Find flights
Deals
Airlines

C$ 180+ Cheap flights to Midway

— MDW
24 Oct — 31 Oct1
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

Tue 6/1010:10 a.m. -
Nonstop1h 50m
Thu 8/103:20 p.m. -
Nonstop1h 40m
Deal found 22/9C$ 289
Sun 11/1010:10 a.m. -
Nonstop1h 50m
Fri 16/1011:45 a.m. -
Nonstop1h 40m
Deal found 19/9C$ 290
Mon 12/101:45 p.m. -
Nonstop1h 50m
Thu 15/103:20 p.m. -
Nonstop1h 40m
Deal found 22/9C$ 292
Sat 17/1010:10 a.m. -
Nonstop1h 50m
Tue 20/1011:45 a.m. -
Nonstop1h 40m
Deal found 20/9C$ 294
Wed 7/101:45 p.m. -
Nonstop1h 50m
Tue 13/103:20 p.m. -
Nonstop1h 40m
Deal found 20/9C$ 302
Thu 15/1010:10 a.m. -
Nonstop1h 50m
Fri 16/103:20 p.m. -
Nonstop1h 40m
Deal found 23/9C$ 306
Mon 5/1010:10 a.m. -
Nonstop1h 50m
Thu 8/103:20 p.m. -
Nonstop1h 40m
Deal found 21/9C$ 309
Wed 14/101:45 p.m. -
Nonstop1h 50m
Tue 20/1011:45 a.m. -
Nonstop1h 40m
Deal found 23/9C$ 310
Wed 7/1010:10 a.m. -
Nonstop1h 50m
Sat 10/1011:45 a.m. -
Nonstop1h 40m
Deal found 23/9C$ 317
Mon 19/1010:10 a.m. -
Nonstop1h 50m
Wed 21/1011:45 a.m. -
Nonstop1h 40m
Deal found 23/9C$ 318
Tue 24/1112:15 p.m. -
1 stop6h 49m
Sat 28/119:30 a.m. -
1 stop6h 50m
Deal found 20/9C$ 320
Tue 6/106:00 a.m. -
1 stop4h 32m
Thu 15/109:29 a.m. -
1 stop3h 07m
Deal found 21/9C$ 321

Find flight deals to Midway Airport

Round-trip from

C$ 286

One-way from

C$ 180

Popular in

October

Cheapest in

February

Average price

C$ 355

Good round-trip deal

C$ 344 or less

Good one-way deal

C$ 256 or less
Air Canada
  • Air Canada
  • 23/10-27/10
  • Nonstop
  • 3h 35m total
  • Toronto to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 13/10-31/12
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 1% potential increase in price (C$ 6 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 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

 
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

Sat 17/10

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

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 183

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 15/10

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

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 183

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 16/10

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

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 183

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 21/10

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

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 185

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Fri 16/10

2:26 p.m.-6:00 p.m.

1 stop4h 34m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 207

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sun 8/11

12:10 p.m.-6:00 p.m.

1 stop6h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 207

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Fri 20/11

12:15 p.m.-6:04 p.m.

1 stop6h 49m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 207

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 28/11

12:15 p.m.-6:04 p.m.

1 stop6h 49m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 207

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sun 4/10

6:00 a.m.-12:39 p.m.

1 stop7h 39m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 209

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 4/11

6:00 a.m.-9:32 a.m.

1 stop4h 32m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 209

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/9

Showing 1-10 of 43 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

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 45 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 Wednesday (4 on average). You will have fewer flight options on Monday, 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$ 222

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

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

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

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
463 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Entertainment

6.9

Overall

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Porter Airlines
8.0
Very good
463 reviews
Porter Airlines
8.0
Very good
463 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Entertainment

6.9

Overall

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

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$ 166, while round-trip flights cost around C$ 237.

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

    A round-trip flight to Midway will typically cost around C$ 262, however they can be found for as little as C$ 237.

  • 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

Search flights to Midway by cabin 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

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.