Flights from Chicago to Port Perry

Cheapest flights from Chicago

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Jun 22 - Tue, Jun 24

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$150 Roundtrip, found 6 days ago

$150

Roundtrip

found 6 days ago

Select United flight, departing Sun, Jun 22 from O'Hare Intl. to Pearson Intl., returning Tue, Jun 24, priced at $150 found 6 days ago

Tue, Jun 24 - Fri, Jun 27

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$183 Roundtrip, found 6 days ago

$183

Roundtrip

found 6 days ago

Select United flight, departing Tue, Jun 24 from O'Hare Intl. to Pearson Intl., returning Fri, Jun 27, priced at $183 found 6 days ago

Tue, Jun 24 - Fri, Jun 27

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$183 Roundtrip, found 6 days ago

$183

Roundtrip

found 6 days ago

Select Air Canada flight, departing Tue, Jun 24 from O'Hare Intl. to Pearson Intl., returning Fri, Jun 27, priced at $183 found 6 days ago

Sun, Jun 22 - Mon, Jun 30

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$188 Roundtrip, found 6 days ago

$188

Roundtrip

found 6 days ago

Select United flight, departing Sun, Jun 22 from O'Hare Intl. to Pearson Intl., returning Mon, Jun 30, priced at $188 found 6 days ago

Wed, Jul 23 - Sun, Aug 3

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$201 Roundtrip, found 15 hours ago

$201

Roundtrip

found 15 hours ago

Select Air Canada flight, departing Wed, Jul 23 from O'Hare Intl. to Pearson Intl., returning Sun, Aug 3, priced at $201 found 15 hours ago

Tue, Jun 24 - Fri, Jun 27

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$206 Roundtrip, found 6 days ago

$206

Roundtrip

found 6 days ago

Select Air Canada flight, departing Tue, Jun 24 from O'Hare Intl. to Pearson Intl., returning Fri, Jun 27, priced at $206 found 6 days ago

Wed, Jul 23 - Sun, Aug 3

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$211 Roundtrip, found 15 hours ago

$211

Roundtrip

found 15 hours ago

Select Delta flight, departing Wed, Jul 23 from O'Hare Intl. to Pearson Intl., returning Sun, Aug 3, priced at $211 found 15 hours ago

Tue, Jul 22 - Tue, Jul 29

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$217 Roundtrip, found 15 hours ago

$217

Roundtrip

found 15 hours ago

Select United flight, departing Tue, Jul 22 from O'Hare Intl. to Pearson Intl., returning Tue, Jul 29, priced at $217 found 15 hours ago

Wed, Jul 23 - Sun, Aug 3

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$218 Roundtrip, found 15 hours ago

$218

Roundtrip

found 15 hours ago

Select Delta flight, departing Wed, Jul 23 from O'Hare Intl. to Pearson Intl., returning Sun, Aug 3, priced at $218 found 15 hours ago

Fri, Jun 27 - Mon, Jun 30

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$222 Roundtrip, found 6 days ago

$222

Roundtrip

found 6 days ago

Select United flight, departing Fri, Jun 27 from O'Hare Intl. to Pearson Intl., returning Mon, Jun 30, priced at $222 found 6 days ago

Mon, Jun 16 - Sat, Jun 21

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$222 Roundtrip, found 2 days ago

$222

Roundtrip

found 2 days ago

Select United flight, departing Mon, Jun 16 from O'Hare Intl. to Pearson Intl., returning Sat, Jun 21, priced at $222 found 2 days ago

Tue, Jun 10 - Tue, Jun 17

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$224 Roundtrip, found 1 day ago

$224

Roundtrip

found 1 day ago

Select Air Canada flight, departing Tue, Jun 10 from O'Hare Intl. to Pearson Intl., returning Tue, Jun 17, priced at $224 found 1 day ago

Wed, Jul 23 - Sun, Aug 3

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$227 Roundtrip, found 15 hours ago

$227

Roundtrip

found 15 hours ago

Select United flight, departing Wed, Jul 23 from O'Hare Intl. to Pearson Intl., returning Sun, Aug 3, priced at $227 found 15 hours ago

Mon, Jun 16 - Sat, Jun 21

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$228 Roundtrip, found 2 days ago

$228

Roundtrip

found 2 days ago

Select American Airlines flight, departing Mon, Jun 16 from O'Hare Intl. to Pearson Intl., returning Sat, Jun 21, priced at $228 found 2 days ago

Tue, Jun 24 - Fri, Jun 27

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$230 Roundtrip, found 6 days ago

$230

Roundtrip

found 6 days ago

Select United flight, departing Tue, Jun 24 from O'Hare Intl. to Pearson Intl., returning Fri, Jun 27, priced at $230 found 6 days ago

Sun, Jun 15 - Tue, Jun 17

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$232 Roundtrip, found 5 days ago

$232

Roundtrip

found 5 days ago

Select American Airlines flight, departing Sun, Jun 15 from O'Hare Intl. to Pearson Intl., returning Tue, Jun 17, priced at $232 found 5 days ago

Fri, Jun 13 - Tue, Jun 17

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$257 Roundtrip, found 5 days ago

$257

Roundtrip

found 5 days ago

Select Delta flight, departing Fri, Jun 13 from O'Hare Intl. to Pearson Intl., returning Tue, Jun 17, priced at $257 found 5 days ago

Tue, Jun 24 - Fri, Jun 27

MDW

Midway Intl.

YYZ

Pearson Intl.

$282 Roundtrip, found 6 days ago

$282

Roundtrip

found 6 days ago

Select Delta flight, departing Tue, Jun 24 from Midway Intl. to Pearson Intl., returning Fri, Jun 27, priced at $282 found 6 days ago

Mon, Jun 16 - Sat, Jun 21

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$460 Roundtrip, found 2 days ago

$460

Roundtrip

found 2 days ago

Select WestJet flight, departing Mon, Jun 16 from O'Hare Intl. to Pearson Intl., returning Sat, Jun 21, priced at $460 found 2 days ago

Fri, Jun 13 - Sun, Jun 15

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$882 Roundtrip, found 1 day ago

$882

Roundtrip

found 1 day ago

Select Alaska Airlines flight, departing Fri, Jun 13 from O'Hare Intl. to Pearson Intl., returning Sun, Jun 15, priced at $882 found 1 day ago