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

One-way options have recently been found by users for as low as C$ 148 on Porter Airlines. Other airlines that offer cheap prices include Air Transat from C$ 156 and Delta from C$ 185 one-way.

What are the most popular routes from Canada to Chicago Midway Airport?

While some choose either Toronto Pearson Intl - Chicago Midway or Montreal Pierre Elliott Trudeau Intl - Chicago Midway, Toronto Island - Chicago Midway is the most popular route from Canada to Chicago Midway Airport.

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

Travellers have found it’s best to book a flight 53 days in advance to save up to 118% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 53 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Canada to Chicago Midway Airport 1-2 weeks in advance for as low as C$ 406, or C$ 667 for flights within the next 24 hours.

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

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, April can be a great choice for travel to Chicago Midway Airport. Flights to Chicago Midway Airport from Canada in April are about C$ 365 on average during April, but can be found for as low as C$ 232.

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

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

How can I find direct flights from Canada to Midway?

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

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

Yes. Cheapflights offers flight deals from Canada 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.

C$ 352+ Flights from Canada to Chicago Midway Airport

Cheap flight deals from Canada to Midway

Round-trip from	C$ 220
One-way from	C$ 148
Popular in	December
Cheapest in	April
Average price	C$ 346
Good round-trip deal	C$ 228 or less
Good one-way deal	C$ 165 or less

Porter Airlines
26/6-29/6
Nonstop
3h 32m total
Canada to Chicago

Search Deals

Porter Airlines
21/7
Nonstop
1h 50m total
Canada to Chicago

Search Deals

Highest demand for flights based on searches. 7% potential increase in price (C$ 40 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease (C$ 7 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in June 2025

Search Deals

Price to beat on a round-trip flight from Canada to Chicago Midway.

Search Deals

Price to beat on a one-way flight from Canada to Chicago Midway.

Search Deals

Find flight deals from Canada to Midway

Cheapest flights from Canada to Midway
Explore the most affordable flight options available from Canada to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 12 June 2025.

Thu 26/67:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Sun 29/69:40 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 12/6C$ 220

Sat 30/87:55 a.m.YTZ - MDW

Nonstop1h 50mAir Transat

Fri 12/99:15 a.m.MDW - YTZ

Nonstop1h 42mAir Transat

Deal found 11/6C$ 254

Mon 18/87:55 a.m.YTZ - MDW

Nonstop1h 50mMultiple Airlines

Tue 19/85:20 p.m.MDW - YTZ

Nonstop1h 42mMultiple Airlines

Deal found 11/6C$ 280

Sat 4/1012:15 p.m.YYZ - MDW

1 stop7h 21mDelta

Wed 15/109:30 a.m.MDW - YYZ

1 stop6h 53mDelta

Deal found 11/6C$ 291

Fri 11/71:10 p.m.YUL - MDW

1 stop4h 14mPorter Airlines

Sun 13/79:40 a.m.MDW - YUL

1 stop5h 20mPorter Airlines

Deal found 10/6C$ 309

Fri 3/107:00 a.m.YUL - MDW

1 stop10h 23mDelta

Wed 8/109:30 a.m.MDW - YUL

1 stop5h 30mDelta

Deal found 10/6C$ 324

Tue 17/66:45 a.m.YYC - MDW

1 stop9h 55mDelta

Tue 24/61:47 p.m.MDW - YYC

1 stop8h 10mDelta

Deal found 11/6C$ 328

Wed 30/78:35 a.m.YOW - MDW

1 stop8h 49mPorter Airlines

Tue 5/89:40 a.m.MDW - YOW

1 stop8h 13mPorter Airlines

Deal found 10/6C$ 357

Tue 5/88:30 p.m.YVR - MDW

2 stops12h 10mMultiple Airlines

Tue 12/811:39 a.m.MDW - YVR

1 stop11h 13mMultiple Airlines

Deal found 11/6C$ 398

Tue 8/79:25 a.m.YEG - MDW

1 stop7h 14mDelta

Tue 15/79:25 a.m.MDW - YEG

2 stops12h 53mDelta

Deal found 10/6C$ 413

Thu 24/76:15 a.m.YVR - MDW

1 stop9h 24mDelta

Tue 29/71:46 p.m.MDW - YVR

1 stop8h 45mDelta

Deal found 11/6C$ 435

Sat 11/107:00 a.m.YUL - MDW

1 stop15h 44mMultiple Airlines

Wed 15/109:15 a.m.MDW - YUL

1 stop8h 30mMultiple Airlines

Deal found 10/6C$ 436

Best flights from Canada to Midway
Discover carefully curated flight deals from Canada to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 12 June 2025.

Thu 26/67:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Sun 29/69:40 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 12/6C$ 220

Sat 30/87:55 a.m.YTZ - MDW

Nonstop1h 50mAir Transat

Fri 12/99:15 a.m.MDW - YTZ

Nonstop1h 42mAir Transat

Deal found 11/6C$ 254

Mon 18/87:55 a.m.YTZ - MDW

Nonstop1h 50mMultiple Airlines

Tue 19/85:20 p.m.MDW - YTZ

Nonstop1h 42mMultiple Airlines

Deal found 11/6C$ 280

Sat 4/1012:15 p.m.YYZ - MDW

1 stop7h 21mDelta

Wed 15/109:30 a.m.MDW - YYZ

1 stop6h 53mDelta

Deal found 11/6C$ 291

Thu 17/71:04 p.m.YYZ - MDW

1 stop5h 35mKLM

Thu 24/76:20 p.m.MDW - YYZ

1 stop3h 38mKLM

Deal found 11/6C$ 483

Fri 3/106:45 a.m.YUL - MDW

2 stops15h 59mWestJet

Wed 8/101:05 p.m.MDW - YUL

2 stops10h 32mWestJet

Deal found 12/6C$ 485

Fri 11/71:10 p.m.YUL - MDW

1 stop4h 14mPorter Airlines

Sun 13/79:40 a.m.MDW - YUL

1 stop5h 20mPorter Airlines

Deal found 10/6C$ 309

Fri 3/107:00 a.m.YUL - MDW

1 stop10h 23mDelta

Wed 8/109:30 a.m.MDW - YUL

1 stop5h 30mDelta

Deal found 10/6C$ 324

Tue 9/96:40 a.m.YYC - MDW

1 stop9h 57mDelta

Wed 17/91:00 p.m.MDW - YYC

2 stops8h 54mDelta

Deal found 11/6C$ 328

Wed 30/78:35 a.m.YOW - MDW

1 stop8h 49mPorter Airlines

Tue 5/89:40 a.m.MDW - YOW

1 stop8h 13mPorter Airlines

Deal found 10/6C$ 357

Tue 5/88:30 p.m.YVR - MDW

2 stops12h 10mMultiple Airlines

Tue 12/811:39 a.m.MDW - YVR

1 stop11h 13mMultiple Airlines

Deal found 11/6C$ 398

Sat 11/107:00 a.m.YUL - MDW

1 stop15h 44mMultiple Airlines

Wed 15/109:15 a.m.MDW - YUL

1 stop8h 30mMultiple Airlines

Deal found 10/6C$ 436

Direct flights from Canada to Midway
Explore direct flight options from Canada to Midway based on user searches, and compare prices and availability for your desired travel dates. Data last updated 12 June 2025.

Thu 26/67:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Sun 29/69:40 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 12/6C$ 220

Sat 30/87:55 a.m.YTZ - MDW

Nonstop1h 50mAir Transat

Fri 12/99:15 a.m.MDW - YTZ

Nonstop1h 42mAir Transat

Deal found 11/6C$ 254

Mon 18/87:55 a.m.YTZ - MDW

Nonstop1h 50mMultiple Airlines

Tue 19/85:20 p.m.MDW - YTZ

Nonstop1h 42mMultiple Airlines

Deal found 11/6C$ 280

Last-minute flights from Canada to Midway
Discover last-minute flight deals from Canada to Midway. Data last updated 12 June 2025 and is based on user searches.

Tue 17/66:45 a.m.YYC - MDW

1 stop9h 55mDelta

Tue 24/61:47 p.m.MDW - YYC

1 stop8h 10mDelta

Deal found 11/6C$ 328

Wed 18/61:10 p.m.YUL - MDW

1 stop4h 44mPorter Airlines

Sat 21/69:40 a.m.MDW - YUL

1 stop7h 15mPorter Airlines

Deal found 10/6C$ 435

Thu 19/610:15 a.m.YOW - MDW

1 stop7h 09mPorter Airlines

Mon 23/69:40 a.m.MDW - YOW

1 stop7h 43mPorter Airlines

Deal found 9/6C$ 547

Thu 19/68:55 a.m.YYC - MDW

1 stop10h 58mMultiple Airlines

Tue 24/611:39 a.m.MDW - YYC

2 stops14h 05mMultiple Airlines

Deal found 10/6C$ 576

Fri 20/67:55 a.m.YTZ - MDW

Nonstop1h 50mAir Transat

Mon 23/69:40 a.m.MDW - YTZ

Nonstop1h 40mAir Transat

Deal found 10/6C$ 261

Fri 20/67:00 a.m.YUL - MDW

1 stop9h 41mDelta

Tue 24/612:44 p.m.MDW - YUL

1 stop10h 10mDelta

Deal found 11/6C$ 498

Fri 20/66:45 a.m.YUL - MDW

2 stops16h 00mWestJet

Thu 3/712:44 p.m.MDW - YUL

2 stops10h 53mWestJet

Deal found 10/6C$ 623

Sat 21/67:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Sat 5/79:40 a.m.MDW - YTZ

Nonstop1h 40mPorter Airlines

Deal found 11/6C$ 227

Sat 21/612:14 p.m.YYZ - MDW

1 stop7h 27mDelta

Tue 24/69:24 a.m.MDW - YYZ

1 stop6h 51mDelta

Deal found 9/6C$ 305

Sat 21/66:20 a.m.YUL - MDW

1 stop7h 46mMultiple Airlines

Tue 24/65:20 p.m.MDW - YUL

1 stop3h 55mMultiple Airlines

Deal found 12/6C$ 491

Sun 22/67:55 a.m.YTZ - MDW

Nonstop1h 50mMultiple Airlines

Thu 26/69:40 a.m.MDW - YTZ

Nonstop1h 40mMultiple Airlines

Deal found 11/6C$ 332

Sun 22/66:25 p.m.YYZ - MDW

1 stop28h 20mWestJet

Thu 26/69:21 a.m.MDW - YYZ

2 stops14h 12mWestJet

Deal found 10/6C$ 569

One-way flights from Canada to Midway
Search for one-way flight options from Canada to Midway. Find affordable one-way fares based on user searches. Data last updated 12 June 2025.

Mon 21/77:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Deal found 12/6C$ 148

Wed 9/73:35 p.m.YTZ - MDW

Nonstop1h 49mAir Transat

Deal found 12/6C$ 156

Sat 6/912:14 p.m.YYZ - MDW

1 stop7h 23mDelta

Deal found 10/6C$ 185

Wed 2/76:45 a.m.YYC - MDW

1 stop9h 55mDelta

Deal found 10/6C$ 190

Mon 14/71:10 p.m.YUL - MDW

1 stop4h 14mPorter Airlines

Deal found 12/6C$ 202

Sun 22/66:30 a.m.YYZ - MDW

1 stop6h 59mKLM

Deal found 11/6C$ 209

Mon 21/78:35 a.m.YOW - MDW

1 stop8h 49mPorter Airlines

Deal found 11/6C$ 215

Sat 11/107:00 a.m.YUL - MDW

1 stop9h 30mDelta

Deal found 11/6C$ 216

Mon 8/98:30 p.m.YVR - MDW

2 stops24h 28mMultiple Airlines

Deal found 10/6C$ 223

Fri 1/89:00 a.m.YWG - MDW

1 stop14h 17mMultiple Airlines

Deal found 12/6C$ 231

Tue 8/712:30 a.m.YYC - MDW

1 stop9h 10mMultiple Airlines

Deal found 11/6C$ 231

Tue 5/88:45 p.m.YEG - MDW

2 stops12h 55mMultiple Airlines

Deal found 10/6C$ 239

Cheapflights Fare Finder

Use the filters below to find and compare flights from Canada to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 26/6

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Sun 29/6

9:40 a.m.-12:22 p.m.

Nonstop1h 42m

C$ 220

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 26/6

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Mon 30/6

9:40 a.m.-12:20 p.m.

Nonstop1h 40m

C$ 261

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 18/8

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Tue 19/8

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 280

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 4/10

12:15 p.m.-6:36 p.m.

1 stop7h 21m

Chicago Midway

Wed 15/10

9:30 a.m.-5:23 p.m.

1 stop6h 53m

C$ 291

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 11/7

1:10 p.m.-4:24 p.m.

1 stop4h 14m

Chicago Midway

Sun 13/7

9:40 a.m.-4:00 p.m.

1 stop5h 20m

C$ 309

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 3/10

7:00 a.m.-4:23 p.m.

1 stop10h 23m

Chicago Midway

Wed 8/10

9:30 a.m.-4:00 p.m.

1 stop5h 30m

C$ 324

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 9/9

6:40 a.m.-5:37 p.m.

1 stop9h 57m

Chicago Midway

Wed 17/9

1:00 p.m.-8:54 p.m.

2 stops8h 54m

C$ 328

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 30/7

8:35 a.m.-4:24 p.m.

1 stop8h 49m

Chicago Midway

Tue 5/8

9:40 a.m.-6:53 p.m.

1 stop8h 13m

C$ 357

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 5/8

8:30 p.m.-10:40 a.m.

2 stops12h 10m

Chicago Midway

Tue 12/8

11:39 a.m.-8:52 p.m.

1 stop11h 13m

C$ 398

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Tue 8/7

9:25 a.m.-5:39 p.m.

1 stop7h 14m

Chicago Midway

Tue 15/7

9:25 a.m.-9:18 p.m.

2 stops12h 53m

C$ 413

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

Showing 1-10 of 60 results

...

Best time to book a flight from Canada to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Canada 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.

Cheapflights Insights

Everything you need to know about your flight from Canada to Chicago Midway Airport

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

Currently, January is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of C$ 243). Flying from Canada to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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.

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

When flying from Canada 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.

Rainfall in Midway by month

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 43.0 mm.

Temperature in Midway by month

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 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

Reviews of airlines servicing Midway

Read through reviews of airlines operating flights from Canada to Chicago, such as Porter Airlines, Delta and KLM. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Porter Airlines

8.0

Very good

288 reviews

Check prices

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

288 reviews

Porter Airlines

8.0

Very good

288 reviews

Check prices

Reviews

1 / 20

4.0

Okay

Mary,Jun 2025

FLL - YYZ

Delta

8.0

Very good

7,950 reviews

Porter Airlines

8.0

Very good

288 reviews

Check prices

Reviews

1 / 20

4.0

Okay

Mary,Jun 2025

FLL - YYZ

KLM

7.8

Good

1,358 reviews

Porter Airlines

8.0

Very good

288 reviews

Check prices

Reviews

1 / 20

4.0

Okay

Mary,Jun 2025

FLL - YYZ

Air Transat

7.8

Good

396 reviews

Porter Airlines

8.0

Very good

288 reviews

Check prices

Reviews

1 / 20

4.0

Okay

Mary,Jun 2025

FLL - YYZ

WestJet

7.2

Good

2,868 reviews

Porter Airlines

8.0

Very good

288 reviews

Check prices

Reviews

1 / 20

4.0

Okay

Mary,Jun 2025

FLL - YYZ

Related info for your journey

What are the cheapest airlines to fly from Canada to Chicago Midway Airport one-way?
One-way options have recently been found by users for as low as C$ 148 on Porter Airlines. Other airlines that offer cheap prices include Air Transat from C$ 156 and Delta from C$ 185 one-way.
What are the most popular routes from Canada to Chicago Midway Airport?
While some choose either Toronto Pearson Intl - Chicago Midway or Montreal Pierre Elliott Trudeau Intl - Chicago Midway, Toronto Island - Chicago Midway is the most popular route from Canada to Chicago Midway Airport.
Can I find deals for flights from Canada to Midway that include hotel bookings?
Yes. In addition to deals on Canada to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Canada to Midway?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Canada to Midway.
Can I find deals for business class flights from Canada to Midway?
Yes. Cheapflights offers flight deals from Canada 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 Canada to Chicago Midway Airport?
Currently, January is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of C$ 243). Flying from Canada to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Canada to Midway

Pearson Intl to O'Hare Intl flights

Toronto Island to Midway flights

Vancouver Intl to O'Hare Intl flights

Pearson Intl to Midway flights

Pierre Elliott Trudeau Intl to O'Hare Intl flights

Pierre Elliott Trudeau Intl to Midway flights

Toronto Island to O'Hare Intl flights

Québec City to O'Hare Intl flights

Calgary to O'Hare Intl flights

Winnipeg to O'Hare Intl flights

Ottawa to O'Hare Intl flights

Vancouver Intl to Midway flights

Region of Waterloo Intl to O'Hare Intl flights

Hamilton to O'Hare Intl flights

Edmonton to O'Hare Intl flights

Québec City to Midway flights

Calgary to Midway flights

Edmonton to Midway flights

Halifax to O'Hare Intl flights

Ottawa to Midway flights

Buffalo to O'Hare Intl flights

St John to O'Hare Intl flights

Detroit to O'Hare Intl flights

Halifax to Midway flights

Saskatoon to O'Hare Intl flights

Moncton to O'Hare Intl flights

Seattle to O'Hare Intl flights

Los Angeles to O'Hare Intl flights

St. John's to O'Hare Intl flights

Regina to O'Hare Intl flights

Kelowna to Midway flights

Kelowna to O'Hare Intl flights

Victoria to O'Hare Intl flights

Comox to O'Hare Intl flights

Saskatoon to Midway flights

Nanaimo to O'Hare Intl flights

Victoria to Midway flights

Grande Prairie to O'Hare Intl flights

Grande Prairie to Midway flights

Top 2 airlines flying from Canada to Midway

Airline	Cheapest	Average	Flexibility	On-time
Porter Airlines	CheapestC$ 237	AverageC$ 440	FlexibilityNo cancel fee	On-time52%	Search Porter Airlines flights
WestJet	CheapestC$ 471	AverageC$ 685	FlexibilityNo cancel fee	On-time60%	Search WestJet flights

Fly with Cheapflights

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

Cheapflights helps you search for flights from Canada to Midway via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from Canada 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 Canada.

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

Yes, we can. To see specific flights from Canada 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 Canada to Midway become cheaper?

Yes! Start tracking prices for Canada to Midway flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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Cheap flights from Canada to Chicago Midway Airport from C$ 148

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 21/7. Fares are subject to change and may not be available on all flights or dates of travel.

Cheap flight deals from Canada to Midway

Keep the following information in mind while searching for Canada to Midway flight deals. Data was last updated 12 June 2025.

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Canada to Midway

Cheapest flights from Canada to MidwayExplore the most affordable flight options available from Canada to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 12 June 2025.

Explore the most affordable flight options available from Canada to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 12 June 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Canada to Chicago Midway Airport that are best for you.

Best time to book a flight from Canada to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Canada with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Canada to Chicago Midway Airport

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

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

Find hourly flight availability from Canada to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 12 June 2025.

Rainfall in Midway by month

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

Temperature in Midway by month

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

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 12 June 2025.

Read through reviews of airlines operating flights from Canada to Chicago, such as Porter Airlines, Delta and KLM. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

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

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

What are the most popular routes from Canada to Chicago Midway Airport?

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

How can I find direct flights from Canada to Midway?

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

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Canada to Midway

See prices for flight routes from nearby airports that may be better suited for you.

Top 2 airlines flying from Canada to Midway

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Cheapest flights from Canada to Midway
Explore the most affordable flight options available from Canada to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 12 June 2025.