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

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

The cheapest flights to Midway Intl. found within the past 7 days were CA $257 round trip and CA $159 one way. Prices and availability subject to change. Additional terms may apply.

Tue, Feb 17 - Sun, Feb 22
YTZ
Toronto
MDW
Chicago
CA $257 Roundtrip, just found
CA $257
Roundtrip
just found
Select Porter Airlines flight, departing Tue, Feb 17 from Toronto to Chicago, returning Sun, Feb 22, priced at CA $257 just found
Thu, Feb 19 - Sat, Feb 21
YTZ
Toronto
MDW
Chicago
CA $258 Roundtrip, found 2 hours ago
CA $258
Roundtrip
found 2 hours ago
Select Porter Airlines flight, departing Thu, Feb 19 from Toronto to Chicago, returning Sat, Feb 21, priced at CA $258 found 2 hours ago
Fri, Jan 30 - Tue, Feb 3
YTZ
Toronto
MDW
Chicago
CA $289 Roundtrip, just found
CA $289
Roundtrip
just found
Select Porter Airlines flight, departing Fri, Jan 30 from Toronto to Chicago, returning Tue, Feb 3, priced at CA $289 just found
Fri, Feb 20 - Sat, Feb 28
YTZ
Toronto
MDW
Chicago
CA $295 Roundtrip, found 1 hour ago
CA $295
Roundtrip
found 1 hour ago
Select Air Transat flight, departing Fri, Feb 20 from Toronto to Chicago, returning Sat, Feb 28, priced at CA $295 found 1 hour ago
Thu, Feb 5 - Sun, Feb 8
YTZ
Toronto
MDW
Chicago
CA $295 Roundtrip, just found
CA $295
Roundtrip
just found
Select Porter Airlines flight, departing Thu, Feb 5 from Toronto to Chicago, returning Sun, Feb 8, priced at CA $295 just found
Tue, Feb 24 - Thu, Feb 26
YTZ
Toronto
MDW
Chicago
CA $297 Roundtrip, found 2 days ago
CA $297
Roundtrip
found 2 days ago
Select Air Transat flight, departing Tue, Feb 24 from Toronto to Chicago, returning Thu, Feb 26, priced at CA $297 found 2 days ago
Tue, Feb 24 - Thu, Feb 26
YTZ
Toronto
MDW
Chicago
CA $297 Roundtrip, found 2 days ago
CA $297
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Tue, Feb 24 from Toronto to Chicago, returning Thu, Feb 26, priced at CA $297 found 2 days ago
Tue, Feb 10 - Sat, Feb 14
YTZ
Toronto
MDW
Chicago
CA $298 Roundtrip, found 1 hour ago
CA $298
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Tue, Feb 10 from Toronto to Chicago, returning Sat, Feb 14, priced at CA $298 found 1 hour ago
Tue, Feb 17 - Sun, Feb 22
YTZ
Toronto
MDW
Chicago
CA $299 Roundtrip, just found
CA $299
Roundtrip
just found
Select Air Transat flight, departing Tue, Feb 17 from Toronto to Chicago, returning Sun, Feb 22, priced at CA $299 just found
Tue, Feb 17 - Sun, Feb 22
YTZ
Toronto
MDW
Chicago
CA $299 Roundtrip, just found
CA $299
Roundtrip
just found
Select Air Transat flight, departing Tue, Feb 17 from Toronto to Chicago, returning Sun, Feb 22, priced at CA $299 just found

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was CA $824, price is now CA $571 per person
CA $571
per person
Feb 13 - Feb 16
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 $1,487, price is now CA $1,005 per person
CA $1,005
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Price was CA $1,746, price is now CA $1,276 per person
CA $1,276
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Price was CA $826, price is now CA $606 per person
CA $606
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Price was CA $789, price is now CA $582 per person
CA $582
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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 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.