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C$ 183+ Cheap flights to Midway

— MDW
19 Sep — 26 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

Wed 9/910:10 a.m. -
Nonstop1h 50m
Thu 10/93:20 p.m. -
Nonstop1h 40m
Deal found 18/8C$ 278
Thu 10/91:45 p.m. -
Nonstop1h 50m
Sun 13/911:45 a.m. -
Nonstop1h 40m
Deal found 15/8C$ 280
Mon 7/910:10 a.m. -
Nonstop1h 50m
Thu 10/93:20 p.m. -
Nonstop1h 40m
Deal found 16/8C$ 283
Fri 11/91:45 p.m. -
Nonstop1h 50m
Sun 13/911:45 a.m. -
Nonstop1h 40m
Deal found 17/8C$ 284
Fri 18/910:10 a.m. -
Nonstop1h 50m
Tue 22/911:45 a.m. -
Nonstop1h 40m
Deal found 17/8C$ 285
Mon 7/910:10 a.m. -
Nonstop1h 50m
Wed 9/93:20 p.m. -
Nonstop1h 40m
Deal found 15/8C$ 288
Tue 8/910:10 a.m. -
Nonstop1h 50m
Sun 13/911:45 a.m. -
Nonstop1h 40m
Deal found 15/8C$ 296
Thu 10/912:08 p.m. -
1 stop5h 49m
Sun 13/96:40 p.m. -
1 stop3h 19m
Deal found 19/8C$ 338
Tue 8/99:45 a.m. -
1 stop8h 12m
Wed 9/95:37 p.m. -
1 stop4h 22m
Deal found 18/8C$ 339
Fri 11/99:50 a.m. -
1 stop7h 32m
Sun 13/96:45 p.m. -
1 stop3h 19m
Deal found 17/8C$ 361
Mon 7/96:10 a.m. -
1 stop7h 29m
Sat 12/95:37 p.m. -
1 stop4h 22m
Deal found 17/8C$ 371
Sat 5/96:10 a.m. -
1 stop4h 07m
Fri 11/99:29 a.m. -
1 stop6h 51m
Deal found 17/8C$ 382

Find flight deals to Midway Airport

Round-trip from

C$ 277

One-way from

C$ 183

Popular in

July

Cheapest in

February

Average price

C$ 369

Good round-trip deal

C$ 280 or less

Good one-way deal

C$ 188 or less
Air Canada
  • Air Canada
  • 24/9-28/9
  • 1 total stop
  • 7h 07m total
  • Toronto to Chicago
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Porter Airlines
  • Porter Airlines
  • 14/9
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 3% potential increase in price (C$ 12 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease (C$ 4 potential savings vs. average RT price).
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Average for round-trip flights in August 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

Sat 19/9

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

Nonstop1h 50m

Chicago Midway

Mon 21/9

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

Nonstop1h 40m

C$ 278

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 18/9

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$ 278

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 17/9

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

Nonstop1h 50m

Chicago Midway

Mon 21/9

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

Nonstop1h 40m

C$ 318

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$ 318

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Mon 7/9

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

Nonstop1h 50m

Chicago Midway

Sun 13/9

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

Nonstop1h 40m

C$ 323

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 15/9

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

1 stop7h 39m

Chicago Midway

Tue 22/9

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

1 stop4h 46m

C$ 339

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Fri 11/9

12:08 p.m.-4:17 p.m.

1 stop5h 09m

Chicago Midway

Sun 13/9

6:40 p.m.-10:59 p.m.

1 stop3h 19m

C$ 339

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

Mon 21/9

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

1 stop6h 51m

C$ 339

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 25/9

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

Nonstop1h 50m

Chicago Midway

Mon 28/9

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

Nonstop1h 40m

C$ 349

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 4/9

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

Nonstop1h 50m

Chicago Midway

Thu 10/9

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

Nonstop1h 40m

C$ 381

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/8

Showing 1-10 of 38 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 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.

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$ 217

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
457 reviews
Check prices

Boarding

8.2

Entertainment

6.9

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.6

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

Boarding

8.2

Entertainment

6.9

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.6

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$ 142, while round-trip flights cost around C$ 228.

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

    A round-trip flight to Midway will typically cost around C$ 315, however they can be found for as little as C$ 228.

  • 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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