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C$ 186+ 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 7/9. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
15 Sep — 22 Sep1
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
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 16 August 2026.

Tue 8/91:45 p.m. -
Nonstop1h 50m
Sat 12/93:20 p.m. -
Nonstop1h 40m
Deal found 13/8C$ 280
Thu 10/91:45 p.m. -
Nonstop1h 50m
Sun 13/911:45 a.m. -
Nonstop1h 40m
Deal found 15/8C$ 282
Mon 7/91:45 p.m. -
Nonstop1h 50m
Thu 10/93:20 p.m. -
Nonstop1h 40m
Deal found 13/8C$ 284
Wed 2/91:45 p.m. -
Nonstop1h 50m
Fri 11/93:20 p.m. -
Nonstop1h 40m
Deal found 13/8C$ 286
Fri 4/910:10 a.m. -
Nonstop1h 50m
Thu 10/93:20 p.m. -
Nonstop1h 40m
Deal found 13/8C$ 287
Sat 5/91:45 p.m. -
Nonstop1h 50m
Sun 13/93:20 p.m. -
Nonstop1h 40m
Deal found 12/8C$ 289
Sun 6/910:10 a.m. -
Nonstop1h 50m
Sun 13/911:45 a.m. -
Nonstop1h 40m
Deal found 14/8C$ 290
Mon 7/910:10 a.m. -
Nonstop1h 50m
Wed 9/93:20 p.m. -
Nonstop1h 40m
Deal found 16/8C$ 291
Fri 4/910:10 a.m. -
Nonstop1h 50m
Sat 12/911:45 a.m. -
Nonstop1h 40m
Deal found 14/8C$ 293
Tue 8/910:10 a.m. -
Nonstop1h 50m
Sun 13/911:45 a.m. -
Nonstop1h 40m
Deal found 13/8C$ 294
Wed 2/91:45 p.m. -
Nonstop1h 50m
Thu 3/911:45 a.m. -
Nonstop1h 40m
Deal found 13/8C$ 295
Wed 9/910:10 a.m. -
Nonstop1h 50m
Thu 10/93:20 p.m. -
Nonstop1h 40m
Deal found 13/8C$ 297

Find flight deals to Midway Airport

Find the latest flights to Midway in 2026, 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 16 August 2026.

Round-trip from

C$ 277

One-way from

C$ 186

Popular in

July

Cheapest in

February

Average price

C$ 372

Good round-trip deal

C$ 281 or less

Good one-way deal

C$ 189 or less
Air Canada
  • Air Canada
  • 1/9-11/9
  • 1 total stop
  • 6h 51m total
  • Toronto to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 7/9
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (C$ 12 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease (C$ 3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
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.
Search Deals

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 16 August 2026.
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
Quickest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 17/9

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Sun 20/9

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 319

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sat 12/9

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

Chicago Midway

Sat 12/9

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 319

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sun 6/9

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Thu 10/9

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

C$ 319

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 2/9

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Wed 9/9

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 323

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 25/9

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

Chicago Midway

Fri 2/10

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 345

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 19/9

12:08 p.m.-6:22 p.m.

1 stop7h 14m

Chicago Midway

Tue 22/9

9:29 a.m.-3:15 p.m.

1 stop4h 46m

C$ 350

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sun 30/8

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

Chicago Midway

Mon 31/8

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 361

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 8/9

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

Chicago Midway

Tue 8/9

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 362

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 24/9

6:00 a.m.-9:07 a.m.

1 stop4h 07m

Chicago Midway

Sun 27/9

9:29 a.m.-5:20 p.m.

1 stop6h 51m

C$ 377

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sun 6/9

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Mon 7/9

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 383

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/8

Showing 1-10 of 43 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
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 33 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 Saturday, 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$ 219

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 16 August 2026.
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
457 reviews
Check prices

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.2

Food

7.6

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Porter Airlines
8.0
Very good
457 reviews
Porter Airlines
8.0
Very good
457 reviews
Check prices

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.2

Food

7.6

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.

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$ 143, while round-trip flights cost around C$ 230.

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

    A round-trip flight to Midway will typically cost around C$ 317, however they can be found for as little as C$ 230.

  • 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 50 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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