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 $293 round trip and CA $186 one way. Prices and availability subject to change. Additional terms may apply.

Mon, Feb 2 - Wed, Feb 18
YYZ
Toronto
MDW
Chicago
CA $293 Roundtrip, found 1 day ago
CA $293
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Feb 2 from Toronto to Chicago, returning Wed, Feb 18, priced at CA $293 found 1 day ago
Fri, Feb 13 - Sun, Feb 15
YYZ
Toronto
MDW
Chicago
CA $294 Roundtrip, found 1 day ago
CA $294
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Feb 13 from Toronto to Chicago, returning Sun, Feb 15, priced at CA $294 found 1 day ago
Tue, Feb 3 - Sun, Feb 8
YYZ
Toronto
MDW
Chicago
CA $296 Roundtrip, found 5 days ago
CA $296
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Feb 3 from Toronto to Chicago, returning Sun, Feb 8, priced at CA $296 found 5 days ago
Sun, Feb 1 - Wed, Feb 4
YYZ
Toronto
MDW
Chicago
CA $298 Roundtrip, found 3 days ago
CA $298
Roundtrip
found 3 days ago
Select Delta flight, departing Sun, Feb 1 from Toronto to Chicago, returning Wed, Feb 4, priced at CA $298 found 3 days ago
Thu, Jan 29 - Tue, Feb 3
YYZ
Toronto
MDW
Chicago
CA $310 Roundtrip, found 1 day ago
CA $310
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Jan 29 from Toronto to Chicago, returning Tue, Feb 3, priced at CA $310 found 1 day ago
Thu, Feb 19 - Sun, Feb 22
YYZ
Toronto
MDW
Chicago
CA $311 Roundtrip, found 1 day ago
CA $311
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Feb 19 from Toronto to Chicago, returning Sun, Feb 22, priced at CA $311 found 1 day ago
Fri, Jan 23 - Sun, Jan 25
YYZ
Toronto
MDW
Chicago
CA $327 Roundtrip, found 1 day ago
CA $327
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jan 23 from Toronto to Chicago, returning Sun, Jan 25, priced at CA $327 found 1 day ago
Fri, Jan 16 - Sun, Jan 18
YYZ
Toronto
MDW
Chicago
CA $327 Roundtrip, found 10 hours ago
CA $327
Roundtrip
found 10 hours ago
Select Delta flight, departing Fri, Jan 16 from Toronto to Chicago, returning Sun, Jan 18, priced at CA $327 found 10 hours ago
Thu, Jan 22 - Mon, Jan 26
YYZ
Toronto
MDW
Chicago
CA $328 Roundtrip, found 4 days ago
CA $328
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Jan 22 from Toronto to Chicago, returning Mon, Jan 26, priced at CA $328 found 4 days ago
Thu, Jan 15 - Sun, Jan 18
YYZ
Toronto
MDW
Chicago
CA $330 Roundtrip, found 2 days ago
CA $330
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Jan 15 from Toronto to Chicago, returning Sun, Jan 18, priced at CA $330 found 2 days ago

Midway Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Price was CA $763, price is now CA $552 per person
CA $552
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Price was CA $1,442, price is now CA $801 per person
CA $801
per person
Jan 14 - Jan 22
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Price was CA $1,305, price is now CA $900 per person
CA $900
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Price was CA $823, price is now CA $592 per person
CA $592
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Price was CA $1,549, price is now CA $1,141 per person
CA $1,141
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip 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.