Cheap flights from Toronto to Chicago Midway

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The best prices from Toronto to Chicago Midway are usually found in April or May, booked 32 days in advance, depart on a Monday or Wednesday and return on a Monday

How to find the cheapest flight from
Toronto (YTO) to Chicago Midway (MDW)

YTO - MDW
Price
C$ 279 - C$ 382
MDW
Temperature
1 - 29 °C
MDW
Rainfall
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

Average price

C$ 323

Average for round-trip flights in October 2020

Round-trip from

C$ 279

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.
What is the cheapest day to fly round-trip from Toronto to Chicago Midway?

Users have found that flying from Toronto to Chicago Midway on a Thursday typically leans towards higher prices. However, this doesn’t mean you still can’t find a deal. Flexibility with other aspects of your flight can still land a great price for your trip.

How far in advance should I book a flight from Toronto to Chicago Midway?

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 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$ 457. For sooner than that we have options available in the next 3 days from C$ 619.

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

Our data shows that April tends to be the cheapest month to fly to Chicago Midway from Toronto. Users have commonly found prices around C$ 333 for the month, but tickets can be as low as C$ 252. Due to multiple factors, prepare for potentially higher prices in January.

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

Unlike in the evening, when flights are generally more expensive, you can save up to 10% on flights from Toronto to Chicago Midway by exploring options for tickets in the afternoon.

Cheap flights from Toronto to Chicago Midway in October, November 2020

The best prices found for YTO to MDW flights for October, November
13 Nov - 17 Nov
C$ 532pp
YYZ
Toronto Pearson Intl
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
YYZ
Toronto Pearson Intl
24 Nov - 21 Jan
C$ 551pp
YYZ
Toronto Pearson Intl
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
YYZ
Toronto Pearson Intl
10 Nov - 19 Nov
C$ 625pp
YYZ
Toronto Pearson Intl
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
YYZ
Toronto Pearson Intl

Toronto to Chicago Midway 2020 flight deals

Cheap flights to Chicago Midway from Toronto found for this year
21 Dec - 4 Jan
C$ 282pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
28 Dec - 1 Jan
C$ 295pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
28 Dec - 1 Jan
C$ 296pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

Direct flights to Chicago Midway from Toronto

Save time with Toronto to Chicago Midway direct flight deals
21 Dec - 4 Jan
C$ 282pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
22 Jan - 5 Feb
C$ 291pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
22 Jan - 5 Feb
C$ 293pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

Last minute flights from Toronto to Chicago Midway

Late deals on round-trip flights to Chicago Midway from Toronto, departing today and this week
5 Nov - 7 Nov
C$ 1,461pp
YYZ
Toronto Pearson Intl
Multiple Airlines
     
3 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
YYZ
Toronto Pearson Intl
5 Nov - 7 Nov
C$ 1,486pp
YYZ
Toronto Pearson Intl
Multiple Airlines
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
YYZ
Toronto Pearson Intl

One-way flights to Chicago Midway from Toronto

The cheapest one-way flights from Toronto to Chicago Midway
3:30 a.m. - 11:18 a.m.
Aeromexico
3 stops
32h 48m
YYZ - MDW
Aeromexico
C$ 528
KAYAK
6:21 a.m. - 11:49 a.m.
Multiple Airlines
3 stops
30h 28m
YYZ - MDW
Multiple Airlines
C$ 1,100
Kiwi.com
1:25 a.m. - 5:30 a.m.
Delta
1 stop
5h 05m
YYZ - MDW
Delta
C$ 1,110
Delta

Related info for your journey

Useful info, stats and facts about Toronto to Chicago Midway flights.

Flight FAQs

From Toronto to Chicago Midway

Can I find flights from Toronto to Chicago Midway for under C$ 395 on Cheapflights?

Yes, there are multiple flights from Toronto to Chicago Midway for under C$ 395. The cheapest flight booked recently is on Porter Airlines for just C$ 282, but on average you can expect to pay C$ 455.

What safety measures are being taken by airlines flying from Toronto to Chicago Midway to control the spread of COVID-19?

Delta is one of the many airlines that have implemented additional safety measures to control the spread of COVID-19. Airline carriers are regularly disinfecting and sanitizing their aircraft. Masks are provided and are mandatory while on board. Pre-flight testing for symptoms and antibodies, alongside socially-distanced seating (for a limited time) will work towards keeping travellers safer while flying from Toronto to Chicago Midway. Policies will vary by airline.

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 Air Canada flying from Toronto to Chicago Midway have implemented new flexible cancellation policies.

Are there direct flights from Toronto to Chicago Midway for under C$ 395 on Cheapflights?

Cheapflights has 6 direct flights from Toronto to Chicago Midway under C$ 395. A good price for a direct flight from Toronto to Chicago Midway is less than C$ 293.

Are there last-minute flights available from Toronto to Chicago Midway for under C$ 1,581?

There are currently 2+ open flights from Toronto to Chicago Midway within the next 7 days for less than C$ 1,581.

What days are direct flights available from Toronto to Chicago Midway?

You can find direct flights on the following days: Sunday, Wednesday, Thursday, Saturday.

Is Toronto weather warmer or cooler than Chicago Midway?

Temperatures around the 29 °C's can be experienced in July. The weather in Chicago Midway is hotter than in Toronto. Plan for potential changes in flight availability as peak weather approaches in this location.

How long is the flight from Toronto to Chicago Midway?

Airlines like Porter Airlines and Delta fly from Toronto to Chicago Midway in about 1h 50m. The time it takes to get you to your destination can typically vary by up to 2h 09m. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

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

Flying on Porter Airlines is currently your cheapest option to Chicago Midway, with prices starting at C$ 283. Another option worth looking into is Delta, starting at C$ 337 round trip. Users have found that Porter Airlines is 14% cheaper than the other options available to this destination.

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

For one-way options, check prices for Delta. According to our data, you can fly for as low as C$ 198. Users have also found tickets on Aeromexico for as little as C$ 470.

Alternative routes for Toronto to Chicago Midway

Destination information for Chicago Midway

Things to know before you go. Useful info for your trip from Toronto to Chicago Midway
Today's exchange rate
C$ 1 = $0.76
Flight duration
1h 43m
Average temperature for October in Chicago Midway
18.0 °C
Avg rainfall for October in Chicago Midway
66.0 mm

Airports servicing Toronto

Billy Bishop Toronto City Airport (YTZ)
Kitchener (YKF)
Hamilton (YHM)

Airports servicing Chicago