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 $413 round trip and CA $245 one way. Prices and availability subject to change. Additional terms may apply.

Wed., 29 Jan. - Tue., 4 Feb.
YYZ
Toronto
MDW
Chicago
CA $413 Roundtrip, found 2 days ago
CA $413
Roundtrip
found 2 days ago
Select Delta flight, departing Wed., 29 Jan. from Toronto to Chicago, returning Tue., 4 Feb., priced at CA $413 found 2 days ago
Sat., 25 Jan. - Tue., 18 Feb.
YYZ
Toronto
MDW
Chicago
CA $413 Roundtrip, found 2 hours ago
CA $413
Roundtrip
found 2 hours ago
Select Delta flight, departing Sat., 25 Jan. from Toronto to Chicago, returning Tue., 18 Feb., priced at CA $413 found 2 hours ago
Sat., 18 Jan. - Mon., 20 Jan.
YYZ
Toronto
MDW
Chicago
CA $435 Roundtrip, found 5 days ago
CA $435
Roundtrip
found 5 days ago
Select Delta flight, departing Sat., 18 Jan. from Toronto to Chicago, returning Mon., 20 Jan., priced at CA $435 found 5 days ago
Thu., 16 Jan. - Thu., 6 Feb.
YYZ
Toronto
MDW
Chicago
CA $435 Roundtrip, found 4 days ago
CA $435
Roundtrip
found 4 days ago
Select Delta flight, departing Thu., 16 Jan. from Toronto to Chicago, returning Thu., 6 Feb., priced at CA $435 found 4 days ago
Tue., 21 Jan. - Sun., 26 Jan.
YYZ
Toronto
MDW
Chicago
CA $439 Roundtrip, found 2 days ago
CA $439
Roundtrip
found 2 days ago
Select Delta flight, departing Tue., 21 Jan. from Toronto to Chicago, returning Sun., 26 Jan., priced at CA $439 found 2 days ago
Fri., 14 Feb. - Fri., 21 Feb.
YYZ
Toronto
MDW
Chicago
CA $441 Roundtrip, found 4 days ago
CA $441
Roundtrip
found 4 days ago
Select Delta flight, departing Fri., 14 Feb. from Toronto to Chicago, returning Fri., 21 Feb., priced at CA $441 found 4 days ago
Tue., 4 Mar. - Mon., 10 Mar.
YYZ
Toronto
MDW
Chicago
CA $445 Roundtrip, found 2 days ago
CA $445
Roundtrip
found 2 days ago
Select Delta flight, departing Tue., 4 Mar. from Toronto to Chicago, returning Mon., 10 Mar., priced at CA $445 found 2 days ago
Mon., 20 Jan. - Fri., 24 Jan.
YYZ
Toronto
MDW
Chicago
CA $456 Roundtrip, found 4 days ago
CA $456
Roundtrip
found 4 days ago
Select Delta flight, departing Mon., 20 Jan. from Toronto to Chicago, returning Fri., 24 Jan., priced at CA $456 found 4 days ago
Sat., 18 Jan. - Sun., 19 Jan.
YYZ
Toronto
MDW
Chicago
CA $461 Roundtrip, found 4 days ago
CA $461
Roundtrip
found 4 days ago
Select Delta flight, departing Sat., 18 Jan. from Toronto to Chicago, returning Sun., 19 Jan., priced at CA $461 found 4 days ago
Mon., 20 Jan. - Wed., 22 Jan.
YYZ
Toronto
MDW
Chicago
CA $465 Roundtrip, found 2 days ago
CA $465
Roundtrip
found 2 days ago
Select Delta flight, departing Mon., 20 Jan. from Toronto to Chicago, returning Wed., 22 Jan., priced at CA $465 found 2 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
Feb. 6 - Feb. 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
per person
Feb. 26 - Mar. 2
found 8 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
per person
Feb. 26 - Mar. 2
found 8 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
per person
Feb. 26 - Mar. 2
found 8 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
Feb. 26 - Mar. 2
found 8 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) 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.