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C$ 182+ Cheap flights to Midway

— MDW
21 Oct — 28 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

Sun 11/1010:10 a.m. -
Nonstop1h 50m
Fri 16/1011:45 a.m. -
Nonstop1h 40m
Deal found 19/9C$ 288
Fri 2/101:45 p.m. -
Nonstop1h 50m
Sun 4/1011:45 a.m. -
Nonstop1h 40m
Deal found 18/9C$ 289
Wed 7/101:45 p.m. -
Nonstop1h 50m
Sun 11/1011:45 a.m. -
Nonstop1h 40m
Deal found 16/9C$ 294
Mon 5/101:45 p.m. -
Nonstop1h 50m
Wed 7/1011:45 a.m. -
Nonstop1h 40m
Deal found 18/9C$ 295
Fri 2/101:45 p.m. -
Nonstop1h 50m
Sat 3/1011:45 a.m. -
Nonstop1h 40m
Deal found 18/9C$ 296
Sun 11/1010:10 a.m. -
Nonstop1h 50m
Sun 18/103:20 p.m. -
Nonstop1h 40m
Deal found 16/9C$ 299
Fri 2/1010:10 a.m. -
Nonstop1h 50m
Fri 2/103:20 p.m. -
Nonstop1h 40m
Deal found 18/9C$ 301
Sat 3/1010:10 a.m. -
Nonstop1h 50m
Sun 4/103:20 p.m. -
Nonstop1h 40m
Deal found 19/9C$ 303
Wed 7/1010:10 a.m. -
Nonstop1h 50m
Fri 9/103:20 p.m. -
Nonstop1h 40m
Deal found 18/9C$ 306
Sat 10/101:45 p.m. -
Nonstop1h 50m
Tue 13/103:20 p.m. -
Nonstop1h 40m
Deal found 19/9C$ 317
Tue 24/1112:15 p.m. -
1 stop6h 49m
Sat 28/119:30 a.m. -
1 stop6h 50m
Deal found 20/9C$ 317
Fri 2/1012:08 p.m. -
1 stop7h 25m
Sat 3/106:40 p.m. -
1 stop3h 19m
Deal found 18/9C$ 319

Find flight deals to Midway Airport

Round-trip from

C$ 288

One-way from

C$ 182

Popular in

October

Cheapest in

February

Average price

C$ 352

Good round-trip deal

C$ 342 or less

Good one-way deal

C$ 254 or less
Porter Airlines
  • Porter Airlines
  • 11/10-16/10
  • Nonstop
  • 3h 30m total
  • Toronto to Chicago
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Porter Airlines
  • Porter Airlines
  • 3/10-31/12
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 1% potential increase in price (C$ 6 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 5 potential savings vs. average RT price).
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Average for round-trip flights in September 2026
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Price to beat on a round-trip flight from Toronto to Chicago Midway.
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Price to beat on a one-way flight from Toronto to Chicago Midway.
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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

Mon 5/10

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$ 182

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sat 10/10

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

Wed 30/9

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

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Fri 2/10

12:08 p.m.-6:33 p.m.

1 stop7h 25m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 201

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 4/11

6:00 a.m.-12:47 p.m.

1 stop7h 47m

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 18/10

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

Sat 17/10

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$ 207

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 1/10

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

1 stop4h 07m

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

Thu 8/10

6:00 a.m.-12:47 p.m.

1 stop7h 47m

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

Wed 11/11

9:45 a.m.-12:51 p.m.

1 stop4h 06m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 207

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/9

Showing 1-10 of 46 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

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 49 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 Monday, which is when the least amount of flights are scheduled (4 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$ 221

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
462 reviews
Check prices

Entertainment

6.9

Overall

8.0

Comfort

8.0

Food

7.6

Crew

8.6

Boarding

8.2

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
462 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Entertainment

6.9

Overall

8.0

Comfort

8.0

Food

7.6

Crew

8.6

Boarding

8.2

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$ 164, while round-trip flights cost around C$ 235.

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

    A round-trip flight to Midway will typically cost around C$ 260, however they can be found for as little as C$ 235.

  • 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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