Cheap flights from Toronto to Midway

Round-trip
Economy
Toronto (YTO)
Chicago (MDW)
Depart
Return
Any month
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How to find the cheapest flight from
Toronto (YTO) to Midway (MDW)

All the information you need to plan the best YTO to MDW flight in 2021: compare Toronto to Midway flight prices with the expected peak season, weather and rainfall in Midway.
YTO - MDW
Price
C$ 268 - C$ 367
MDW
Temperature
1 - 29 °C
MDW
Precipitation
17 - 109 mm

Popular in

July

High demand for flights, 14% potential price rise

Cheapest in

April

Best time to find cheap flights, 15% potential price drop

Round-trip from

C$ 268

From Toronto to Chicago Midway

One-way from

C$ 246

One-way flight from Toronto to Chicago Midway

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
How far in advance should I book a flight from Toronto to Chicago Midway Airport?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 34 days in advance, which can save you up to 86% on flights from Toronto to Chicago Midway Airport compared to booking the week you need them. Waiting 34 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at C$ 439. For sooner than that we have options available in the next 3 days from C$ 595.

What is the cheapest month to fly from Toronto to Chicago Midway Airport?

April can be a great time to fly to Chicago Midway Airport from Toronto with a flight ticket averaging about C$ 320. Cheapflights users have found deals in the month of April for as cheap as C$ 242. The most expensive prices can be found in the month of January.

When is the cheapest time to fly from Toronto to Chicago Midway Airport (YTO - MDW)?

When flying from Toronto to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap flights from Toronto to Midway in September, October 2021

The best prices found for YTO to MDW flights for September, October
22 Oct - 24 Oct
C$ 265pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
8 Oct - 12 Oct
C$ 280pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
24 Oct - 26 Oct
C$ 281pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

Toronto to Midway 2021 flight deals

Cheap flights to Midway from Toronto found for this year
22 Oct - 24 Oct
C$ 265pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
8 Oct - 12 Oct
C$ 280pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
24 Oct - 26 Oct
C$ 281pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

Direct flights to Midway from Toronto

Save time with Toronto to Midway direct flight deals
8 Oct - 12 Oct
C$ 280pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
24 Oct - 26 Oct
C$ 281pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
15 Dec - 29 Dec
C$ 294pp
YTZ
Toronto Island
Major Airline
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Major Airline
Direct
YTZ
Toronto Island

Last minute flights from Toronto to Midway

Late deals on round-trip flights to Midway from Toronto, departing today and this week
26 Sep - 4 Oct
C$ 399pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
26 Sep - 15 Oct
C$ 417pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
21 Sep - 28 Sep
C$ 424pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

One-way flights to Midway from Toronto

The cheapest one-way flights from Toronto to Midway
12:00 p.m. - 7:41 p.m.
Delta
2 stops
8h 41m
YYZ - MDW
Delta
C$ 246
Delta
4:55 a.m. - 5:42 a.m.
Porter Airlines
Direct
1h 47m
YTZ - MDW
Porter Airlines
C$ 249
mytrip.com
8:43 a.m. - 1:25 p.m.
Aeromexico
1 stop
5h 42m
YYZ - MDW
Aeromexico
C$ 255
Gate1.ca

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Toronto</span> to <span class="emphasized">Midway</span> flights.

Flight FAQs

From Toronto to Midway

Which airlines flying from Toronto to Chicago Midway have flexible cancellations due to COVID-19?

Due to the rapidly changing circumstances due to COVID-19, airlines like Porter Airlines, Delta, and WestJet flying from Toronto to Chicago Midway have implemented new flexible cancellation policies.

Can I find flights from Toronto to Chicago Midway Airport for under C$ 300 on Cheapflights?

Yes, there are multiple flights from Toronto to Chicago Midway Airport for under C$ 300. The cheapest flight booked recently is on Porter Airlines for just C$ 265, but on average you can expect to pay C$ 305.

Are there direct flights from Toronto to Chicago Midway Airport for under C$ 300 on Cheapflights?

Cheapflights has 20 direct flights from Toronto to Chicago Midway Airport under C$ 300. A good price for a direct flight from Toronto to Chicago Midway Airport is less than C$ 309.

Are there last-minute flights available from Toronto to Chicago Midway Airport for under C$ 400?

There are currently 20+ open flights from Toronto to Chicago Midway Airport within the next 7 days for less than C$ 400.

What are the cheapest airlines flying from Toronto to Chicago Midway Airport round-trip?

Cheapflights users have booked flights from Toronto to Chicago Midway Airport round-trip from C$ 265. Other airlines that can offer you cheap pricing are Major Airline, from C$ 294, and Delta, from C$ 344. Porter Airlines is priced at 16% lower than the current average price of a flight leaving 3 months from now.

What are the cheapest airlines to fly from Toronto to Chicago Midway Airport one-way?

For one-way options, check prices for Porter Airlines. According to our data, you can fly for as low as C$ 158. Users have also found prices from C$ 204 and C$ 255 on Porter Airlines and Delta, respectively.

Related searches

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Rent a Car

Car Rentals in Midway Car Rentals in USA

COVID Restrictions

View COVID Travel Restrictions for Midway (MDW)

Do I need a COVID test to fly to Midway from Toronto?

Information is based on travel restrictions from Toronto to Chicago Midway

Most visitors from Toronto need to provide a negative COVID-19 test result and/or quarantine to enter Chicago Midway.

COVID-19 testing requirements
Visitors from Toronto must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago Midway.

Quarantine requirements
Visitors from Toronto are not required to quarantine after entering Chicago Midway.

Do I need a test to fly back to Toronto from Midway?

Returning to Toronto from Chicago Midway

COVID-19 testing requirements
Visitors from Chicago Midway must present a negative RT-PCR (NAAT) test taken 72 hours before departing to Toronto.

Quarantine requirements
Visitors from Chicago Midway are not required to quarantine after entering Toronto.

Hide COVID Travel Restrictions for Midway (MDW)

Alternative routes for Toronto to Midway

See prices for flight routes from nearby airports that may be better suited for you.

Destination information for Midway

Things to know before you go - useful duration and weather info for your trip from Toronto to Midway.
Today's exchange rate
C$ 1 = $0.79
Flight duration from Toronto to Chicago Midway
1h 44m
Average temperature for September in Midway
25.0 °C
Avg rainfall for September in Midway
60.0 mm

Airports servicing Toronto

Toronto Island (YTZ)
Hamilton (YHM)
Kitchener-Waterloo (YKF)

Airports servicing Chicago

Top 4 airlines flying from Toronto to Chicago Midway

The chart below displays the airlines Cheapflights users travelling from Toronto to Midway choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Porter Airlines
C$ 171 C$ 286 No cancel fee 52%
Search Porter Airlines flights
Air Canada
C$ 221 C$ 300 No cancel fee 67%
Search Air Canada flights
WestJet
C$ 210 C$ 384 No cancel fee 60%
Search WestJet flights
Delta
C$ 209 C$ 433 No cancel fee N/A
Search Delta flights
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