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C$ 145+ 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 26/11. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
23 Aug — 30 Aug1
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 18 August 2025.

Round-trip from

C$ 203

One-way from

C$ 145

Popular in

December

Cheapest in

July

Average price

C$ 356

Good round-trip deal

C$ 241 or less

Good one-way deal

C$ 154 or less
United Airlines
  • United Airlines
  • 4/11-11/11
  • Nonstop
  • 3h 52m total
  • Toronto to Chicago
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Porter Airlines
  • Porter Airlines
  • 10/11
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 8% potential increase in price (C$ 44 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 August 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 18 August 2025.

Thu 11/93:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sat 13/99:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/8C$ 239
Thu 25/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sat 27/99:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/8C$ 242
Fri 12/93:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Thu 18/99:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/8C$ 245
Thu 2/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 5/105:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/8C$ 246
Thu 2/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Mon 6/105:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/8C$ 247
Wed 10/93:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sat 13/99:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/8C$ 250
Fri 19/93:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 21/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/8C$ 251
Sun 7/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Wed 10/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/8C$ 253
Fri 12/93:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Fri 19/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/8C$ 254
Thu 23/103:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 26/1011:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 16/8C$ 256
Sat 27/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Wed 1/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/8C$ 261
Tue 4/116:15 a.m.YYZ - MDW
1 stop7h 13mDelta
Sat 8/1111:10 a.m.MDW - YYZ
1 stop5h 09mDelta
Deal found 16/8C$ 280

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 18 August 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

Fri 24/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Sun 26/10

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 239

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 11/9

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

Nonstop1h 49m

Chicago Midway

Sat 13/9

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 239

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 19/9

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

Nonstop1h 49m

Chicago Midway

Sun 21/9

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 239

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 15/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Mon 20/10

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

Nonstop1h 42m

C$ 239

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 25/9

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Sun 28/9

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 242

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 19/9

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

Nonstop1h 49m

Chicago Midway

Thu 25/9

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 242

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 28/9

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Tue 7/10

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

Nonstop1h 42m

C$ 242

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 2/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Sun 5/10

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

Nonstop1h 42m

C$ 242

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 24/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Mon 27/10

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 242

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 25/9

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Sat 27/9

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 242

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/8

Showing 1-10 of 44 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 8 August 2025.

To ensure you get the cheapest price possible for a flight to Midway, you should look to book at least 75 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 36 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 20 October 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 Monday evenings, 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$ 137
Air Transat
Air Transat
From C$ 189
WestJet
WestJet
From C$ 345

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 18 August 2025.
Check out reviews from past customers who have flown Porter Airlines and Air 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
333 reviews
Check prices

Overall

8.0

Entertainment

7.0

Crew

8.7

Comfort

8.0

Boarding

8.2

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
333 reviews
Porter Airlines
8.0
Very good
333 reviews
Check prices

Overall

8.0

Entertainment

7.0

Crew

8.7

Comfort

8.0

Boarding

8.2

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Transat
7.7
Good
428 reviews
Porter Airlines
8.0
Very good
333 reviews
Check prices

Overall

8.0

Entertainment

7.0

Crew

8.7

Comfort

8.0

Boarding

8.2

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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$ 63, while round-trip flights cost around C$ 106.

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

    A round-trip flight to Midway will typically cost around C$ 258, however they can be found for as little as C$ 77.

  • 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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