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C$ 274+ Cheap flights to Midway

— MDW
18 Nov — 25 Nov1
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

Mon 9/1112:15 p.m. -
1 stop6h 49m
Tue 1/126:41 p.m. -
1 stop3h 26m
Deal found 14/10C$ 465
Sat 7/119:40 a.m. -
1 stop4h 07m
Sun 8/119:29 a.m. -
1 stop3h 07m
Deal found 17/10C$ 466
Fri 20/116:00 a.m. -
1 stop4h 46m
Tue 24/119:30 a.m. -
1 stop6h 50m
Deal found 14/10C$ 469
Sun 8/1112:10 p.m. -
1 stop6h 50m
Fri 13/119:30 a.m. -
1 stop6h 50m
Deal found 18/10C$ 472
Fri 13/116:00 a.m. -
1 stop7h 51m
Sun 15/119:30 a.m. -
1 stop6h 50m
Deal found 14/10C$ 506
Sat 28/116:00 a.m. -
1 stop4h 46m
Thu 3/129:37 a.m. -
1 stop6h 43m
Deal found 17/10C$ 507
Sun 15/1112:15 p.m. -
1 stop6h 49m
Sun 22/119:30 a.m. -
1 stop6h 50m
Deal found 18/10C$ 509
Thu 5/1112:10 p.m. -
1 stop6h 50m
Sun 8/111:27 p.m. -
1 stop8h 29m
Deal found 14/10C$ 510
Fri 6/116:05 a.m. -
1 stop7h 47m
Sun 8/119:34 a.m. -
1 stop6h 50m
Deal found 16/10C$ 517
Sat 7/119:45 a.m. -
1 stop4h 07m
Sun 8/119:34 a.m. -
1 stop3h 07m
Deal found 17/10C$ 519
Wed 18/119:10 a.m. -
2 stops15h 37m
Sun 22/111:16 p.m. -
2 stops22h 34m
Deal found 14/10C$ 697
Tue 1/127:10 p.m. -
2 stops17h 23m
Sat 5/1212:28 p.m. -
2 stops20h 11m
Deal found 16/10C$ 698

Find flight deals to Midway Airport

Round-trip from

C$ 324

One-way from

C$ 274

Popular in

October

Cheapest in

February

Average price

C$ 431

Good round-trip deal

C$ 344 or less

Good one-way deal

C$ 188 or less
Air Canada
  • Air Canada
  • 24/10-30/10
  • Nonstop
  • 3h 57m total
  • Toronto to Chicago
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Delta
  • Delta
  • 18/11-31/12
  • 1 total stop
  • 7h 51m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 2% potential increase in price (C$ 9 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 October 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

Mon 30/11

6:00 a.m.-12:51 p.m.

1 stop7h 51m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 276

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 28/11

6:00 a.m.-9:46 a.m.

1 stop4h 46m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 276

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 25/11

6:00 a.m.-9:46 a.m.

1 stop4h 46m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 276

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 8/12

6:00 a.m.-1:01 p.m.

1 stop8h 01m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 276

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 17/11

2:20 p.m.-6:04 p.m.

1 stop4h 44m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 277

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 11/11

2:20 p.m.-6:04 p.m.

1 stop4h 44m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 277

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 5/12

6:00 a.m.-9:37 a.m.

1 stop4h 37m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 277

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 21/11

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$ 277

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 2/12

2:25 p.m.-6:01 p.m.

1 stop4h 36m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 277

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sun 15/11

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$ 277

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/10

Showing 1-10 of 42 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 44 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$ 223

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
468 reviews
Check prices

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.6

Entertainment

7.0

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
468 reviews
Porter Airlines
8.0
Very good
468 reviews
Check prices

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.6

Entertainment

7.0

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$ 83, while round-trip flights cost around C$ 238.

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

    A round-trip flight to Midway will typically cost around C$ 263, however they can be found for as little as C$ 238.

  • 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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