How long is the flight from Canada to Chicago Midway Airport?

Departing from Canada to Chicago Midway Airport will take you 6h 24m. The distance from Canada to Chicago Midway Airport is about 1411 km. This flight may include one or multiple stops.

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$ 181 on Porter Airlines. Other airlines that offer cheap prices include Delta from C$ 191 and WestJet from C$ 220 one-way.

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.

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).

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

While some choose either Toronto Island - Chicago Midway or Montreal Pierre Elliott Trudeau Intl - Chicago Midway, Toronto Pearson Intl - 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 135% 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$ 428, or C$ 680 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, July can be a great choice for travel to Chicago Midway Airport. Flights to Chicago Midway Airport from Canada in July are about C$ 353 on average during July, but can be found for as low as C$ 192.

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$ 167+ Cheap Flights from Canada to Chicago Midway Airport

Cheap flight deals from Canada to Midway

Round-trip from	C$ 238
One-way from	C$ 167
Popular in	December
Cheapest in	July
Average price	C$ 352
Good round-trip deal	C$ 243 or less
Good one-way deal	C$ 226 or less

Porter Airlines
3/10-7/10
2 total stops
11h 44m total
Canada to Chicago

Search Deals

20/10
2 total stops
15h 08m total
Canada to Chicago

Search Deals

Highest demand for flights based on searches. 8% potential increase in price (C$ 42 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease (C$ 8 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in September 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 15 September 2025.

Fri 3/1011:00 a.m.YQB - MDW

1 stop6h 24mPorter Airlines

Tue 7/109:35 a.m.MDW - YQB

1 stop5h 20mPorter Airlines

Deal found 14/9C$ 238

Wed 29/1011:00 p.m.YVR - MDW

1 stop17h 39mMultiple Airlines

Wed 5/112:06 p.m.MDW - YVR

1 stop23h 06mMultiple Airlines

Deal found 14/9C$ 277

Mon 20/108:30 p.m.YVR - MDW

2 stops15h 08mMultiple Airlines

Wed 22/108:05 a.m.MDW - YVR

1 stop14h 43mMultiple Airlines

Deal found 14/9C$ 280

Thu 2/109:30 a.m.YVR - MDW

1 stop12h 11mMultiple Airlines

Mon 6/106:20 a.m.MDW - YVR

1 stop16h 28mMultiple Airlines

Deal found 13/9C$ 282

Sat 4/109:30 a.m.YVR - MDW

1 stop12h 11mMultiple Airlines

Tue 7/108:05 a.m.MDW - YVR

1 stop14h 43mMultiple Airlines

Deal found 13/9C$ 285

Fri 17/109:00 a.m.YWG - MDW

1 stop14h 46mMultiple Airlines

Wed 29/102:06 p.m.MDW - YWG

2 stops34h 35mMultiple Airlines

Deal found 14/9C$ 295

Fri 17/1011:00 a.m.YQB - MDW

1 stop6h 24mPorter Airlines

Sun 19/109:35 a.m.MDW - YQB

1 stop5h 20mPorter Airlines

Deal found 14/9C$ 299

Thu 30/109:00 p.m.YWG - MDW

2 stops21h 39mMultiple Airlines

Thu 6/111:37 p.m.MDW - YWG

1 stop25h 30mMultiple Airlines

Deal found 15/9C$ 302

Mon 3/118:35 p.m.YEG - MDW

2 stops14h 03mMultiple Airlines

Sat 8/111:37 p.m.MDW - YEG

1 stop23h 34mMultiple Airlines

Deal found 12/9C$ 302

Sat 1/116:00 a.m.YEG - MDW

2 stops11h 39mMultiple Airlines

Sat 8/111:37 p.m.MDW - YEG

1 stop23h 34mMultiple Airlines

Deal found 12/9C$ 305

Sun 9/118:30 a.m.YHZ - MDW

1 stop8h 50mPorter Airlines

Thu 20/1111:00 a.m.MDW - YHZ

1 stop7h 05mPorter Airlines

Deal found 15/9C$ 317

Fri 31/107:30 a.m.YWG - MDW

1 stop11h 09mMultiple Airlines

Sun 2/115:20 a.m.MDW - YWG

1 stop8h 47mMultiple Airlines

Deal found 15/9C$ 320

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 15 September 2025.

Thu 2/109:30 a.m.YVR - MDW

1 stop12h 11mMultiple Airlines

Mon 6/105:33 p.m.MDW - YVR

2 stops22h 03mMultiple Airlines

Deal found 13/9C$ 284

Fri 17/1011:00 a.m.YQB - MDW

1 stop6h 24mPorter Airlines

Sun 19/109:35 a.m.MDW - YQB

1 stop5h 20mPorter Airlines

Deal found 14/9C$ 299

Sun 26/106:45 a.m.YYC - MDW

1 stop9h 58mDelta

Sat 1/1110:40 a.m.MDW - YYC

2 stops13h 22mDelta

Deal found 13/9C$ 336

Fri 7/116:00 p.m.YYZ - MDW

1 stop16h 40mWestJet

Sun 9/1110:47 a.m.MDW - YYZ

1 stop5h 13mWestJet

Deal found 14/9C$ 361

Sat 4/109:30 a.m.YVR - MDW

1 stop12h 11mMultiple Airlines

Tue 7/108:05 a.m.MDW - YVR

1 stop14h 43mMultiple Airlines

Deal found 13/9C$ 285

Sun 9/118:30 a.m.YHZ - MDW

1 stop8h 50mPorter Airlines

Thu 20/1111:00 a.m.MDW - YHZ

1 stop7h 05mPorter Airlines

Deal found 15/9C$ 317

Thu 30/109:00 p.m.YWG - MDW

2 stops21h 39mMultiple Airlines

Thu 6/111:37 p.m.MDW - YWG

1 stop25h 30mMultiple Airlines

Deal found 15/9C$ 302

Tue 28/106:45 a.m.YYC - MDW

1 stop9h 58mDelta

Tue 4/119:20 a.m.MDW - YYC

1 stop5h 34mDelta

Deal found 13/9C$ 336

Fri 17/101:10 p.m.YUL - MDW

1 stop4h 14mPorter Airlines

Mon 20/109:35 a.m.MDW - YUL

1 stop5h 25mPorter Airlines

Deal found 14/9C$ 325

Sat 11/106:45 a.m.YYC - MDW

1 stop9h 58mDelta

Sat 18/103:00 p.m.MDW - YYC

1 stop6h 47mDelta

Deal found 13/9C$ 336

Fri 31/1012:45 a.m.YEG - MDW

1 stop16h 54mMultiple Airlines

Sat 8/111:37 p.m.MDW - YEG

1 stop23h 34mMultiple Airlines

Deal found 12/9C$ 307

Sat 25/106:20 a.m.YYZ - MDW

1 stop5h 10mWestJet

Sat 25/103:00 p.m.MDW - YYZ

1 stop7h 18mWestJet

Deal found 13/9C$ 381

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 15 September 2025.

Sat 18/107:50 a.m.YTZ - MDW

Nonstop1h 49mPorter Airlines

Sat 25/109:35 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 14/9C$ 332

Thu 16/103:35 p.m.YTZ - MDW

Nonstop1h 49mPorter Airlines

Sun 19/109:35 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 15/9C$ 334

Sat 18/107:50 a.m.YTZ - MDW

Nonstop1h 49mPorter Airlines

Mon 20/109:35 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 14/9C$ 336

Tue 28/109:15 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Tue 4/114:15 p.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 13/9C$ 338

Fri 17/107:50 a.m.YTZ - MDW

Nonstop1h 49mPorter Airlines

Mon 20/109:35 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 13/9C$ 339

Wed 15/107:50 a.m.YTZ - MDW

Nonstop1h 49mPorter Airlines

Thu 16/109:35 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 15/9C$ 340

Mon 6/107:50 a.m.YTZ - MDW

Nonstop1h 49mPorter Airlines

Thu 9/109:35 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 14/9C$ 342

Wed 15/103:35 p.m.YTZ - MDW

Nonstop1h 49mPorter Airlines

Mon 20/105:20 p.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 13/9C$ 345

Sun 12/107:50 a.m.YTZ - MDW

Nonstop1h 49mPorter Airlines

Sun 19/109:35 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 14/9C$ 346

Wed 15/103:35 p.m.YTZ - MDW

Nonstop1h 49mPorter Airlines

Fri 17/109:35 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 15/9C$ 347

Sun 12/107:50 a.m.YTZ - MDW

Nonstop1h 49mPorter Airlines

Tue 21/109:35 a.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 15/9C$ 349

Last-minute flights from Canada to Midway
Discover last-minute flight deals from Canada to Midway. Data last updated 15 September 2025 and is based on user searches.

Thu 2/109:30 a.m.YVR - MDW

1 stop12h 11mMultiple Airlines

Mon 6/106:20 a.m.MDW - YVR

1 stop16h 28mMultiple Airlines

Deal found 13/9C$ 282

Fri 3/1011:00 a.m.YQB - MDW

1 stop6h 24mPorter Airlines

Tue 7/109:35 a.m.MDW - YQB

1 stop5h 20mPorter Airlines

Deal found 14/9C$ 238

Sat 4/109:30 a.m.YVR - MDW

1 stop12h 11mMultiple Airlines

Tue 7/108:05 a.m.MDW - YVR

1 stop14h 43mMultiple Airlines

Deal found 13/9C$ 285

Tue 14/107:30 p.m.YTZ - MDW

1 stop4h 55mMultiple Airlines

Wed 22/109:35 a.m.MDW - YTZ

Nonstop1h 42mMultiple Airlines

Deal found 15/9C$ 324

Fri 17/109:00 a.m.YWG - MDW

1 stop14h 46mMultiple Airlines

Wed 29/102:06 p.m.MDW - YWG

2 stops34h 35mMultiple Airlines

Deal found 14/9C$ 295

Fri 17/1011:00 a.m.YQB - MDW

1 stop6h 24mPorter Airlines

Sun 19/109:35 a.m.MDW - YQB

1 stop5h 20mPorter Airlines

Deal found 14/9C$ 299

Mon 20/108:30 p.m.YVR - MDW

2 stops15h 08mMultiple Airlines

Wed 22/108:05 a.m.MDW - YVR

1 stop14h 43mMultiple Airlines

Deal found 14/9C$ 280

Wed 29/1011:00 p.m.YVR - MDW

1 stop17h 39mMultiple Airlines

Wed 5/112:06 p.m.MDW - YVR

1 stop23h 06mMultiple Airlines

Deal found 14/9C$ 277

Wed 29/1011:00 p.m.YVR - MDW

1 stop17h 39mMultiple Airlines

Mon 3/111:37 p.m.MDW - YVR

2 stops29h 17mMultiple Airlines

Deal found 13/9C$ 320

Thu 30/109:00 p.m.YWG - MDW

2 stops21h 39mMultiple Airlines

Thu 6/111:37 p.m.MDW - YWG

1 stop25h 30mMultiple Airlines

Deal found 15/9C$ 302

Fri 31/1012:45 a.m.YEG - MDW

1 stop16h 54mMultiple Airlines

Sat 8/111:37 p.m.MDW - YEG

1 stop23h 34mMultiple Airlines

Deal found 12/9C$ 307

Fri 31/107:30 a.m.YWG - MDW

1 stop11h 09mMultiple Airlines

Sun 2/115:20 a.m.MDW - YWG

1 stop8h 47mMultiple Airlines

Deal found 15/9C$ 320

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 15 September 2025.

Mon 20/108:30 p.m.YVR - MDW

2 stops15h 08mMultiple Airlines

Deal found 13/9C$ 167

Wed 1/108:30 p.m.YVR - MDW

2 stops17h 28mMultiple Airlines

Deal found 13/9C$ 169

Fri 31/107:30 a.m.YWG - MDW

1 stop14h 15mMultiple Airlines

Deal found 15/9C$ 174

Mon 6/108:30 p.m.YVR - MDW

2 stops15h 08mMultiple Airlines

Deal found 13/9C$ 176

Wed 29/106:55 p.m.YWG - MDW

3 stops27h 08mMultiple Airlines

Deal found 14/9C$ 181

Wed 29/108:30 a.m.YHZ - MDW

1 stop8h 50mPorter Airlines

Deal found 14/9C$ 181

Sun 12/108:55 a.m.YYC - MDW

1 stop23h 36mMultiple Airlines

Deal found 14/9C$ 187

Thu 13/118:35 p.m.YEG - MDW

2 stops21h 04mMultiple Airlines

Deal found 15/9C$ 187

Wed 29/109:45 p.m.YYC - MDW

2 stops23h 18mMultiple Airlines

Deal found 14/9C$ 188

Sun 19/107:50 a.m.YTZ - MDW

Nonstop1h 49mPorter Airlines

Deal found 13/9C$ 188

Thu 30/108:35 p.m.YEG - MDW

2 stops21h 04mMultiple Airlines

Deal found 15/9C$ 188

Fri 24/103:35 p.m.YTZ - MDW

Nonstop1h 49mPorter Airlines

Deal found 14/9C$ 190

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

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 2/10

9:30 a.m.-11:41 p.m.

1 stop12h 11m

Chicago Midway

Mon 6/10

5:33 p.m.-1:36 p.m.

2 stops22h 03m

C$ 284

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 4/10

9:30 a.m.-11:41 p.m.

1 stop12h 11m

Chicago Midway

Tue 7/10

8:05 a.m.-8:48 p.m.

1 stop14h 43m

C$ 285

Québec CityChicago

YQB - MDW

YQBMDW

Québec City

Fri 17/10

11:00 a.m.-4:24 p.m.

1 stop6h 24m

Chicago Midway

Sun 19/10

9:35 a.m.-3:55 p.m.

1 stop5h 20m

C$ 299

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Thu 30/10

9:00 p.m.-6:39 p.m.

2 stops21h 39m

Chicago Midway

Thu 6/11

1:37 p.m.-3:07 p.m.

1 stop25h 30m

C$ 302

EdmontonChicago

YEG - MDW

YEGMDW

Edmonton

Fri 31/10

12:45 a.m.-6:39 p.m.

1 stop16h 54m

Chicago Midway

Sat 8/11

1:37 p.m.-12:11 p.m.

1 stop23h 34m

C$ 307

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sun 9/11

8:30 a.m.-3:20 p.m.

1 stop8h 50m

Chicago Midway

Thu 20/11

11:00 a.m.-8:05 p.m.

1 stop7h 05m

C$ 317

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 14/10

7:30 p.m.-11:25 p.m.

1 stop4h 55m

Chicago Midway

Wed 22/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 324

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 14/10

7:30 p.m.-11:25 p.m.

1 stop4h 55m

Chicago Midway

Thu 23/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 324

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 17/10

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

1 stop4h 14m

Chicago Midway

Mon 20/10

9:35 a.m.-4:00 p.m.

1 stop5h 25m

C$ 325

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 13/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Tue 21/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 332

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/9

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, September is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of C$ 209). 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.

Reviews of airlines servicing Midway

Check out reviews from past customers who have flown with Porter Airlines,Air Transat, andWestJet from Canada to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Porter Airlines

7.9

Good

363 reviews

Check prices

Reviews

1 / 20

2.0

Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

Porter Airlines

7.9

Good

363 reviews

Porter Airlines

7.9

Good

363 reviews

Check prices

Reviews

1 / 20

2.0

Mediocre

Anonymous,Sep 2025

YYZ - OPO

Air Transat

7.7

Good

438 reviews

Porter Airlines

7.9

Good

363 reviews

Check prices

Reviews

1 / 20

2.0

Mediocre

Anonymous,Sep 2025

YYZ - OPO

WestJet

7.2

Good

3,091 reviews

Porter Airlines

7.9

Good

363 reviews

Check prices

Reviews

1 / 20

2.0

Mediocre

Anonymous,Sep 2025

YYZ - OPO

Related info for your journey

How long is the flight from Canada to Chicago Midway Airport?
Departing from Canada to Chicago Midway Airport will take you 6h 24m. The distance from Canada to Chicago Midway Airport is about 1411 km. This flight may include one or multiple stops.
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$ 181 on Porter Airlines. Other airlines that offer cheap prices include Delta from C$ 191 and WestJet from C$ 220 one-way.
What are the most popular routes from Canada to Chicago Midway Airport?
While some choose either Toronto Island - Chicago Midway or Montreal Pierre Elliott Trudeau Intl - Chicago Midway, Toronto Pearson Intl - 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, September is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of C$ 209). 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

Vancouver Intl to O'Hare Intl flights

Pierre Elliott Trudeau Intl to O'Hare Intl flights

Pearson Intl to Midway flights

Toronto Island to Midway flights

Pierre Elliott Trudeau Intl to Midway flights

Vancouver Intl to Midway flights

Calgary to O'Hare Intl flights

Québec City to O'Hare Intl flights

Toronto Island to O'Hare Intl flights

Ottawa to O'Hare Intl flights

Halifax to O'Hare Intl flights

Calgary to Midway flights

Winnipeg to O'Hare Intl flights

Québec City to Midway flights

Edmonton to O'Hare Intl flights

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Ottawa to Midway flights

Buffalo to O'Hare Intl flights

Halifax to Midway flights

Victoria to O'Hare Intl flights

Edmonton to Midway flights

Detroit to O'Hare Intl flights

Region of Waterloo Intl to O'Hare Intl flights

Nanaimo to O'Hare Intl flights

Saskatoon to O'Hare Intl flights

Kelowna to O'Hare Intl flights

Kelowna to Midway flights

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Victoria to Midway flights

Hamilton to O'Hare Intl flights

Saskatoon to Midway flights

Regina to O'Hare Intl flights

Mexico City to O'Hare Intl flights

Top 2 airlines flying from Canada to Midway

Airline	Cheapest	Average	Flexibility	On-time
Porter Airlines	CheapestC$ 197	AverageC$ 446	FlexibilityNo cancel fee	On-time52%	Search Porter Airlines flights
WestJet	CheapestC$ 421	AverageC$ 678	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$ 167

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 20/10. 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 15 September 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 15 September 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 15 September 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 15 September 2025.

Reviews of airlines servicing Midway

Check out reviews from past customers who have flown with Porter Airlines,Air Transat, andWestJet from Canada to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up 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.

How long is the flight from Canada to Chicago Midway Airport?

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?

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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 15 September 2025.