Skip to main content
An airplane exhibit labeled "Concourse A" in an airport terminal.

￥24,460 Cheap Flights from Toronto (YYZ) to Chicago (MDW)

Photo by by Midway Intl Airport
Open Photo by by Midway Intl Airport

Cheap Flights from Toronto to Chicago (YYZ-MDW)

Prices were available within the past 7 days and start at ￥24,460 for one-way flights and ￥40,560 for roundtrip, for the period specified. Prices and availability are subject to change.
Delta
Tue, Jul 28 - Sat, Aug 1
YYZ
Toronto
MDW
Chicago
￥40,560
Roundtrip
Found 5 days ago
Select Delta flight, departing Tue, Jul 28 from Toronto to Chicago, returning Sat, Aug 1, priced at ￥40,560 Found 5 days ago
Delta
Tue, Aug 18 - Fri, Aug 21
YYZ
Toronto
MDW
Chicago
￥44,180
Roundtrip
Found 5 days ago
Select Delta flight, departing Tue, Aug 18 from Toronto to Chicago, returning Fri, Aug 21, priced at ￥44,180 Found 5 days ago
Delta
Tue, Jul 28 - Sat, Aug 1
YYZ
Toronto
MDW
Chicago
￥44,340
Roundtrip
Found 5 days ago
Select Delta flight, departing Tue, Jul 28 from Toronto to Chicago, returning Sat, Aug 1, priced at ￥44,340 Found 5 days ago
Delta
Thu, Sep 17 - Tue, Sep 22
YYZ
Toronto
MDW
Chicago
￥45,310
Roundtrip
Found 1 day ago
Select Delta flight, departing Thu, Sep 17 from Toronto to Chicago, returning Tue, Sep 22, priced at ￥45,310 Found 1 day ago
Delta
Tue, Aug 11 - Thu, Aug 13
YYZ
Toronto
MDW
Chicago
￥46,970
Roundtrip
Found 1 day ago
Select Delta flight, departing Tue, Aug 11 from Toronto to Chicago, returning Thu, Aug 13, priced at ￥46,970 Found 1 day ago
Delta
Tue, Sep 1 - Thu, Sep 3
YYZ
Toronto
MDW
Chicago
￥47,030
Roundtrip
Found 2 days ago
Select Delta flight, departing Tue, Sep 1 from Toronto to Chicago, returning Thu, Sep 3, priced at ￥47,030 Found 2 days ago
Delta
Fri, Aug 14 - Mon, Aug 17
YYZ
Toronto
MDW
Chicago
￥47,820
Roundtrip
Found 4 days ago
Select Delta flight, departing Fri, Aug 14 from Toronto to Chicago, returning Mon, Aug 17, priced at ￥47,820 Found 4 days ago
Delta
Tue, Jul 28 - Sat, Aug 1
YYZ
Toronto
MDW
Chicago
￥47,860
Roundtrip
Found 5 days ago
Select Delta flight, departing Tue, Jul 28 from Toronto to Chicago, returning Sat, Aug 1, priced at ￥47,860 Found 5 days ago
Delta
Fri, Aug 7 - Mon, Aug 24
YYZ
Toronto
MDW
Chicago
￥47,980
Roundtrip
Found 3 days ago
Select Delta flight, departing Fri, Aug 7 from Toronto to Chicago, returning Mon, Aug 24, priced at ￥47,980 Found 3 days ago
WestJet
Sun, Dec 20 - Tue, Dec 22
YYZ
Toronto
MDW
Chicago
￥83,320
Roundtrip
Found 6 hours ago
Select WestJet flight, departing Sun, Dec 20 from Toronto to Chicago, returning Tue, Dec 22, priced at ￥83,320 Found 6 hours ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from ￥57,280
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from ￥57,280

Find the cheapest month to fly from Toronto (YYZ) to Chicago (MDW)

May is typically the cheapest month to fly

From ￥33,696 - ￥56,347 per traveler.

Travel information

Origin airport
Toronto Pearson Intl. Airport
Destination airport
Chicago Midway Airport
Distance
696 km away
Airlines serving
WestJet, Delta
Popular airline
WestJet
Roundtrip price
￥40,560
*Available to One Key members.