Flights from Chicago to Owen Sound

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.

Wed, Sep 3 - Wed, Sep 10

MDW

Midway Intl.

YTZ

Billy Bishop Toronto City

$234 Roundtrip, found 2 days ago

$234

Roundtrip

found 2 days ago

Select Air Transat flight, departing Wed, Sep 3 from Midway Intl. to Billy Bishop Toronto City, returning Wed, Sep 10, priced at $234 found 2 days ago

Sun, Aug 31 - Sun, Sep 7

MDW

Midway Intl.

YTZ

Billy Bishop Toronto City

$237 Roundtrip, found 2 days ago

$237

Roundtrip

found 2 days ago

Select Porter Airlines flight, departing Sun, Aug 31 from Midway Intl. to Billy Bishop Toronto City, returning Sun, Sep 7, priced at $237 found 2 days ago

Wed, Sep 3 - Wed, Sep 10

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$243 Roundtrip, found 2 days ago

$243

Roundtrip

found 2 days ago

Select Air Canada flight, departing Wed, Sep 3 from O'Hare Intl. to Pearson Intl., returning Wed, Sep 10, priced at $243 found 2 days ago

Wed, Sep 3 - Wed, Sep 10

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$243 Roundtrip, found 2 days ago

$243

Roundtrip

found 2 days ago

Select United flight, departing Wed, Sep 3 from O'Hare Intl. to Pearson Intl., returning Wed, Sep 10, priced at $243 found 2 days ago

Wed, Sep 3 - Wed, Sep 10

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$248 Roundtrip, found 2 days ago

$248

Roundtrip

found 2 days ago

Select Air Canada flight, departing Wed, Sep 3 from O'Hare Intl. to Pearson Intl., returning Wed, Sep 10, priced at $248 found 2 days ago

Mon, Sep 1 - Thu, Sep 11

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$253 Roundtrip, found 2 days ago

$253

Roundtrip

found 2 days ago

Select American Airlines flight, departing Mon, Sep 1 from O'Hare Intl. to Pearson Intl., returning Thu, Sep 11, priced at $253 found 2 days ago

Wed, Sep 3 - Wed, Sep 10

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$258 Roundtrip, found 2 days ago

$258

Roundtrip

found 2 days ago

Select United flight, departing Wed, Sep 3 from O'Hare Intl. to Pearson Intl., returning Wed, Sep 10, priced at $258 found 2 days ago

Wed, Sep 3 - Wed, Sep 10

MDW

Midway Intl.

YTZ

Billy Bishop Toronto City

$268 Roundtrip, found 2 days ago

$268

Roundtrip

found 2 days ago

Select Air Transat flight, departing Wed, Sep 3 from Midway Intl. to Billy Bishop Toronto City, returning Wed, Sep 10, priced at $268 found 2 days ago

Wed, Sep 3 - Wed, Sep 10

MDW

Midway Intl.

YYZ

Pearson Intl.

$268 Roundtrip, found 2 days ago

$268

Roundtrip

found 2 days ago

Select Delta flight, departing Wed, Sep 3 from Midway Intl. to Pearson Intl., returning Wed, Sep 10, priced at $268 found 2 days ago

Wed, Sep 3 - Wed, Sep 10

MDW

Midway Intl.

YTZ

Billy Bishop Toronto City

$282 Roundtrip, found 2 days ago

$282

Roundtrip

found 2 days ago

Select Air Transat flight, departing Wed, Sep 3 from Midway Intl. to Billy Bishop Toronto City, returning Wed, Sep 10, priced at $282 found 2 days ago

Mon, Sep 1 - Sun, Sep 7

MDW

Midway Intl.

YTZ

Billy Bishop Toronto City

$284 Roundtrip, found 2 days ago

$284

Roundtrip

found 2 days ago

Select Porter Airlines flight, departing Mon, Sep 1 from Midway Intl. to Billy Bishop Toronto City, returning Sun, Sep 7, priced at $284 found 2 days ago

Wed, Sep 3 - Wed, Sep 10

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$300 Roundtrip, found 2 days ago

$300

Roundtrip

found 2 days ago

Select American Airlines flight, departing Wed, Sep 3 from O'Hare Intl. to Pearson Intl., returning Wed, Sep 10, priced at $300 found 2 days ago

Wed, Sep 3 - Wed, Sep 10

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$305 Roundtrip, found 2 days ago

$305

Roundtrip

found 2 days ago

Select United flight, departing Wed, Sep 3 from O'Hare Intl. to Pearson Intl., returning Wed, Sep 10, priced at $305 found 2 days ago

Wed, Sep 3 - Wed, Sep 10

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$316 Roundtrip, found 2 days ago

$316

Roundtrip

found 2 days ago

Select American Airlines flight, departing Wed, Sep 3 from O'Hare Intl. to Pearson Intl., returning Wed, Sep 10, priced at $316 found 2 days ago

Wed, Sep 3 - Wed, Sep 10

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$327 Roundtrip, found 2 days ago

$327

Roundtrip

found 2 days ago

Select American Airlines flight, departing Wed, Sep 3 from O'Hare Intl. to Pearson Intl., returning Wed, Sep 10, priced at $327 found 2 days ago

Wed, Sep 3 - Wed, Sep 10

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$331 Roundtrip, found 2 days ago

$331

Roundtrip

found 2 days ago

Select WestJet flight, departing Wed, Sep 3 from O'Hare Intl. to Pearson Intl., returning Wed, Sep 10, priced at $331 found 2 days ago

Wed, Sep 3 - Wed, Sep 10

ORD

O'Hare Intl.

YYZ

Pearson Intl.

$333 Roundtrip, found 2 days ago

$333

Roundtrip

found 2 days ago

Select American Airlines flight, departing Wed, Sep 3 from O'Hare Intl. to Pearson Intl., returning Wed, Sep 10, priced at $333 found 2 days ago

Wed, Sep 3 - Wed, Sep 10

ORD

O'Hare Intl.

YKF

Region of Waterloo Intl.

$338 Roundtrip, found 2 days ago

$338

Roundtrip

found 2 days ago

Select Air Canada flight, departing Wed, Sep 3 from O'Hare Intl. to Region of Waterloo Intl., returning Wed, Sep 10, priced at $338 found 2 days ago

Wed, Sep 3 - Wed, Sep 10

ORD

O'Hare Intl.

YHM

John C. Munro Hamilton Intl.

$339 Roundtrip, found 2 days ago

$339

Roundtrip

found 2 days ago

Select Air Canada flight, departing Wed, Sep 3 from O'Hare Intl. to John C. Munro Hamilton Intl., returning Wed, Sep 10, priced at $339 found 2 days ago

Wed, Sep 3 - Wed, Sep 10

ORD

O'Hare Intl.

YTZ

Billy Bishop Toronto City

$344 Roundtrip, found 2 days ago

$344

Roundtrip

found 2 days ago

Select Air Canada flight, departing Wed, Sep 3 from O'Hare Intl. to Billy Bishop Toronto City, returning Wed, Sep 10, priced at $344 found 2 days ago