Cheap Flights From Billy Bishop Toronto City (YTZ) To Midway Intl. (MDW)

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Find The Best Dates To Fly

Cheapest Flights from Toronto (YTZ) to Chicago (MDW)

The cheapest flights to Midway Intl. found within the past 7 days were CA $249 round trip and CA $155 one way. Prices and availability subject to change. Additional terms may apply.

Fri, Apr 17 - Sat, Apr 25
YTZ
Toronto
MDW
Chicago
CA $249 Roundtrip, just found
CA $249
Roundtrip
just found
Select Air Transat flight, departing Fri, Apr 17 from Toronto to Chicago, returning Sat, Apr 25, priced at CA $249 just found
Fri, Apr 17 - Sat, Apr 25
YTZ
Toronto
MDW
Chicago
CA $249 Roundtrip, just found
CA $249
Roundtrip
just found
Select Porter Airlines flight, departing Fri, Apr 17 from Toronto to Chicago, returning Sat, Apr 25, priced at CA $249 just found
Mon, Jan 12 - Tue, Jan 20
YTZ
Toronto
MDW
Chicago
CA $250 Roundtrip, just found
CA $250
Roundtrip
just found
Select Air Transat flight, departing Mon, Jan 12 from Toronto to Chicago, returning Tue, Jan 20, priced at CA $250 just found
Mon, Jan 12 - Tue, Jan 20
YTZ
Toronto
MDW
Chicago
CA $267 Roundtrip, just found
CA $267
Roundtrip
just found
Select Air Transat flight, departing Mon, Jan 12 from Toronto to Chicago, returning Tue, Jan 20, priced at CA $267 just found
Fri, Mar 13 - Thu, Mar 19
YTZ
Toronto
MDW
Chicago
CA $311 Roundtrip, found 19 hours ago
CA $311
Roundtrip
found 19 hours ago
Select Air Transat flight, departing Fri, Mar 13 from Toronto to Chicago, returning Thu, Mar 19, priced at CA $311 found 19 hours ago
Thu, Apr 16 - Sun, Apr 19
YTZ
Toronto
MDW
Chicago
CA $312 Roundtrip, found 5 hours ago
CA $312
Roundtrip
found 5 hours ago
Select Air Transat flight, departing Thu, Apr 16 from Toronto to Chicago, returning Sun, Apr 19, priced at CA $312 found 5 hours ago
Thu, Jan 15 - Fri, Jan 16
YTZ
Toronto
MDW
Chicago
CA $314 Roundtrip, found 4 days ago
CA $314
Roundtrip
found 4 days ago
Select Air Transat flight, departing Thu, Jan 15 from Toronto to Chicago, returning Fri, Jan 16, priced at CA $314 found 4 days ago
Sat, Nov 22 - Tue, Jan 20
YTZ
Toronto
MDW
Chicago
CA $316 Roundtrip, found 3 days ago
CA $316
Roundtrip
found 3 days ago
Select Air Transat flight, departing Sat, Nov 22 from Toronto to Chicago, returning Tue, Jan 20, priced at CA $316 found 3 days ago
Sat, Nov 22 - Tue, Jan 20
YTZ
Toronto
MDW
Chicago
CA $316 Roundtrip, found 3 days ago
CA $316
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Sat, Nov 22 from Toronto to Chicago, returning Tue, Jan 20, priced at CA $316 found 3 days ago
Fri, Mar 13 - Tue, Mar 17
YTZ
Toronto
MDW
Chicago
CA $330 Roundtrip, found 1 day ago
CA $330
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Fri, Mar 13 from Toronto to Chicago, returning Tue, Mar 17, priced at CA $330 found 1 day ago

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Price was CA $787, price is now CA $496 per person
CA $496
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Price was CA $2,175, price is now CA $1,293 per person
CA $1,293
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Price was CA $2,112, price is now CA $1,281 per person
CA $1,281
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Price was CA $843, price is now CA $538 per person
CA $538
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Price was CA $912, price is now CA $587 per person
CA $587
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Don't see what you're looking for?
See all available trips from Billy Bishop Toronto City to Midway Intl.
View all trips

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 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?
Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you're looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you're browsing flight deals.
What are the cheapest days to fly?
Frequent travellers may already know this, but earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.
How far in advance can you book a flight?
Here's the deal: It is typically possible to start comparing international airfares on Travelocity.ca 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 2-4 weeks prior to their travel dates.*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

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.