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 $351 round trip and CA $236 one way. Prices and availability subject to change. Additional terms may apply.

Fri, May 8 - Fri, May 15
YYZ
Toronto
MDW
Chicago
CA $351 Roundtrip, found 6 days ago
CA $351
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, May 8 from Toronto to Chicago, returning Fri, May 15, priced at CA $351 found 6 days ago
Sat, May 9 - Fri, May 15
YYZ
Toronto
MDW
Chicago
CA $353 Roundtrip, found 6 days ago
CA $353
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, May 9 from Toronto to Chicago, returning Fri, May 15, priced at CA $353 found 6 days ago
Mon, May 4 - Mon, May 11
YYZ
Toronto
MDW
Chicago
CA $372 Roundtrip, found 2 days ago
CA $372
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, May 4 from Toronto to Chicago, returning Mon, May 11, priced at CA $372 found 2 days ago
Mon, Apr 20 - Mon, Apr 27
YYZ
Toronto
MDW
Chicago
CA $373 Roundtrip, found 4 days ago
CA $373
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Apr 20 from Toronto to Chicago, returning Mon, Apr 27, priced at CA $373 found 4 days ago
Sun, May 24 - Sat, May 30
YYZ
Toronto
MDW
Chicago
CA $374 Roundtrip, found 4 days ago
CA $374
Roundtrip
found 4 days ago
Select Delta flight, departing Sun, May 24 from Toronto to Chicago, returning Sat, May 30, priced at CA $374 found 4 days ago
Thu, Apr 23 - Thu, Apr 30
YYZ
Toronto
MDW
Chicago
CA $383 Roundtrip, found 4 days ago
CA $383
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Apr 23 from Toronto to Chicago, returning Thu, Apr 30, priced at CA $383 found 4 days ago
Sat, May 2 - Sun, May 3
YYZ
Toronto
MDW
Chicago
CA $393 Roundtrip, found 1 hour ago
CA $393
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, May 2 from Toronto to Chicago, returning Sun, May 3, priced at CA $393 found 1 hour ago
Thu, Jun 11 - Sun, Jun 14
YYZ
Toronto
MDW
Chicago
CA $394 Roundtrip, found 1 day ago
CA $394
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Jun 11 from Toronto to Chicago, returning Sun, Jun 14, priced at CA $394 found 1 day ago
Fri, Apr 10 - Fri, Apr 17
YYZ
Toronto
MDW
Chicago
CA $400 Roundtrip, found 5 hours ago
CA $400
Roundtrip
found 5 hours ago
Select Delta flight, departing Fri, Apr 10 from Toronto to Chicago, returning Fri, Apr 17, priced at CA $400 found 5 hours ago
Fri, May 1 - Sun, May 3
YYZ
Toronto
MDW
Chicago
CA $403 Roundtrip, found 1 day ago
CA $403
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, May 1 from Toronto to Chicago, returning Sun, May 3, priced at CA $403 found 1 day ago

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Price was CA $1,064, price is now CA $827 per person
CA $827
per person
May 7 - May 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Price was CA $1,319, price is now CA $879 per person
CA $879
per person
Apr 16 - Apr 19
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Price was CA $1,890, price is now CA $1,310 per person
CA $1,310
per person
May 6 - May 10
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Price was CA $1,886, price is now CA $1,323 per person
CA $1,323
per person
May 7 - May 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was CA $1,330, price is now CA $958 per person
CA $958
per person
Apr 24 - Apr 27
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
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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.