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 $300 round trip and CA $181 one way. Prices and availability subject to change. Additional terms may apply.

Thu, May 28 - Sun, May 31
YTZ
Toronto
MDW
Chicago
CA $300 Roundtrip, just found
CA $300
Roundtrip
just found
Select Porter Airlines flight, departing Thu, May 28 from Toronto to Chicago, returning Sun, May 31, priced at CA $300 just found
Tue, May 5 - Mon, May 11
YTZ
Toronto
MDW
Chicago
CA $305 Roundtrip, found 7 hours ago
CA $305
Roundtrip
found 7 hours ago
Select Porter Airlines flight, departing Tue, May 5 from Toronto to Chicago, returning Mon, May 11, priced at CA $305 found 7 hours ago
Thu, May 7 - Fri, May 15
YTZ
Toronto
MDW
Chicago
CA $310 Roundtrip, found 4 days ago
CA $310
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Thu, May 7 from Toronto to Chicago, returning Fri, May 15, priced at CA $310 found 4 days ago
Sun, May 24 - Fri, Jul 3
YTZ
Toronto
MDW
Chicago
CA $320 Roundtrip, found 6 days ago
CA $320
Roundtrip
found 6 days ago
Select Porter Airlines flight, departing Sun, May 24 from Toronto to Chicago, returning Fri, Jul 3, priced at CA $320 found 6 days ago
Fri, May 29 - Tue, Jun 2
YTZ
Toronto
MDW
Chicago
CA $325 Roundtrip, just found
CA $325
Roundtrip
just found
Select Porter Airlines flight, departing Fri, May 29 from Toronto to Chicago, returning Tue, Jun 2, priced at CA $325 just found
Sat, Jul 18 - Sat, Jul 25
YTZ
Toronto
MDW
Chicago
CA $330 Roundtrip, just found
CA $330
Roundtrip
just found
Select Porter Airlines flight, departing Sat, Jul 18 from Toronto to Chicago, returning Sat, Jul 25, priced at CA $330 just found
Fri, Jul 31 - Tue, Aug 4
YTZ
Toronto
MDW
Chicago
CA $335 Roundtrip, found 6 hours ago
CA $335
Roundtrip
found 6 hours ago
Select Porter Airlines flight, departing Fri, Jul 31 from Toronto to Chicago, returning Tue, Aug 4, priced at CA $335 found 6 hours ago
Fri, Aug 7 - Mon, Aug 10
YTZ
Toronto
MDW
Chicago
CA $340 Roundtrip, just found
CA $340
Roundtrip
just found
Select Porter Airlines flight, departing Fri, Aug 7 from Toronto to Chicago, returning Mon, Aug 10, priced at CA $340 just found
Thu, May 28 - Sun, May 31
YTZ
Toronto
MDW
Chicago
CA $342 Roundtrip, just found
CA $342
Roundtrip
just found
Select Air Transat flight, departing Thu, May 28 from Toronto to Chicago, returning Sun, May 31, priced at CA $342 just found
Thu, May 28 - Sun, May 31
YTZ
Toronto
MDW
Chicago
CA $344 Roundtrip, just found
CA $344
Roundtrip
just found
Select Air Transat flight, departing Thu, May 28 from Toronto to Chicago, returning Sun, May 31, priced at CA $344 just found

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Price was CA $991, price is now CA $699 per person
CA $699
per person
May 26 - May 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
Price was CA $1,230, price is now CA $790 per person
CA $790
per person
May 22 - May 25
found 1 hour ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Price was CA $1,342, price is now CA $921 per person
CA $921
per person
May 26 - May 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Price was CA $1,178, price is now CA $849 per person
CA $849
per person
May 23 - May 25
just found
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

4.5 out of 5
Price was CA $1,321, price is now CA $956 per person
CA $956
per person
Jun 12 - Jun 15
found 22 hours ago
Roundtrip 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.

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*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.