Cheap Flights From Pearson Intl. (YYZ) To Midway Intl. (MDW)

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

The cheapest flights to Midway Intl. found within the past 7 days were CA $365 round trip and CA $221 one way. Prices and availability subject to change. Additional terms may apply.

Fri., 7 Feb. - Tue., 11 Feb.
YYZ
Toronto
MDW
Chicago
CA $365 Roundtrip, found 5 days ago
CA $365
Roundtrip
found 5 days ago
Select Delta flight, departing Fri., 7 Feb. from Toronto to Chicago, returning Tue., 11 Feb., priced at CA $365 found 5 days ago
Mon., 13 Jan. - Wed., 15 Jan.
YYZ
Toronto
MDW
Chicago
CA $367 Roundtrip, found 4 days ago
CA $367
Roundtrip
found 4 days ago
Select Delta flight, departing Mon., 13 Jan. from Toronto to Chicago, returning Wed., 15 Jan., priced at CA $367 found 4 days ago
Fri., 7 Feb. - Sun., 9 Feb.
YYZ
Toronto
MDW
Chicago
CA $371 Roundtrip, found 2 days ago
CA $371
Roundtrip
found 2 days ago
Select Delta flight, departing Fri., 7 Feb. from Toronto to Chicago, returning Sun., 9 Feb., priced at CA $371 found 2 days ago
Fri., 7 Feb. - Mon., 10 Feb.
YYZ
Toronto
MDW
Chicago
CA $372 Roundtrip, found 2 days ago
CA $372
Roundtrip
found 2 days ago
Select Delta flight, departing Fri., 7 Feb. from Toronto to Chicago, returning Mon., 10 Feb., priced at CA $372 found 2 days ago
Thu., 30 Jan. - Sun., 2 Feb.
YYZ
Toronto
MDW
Chicago
CA $372 Roundtrip, found 3 days ago
CA $372
Roundtrip
found 3 days ago
Select Delta flight, departing Thu., 30 Jan. from Toronto to Chicago, returning Sun., 2 Feb., priced at CA $372 found 3 days ago
Wed., 22 Jan. - Fri., 24 Jan.
YYZ
Toronto
MDW
Chicago
CA $375 Roundtrip, found 6 days ago
CA $375
Roundtrip
found 6 days ago
Select Delta flight, departing Wed., 22 Jan. from Toronto to Chicago, returning Fri., 24 Jan., priced at CA $375 found 6 days ago
Wed., 29 Jan. - Fri., 31 Jan.
YYZ
Toronto
MDW
Chicago
CA $375 Roundtrip, found 2 hours ago
CA $375
Roundtrip
found 2 hours ago
Select Delta flight, departing Wed., 29 Jan. from Toronto to Chicago, returning Fri., 31 Jan., priced at CA $375 found 2 hours ago
Wed., 29 Jan. - Fri., 31 Jan.
YYZ
Toronto
MDW
Chicago
CA $376 Roundtrip, found 2 hours ago
CA $376
Roundtrip
found 2 hours ago
Select Delta flight, departing Wed., 29 Jan. from Toronto to Chicago, returning Fri., 31 Jan., priced at CA $376 found 2 hours ago
Fri., 17 Jan. - Mon., 20 Jan.
YYZ
Toronto
MDW
Chicago
CA $385 Roundtrip, found 1 day ago
CA $385
Roundtrip
found 1 day ago
Select Delta flight, departing Fri., 17 Jan. from Toronto to Chicago, returning Mon., 20 Jan., priced at CA $385 found 1 day ago
Mon., 20 Jan. - Sat., 25 Jan.
YYZ
Toronto
MDW
Chicago
CA $385 Roundtrip, found 5 days ago
CA $385
Roundtrip
found 5 days ago
Select Delta flight, departing Mon., 20 Jan. from Toronto to Chicago, returning Sat., 25 Jan., priced at CA $385 found 5 days ago

Best Midway Intl. Flight and Hotel Packages

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago

Hilton Chicago

4 out of 5
per person
Jan. 13 - Jan. 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Save 100% on your flight
per person
Jan. 13 - Jan. 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
per person
Jan. 13 - Jan. 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
per person
Jan. 13 - Jan. 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
per person
Jan. 13 - Jan. 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
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Popular Flight Routes from Toronto (YYZ)

Travelers at YYZ love to visit these top cities. Roam to the top destinations from Toronto (YYZ) 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.