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C$ 275+ Cheap flights to Midway

— MDW
9 Dec — 16 Dec1
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

Thu 3/126:00 a.m. -
1 stop4h 37m
Sun 6/121:41 p.m. -
1 stop8h 26m
Deal found 8/11C$ 468
Thu 10/129:45 a.m. -
1 stop4h 16m
Mon 14/121:41 p.m. -
1 stop8h 26m
Deal found 6/11C$ 475
Thu 26/116:00 a.m. -
1 stop6h 25m
Sun 29/111:31 p.m. -
1 stop8h 26m
Deal found 5/11C$ 486
Wed 16/129:45 a.m. -
1 stop4h 16m
Thu 7/11:59 p.m. -
1 stop8h 00m
Deal found 4/11C$ 499
Fri 4/126:00 a.m. -
1 stop4h 37m
Sun 6/126:41 p.m. -
1 stop3h 26m
Deal found 8/11C$ 516
Fri 27/116:00 a.m. -
1 stop6h 25m
Sun 29/119:30 a.m. -
1 stop3h 00m
Deal found 6/11C$ 528
Wed 25/116:00 a.m. -
1 stop4h 46m
Mon 30/111:31 p.m. -
1 stop8h 26m
Deal found 8/11C$ 534
Thu 26/116:04 a.m. -
1 stop6h 25m
Sun 29/111:35 p.m. -
1 stop8h 26m
Deal found 5/11C$ 535
Mon 7/122:25 p.m. -
1 stop4h 36m
Mon 14/121:41 p.m. -
1 stop8h 26m
Deal found 8/11C$ 548
Mon 7/127:10 p.m. -
2 stops17h 23m
Wed 9/1212:28 p.m. -
2 stops24h 06m
Deal found 5/11C$ 685
Thu 10/127:10 p.m. -
2 stops21h 56m
Sun 13/125:02 p.m. -
2 stops17h 17m
Deal found 4/11C$ 708
Fri 4/124:15 p.m. -
2 stops20h 18m
Mon 7/125:02 p.m. -
2 stops15h 37m
Deal found 4/11C$ 711

Find flight deals to Midway Airport

Round-trip from

C$ 350

One-way from

C$ 275

Popular in

October

Cheapest in

February

Average price

C$ 418

Good round-trip deal

C$ 470 or less

Good one-way deal

C$ 324 or less
17/2-24/2
  • 17/2-24/2
  • 2 total stops
  • 39h 34m total
  • Toronto to Chicago
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Delta
  • Delta
  • 6/12-31/12
  • 1 total stop
  • 4h 16m 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. 1% potential price decrease (C$ 5 potential savings vs. average RT price).
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Average for round-trip flights in November 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

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$ 277

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 17/12

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$ 277
Quickest round-trip

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$ 284

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 1/12

12:15 p.m.-6:01 p.m.

1 stop6h 46m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 284

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Thu 26/11

6:00 a.m.-11:25 a.m.

1 stop6h 25m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 285

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 19/1

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$ 297

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 23/1

7:45 a.m.-1:01 p.m.

1 stop6h 16m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 298

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$ 328

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$ 342

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Mon 14/12

4:15 p.m.-11:33 a.m.

2 stops20h 18m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 346

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 35 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 9 hours 51 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$ 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

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
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

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$ 218.

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

    A round-trip flight to Midway will typically cost around C$ 220, however they can be found for as little as C$ 218.

  • 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 (3 hours 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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