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C$ 165+ 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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
22 May — 29 May1
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 17 May 2025.

Round-trip from

C$ 236

One-way from

C$ 165

Popular in

December

Cheapest in

April

Average price

C$ 356

Good round-trip deal

C$ 234 or less

Good one-way deal

C$ 164 or less
Porter Airlines
  • Porter Airlines
  • 8/8-17/8
  • Nonstop
  • 3h 29m total
  • Toronto to Chicago
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Air Transat
  • Air Transat
  • 11/6
  • Nonstop
  • 1h 49m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 6% potential increase in price (C$ 37 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 7 potential savings vs. average RT price).
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Average for round-trip flights in May 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 17 May 2025.

Fri 8/83:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 17/89:40 a.m.MDW - YTZ
Nonstop1h 40mPorter Airlines
Deal found 15/5C$ 236
Sat 28/67:55 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Tue 1/79:40 a.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 16/5C$ 276
Sat 4/1012:15 p.m.YYZ - MDW
1 stop7h 21mDelta
Wed 15/101:00 p.m.MDW - YYZ
1 stop3h 23mDelta
Deal found 16/5C$ 293
Thu 19/63:35 p.m.YTZ - MDW
Nonstop1h 49mMultiple Airlines
Fri 20/65:50 p.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 16/5C$ 296
Thu 31/77:15 a.m.YYZ - MDW
1 stop14h 07mMultiple Airlines
Mon 4/88:35 a.m.MDW - YYZ
1 stop13h 09mMultiple Airlines
Deal found 16/5C$ 468
Sat 14/61:04 p.m.YYZ - MDW
1 stop5h 08mWestJet
Sat 21/61:47 p.m.MDW - YYZ
1 stop8h 36mWestJet
Deal found 15/5C$ 469
Sat 17/56:30 a.m.YYZ - MDW
1 stop7h 45mKLM
Mon 19/51:55 p.m.MDW - YYZ
1 stop8h 19mKLM
Deal found 15/5C$ 835

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 17 May 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 8/8

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

Nonstop1h 49m

Chicago Midway

Sun 17/8

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

Nonstop1h 40m

C$ 236

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 28/6

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

Nonstop1h 50m

Chicago Midway

Tue 1/7

9:40 a.m.-12:22 p.m.

Nonstop1h 42m

C$ 276

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 19/6

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

Nonstop1h 49m

Chicago Midway

Fri 20/6

5:50 p.m.-8:32 p.m.

Nonstop1h 42m

C$ 296

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 6/6

6:30 a.m.-8:40 a.m.

1 stop3h 10m

Chicago Midway

Tue 10/6

9:21 a.m.-6:34 p.m.

1 stop8h 13m

C$ 304

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 31/7

7:15 a.m.-8:22 p.m.

1 stop14h 07m

Chicago Midway

Mon 4/8

8:35 a.m.-10:44 p.m.

1 stop13h 09m

C$ 468

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 14/6

1:04 p.m.-5:12 p.m.

1 stop5h 08m

Chicago Midway

Sat 21/6

1:47 p.m.-11:23 p.m.

1 stop8h 36m

C$ 469

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 11/6

4:05 p.m.-4:54 p.m.

Nonstop1h 49m

C$ 165

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 24/6

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

Nonstop1h 50m

C$ 176

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 5/6

6:30 a.m.-8:40 a.m.

1 stop3h 10m

C$ 197

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 11/7

8:45 a.m.-5:35 p.m.

1 stop9h 50m

C$ 258

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/5

Showing 1-10 of 12 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 9 May 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 29 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 Tuesday, 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$ 188
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 17 May 2025.
Read reviews from past customers who have flown Porter Airlines, Delta and Air Transat to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
286 reviews
Check prices

Comfort

8.1

Overall

8.0

Crew

8.7

Boarding

8.2

Entertainment

7.0

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
286 reviews
Porter Airlines
8.0
Very good
286 reviews
Check prices

Comfort

8.1

Overall

8.0

Crew

8.7

Boarding

8.2

Entertainment

7.0

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Delta
8.0
Very good
7,949 reviews
Porter Airlines
8.0
Very good
286 reviews
Check prices

Comfort

8.1

Overall

8.0

Crew

8.7

Boarding

8.2

Entertainment

7.0

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air Transat
7.8
Good
388 reviews
Porter Airlines
8.0
Very good
286 reviews
Check prices

Comfort

8.1

Overall

8.0

Crew

8.7

Boarding

8.2

Entertainment

7.0

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
WestJet
7.2
Good
2,844 reviews
Porter Airlines
8.0
Very good
286 reviews
Check prices

Comfort

8.1

Overall

8.0

Crew

8.7

Boarding

8.2

Entertainment

7.0

Food

7.6

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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$ 54, while round-trip flights cost around C$ 163.

  • 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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