Flights from Chicago to Waterloo

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.

Fri, Jun 13 - Sat, Jun 14

ORD

O'Hare Intl.

YUL

Pierre Elliott Trudeau Intl.

$282 Roundtrip, found 6 days ago

$282

Roundtrip

found 6 days ago

Select American Airlines flight, departing Fri, Jun 13 from O'Hare Intl. to Pierre Elliott Trudeau Intl., returning Sat, Jun 14, priced at $282 found 6 days ago

Wed, Jun 18 - Sun, Jun 22

ORD

O'Hare Intl.

YUL

Pierre Elliott Trudeau Intl.

$285 Roundtrip, found 1 day ago

$285

Roundtrip

found 1 day ago

Select Air Canada flight, departing Wed, Jun 18 from O'Hare Intl. to Pierre Elliott Trudeau Intl., returning Sun, Jun 22, priced at $285 found 1 day ago

Wed, Jun 18 - Sun, Jun 22

ORD

O'Hare Intl.

YUL

Pierre Elliott Trudeau Intl.

$289 Roundtrip, found 1 day ago

$289

Roundtrip

found 1 day ago

Select American Airlines flight, departing Wed, Jun 18 from O'Hare Intl. to Pierre Elliott Trudeau Intl., returning Sun, Jun 22, priced at $289 found 1 day ago

Wed, Jun 18 - Sun, Jun 22

ORD

O'Hare Intl.

YUL

Pierre Elliott Trudeau Intl.

$291 Roundtrip, found 1 day ago

$291

Roundtrip

found 1 day ago

Select Air Canada flight, departing Wed, Jun 18 from O'Hare Intl. to Pierre Elliott Trudeau Intl., returning Sun, Jun 22, priced at $291 found 1 day ago

Sat, Jun 14 - Sat, Jun 14

ORD

O'Hare Intl.

YUL

Pierre Elliott Trudeau Intl.

$298 Roundtrip, found 6 days ago

$298

Roundtrip

found 6 days ago

Select American Airlines flight, departing Sat, Jun 14 from O'Hare Intl. to Pierre Elliott Trudeau Intl., returning Sat, Jun 14, priced at $298 found 6 days ago

Sat, Jun 21 - Wed, Jun 25

ORD

O'Hare Intl.

YUL

Pierre Elliott Trudeau Intl.

$306 Roundtrip, found 6 days ago

$306

Roundtrip

found 6 days ago

Select Air Canada flight, departing Sat, Jun 21 from O'Hare Intl. to Pierre Elliott Trudeau Intl., returning Wed, Jun 25, priced at $306 found 6 days ago

Tue, Jun 17 - Wed, Jun 25

ORD

O'Hare Intl.

YUL

Pierre Elliott Trudeau Intl.

$311 Roundtrip, found 6 days ago

$311

Roundtrip

found 6 days ago

Select Air Canada flight, departing Tue, Jun 17 from O'Hare Intl. to Pierre Elliott Trudeau Intl., returning Wed, Jun 25, priced at $311 found 6 days ago

Wed, Jun 18 - Sun, Jun 22

ORD

O'Hare Intl.

YUL

Pierre Elliott Trudeau Intl.

$311 Roundtrip, found 1 day ago

$311

Roundtrip

found 1 day ago

Select Air Canada flight, departing Wed, Jun 18 from O'Hare Intl. to Pierre Elliott Trudeau Intl., returning Sun, Jun 22, priced at $311 found 1 day ago

Wed, Jun 18 - Sun, Jun 22

ORD

O'Hare Intl.

YUL

Pierre Elliott Trudeau Intl.

$313 Roundtrip, found 1 day ago

$313

Roundtrip

found 1 day ago

Select American Airlines flight, departing Wed, Jun 18 from O'Hare Intl. to Pierre Elliott Trudeau Intl., returning Sun, Jun 22, priced at $313 found 1 day ago

Wed, Jun 18 - Sun, Jun 22

ORD

O'Hare Intl.

YUL

Pierre Elliott Trudeau Intl.

$315 Roundtrip, found 1 day ago

$315

Roundtrip

found 1 day ago

Select Air Canada flight, departing Wed, Jun 18 from O'Hare Intl. to Pierre Elliott Trudeau Intl., returning Sun, Jun 22, priced at $315 found 1 day ago

Fri, Jun 20 - Wed, Jun 25

ORD

O'Hare Intl.

YUL

Pierre Elliott Trudeau Intl.

$316 Roundtrip, found 1 day ago

$316

Roundtrip

found 1 day ago

Select United flight, departing Fri, Jun 20 from O'Hare Intl. to Pierre Elliott Trudeau Intl., returning Wed, Jun 25, priced at $316 found 1 day ago

Wed, Jun 18 - Sun, Jun 22

ORD

O'Hare Intl.

YUL

Pierre Elliott Trudeau Intl.

$316 Roundtrip, found 1 day ago

$316

Roundtrip

found 1 day ago

Select United flight, departing Wed, Jun 18 from O'Hare Intl. to Pierre Elliott Trudeau Intl., returning Sun, Jun 22, priced at $316 found 1 day ago

Thu, Jun 19 - Tue, Jun 24

MDW

Midway Intl.

YUL

Pierre Elliott Trudeau Intl.

$316 Roundtrip, found 1 day ago

$316

Roundtrip

found 1 day ago

Select Porter Airlines flight, departing Thu, Jun 19 from Midway Intl. to Pierre Elliott Trudeau Intl., returning Tue, Jun 24, priced at $316 found 1 day ago

Wed, Jun 18 - Sun, Jun 22

ORD

O'Hare Intl.

YUL

Pierre Elliott Trudeau Intl.

$317 Roundtrip, found 1 day ago

$317

Roundtrip

found 1 day ago

Select American Airlines flight, departing Wed, Jun 18 from O'Hare Intl. to Pierre Elliott Trudeau Intl., returning Sun, Jun 22, priced at $317 found 1 day ago

Sat, Jun 21 - Sat, Jun 21

ORD

O'Hare Intl.

YUL

Pierre Elliott Trudeau Intl.

$322 Roundtrip, found 6 days ago

$322

Roundtrip

found 6 days ago

Select United flight, departing Sat, Jun 21 from O'Hare Intl. to Pierre Elliott Trudeau Intl., returning Sat, Jun 21, priced at $322 found 6 days ago

Wed, Jun 18 - Sun, Jun 22

ORD

O'Hare Intl.

YUL

Pierre Elliott Trudeau Intl.

$322 Roundtrip, found 1 day ago

$322

Roundtrip

found 1 day ago

Select Air Canada flight, departing Wed, Jun 18 from O'Hare Intl. to Pierre Elliott Trudeau Intl., returning Sun, Jun 22, priced at $322 found 1 day ago

Wed, Jun 18 - Sun, Jun 22

ORD

O'Hare Intl.

YUL

Pierre Elliott Trudeau Intl.

$430 Roundtrip, found 1 day ago

$430

Roundtrip

found 1 day ago

Select United flight, departing Wed, Jun 18 from O'Hare Intl. to Pierre Elliott Trudeau Intl., returning Sun, Jun 22, priced at $430 found 1 day ago

Thu, Jun 12 - Tue, Jun 17

ORD

O'Hare Intl.

YUL

Pierre Elliott Trudeau Intl.

$444 Roundtrip, found 6 days ago

$444

Roundtrip

found 6 days ago

Select WestJet flight, departing Thu, Jun 12 from O'Hare Intl. to Pierre Elliott Trudeau Intl., returning Tue, Jun 17, priced at $444 found 6 days ago

Thu, Jun 12 - Sun, Jun 15

ORD

O'Hare Intl.

YUL

Pierre Elliott Trudeau Intl.

$510 Roundtrip, found 6 days ago

$510

Roundtrip

found 6 days ago

Select Delta flight, departing Thu, Jun 12 from O'Hare Intl. to Pierre Elliott Trudeau Intl., returning Sun, Jun 15, priced at $510 found 6 days ago

Mon, Jun 9 - Sat, Jun 14

ORD

O'Hare Intl.

YHU

Montreal Metropolitan Airport

$1,064 Roundtrip, found 6 days ago

$1,064

Roundtrip

found 6 days ago

Select Air Canada flight, departing Mon, Jun 9 from O'Hare Intl. to Montreal Metropolitan Airport, returning Sat, Jun 14, priced at $1,064 found 6 days ago