Flights from Chicago to Zephyr

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.

Tue, Sep 9 - Tue, Sep 9

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$153 Roundtrip, found 6 days ago

$153

Roundtrip

found 6 days ago

Select United flight, departing Tue, Sep 9 from O'Hare Intl. to Pearson Intl., returning Tue, Sep 9, priced at $153 found 6 days ago

Fri, Sep 5 - Tue, Sep 9

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$167 Roundtrip, found 6 days ago

$167

Roundtrip

found 6 days ago

Select Air Canada flight, departing Fri, Sep 5 from O'Hare Intl. to Pearson Intl., returning Tue, Sep 9, priced at $167 found 6 days ago

Thu, Aug 7 - Thu, Aug 7

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$213 Roundtrip, found 4 days ago

$213

Roundtrip

found 4 days ago

Select Air Canada flight, departing Thu, Aug 7 from O'Hare Intl. to Pearson Intl., returning Thu, Aug 7, priced at $213 found 4 days ago

Thu, Aug 28 - Fri, Aug 29

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$224 Roundtrip, found 1 day ago

$224

Roundtrip

found 1 day ago

Select Delta flight, departing Thu, Aug 28 from O'Hare Intl. to Pearson Intl., returning Fri, Aug 29, priced at $224 found 1 day ago

Sun, Aug 3 - Mon, Aug 11

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$232 Roundtrip, found 4 days ago

$232

Roundtrip

found 4 days ago

Select United flight, departing Sun, Aug 3 from O'Hare Intl. to Pearson Intl., returning Mon, Aug 11, priced at $232 found 4 days ago

Tue, Aug 26 - Fri, Aug 29

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$232 Roundtrip, found 1 day ago

$232

Roundtrip

found 1 day ago

Select Air Canada flight, departing Tue, Aug 26 from O'Hare Intl. to Pearson Intl., returning Fri, Aug 29, priced at $232 found 1 day ago

Thu, Aug 28 - Fri, Aug 29

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$237 Roundtrip, found 1 day ago

$237

Roundtrip

found 1 day ago

Select Air Canada flight, departing Thu, Aug 28 from O'Hare Intl. to Pearson Intl., returning Fri, Aug 29, priced at $237 found 1 day ago

Thu, Aug 28 - Fri, Aug 29

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$250 Roundtrip, found 1 day ago

$250

Roundtrip

found 1 day ago

Select Air Canada flight, departing Thu, Aug 28 from O'Hare Intl. to Pearson Intl., returning Fri, Aug 29, priced at $250 found 1 day ago

Thu, Aug 28 - Fri, Aug 29

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$252 Roundtrip, found 1 day ago

$252

Roundtrip

found 1 day ago

Select American Airlines flight, departing Thu, Aug 28 from O'Hare Intl. to Pearson Intl., returning Fri, Aug 29, priced at $252 found 1 day ago

Thu, Aug 28 - Fri, Aug 29

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$257 Roundtrip, found 1 day ago

$257

Roundtrip

found 1 day ago

Select Delta flight, departing Thu, Aug 28 from O'Hare Intl. to Pearson Intl., returning Fri, Aug 29, priced at $257 found 1 day ago

Thu, Aug 28 - Fri, Aug 29

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$262 Roundtrip, found 1 day ago

$262

Roundtrip

found 1 day ago

Select Delta flight, departing Thu, Aug 28 from O'Hare Intl. to Pearson Intl., returning Fri, Aug 29, priced at $262 found 1 day ago

Thu, Aug 28 - Fri, Aug 29

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$270 Roundtrip, found 1 day ago

$270

Roundtrip

found 1 day ago

Select American Airlines flight, departing Thu, Aug 28 from O'Hare Intl. to Pearson Intl., returning Fri, Aug 29, priced at $270 found 1 day ago

Thu, Aug 28 - Fri, Aug 29

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$280 Roundtrip, found 1 day ago

$280

Roundtrip

found 1 day ago

Select Air Canada flight, departing Thu, Aug 28 from O'Hare Intl. to Pearson Intl., returning Fri, Aug 29, priced at $280 found 1 day ago

Thu, Aug 28 - Fri, Aug 29

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$285 Roundtrip, found 1 day ago

$285

Roundtrip

found 1 day ago

Select American Airlines flight, departing Thu, Aug 28 from O'Hare Intl. to Pearson Intl., returning Fri, Aug 29, priced at $285 found 1 day ago

Thu, Aug 28 - Fri, Aug 29

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$288 Roundtrip, found 1 day ago

$288

Roundtrip

found 1 day ago

Select Air Canada flight, departing Thu, Aug 28 from O'Hare Intl. to Pearson Intl., returning Fri, Aug 29, priced at $288 found 1 day ago

Thu, Aug 28 - Fri, Aug 29

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$290 Roundtrip, found 1 day ago

$290

Roundtrip

found 1 day ago

Select American Airlines flight, departing Thu, Aug 28 from O'Hare Intl. to Pearson Intl., returning Fri, Aug 29, priced at $290 found 1 day ago

Thu, Aug 28 - Fri, Aug 29

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$294 Roundtrip, found 1 day ago

$294

Roundtrip

found 1 day ago

Select Delta flight, departing Thu, Aug 28 from O'Hare Intl. to Pearson Intl., returning Fri, Aug 29, priced at $294 found 1 day ago

Thu, Aug 28 - Fri, Aug 29

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$373 Roundtrip, found 1 day ago

$373

Roundtrip

found 1 day ago

Select United flight, departing Thu, Aug 28 from O'Hare Intl. to Pearson Intl., returning Fri, Aug 29, priced at $373 found 1 day ago

Mon, Dec 29 - Mon, Jan 5

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$483 Roundtrip, found 4 days ago

$483

Roundtrip

found 4 days ago

Select WestJet flight, departing Mon, Dec 29 from O'Hare Intl. to Pearson Intl., returning Mon, Jan 5, priced at $483 found 4 days ago

Mon, Dec 29 - Mon, Jan 5

MDW

Midway Intl.

YYZ

Pearson Intl.

$598 Roundtrip, found 4 days ago

$598

Roundtrip

found 4 days ago

Select WestJet flight, departing Mon, Dec 29 from Midway Intl. to Pearson Intl., returning Mon, Jan 5, priced at $598 found 4 days ago