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C$ 183+ Cheap flights to Midway

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 7/11. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
23 Nov — 30 Nov1
1 adult
1 adult, Economy, 0 bags

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Cheapest flights to Midway Airport
Explore the most affordable flight options available to Midway Airport. Find the lowest fares based on data from user searches, with prices last updated on 24 October 2025.

Sun 9/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 15/1112:45 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 23/10C$ 260
Fri 7/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 17/114:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 23/10C$ 273
Fri 21/116:05 a.m.YYZ - MDW
1 stop3h 49mKLM
Mon 24/116:48 p.m.MDW - YYZ
1 stop3h 17mKLM
Deal found 23/10C$ 288
Thu 4/1212:13 p.m.YYZ - MDW
1 stop6h 47mDelta
Mon 8/126:40 p.m.MDW - YYZ
1 stop3h 31mDelta
Deal found 22/10C$ 294
Fri 21/112:30 p.m.YTZ - MDW
Nonstop1h 50mAir Transat
Sun 23/1111:00 a.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 23/10C$ 295
Fri 21/116:05 a.m.YYZ - MDW
1 stop7h 29mDelta
Sun 23/116:48 p.m.MDW - YYZ
1 stop3h 17mDelta
Deal found 23/10C$ 295
Sat 8/116:15 a.m.YYZ - MDW
1 stop3h 25mDelta
Mon 17/116:48 p.m.MDW - YYZ
1 stop3h 17mDelta
Deal found 23/10C$ 298
Mon 8/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 15/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 23/10C$ 301
Fri 21/112:30 p.m.YTZ - MDW
Nonstop1h 50mAir Transat
Mon 24/114:15 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 23/10C$ 309
Mon 17/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 19/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 22/10C$ 311
Fri 14/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 16/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 21/10C$ 312
Mon 10/1112:08 p.m.YYZ - MDW
1 stop7h 00mDelta
Fri 14/116:48 p.m.MDW - YYZ
1 stop3h 17mDelta
Deal found 23/10C$ 312

Flights to Midway in 2025

Find the latest flights to Midway in 2025, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 629,999 searches and data was last updated on 24 October 2025.

Round-trip from

C$ 256

One-way from

C$ 183

Popular in

October

Cheapest in

July

Average price

C$ 407

Good round-trip deal

C$ 347 or less

Good one-way deal

C$ 197 or less
American Airlines
  • American Airlines
  • 20/11-27/11
  • 2 total stops
  • 18h 08m total
  • Toronto to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 7/11
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Toronto to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Toronto to Chicago Midway.
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Cheapflights Fare Finder

 
Locate flights to Midway that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 629,999 searches and data was last updated on 24 October 2025.
Use the filters below to find and compare flights to Chicago Midway Airport that are best for you.

Fly from

Toronto

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 25/2

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Thu 5/3

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 266

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 7/11

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Mon 17/11

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 273

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 7/11

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Fri 14/11

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 273

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 6/2

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Sun 8/2

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 274

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 21/11

6:05 a.m.-8:54 a.m.

1 stop3h 49m

Chicago Midway

Mon 24/11

6:48 p.m.-11:05 p.m.

1 stop3h 17m

C$ 288

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 27/11

6:05 a.m.-8:54 a.m.

1 stop3h 49m

Chicago Midway

Mon 1/12

1:47 p.m.-11:21 p.m.

1 stop8h 34m

C$ 294

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 6/12

6:30 a.m.-1:08 p.m.

1 stop7h 38m

Chicago Midway

Sat 13/12

6:46 p.m.-11:11 p.m.

1 stop3h 25m

C$ 294

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 4/12

12:13 p.m.-6:00 p.m.

1 stop6h 47m

Chicago Midway

Mon 8/12

6:40 p.m.-11:11 p.m.

1 stop3h 31m

C$ 294

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 27/11

6:05 a.m.-8:54 a.m.

1 stop3h 49m

Chicago Midway

Sun 30/11

9:34 a.m.-5:15 p.m.

1 stop6h 41m

C$ 294

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 26/11

6:05 a.m.-12:34 p.m.

1 stop7h 29m

Chicago Midway

Mon 1/12

1:47 p.m.-11:21 p.m.

1 stop8h 34m

C$ 294

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/10

Showing 1-10 of 42 results
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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
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 to Chicago Midway Airport

How long is the flight to Midway?

On average, a flight from Toronto to Midway takes 2 hours 35 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.

When is the cheapest time to fly to Midway?

Use this chart to determine the cheapest time to fly round-trip from Toronto to Midway. Price data was last updated on 20 October 2024.

Users looking for the lowest fares to Midway should consider flying on Tuesday afternoons, when prices are typically cheapest. Budget-minded travellers will want to avoid Monday evenings, when prices are usually at their highest.

What are the most popular airlines that fly to Midway?

The most popular airlines flying from Toronto to Midway are Porter Airlines and WestJet.

Porter Airlines
Porter Airlines
From C$ 191
Air Transat
Air Transat
From C$ 264
WestJet
WestJet
From C$ 556

What are the cheapest airlines that fly to Midway?

The cheapest airlines flying from Toronto to Midway are Porter Airlines and WestJet.

Rainfall in Midway by month

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

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

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 24 October 2025.
Check out reviews from past customers who have flown Porter Airlines and Air Transat 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
383 reviews
Check prices

Comfort

8.0

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.6

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
8.0
Very good
383 reviews
Porter Airlines
8.0
Very good
383 reviews
Check prices

Comfort

8.0

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.6

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.
Air Transat
7.8
Good
469 reviews
Porter Airlines
8.0
Very good
383 reviews
Check prices

Comfort

8.0

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.6

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.

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$ 60, while round-trip flights cost around C$ 136.

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

    A round-trip flight to Midway will typically cost around C$ 362, however they can be found for as little as C$ 136.

  • 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 (1 hour 49 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 Kitch is the closest property to Chicago Midway (0.0 km away from Chicago Midway).

See more FAQs

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