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C$ 195+ Cheap flights to Midway

— MDW
6 Oct — 13 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 13/101:45 p.m. -
Nonstop1h 50m
Tue 20/103:20 p.m. -
Nonstop1h 40m
Deal found 5/9C$ 286
Mon 12/101:45 p.m. -
Nonstop1h 50m
Wed 14/103:20 p.m. -
Nonstop1h 40m
Deal found 5/9C$ 289
Fri 25/91:45 p.m. -
Nonstop1h 50m
Sun 27/911:45 a.m. -
Nonstop1h 40m
Deal found 4/9C$ 292
Sat 17/101:45 p.m. -
Nonstop1h 50m
Sun 18/103:20 p.m. -
Nonstop1h 40m
Deal found 2/9C$ 300
Wed 30/910:10 a.m. -
Nonstop1h 50m
Fri 2/1011:45 a.m. -
Nonstop1h 40m
Deal found 2/9C$ 306
Sat 19/910:10 a.m. -
Nonstop1h 50m
Sat 26/911:45 a.m. -
Nonstop1h 40m
Deal found 4/9C$ 307
Thu 1/1010:10 a.m. -
Nonstop1h 50m
Sun 4/103:20 p.m. -
Nonstop1h 40m
Deal found 6/9C$ 309
Thu 1/1010:10 a.m. -
Nonstop1h 50m
Thu 8/103:20 p.m. -
Nonstop1h 40m
Deal found 3/9C$ 314
Tue 22/910:10 a.m. -
Nonstop1h 50m
Sat 26/911:45 a.m. -
Nonstop1h 40m
Deal found 4/9C$ 317
Thu 24/96:00 a.m. -
1 stop7h 39m
Sun 27/99:29 a.m. -
1 stop6h 51m
Deal found 3/9C$ 317
Tue 22/91:45 p.m. -
Nonstop1h 50m
Tue 29/911:45 a.m. -
Nonstop1h 40m
Deal found 2/9C$ 318
Tue 22/91:45 p.m. -
Nonstop1h 50m
Fri 25/93:20 p.m. -
Nonstop1h 40m
Deal found 2/9C$ 321

Find flight deals to Midway Airport

Round-trip from

C$ 285

One-way from

C$ 195

Popular in

October

Cheapest in

February

Average price

C$ 365

Good round-trip deal

C$ 292 or less

Good one-way deal

C$ 285 or less
Lufthansa
  • Lufthansa
  • 26/9-27/9
  • Nonstop
  • 3h 47m total
  • Toronto to Chicago
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Air Transat
  • Air Transat
  • 27/9-31/12
  • 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. 0% potential price decrease (C$ 3 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

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Fri 25/9

2:24 p.m.-6:33 p.m.

1 stop5h 09m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 199

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Mon 12/10

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$ 199

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 23/9

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$ 199

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 29/9

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$ 199

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$ 199
Quickest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 24/9

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$ 205

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Mon 28/9

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$ 210

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 3/10

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$ 210

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$ 210

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 4/11

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$ 210

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/9

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

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 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$ 218

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
458 reviews
Check prices

Entertainment

6.9

Boarding

8.2

Crew

8.6

Food

7.6

Comfort

8.0

Overall

8.0

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
458 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Entertainment

6.9

Boarding

8.2

Crew

8.6

Food

7.6

Comfort

8.0

Overall

8.0

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$ 153, while round-trip flights cost around C$ 233.

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

    A round-trip flight to Midway will typically cost around C$ 257, however they can be found for as little as C$ 233.

  • 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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