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C$ 144+ Cheap flights to Midway

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
8 Jul — 15 Jul1
1 adult

Flights to Midway in 2025

Find the latest flights to Midway in 2025, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 629,999 searches and data was last updated on 3 July 2025.

Round-trip from

C$ 221

One-way from

C$ 144

Popular in

December

Cheapest in

April

Average price

C$ 343

Good round-trip deal

C$ 228 or less

Good one-way deal

C$ 154 or less
Porter Airlines
  • Porter Airlines
  • 15/7-15/7
  • Nonstop
  • 3h 32m total
  • Toronto to Chicago
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Porter Airlines
  • Porter Airlines
  • 12/9
  • Nonstop
  • 1h 49m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 7% potential increase in price (C$ 40 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 8 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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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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Find flight deals to Midway Airport

Cheapest flights to Midway Airport
Explore the most affordable flight options available to Midway Airport. Find the lowest fares based on data from user searches, with prices last updated on 3 July 2025.

Fri 11/77:55 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 14/79:40 a.m.MDW - YTZ
Nonstop1h 40mPorter Airlines
Deal found 2/7C$ 221
Fri 5/97:30 a.m.YTZ - MDW
Nonstop1h 49mMultiple Airlines
Mon 8/99:15 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 1/7C$ 224
Wed 30/77:55 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Wed 6/89:40 a.m.MDW - YTZ
Nonstop1h 40mAir Transat
Deal found 1/7C$ 228
Sat 4/1012:14 p.m.YYZ - MDW
1 stop7h 21mDelta
Wed 15/102:00 p.m.MDW - YYZ
1 stop7h 55mDelta
Deal found 1/7C$ 292
Fri 15/87:21 p.m.YYZ - MDW
1 stop18h 42mWestJet
Fri 22/812:43 p.m.MDW - YYZ
1 stop8h 15mWestJet
Deal found 2/7C$ 349

Cheapflights Fare Finder

Locate flights to Midway that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 629,999 searches and data was last updated on 3 July 2025.
Use the filters below to find and compare flights to Chicago Midway Airport that are best for you.

Fly from

Toronto

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 15/7

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Tue 15/7

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 221

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 5/9

7:30 a.m.-8:19 a.m.

Nonstop1h 49m

Chicago Midway

Mon 8/9

9:15 a.m.-11:57 a.m.

Nonstop1h 42m

C$ 224

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 30/7

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Wed 6/8

9:40 a.m.-12:20 p.m.

Nonstop1h 40m

C$ 228

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 4/10

12:14 p.m.-6:35 p.m.

1 stop7h 21m

Chicago Midway

Wed 15/10

2:00 p.m.-10:55 p.m.

1 stop7h 55m

C$ 292

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 15/8

7:21 p.m.-1:03 p.m.

1 stop18h 42m

Chicago Midway

Fri 22/8

12:43 p.m.-9:58 p.m.

1 stop8h 15m

C$ 349

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 12/9

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

C$ 144

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 19/7

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

C$ 147

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 1/9

12:14 p.m.-6:37 p.m.

1 stop7h 23m

C$ 184

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 21/8

8:45 a.m.-5:05 p.m.

1 stop9h 20m

C$ 211

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 30/8

1:20 p.m.-9:12 p.m.

1 stop8h 52m

C$ 211

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/7

Showing 1-10 of 11 results
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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
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight to Chicago Midway Airport

When is the best time to book a flight to Midway?

Use this chart to determine the optimal time to book a round-trip flight from Toronto to Midway. Price data was last updated on 27 June 2025.

To ensure you get the cheapest price possible for a flight to Midway, you should look to book at least 34 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

How long is the flight to Midway?

On average, a flight from Toronto to Midway takes 2 hours 37 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.

When is the cheapest time to fly to Midway?

Use this chart to determine the cheapest time to fly round-trip from Toronto to Midway. Price data was last updated on 30 June 2024.

Users looking for the lowest fares to Midway should consider flying on Monday at noon, when prices are typically cheapest. Budget-minded travellers will want to avoid Sunday at noon, when prices are usually at their highest.

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 Saturday, which is when the least amount of flights are scheduled (2 on average).

What are the most popular airlines that fly to Midway?

The most popular airlines flying from Toronto to Midway are Porter Airlines and WestJet.

Porter Airlines
Porter Airlines
From C$ 168
WestJet
WestJet
From C$ 345
Air Transat
Air Transat
From C$ 186

What are the cheapest airlines that fly to Midway?

The cheapest airlines flying from Toronto to Midway are Porter Airlines and WestJet.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals 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

Plan your trip to Midway by taking into account the average temperature totals 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

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated 3 July 2025.
Check out reviews from past customers who have flown Porter Airlines,Delta, andAir Transat 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
298 reviews
Check prices

Boarding

8.2

Crew

8.7

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
298 reviews
Porter Airlines
8.0
Very good
298 reviews
Check prices

Boarding

8.2

Crew

8.7

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,982 reviews
Porter Airlines
8.0
Very good
298 reviews
Check prices

Boarding

8.2

Crew

8.7

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Air Transat
7.8
Good
407 reviews
Porter Airlines
8.0
Very good
298 reviews
Check prices

Boarding

8.2

Crew

8.7

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
WestJet
7.2
Good
2,917 reviews
Porter Airlines
8.0
Very good
298 reviews
Check prices

Boarding

8.2

Crew

8.7

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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$ 134, while round-trip flights cost around C$ 159.

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

    A round-trip flight to Midway will typically cost around C$ 423, however they can be found for as little as C$ 117.

  • 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 49 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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