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Cheap flights from Canada to Chicago Midway Airport from C$ 275

YYZ — MDW
9 Dec — 16 Dec1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Canada to Midway

Enter your travel dates to find the best prices.

Cheapest flights from Canada to Midway

Thu 3/126:00 a.m. -
1 stop4h 37m
Sun 6/121:41 p.m. -
1 stop8h 26m
Deal found 8/11C$ 468
Thu 10/129:45 a.m. -
1 stop4h 16m
Mon 14/121:41 p.m. -
1 stop8h 26m
Deal found 6/11C$ 475
Fri 4/126:00 a.m. -
1 stop4h 37m
Sun 13/126:00 a.m. -
1 stop10h 33m
Deal found 8/11C$ 482
Thu 3/127:00 a.m. -
1 stop10h 16m
Mon 7/125:30 p.m. -
1 stop5h 11m
Deal found 7/11C$ 483
Thu 3/126:00 a.m. -
1 stop4h 37m
Sun 6/126:41 p.m. -
1 stop3h 52m
Deal found 6/11C$ 486
Thu 26/116:00 a.m. -
1 stop6h 25m
Sun 29/111:31 p.m. -
1 stop8h 26m
Deal found 5/11C$ 486
Wed 16/122:25 p.m. -
1 stop4h 36m
Sat 9/19:38 a.m. -
1 stop5h 41m
Deal found 4/11C$ 499
Fri 4/126:00 a.m. -
1 stop4h 37m
Sun 6/126:00 a.m. -
1 stop10h 33m
Deal found 5/11C$ 509
Fri 4/126:00 a.m. -
1 stop4h 37m
Sun 6/126:41 p.m. -
1 stop3h 26m
Deal found 8/11C$ 516
Wed 25/116:00 a.m. -
1 stop4h 46m
Sun 29/111:31 p.m. -
1 stop8h 56m
Deal found 8/11C$ 525
Wed 25/117:10 a.m. -
1 stop5h 40m
Sun 6/126:41 p.m. -
1 stop3h 52m
Deal found 7/11C$ 527
Fri 27/116:00 a.m. -
1 stop6h 25m
Sun 29/119:30 a.m. -
1 stop3h 00m
Deal found 6/11C$ 528

Find flight deals from Canada to Midway

Round-trip from

C$ 468

One-way from

C$ 275

Popular in

October

Cheapest in

February

Average price

C$ 418

Good round-trip deal

C$ 470 or less

Good one-way deal

C$ 324 or less
Delta
  • Delta
  • 3/12-6/12
  • 2 total stops
  • 13h 03m total
  • Canada to Chicago
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Delta
  • Delta
  • 6/12-31/12
  • 1 total stop
  • 8h 01m total
  • Canada to Chicago
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (C$ 17 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 7 potential savings vs. average RT price).
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Average for round-trip flights in November 2026
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Price to beat on a round-trip flight from Canada to Chicago Midway.
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Price to beat on a one-way flight from Canada to Chicago Midway.
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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

Cheapest round-trip
Quickest round-trip

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sun 10/1

6:10 a.m.-9:16 a.m.

1 stop4h 06m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 275

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Mon 11/1

6:10 a.m.-1:17 p.m.

1 stop8h 07m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 275

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Mon 14/12

6:00 a.m.-9:37 a.m.

1 stop4h 37m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 277

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 17/12

6:00 a.m.-1:01 p.m.

1 stop8h 01m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 277

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 15/12

6:00 a.m.-1:01 p.m.

1 stop8h 01m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 283

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 30/11

6:00 a.m.-12:51 p.m.

1 stop7h 51m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 283

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 14/12

7:10 a.m.-4:50 p.m.

1 stop10h 40m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 284

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 28/11

6:00 a.m.-9:46 a.m.

1 stop4h 46m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 284

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 15/12

6:00 a.m.-9:37 a.m.

1 stop4h 37m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 285

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sun 6/12

9:45 a.m.-1:01 p.m.

1 stop4h 16m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 285

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 60 resultsSorted by cheapest first
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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

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$ 288). Flying from Canada to Chicago Midway Airport in October is currently the most expensive (average of C$ 712). 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.

How often are flights from Canada to Chicago delayed?

About 16% of weekly flights between Canada and Chicago have experienced delays in the past year, with the average delay time being 107 minutes.

What is the most punctual flight time for Canada to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Canada to Chicago flights?

Over the past year, Porter Airlines has had the lowest number of delays on this route, with just 16% of flights being delayed.

Reviews of airlines servicing Midway

Check out reviews from past customers who have flown with Porter Airlines 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
8.0
Very good
468 reviews
Check prices

Overall

8.0

Entertainment

6.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Porter Airlines
8.0
Very good
468 reviews
Porter Airlines
8.0
Very good
468 reviews
Check prices

Overall

8.0

Entertainment

6.9

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

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 8h 01m. The distance from Canada to Chicago Midway Airport is about 695 km. This flight may include one or multiple stops.

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

    While some choose either Montreal Pierre Elliott Trudeau Intl - Chicago Midway or Vancouver 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, January is the cheapest month in which you can book a flight from Canada to Chicago Midway Airport (average of C$ 288). Flying from Canada to Chicago Midway Airport in October is currently the most expensive (average of C$ 712). 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

Top airline flying from Canada to Midway

AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 247AverageC$ 403FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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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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