$100 Cheap flights from Billy Bishop Toronto City to Midway Intl. (YTZ to MDW)

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Find The Best Dates To Fly from Billy Bishop Toronto City to Midway Intl.

Compare Flight Prices from Toronto to Chicago

Affordable Airfare Tickets from YTZ to MDW Airport

The cheapest flights to Midway Intl. found within the past 7 days were $156 round trip and $100 one way. Prices and availability subject to change. Additional terms may apply.

Thu, May 22 - Mon, May 26
YTZ
Toronto
MDW
Chicago
$156 Roundtrip, found 1 hour ago
$156
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Thu, May 22 from Toronto to Chicago, returning Mon, May 26, priced at $156 found 1 hour ago
Tue, May 13 - Fri, May 16
YTZ
Toronto
MDW
Chicago
$176 Roundtrip, found 8 hours ago
$176
Roundtrip
found 8 hours ago
Select Porter Airlines flight, departing Tue, May 13 from Toronto to Chicago, returning Fri, May 16, priced at $176 found 8 hours ago
Fri, Jul 18 - Mon, Jul 21
YTZ
Toronto
MDW
Chicago
$192 Roundtrip, found 2 days ago
$192
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Fri, Jul 18 from Toronto to Chicago, returning Mon, Jul 21, priced at $192 found 2 days ago
Mon, May 5 - Fri, May 9
YTZ
Toronto
MDW
Chicago
$196 Roundtrip, found 2 days ago
$196
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Mon, May 5 from Toronto to Chicago, returning Fri, May 9, priced at $196 found 2 days ago
Sun, Jun 15 - Wed, Jun 18
YTZ
Toronto
MDW
Chicago
$197 Roundtrip, found 5 days ago
$197
Roundtrip
found 5 days ago
Select Porter Airlines flight, departing Sun, Jun 15 from Toronto to Chicago, returning Wed, Jun 18, priced at $197 found 5 days ago
Tue, May 13 - Sat, May 17
YTZ
Toronto
MDW
Chicago
$198 Roundtrip, found 6 days ago
$198
Roundtrip
found 6 days ago
Select Porter Airlines flight, departing Tue, May 13 from Toronto to Chicago, returning Sat, May 17, priced at $198 found 6 days ago
Mon, Jun 2 - Wed, Jul 16
YTZ
Toronto
MDW
Chicago
$205 Roundtrip, found 6 days ago
$205
Roundtrip
found 6 days ago
Select Porter Airlines flight, departing Mon, Jun 2 from Toronto to Chicago, returning Wed, Jul 16, priced at $205 found 6 days ago
Thu, May 1 - Thu, May 8
YTZ
Toronto
MDW
Chicago
$209 Roundtrip, found 6 days ago
$209
Roundtrip
found 6 days ago
Select Porter Airlines flight, departing Thu, May 1 from Toronto to Chicago, returning Thu, May 8, priced at $209 found 6 days ago
Fri, Aug 22 - Sun, Aug 24
YTZ
Toronto
MDW
Chicago
$212 Roundtrip, found 5 days ago
$212
Roundtrip
found 5 days ago
Select Porter Airlines flight, departing Fri, Aug 22 from Toronto to Chicago, returning Sun, Aug 24, priced at $212 found 5 days ago
Fri, Aug 8 - Sun, Aug 10
YTZ
Toronto
MDW
Chicago
$213 Roundtrip, found 3 days ago
$213
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Fri, Aug 8 from Toronto to Chicago, returning Sun, Aug 10, priced at $213 found 3 days ago

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Marriott Chicago Schaumburg

Marriott Chicago Schaumburg

3.5 out of 5
per person
May 30 - Jun 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Ambassador Hotel Chicago

Ambassador Hotel Chicago

4 out of 5
Save 100% on your flight
per person
May 29 - Jun 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Courtyard by Marriott Chicago Wood Dale

Courtyard by Marriott Chicago Wood Dale

3 out of 5
per person
May 30 - Jun 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Chicago Marriott Oak Brook

Chicago Marriott Oak Brook

3.5 out of 5
per person
May 30 - Jun 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
SpringHill Suites by Marriott Chicago Naperville/Warrenville

SpringHill Suites by Marriott Chicago Naperville/Warrenville

3 out of 5
per person
May 30 - Jun 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
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Frequently asked questions

Are there direct flights from Billy Bishop Toronto City Airport (YTZ) to Midway Airport?
If you’re not so fond of layovers, it’s smart to plan your flight from YTZ to MDW as early as possible. Porter Airlines is the only carrier that offers direct flights to Chicago from Toronto.
What is the flight distance from YTZ to Midway Intl. Airport (MDW)?
With only 440 mi separating YTZ and Midway Intl. Airport (MDW), time will whiz by between the seat belt sign turning off and the captain asking you to prepare for landing.
What airlines fly from Billy Bishop Airport to Midway Intl. Airport (MDW)?
Ready to book the airfare for your next big adventure? Want to travel from Billy Bishop Airport to Chicago Airport in the shortest time possible? Hop on one of the 65 direct flights offered by Porter Airlines every month, and you’ll be landing before you can utter ‘Are we there yet?’
What is the best day to buy a plane ticket?
This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2021. Tuesday and Wednesday prices are also good, but you may want to prepare your budget if booking during the weekend, as data shows that is when prices are generally at their highest.
What are the cheapest days to fly?
Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2021, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.
How far in advance can you book a flight?
Trying to figure out how early you should book your flight? It’s possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 0-2 weeks prior to their travel dates.*According to flight demand on Travelocity.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Flight information from Toronto to Chicago

 

Traveling From
Billy Bishop Toronto City
Traveling To
Midway Intl.
Shortest Flight Time
 hours mins
Earliest Departure Time
Latest Departure Time
Lowest Flight Price
$156

Discover our best flights from Toronto YTZ to Chicago MDW. 

With 20 airlines to choose from on Travelocity, you can easily find the best option for you. Use our filters to sort by price, compare airlines, and find the most convenient flight times. 

 

Find our best return flights from Toronto YTZ to Chicago MDW at the right price  

Airfares to Chicago MDW from Toronto YTZ currently cost between $156 and $213. It’s usually cheaper to book a round trip than two separate one-way flights. Prices and availability subject to change. Additional terms may apply. 

 

Book one-way flights from Toronto YTZ to Chicago MDW 

If you want to be flexible about when you return, or keep your travel options open ended, a one-way flight could be just the ticket! You’ll find one-way airfares from Toronto YTZ to Chicago MDW on Travelocity starting at $100. Prices and availability subject to change. Additional terms may apply. 

 

Get to Chicago MDW from Toronto YTZ quicker with direct flights. 

Get to Chicago faster, without the hassle of changing planes and moving baggage, by booking a direct flight. Expect your direct flight to MDW from YTZ to take around hour(s) min(s).  

 

Find our cheapest airfares for flights from Toronto YTZ to Chicago MDW

Find cheap flight deals by using our search filters to sort results starting with the lowest price airfares to MDW from YTZ. Our Price Match Promise means if you find a lower rate on Travelocity.com or on another US-based website within 24 hours of booking, we’ll credit or refund the difference.  

 

Get our best airfare deals for your flight from Toronto YTZ to Chicago MDW today 

If you’re flexible about when you travel, May is usually the cheapest month to fly from Toronto YTZ to Chicago MDW. If you need to be more specific, search by date and arrival and departure times.Then, compare prices across different airlines, and sort results by lowest price first. 

 

Book flexible airline tickets for flights to Chicago MDW from Toronto YTZ 

Some airlines let you change your travel dates without charging a fee. Use our ‘no change fee’ filter to see which flights to MDW from YTZ have this option.  

 

Travel with confidence when you book flights to Chicago MDW from Toronto YTZ with Travelocity 

We’ve secured fantastic deals with all the main airline carriers and it’s easy to compare, choose, and book with Travelocity. With 24/7 customer service and our free 'App', we’ll always keep you moving. 

Popular Flight Routes from Toronto (YTZ)

Travelers at YTZ love to visit these top cities. Roam to the top destinations from Toronto (YTZ) today with the cheap prices from Travelocity!

Popular Flight Routes from Chicago (MDW)

Travelers at MDW love to visit these top cities. Roam to the top destinations from Chicago(MDW) today with the cheap prices from Travelocity!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.