 7 days for less than C$ 500.

  • 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 21/4.

See more FAQs

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Alternative routes for Calgary to Midway
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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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