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C$ 172+ 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 29/12. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
20 dic. — 27 dic.1
1 adult
1 adult, Economy, 0 bags

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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 20 noviembre 2025.

mar. 2/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
vie. 5/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/11C$ 252
lun. 22/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
lun. 5/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/11C$ 256
mar. 23/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
mar. 6/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/11C$ 266
sáb. 20/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
lun. 5/14:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 19/11C$ 269
vie. 5/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
lun. 8/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 19/11C$ 273
mar. 2/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
jue. 4/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/11C$ 276
dom. 7/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
mié. 10/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 19/11C$ 279
mar. 23/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
sáb. 27/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/11C$ 288
vie. 19/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
mar. 30/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 19/11C$ 294
jue. 11/126:05 a.m.YYZ - MDW
1 stop7h 29mDelta
mar. 16/129:34 a.m.MDW - YYZ
1 stop4h 14mDelta
Deal found 18/11C$ 295
dom. 7/126:05 a.m.YYZ - MDW
1 stop3h 49mDelta
sáb. 13/121:14 p.m.MDW - YYZ
1 stop3h 01mDelta
Deal found 17/11C$ 312
vie. 5/123:38 p.m.YYZ - MDW
1 stop3h 22mDelta
lun. 8/126:40 p.m.MDW - YYZ
1 stop3h 31mDelta
Deal found 19/11C$ 329

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 20 noviembre 2025.

Round-trip from

C$ 252

One-way from

C$ 172

Popular in

December

Cheapest in

July

Average price

C$ 395

Good round-trip deal

C$ 348 or less

Good one-way deal

C$ 198 or less
Porter Airlines
  • Porter Airlines
  • 2/12-5/12
  • Nonstop
  • 3h 32m total
  • Toronto to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 29/12
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Toronto to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Toronto to Chicago Midway.
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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 20 noviembre 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

vie. 26/12

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

mar. 6/1

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

Nonstop1h 42m

C$ 256

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

sáb. 27/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

lun. 5/1

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

Nonstop1h 42m

C$ 256

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

lun. 22/12

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

lun. 5/1

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

Nonstop1h 42m

C$ 256

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

mié. 24/12

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

mar. 6/1

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

Nonstop1h 42m

C$ 266

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

mar. 23/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

lun. 5/1

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

Nonstop1h 42m

C$ 269

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

dom. 21/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

lun. 5/1

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

Nonstop1h 42m

C$ 269

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

sáb. 20/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

lun. 5/1

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 269

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

jue. 25/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

mar. 6/1

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

Nonstop1h 42m

C$ 269

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

mié. 24/12

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

lun. 5/1

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

Nonstop1h 42m

C$ 269

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

mar. 23/12

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

mar. 6/1

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

Nonstop1h 42m

C$ 269

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/11

Showing 1-10 of 40 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

How long is the flight to Midway?

On average, a flight from Toronto to Midway takes 2 hours 35 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 16 December 2024.

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

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$ 192
Air Transat
Air Transat
From C$ 266
WestJet
WestJet
From C$ 559

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 20 noviembre 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
393 reviews
Check prices

Crew

8.6

Comfort

8.0

Food

7.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
8.0
Very good
393 reviews
Porter Airlines
8.0
Very good
393 reviews
Check prices

Crew

8.6

Comfort

8.0

Food

7.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Transat
7.8
Good
475 reviews
Porter Airlines
8.0
Very good
393 reviews
Check prices

Crew

8.6

Comfort

8.0

Food

7.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

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$ 62, while round-trip flights cost around C$ 180.

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

    A round-trip flight to Midway will typically cost around C$ 407, however they can be found for as little as C$ 180.

  • 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 Kitch is the closest property to Chicago Midway (0.0 km away from Chicago Midway).

See more FAQs

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