Find flights
Deals
Airlines

C$ 192+ 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 31/7. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
28 Jul — 4 Aug1
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 28 June 2026.

Thu 9/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 12/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 25/6C$ 288
Sun 12/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 15/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 26/6C$ 290
Sat 25/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 29/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 25/6C$ 291
Fri 10/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 12/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 26/6C$ 292
Fri 24/71:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Fri 31/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 26/6C$ 294
Fri 17/71:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 21/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 27/6C$ 295
Thu 16/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 21/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 27/6C$ 297
Fri 10/71:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 16/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 26/6C$ 299
Thu 9/71:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 26/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 25/6C$ 302
Thu 16/71:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 18/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 25/6C$ 305
Wed 16/912:08 p.m.
YYZ
-
MDW
1 stop7h 25m
Delta
Wed 23/99:29 a.m.
MDW
-
YYZ
1 stop6h 51m
Delta
Deal found 27/6C$ 362
Wed 14/109:45 a.m.
YYZ
-
MDW
1 stop3h 48m
Delta
Sat 17/106:30 p.m.
MDW
-
YYZ
1 stop3h 30m
Delta
Deal found 25/6C$ 363

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 28 June 2026.

Round-trip from

C$ 285

One-way from

C$ 192

Popular in

June

Cheapest in

September

Average price

C$ 417

Good round-trip deal

C$ 305 or less

Good one-way deal

C$ 176 or less
Porter Airlines
  • Porter Airlines
  • 25/9-27/9
  • Nonstop
  • 3h 35m total
  • Toronto to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 31/7
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 28 June 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 - MDW

YTZMDW

Toronto Island

Tue 14/7

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

Nonstop1h 50m

Chicago Midway

Fri 17/7

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

Nonstop1h 40m

C$ 291

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 17/7

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

Nonstop1h 50m

Chicago Midway

Tue 21/7

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

Nonstop1h 40m

C$ 295

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 20/7

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

Nonstop1h 50m

Chicago Midway

Thu 23/7

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

Nonstop1h 40m

C$ 302

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 16/7

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

Nonstop1h 50m

Chicago Midway

Tue 21/7

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

Nonstop1h 40m

C$ 302

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 18/7

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

Nonstop1h 50m

Chicago Midway

Sun 19/7

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

Nonstop1h 40m

C$ 305

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 23/7

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

Nonstop1h 50m

Chicago Midway

Mon 27/7

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

Nonstop1h 40m

C$ 308

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 31/7

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

Nonstop1h 50m

Chicago Midway

Mon 3/8

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

Nonstop1h 40m

C$ 331

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 30/7

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

Nonstop1h 50m

Chicago Midway

Mon 3/8

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

Nonstop1h 40m

C$ 346

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 29/7

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

Nonstop1h 50m

Chicago Midway

Mon 3/8

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

Nonstop1h 40m

C$ 348

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 5/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Sun 9/8

10:20 a.m.-1:00 p.m.

Nonstop1h 40m

C$ 353

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/6

Showing 1-10 of 46 resultsSorted by cheapest first
1
2
3
...
5

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 36 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$ 116

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 28 June 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
441 reviews
Check prices

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.5

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Porter Airlines
8.0
Very good
441 reviews
Porter Airlines
8.0
Very good
441 reviews
Check prices

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.5

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.

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$ 164, while round-trip flights cost around C$ 257.

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

    A round-trip flight to Midway will typically cost around C$ 371, however they can be found for as little as C$ 257.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Search flights to Midway by cabin class

Find flights to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First class flights to Chicago Midway Airport
Business class flights to Chicago Midway Airport
Prem Economy class flights to Chicago Midway Airport
Economy class flights to Chicago Midway Airport

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights to Midway?

When you search for this flight to Midway, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the best flight for you.

Why should you use Cheapflights to find cheap flight tickets to Midway?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Midway.

Can Cheapflights find flights to Midway with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights to Midway flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights to Midway become cheaper?

Yes! Start tracking prices for Midway flights today and get alerted when prices change. To subscribe and begin receiving alerts, click the bell icon next to the flight deals above and provide your email address.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.