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C$ 165+ 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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
11 Jan — 18 Jan1
1 adult
1 adult, Economy, 0 bags

Flights to Midway in 2025

Enter your travel dates to find the best prices.

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 12 December 2025.

Wed 31/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 1/14:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/12C$ 374
Wed 24/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 18/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 9/12C$ 379
Sat 27/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 6/111:05 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/12C$ 408
Wed 31/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 5/14:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/12C$ 414
Sat 27/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 5/14:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/12C$ 419
Mon 29/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 5/14:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/12C$ 429
Fri 26/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 31/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/12C$ 430
Wed 31/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 4/14:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/12C$ 441
Sun 28/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 2/111:05 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/12C$ 443
Wed 24/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 31/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/12C$ 450
Wed 31/127:15 a.m.YYZ - MDW
1 stop15h 43mMultiple Airlines
Sun 4/17:44 a.m.MDW - YYZ
2 stops31h 41mMultiple Airlines
Deal found 10/12C$ 583
Tue 30/128:20 p.m.YYZ - MDW
2 stops26h 52mMultiple Airlines
Sun 4/16:08 p.m.MDW - YYZ
1 stop13h 56mMultiple Airlines
Deal found 10/12C$ 607

Find flight deals to Midway Airport

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 12 December 2025.

Round-trip from

C$ 247

One-way from

C$ 165

Popular in

December

Cheapest in

July

Average price

C$ 441

Good round-trip deal

C$ 244 or less

Good one-way deal

C$ 152 or less
25/1-28/1
  • 25/1-28/1
  • 4 total stops
  • 48h 48m total
  • Toronto to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 11/2
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 12 December 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

Fri 20/2

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

Nonstop1h 50m

Chicago Midway

Mon 23/2

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

Nonstop1h 42m

C$ 247

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 25/1

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

Nonstop1h 50m

Chicago Midway

Sun 1/2

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

Nonstop1h 42m

C$ 258

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 26/1

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

Nonstop1h 50m

Chicago Midway

Thu 29/1

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

Nonstop1h 42m

C$ 269

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 23/2

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

Chicago Midway

Mon 16/3

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

Nonstop1h 42m

C$ 281

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 5/2

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$ 288

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 5/2

7:45 a.m.-12:46 p.m.

1 stop6h 01m

Chicago Midway

Sun 8/2

1:26 p.m.-7:08 p.m.

1 stop4h 42m

C$ 292

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 29/1

7:45 a.m.-12:46 p.m.

1 stop6h 01m

Chicago Midway

Sun 1/2

1:26 p.m.-7:08 p.m.

1 stop4h 42m

C$ 310

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 15/1

7:45 a.m.-12:48 p.m.

1 stop6h 03m

Chicago Midway

Mon 19/1

1:26 p.m.-7:08 p.m.

1 stop4h 42m

C$ 325

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 7/1

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

Nonstop1h 50m

Chicago Midway

Wed 14/1

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

Nonstop1h 42m

C$ 325

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 26/1

6:00 a.m.-12:46 p.m.

1 stop7h 46m

Chicago Midway

Thu 29/1

1:26 p.m.-10:42 p.m.

1 stop8h 16m

C$ 327

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 36 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.

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$ 188
Air Transat
Air Transat
From C$ 260

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

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 12 December 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
397 reviews
Check prices

Crew

8.6

Food

7.6

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
8.0
Very good
397 reviews
Porter Airlines
8.0
Very good
397 reviews
Check prices

Crew

8.6

Food

7.6

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Transat
7.8
Good
480 reviews
Porter Airlines
8.0
Very good
397 reviews
Check prices

Crew

8.6

Food

7.6

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

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$ 61, while round-trip flights cost around C$ 125.

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

    A round-trip flight to Midway will typically cost around C$ 131, however they can be found for as little as C$ 125.

  • 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 Kitchen is the closest property to Chicago Midway (0.0 km away from Chicago Midway).

See more FAQs

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