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C$ 218+ Cheap flights to Midway

— MDW
29 Nov — 6 Dec1
1 adult
1 adult, Economy, 0 bags

Flights to Midway in 2026

Enter your travel dates to find the best prices.

Cheapest flights to Midway Airport

Thu 19/119:45 a.m. -
1 stop4h 06m
Mon 23/119:30 a.m. -
1 stop3h 00m
Deal found 27/10C$ 364
Sat 21/119:45 a.m. -
1 stop4h 06m
Wed 25/119:30 a.m. -
1 stop3h 00m
Deal found 27/10C$ 365
Sat 28/116:00 a.m. -
1 stop7h 51m
Tue 1/126:41 p.m. -
1 stop3h 26m
Deal found 27/10C$ 401
Sat 14/116:00 a.m. -
1 stop4h 46m
Wed 18/119:30 a.m. -
1 stop3h 00m
Deal found 27/10C$ 411
Mon 9/1112:15 p.m. -
1 stop6h 49m
Wed 2/126:41 p.m. -
1 stop3h 26m
Deal found 26/10C$ 413
Fri 25/1212:20 p.m. -
1 stop6h 24m
Fri 1/16:15 p.m. -
1 stop3h 44m
Deal found 28/10C$ 456
Thu 19/116:00 a.m. -
1 stop4h 46m
Sun 22/119:30 a.m. -
1 stop6h 50m
Deal found 27/10C$ 457
Thu 12/1112:15 p.m. -
1 stop6h 49m
Mon 16/111:31 p.m. -
1 stop8h 26m
Deal found 28/10C$ 459
Sat 5/126:00 a.m. -
1 stop4h 37m
Mon 7/129:37 a.m. -
1 stop6h 43m
Deal found 25/10C$ 470
Thu 12/116:00 a.m. -
1 stop7h 51m
Sun 15/111:31 p.m. -
1 stop8h 26m
Deal found 29/10C$ 481
Fri 27/116:00 a.m. -
1 stop6h 25m
Sun 29/119:30 a.m. -
1 stop6h 50m
Deal found 27/10C$ 495
Tue 1/127:10 p.m. -
2 stops17h 23m
Thu 3/125:02 p.m. -
2 stops15h 37m
Deal found 26/10C$ 611

Find flight deals to Midway Airport

Round-trip from

C$ 298

One-way from

C$ 218

Popular in

October

Cheapest in

February

Average price

C$ 442

Good round-trip deal

C$ 429 or less

Good one-way deal

C$ 186 or less
Porter Airlines
  • Porter Airlines
  • 19/11-23/11
  • Nonstop
  • 3h 50m total
  • Toronto to Chicago
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Delta
  • Delta
  • 21/11-31/12
  • 1 total stop
  • 4h 06m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 3% potential increase in price (C$ 16 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 5 potential savings vs. average RT price).
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Average for round-trip flights in October 2026
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Price to beat on a round-trip flight from Toronto to Chicago Midway.
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Price to beat on a one-way flight from Toronto to Chicago Midway.
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Cheapflights Fare Finder

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

Fly from

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 25/11

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$ 218

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 24/11

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$ 224

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 26/11

6:00 a.m.-11:25 a.m.

1 stop6h 25m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 224

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 3/12

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$ 224

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 28/11

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$ 260

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Fri 25/12

12:20 p.m.-5:44 p.m.

1 stop6h 24m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 270

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sun 6/12

12:15 p.m.-6:01 p.m.

1 stop6h 46m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 270

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Mon 9/11

12:15 p.m.-6:04 p.m.

1 stop6h 49m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 271
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$ 273

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 17/11

9:45 a.m.-12:51 p.m.

1 stop4h 06m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 276

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/10

Showing 1-10 of 40 resultsSorted by cheapest first
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Best time to book a flight to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

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

How long is the flight to Midway?

On average, a flight from Toronto to Midway takes 7 hours 25 minutes. Flights to Midway from other popular cities in Canada will vary in length. Below are a few examples of popular routes and their flight times.

What are the most popular airlines that fly to Midway?

The most popular airline flying from Toronto to Midway is Porter Airlines.

Porter Airlines
Porter Airlines
From C$ 221

What are the cheapest airlines that fly to Midway?

The cheapest airline flying from Toronto to Midway is Porter Airlines.

Rainfall in Midway by month

In terms of precipitation, rainfall in Midway 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 Midway when rainfall is around 43.0 mm.

Temperature in Midway by month

If weather is an important factor for your trip to Midway, 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

Check out reviews from past customers who have flown Porter Airlines to the United States to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
468 reviews
Check prices

Crew

8.6

Entertainment

6.9

Food

7.6

Boarding

8.2

Comfort

8.0

Overall

8.0

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

Crew

8.6

Entertainment

6.9

Food

7.6

Boarding

8.2

Comfort

8.0

Overall

8.0

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.

FAQs about flying to Midway

  • Can I find cheaper flights to Midway if I am willing to have layovers?

    Yes, flights with layovers are often cheaper than direct flights. Keep an eye out for flight deals to Midway on Cheapflights that require 1 or 2 stops for potential cost savings.

  • What is the best airline to fly to Midway?

    Based on reviews from Cheapflights users, Porter Airlines is rated the highest out of the airlines that fly to Midway.

  • What is the cheapest airport to fly to in Midway?

    Chicago Midway is currently the cheapest airport to fly to in Midway. One-way flights to Chicago Midway typically cost C$ 82, while round-trip flights cost around C$ 216.

  • How much is a round-trip flight to Midway?

    A round-trip flight to Midway will typically cost around C$ 218, however they can be found for as little as C$ 216.

  • Where does the fastest flight to Midway depart from?

    For those looking to save time traveling to Midway, Toronto offers the quickest one-way flight (3 hours 38 minutes).

  • Does Chicago Midway have rental cars?

    Yes. Those touching down at Chicago Midway can take advantage of the rental car services offered upon their arrival.

  • Are there hotels close to Chicago Midway?

    Yes. Chicago Midway has hotels nearby for those requiring accommodations. Midway Airport 2 Bedroom With Full Kitchen is the closest property to Chicago Midway (0.0 km away from Chicago Midway).

See more FAQs

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