$118 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 $191 round trip and $118 one way. Prices and availability subject to change. Additional terms may apply.

Fri, Aug 21 - Sun, Aug 23
YTZ
Toronto
MDW
Chicago
$191 Roundtrip, found 4 days ago
$191
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Fri, Aug 21 from Toronto to Chicago, returning Sun, Aug 23, priced at $191 found 4 days ago
Mon, Sep 28 - Sun, Oct 11
YTZ
Toronto
MDW
Chicago
$192 Roundtrip, found 3 days ago
$192
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Mon, Sep 28 from Toronto to Chicago, returning Sun, Oct 11, priced at $192 found 3 days ago
Wed, Sep 9 - Sat, Sep 12
YTZ
Toronto
MDW
Chicago
$201 Roundtrip, found 4 days ago
$201
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Wed, Sep 9 from Toronto to Chicago, returning Sat, Sep 12, priced at $201 found 4 days ago
Fri, Sep 11 - Sun, Sep 13
YTZ
Toronto
MDW
Chicago
$202 Roundtrip, found 1 hour ago
$202
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Fri, Sep 11 from Toronto to Chicago, returning Sun, Sep 13, priced at $202 found 1 hour ago
Sun, Aug 30 - Tue, Sep 8
YTZ
Toronto
MDW
Chicago
$213 Roundtrip, found 13 hours ago
$213
Roundtrip
found 13 hours ago
Select Porter Airlines flight, departing Sun, Aug 30 from Toronto to Chicago, returning Tue, Sep 8, priced at $213 found 13 hours ago
Tue, Sep 1 - Thu, Sep 10
YTZ
Toronto
MDW
Chicago
$219 Roundtrip, found 2 hours ago
$219
Roundtrip
found 2 hours ago
Select Porter Airlines flight, departing Tue, Sep 1 from Toronto to Chicago, returning Thu, Sep 10, priced at $219 found 2 hours ago
Mon, Aug 31 - Fri, Sep 11
YTZ
Toronto
MDW
Chicago
$221 Roundtrip, found 5 days ago
$221
Roundtrip
found 5 days ago
Select Porter Airlines flight, departing Mon, Aug 31 from Toronto to Chicago, returning Fri, Sep 11, priced at $221 found 5 days ago
Thu, Aug 27 - Thu, Sep 10
YTZ
Toronto
MDW
Chicago
$222 Roundtrip, found 6 days ago
$222
Roundtrip
found 6 days ago
Select Porter Airlines flight, departing Thu, Aug 27 from Toronto to Chicago, returning Thu, Sep 10, priced at $222 found 6 days ago
Sat, Aug 29 - Sat, Sep 5
YTZ
Toronto
MDW
Chicago
$229 Roundtrip, found 3 days ago
$229
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Sat, Aug 29 from Toronto to Chicago, returning Sat, Sep 5, priced at $229 found 3 days ago
Fri, Sep 11 - Mon, Sep 14
YTZ
Toronto
MDW
Chicago
$230 Roundtrip, found 16 hours ago
$230
Roundtrip
found 16 hours ago
Select Porter Airlines flight, departing Fri, Sep 11 from Toronto to Chicago, returning Mon, Sep 14, priced at $230 found 16 hours ago

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $765, price is now $534 per person
$534
per person
Sep 10 - Sep 13
just found
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $882, price is now $595 per person
$595
per person
Sep 10 - Sep 13
just found
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $980, price is now $717 per person
$717
per person
Sep 10 - Sep 13
just found
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Price was $708, price is now $572 per person
$572
per person
Sep 10 - Sep 13
just found
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Price was $827, price is now $680 per person
$680
per person
Sep 10 - Sep 13
just found
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
$191

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 $191 and $230. 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 $118. 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, August 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. 

Explore More Ways to Travel with 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.