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C$ 160+ 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 18/1. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
16 Jan — 23 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 17 December 2025.

Tue 30/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 1/211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/12C$ 372
Wed 31/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 3/211:05 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/12C$ 400
Mon 22/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 6/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/12C$ 457
Thu 18/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 22/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/12C$ 475
Mon 29/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 6/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 16/12C$ 478
Wed 31/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 2/211:05 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/12C$ 489
Mon 22/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 8/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/12C$ 490
Fri 19/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 23/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/12C$ 493
Thu 18/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 23/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/12C$ 494
Sat 20/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 22/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/12C$ 495
Mon 29/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 1/14:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/12C$ 497
Tue 23/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 7/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/12C$ 498

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 17 December 2025.

Round-trip from

C$ 250

One-way from

C$ 160

Popular in

December

Cheapest in

July

Average price

C$ 442

Good round-trip deal

C$ 245 or less

Good one-way deal

C$ 152 or less
American Airlines
  • American Airlines
  • 23/1-1/2
  • Nonstop
  • 3h 53m total
  • Toronto to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 18/1
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 10 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 17 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

Thu 29/1

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

Nonstop1h 50m

Chicago Midway

Thu 5/2

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

C$ 256

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$ 257

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 25/1

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

Nonstop1h 50m

Chicago Midway

Wed 28/1

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

Nonstop1h 42m

C$ 275

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 14/1

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

Nonstop1h 50m

Chicago Midway

Sun 18/1

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

Nonstop1h 42m

C$ 290

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 5/2

6:00 a.m.-8:52 a.m.

1 stop3h 52m

Chicago Midway

Sun 8/2

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

1 stop4h 42m

C$ 293

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 10/2

6:00 a.m.-8:52 a.m.

1 stop3h 52m

Chicago Midway

Sun 15/2

5:00 p.m.-11:11 p.m.

1 stop5h 11m

C$ 293

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 5/2

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

1 stop6h 01m

Chicago Midway

Wed 11/2

9:53 a.m.-3:59 p.m.

1 stop5h 06m

C$ 293

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 9/2

12:12 p.m.-5:55 p.m.

1 stop6h 43m

Chicago Midway

Wed 11/2

9:53 a.m.-3:59 p.m.

1 stop5h 06m

C$ 293

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 30/1

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

Nonstop1h 50m

Chicago Midway

Fri 6/2

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

Nonstop1h 42m

C$ 301

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 14/2

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

1 stop6h 01m

Chicago Midway

Fri 20/2

6:17 p.m.-10:40 p.m.

1 stop3h 23m

C$ 304

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/12

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.

Weekly flight availability to Midway

The most flights from Toronto to Midway are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

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 17 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
399 reviews
Check prices

Food

7.6

Overall

8.0

Comfort

7.9

Crew

8.6

Entertainment

7.0

Boarding

8.2

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
399 reviews
Porter Airlines
8.0
Very good
399 reviews
Check prices

Food

7.6

Overall

8.0

Comfort

7.9

Crew

8.6

Entertainment

7.0

Boarding

8.2

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
483 reviews
Porter Airlines
8.0
Very good
399 reviews
Check prices

Food

7.6

Overall

8.0

Comfort

7.9

Crew

8.6

Entertainment

7.0

Boarding

8.2

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$ 183.

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

    A round-trip flight to Midway will typically cost around C$ 290, however they can be found for as little as C$ 183.

  • 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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