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 $244 round trip and CA $166 one way. Prices and availability subject to change. Additional terms may apply.

Thu., Jun. 19 - Fri., Oct. 3
YTZ
Toronto
MDW
Chicago
CA $244 Roundtrip, found 1 day ago
CA $244
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Thu., Jun. 19 from Toronto to Chicago, returning Fri., Oct. 3, priced at CA $244 found 1 day ago
Mon., Sep. 1 - Fri., Sep. 5
YTZ
Toronto
MDW
Chicago
CA $251 Roundtrip, found 2 days ago
CA $251
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Mon., Sep. 1 from Toronto to Chicago, returning Fri., Sep. 5, priced at CA $251 found 2 days ago
Tue., Aug. 26 - Sat., Sep. 6
YTZ
Toronto
MDW
Chicago
CA $257 Roundtrip, found 3 days ago
CA $257
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Tue., Aug. 26 from Toronto to Chicago, returning Sat., Sep. 6, priced at CA $257 found 3 days ago
Thu., Jun. 12 - Wed., Oct. 29
YTZ
Toronto
MDW
Chicago
CA $265 Roundtrip, found 1 day ago
CA $265
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Thu., Jun. 12 from Toronto to Chicago, returning Wed., Oct. 29, priced at CA $265 found 1 day ago
Thu., Nov. 27 - Sun., Nov. 30
YTZ
Toronto
MDW
Chicago
CA $271 Roundtrip, found 3 days ago
CA $271
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Thu., Nov. 27 from Toronto to Chicago, returning Sun., Nov. 30, priced at CA $271 found 3 days ago
Thu., Jun. 19 - Fri., Oct. 3
YTZ
Toronto
MDW
Chicago
CA $276 Roundtrip, found 1 day ago
CA $276
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Thu., Jun. 19 from Toronto to Chicago, returning Fri., Oct. 3, priced at CA $276 found 1 day ago
Thu., Nov. 27 - Sun., Nov. 30
YTZ
Toronto
MDW
Chicago
CA $277 Roundtrip, found 3 days ago
CA $277
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Thu., Nov. 27 from Toronto to Chicago, returning Sun., Nov. 30, priced at CA $277 found 3 days ago
Thu., Nov. 27 - Sun., Nov. 30
YTZ
Toronto
MDW
Chicago
CA $279 Roundtrip, found 3 days ago
CA $279
Roundtrip
found 3 days ago
Select Air Transat flight, departing Thu., Nov. 27 from Toronto to Chicago, returning Sun., Nov. 30, priced at CA $279 found 3 days ago
Thu., Oct. 2 - Sun., Oct. 5
YTZ
Toronto
MDW
Chicago
CA $280 Roundtrip, found 3 days ago
CA $280
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Thu., Oct. 2 from Toronto to Chicago, returning Sun., Oct. 5, priced at CA $280 found 3 days ago
Thu., Nov. 6 - Mon., Nov. 10
YTZ
Toronto
MDW
Chicago
CA $280 Roundtrip, found 4 days ago
CA $280
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Thu., Nov. 6 from Toronto to Chicago, returning Mon., Nov. 10, priced at CA $280 found 4 days ago

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Chicago River Side Suites

Chicago River Side Suites

2 out of 5
Save 100% on your flight
per person
Jul 19 - Jul 21
found 13 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
per person
Jul 19 - Jul 21
found 13 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
per person
Jul 19 - Jul 21
found 13 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
per person
Jul 19 - Jul 21
found 13 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
per person
Jul 19 - Jul 21
found 13 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
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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.