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C$ 219+ Cheap flights to Midway

— MDW
21 Nov — 28 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

Fri 25/126:10 a.m. -
1 stop3h 40m
Fri 1/16:15 p.m. -
1 stop3h 44m
Deal found 22/10C$ 356
Sat 21/116:00 a.m. -
1 stop4h 46m
Wed 25/111:31 p.m. -
1 stop8h 26m
Deal found 21/10C$ 365
Thu 19/116:00 a.m. -
1 stop4h 46m
Mon 23/119:30 a.m. -
1 stop3h 00m
Deal found 20/10C$ 378
Fri 25/1212:20 p.m. -
1 stop6h 24m
Tue 5/11:00 p.m. -
1 stop5h 07m
Deal found 20/10C$ 389
Thu 19/116:00 a.m. -
1 stop4h 46m
Mon 23/119:30 a.m. -
1 stop3h 00m
Deal found 20/10C$ 396
Wed 2/1212:15 p.m. -
1 stop6h 46m
Wed 9/121:41 p.m. -
1 stop8h 26m
Deal found 21/10C$ 398
Fri 13/1112:15 p.m. -
1 stop6h 49m
Tue 17/119:30 a.m. -
1 stop6h 50m
Deal found 21/10C$ 402
Thu 26/116:00 a.m. -
1 stop6h 25m
Sun 29/119:30 a.m. -
1 stop3h 00m
Deal found 19/10C$ 410
Thu 12/1112:15 p.m. -
1 stop6h 49m
Sun 15/119:30 a.m. -
1 stop6h 50m
Deal found 21/10C$ 426
Mon 30/116:00 a.m. -
1 stop7h 51m
Thu 10/129:37 a.m. -
1 stop6h 43m
Deal found 21/10C$ 434
Wed 11/119:10 a.m. -
2 stops15h 37m
Sat 14/117:15 a.m. -
2 stops28h 35m
Deal found 21/10C$ 538
Fri 4/124:15 p.m. -
2 stops20h 18m
Fri 11/1211:00 a.m. -
3 stops30h 15m
Deal found 20/10C$ 585

Find flight deals to Midway Airport

Round-trip from

C$ 302

One-way from

C$ 219

Popular in

October

Cheapest in

February

Average price

C$ 444

Good round-trip deal

C$ 342 or less

Good one-way deal

C$ 187 or less
Porter Airlines
  • Porter Airlines
  • 17/11-1/12
  • Nonstop
  • 3h 50m total
  • Toronto to Chicago
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Delta
  • Delta
  • 22/11-31/12
  • 1 total stop
  • 4h 46m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 3% potential increase in price (C$ 13 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 6 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

Fri 20/11

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$ 225

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$ 225

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 17/12

9:45 a.m.-1:01 p.m.

1 stop4h 16m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 225

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$ 239

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 3/12

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$ 239

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$ 240
Quickest round-trip

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Fri 25/12

6:10 a.m.-8:50 a.m.

1 stop3h 40m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 240

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Wed 18/11

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$ 240

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 2/12

9:10 a.m.-2:55 p.m.

2 stops30h 45m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 263

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 20/11

4:15 p.m.-7:33 a.m.

2 stops16h 18m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 274

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/10

Showing 1-10 of 40 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 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.

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
467 reviews
Check prices

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.6

Entertainment

6.9

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
467 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.6

Entertainment

6.9

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$ 82, while round-trip flights cost around C$ 236.

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

    A round-trip flight to Midway will typically cost around C$ 261, however they can be found for as little as C$ 236.

  • 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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