Find flights
Deals

C$ 126+ Direct flights from Chicago Midway Airport

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 8/7. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
MDW — YTZ
17 May — 24 May1
1 adult
1 adult, Economy, 0 bags

Find direct flights from Midway within your budget

 
Use the slider to find direct flights from Midway within your budget. Price data is based on user searches made on Cheapflights. Over the past seven days, Cheapflights users made 629,999 searches. This data was last updated on 17 April 2026.

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 8/5

10:30 a.m.-1:10 p.m.

Nonstop1h 40m

Toronto Island

Mon 11/5

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

C$ 298

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 29/5

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

Toronto Island

Fri 5/6

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

C$ 304

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 28/5

10:30 a.m.-1:10 p.m.

Nonstop1h 40m

Toronto Island

Thu 4/6

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

C$ 310

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 18/7

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

Toronto Island

Sun 26/7

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

C$ 318

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 15/7

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

Toronto Island

Mon 20/7

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

C$ 320

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 20/5

10:30 a.m.-1:10 p.m.

Nonstop1h 40m

Toronto Island

Wed 27/5

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

C$ 321

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 4/6

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

Toronto Island

Wed 10/6

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

C$ 321

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 3/7

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

Toronto Island

Mon 6/7

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

C$ 322

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 1/5

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

Toronto Island

Mon 4/5

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

C$ 342

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 1/5

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

Toronto Island

Sun 3/5

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

C$ 342

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/4

Showing 1-10 of 23 resultsSorted by cheapest first
1
2
3

Best time to book a flight from Midway

Have a flexible travel schedule? Discover the best time to fly from 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.

Related info for your journey

Access useful and relevant information related to your journey from Midway. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated 17 April 2026.

  • Where can you fly direct from Chicago Midway Airport?

    Currently, the most popular direct flight destination from Chicago Midway Airport is Toronto Island Airport.

  • How much are direct flights from Chicago Midway Airport?

    On average, a one-way direct flight from Chicago Midway Airport will cost users approximately C$ 169. If you're looking for a direct round-trip flight from Chicago Midway Airport, you can expect to pay around C$ 207.

  • How long is a direct flight from Chicago Midway Airport?

    While the flight duration depends heavily on the destination, on average, travelers can expect non-stop flights from Chicago Midway Airport to last approximately 1h 40m on average. The quickest direct flight from Chicago Midway Airport at this time departs from Chicago Midway Airport (1h 40m), while the longest leaves from Chicago Midway Airport (1h 40m).

  • What is the best time of year to fly direct from Chicago Midway Airport?

    If you're seeking the lowest price on a direct flight from Chicago Midway Airport, October is worth consideration as prices are at their lowest, on average. In terms of the number of daily non-stop flights, January offers travelers the most options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Direct flights from Illinois cities

Book a direct flight from one of these other cities located in Illinois.
Direct flights from Peoria

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.