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Cheap flights to Midway

— MDW
2 May — 9 May1
1 adult
1 adult, Economy, 0 bags

Find flight deals to Midway Airport

Find the latest flights to Midway in 2026, 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 2 April 2026.

Round-trip from

C$ 272

One-way from

C$ 172

Popular in

December

Cheapest in

July

Average price

C$ 342

Good round-trip deal

C$ 293 or less

Good one-way deal

C$ 264 or less
Air Canada
  • Air Canada
  • 9/7-19/7
  • 1 total stop
  • 6h 46m total
  • Toronto to Chicago
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Air Transat
  • Air Transat
  • 6/5
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 6% potential increase in price (C$ 23 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 April 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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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

What are the cheapest airlines that fly to Midway?

The cheapest airline flying from Toronto to Midway is Porter Airlines.

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 2 April 2026.
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
430 reviews
Check prices

Entertainment

7.0

Comfort

8.0

Crew

8.6

Food

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
430 reviews
Porter Airlines
8.0
Very good
430 reviews
Check prices

Entertainment

7.0

Comfort

8.0

Crew

8.6

Food

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Air Transat
7.7
Good
531 reviews
Porter Airlines
8.0
Very good
430 reviews
Check prices

Entertainment

7.0

Comfort

8.0

Crew

8.6

Food

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

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$ 152, while round-trip flights cost around C$ 155.

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

    A round-trip flight to Midway will typically cost around C$ 371, however they can be found for as little as C$ 155.

  • 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 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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