Flights from Montreal to Chicago

Cheapest flights from Montreal

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, Jul 22 - Wed, Jul 23

YUL

Pierre Elliott Trudeau Intl.

MDW

Midway Intl.

$274 Roundtrip, found 2 days ago

$274

Roundtrip

found 2 days ago

Select Porter Airlines flight, departing Tue, Jul 22 from Pierre Elliott Trudeau Intl. to Midway Intl., returning Wed, Jul 23, priced at $274 found 2 days ago

Fri, Jul 25 - Sun, Jul 27

YUL

Pierre Elliott Trudeau Intl.

MDW

Midway Intl.

$275 Roundtrip, found 2 days ago

$275

Roundtrip

found 2 days ago

Select Porter Airlines flight, departing Fri, Jul 25 from Pierre Elliott Trudeau Intl. to Midway Intl., returning Sun, Jul 27, priced at $275 found 2 days ago

Sat, Jul 26 - Mon, Jul 28

YUL

Pierre Elliott Trudeau Intl.

ORD

O'Hare Intl.

$276 Roundtrip, found 2 days ago

$276

Roundtrip

found 2 days ago

Select Air Canada flight, departing Sat, Jul 26 from Pierre Elliott Trudeau Intl. to O'Hare Intl., returning Mon, Jul 28, priced at $276 found 2 days ago

Mon, Jul 28 - Mon, Jul 28

YUL

Pierre Elliott Trudeau Intl.

ORD

O'Hare Intl.

$277 Roundtrip, found 2 days ago

$277

Roundtrip

found 2 days ago

Select United flight, departing Mon, Jul 28 from Pierre Elliott Trudeau Intl. to O'Hare Intl., returning Mon, Jul 28, priced at $277 found 2 days ago

Sat, Jul 26 - Sat, Jul 26

YUL

Pierre Elliott Trudeau Intl.

ORD

O'Hare Intl.

$283 Roundtrip, found 2 days ago

$283

Roundtrip

found 2 days ago

Select Delta flight, departing Sat, Jul 26 from Pierre Elliott Trudeau Intl. to O'Hare Intl., returning Sat, Jul 26, priced at $283 found 2 days ago

Tue, Jul 22 - Tue, Jul 22

YUL

Pierre Elliott Trudeau Intl.

ORD

O'Hare Intl.

$288 Roundtrip, found 2 days ago

$288

Roundtrip

found 2 days ago

Select Air Canada flight, departing Tue, Jul 22 from Pierre Elliott Trudeau Intl. to O'Hare Intl., returning Tue, Jul 22, priced at $288 found 2 days ago

Fri, Jul 25 - Sun, Jul 27

YUL

Pierre Elliott Trudeau Intl.

ORD

O'Hare Intl.

$289 Roundtrip, found 2 days ago

$289

Roundtrip

found 2 days ago

Select Air Canada flight, departing Fri, Jul 25 from Pierre Elliott Trudeau Intl. to O'Hare Intl., returning Sun, Jul 27, priced at $289 found 2 days ago

Mon, Jul 28 - Wed, Jul 30

YUL

Pierre Elliott Trudeau Intl.

ORD

O'Hare Intl.

$289 Roundtrip, found 2 days ago

$289

Roundtrip

found 2 days ago

Select United flight, departing Mon, Jul 28 from Pierre Elliott Trudeau Intl. to O'Hare Intl., returning Wed, Jul 30, priced at $289 found 2 days ago

Fri, Jul 25 - Sun, Jul 27

YUL

Pierre Elliott Trudeau Intl.

ORD

O'Hare Intl.

$291 Roundtrip, found 2 days ago

$291

Roundtrip

found 2 days ago

Select United flight, departing Fri, Jul 25 from Pierre Elliott Trudeau Intl. to O'Hare Intl., returning Sun, Jul 27, priced at $291 found 2 days ago

Tue, Jul 22 - Sat, Aug 2

YUL

Pierre Elliott Trudeau Intl.

MDW

Midway Intl.

$298 Roundtrip, found 2 days ago

$298

Roundtrip

found 2 days ago

Select Porter Airlines flight, departing Tue, Jul 22 from Pierre Elliott Trudeau Intl. to Midway Intl., returning Sat, Aug 2, priced at $298 found 2 days ago

Fri, Jul 25 - Sun, Jul 27

YUL

Pierre Elliott Trudeau Intl.

MDW

Midway Intl.

$299 Roundtrip, found 2 days ago

$299

Roundtrip

found 2 days ago

Select Porter Airlines flight, departing Fri, Jul 25 from Pierre Elliott Trudeau Intl. to Midway Intl., returning Sun, Jul 27, priced at $299 found 2 days ago

Sun, Jul 27 - Wed, Jul 30

YUL

Pierre Elliott Trudeau Intl.

MDW

Midway Intl.

$302 Roundtrip, found 2 days ago

$302

Roundtrip

found 2 days ago

Select Delta flight, departing Sun, Jul 27 from Pierre Elliott Trudeau Intl. to Midway Intl., returning Wed, Jul 30, priced at $302 found 2 days ago

Fri, Jul 25 - Sun, Jul 27

YUL

Pierre Elliott Trudeau Intl.

ORD

O'Hare Intl.

$305 Roundtrip, found 2 days ago

$305

Roundtrip

found 2 days ago

Select United flight, departing Fri, Jul 25 from Pierre Elliott Trudeau Intl. to O'Hare Intl., returning Sun, Jul 27, priced at $305 found 2 days ago

Sun, Jul 27 - Mon, Jul 28

YUL

Pierre Elliott Trudeau Intl.

MDW

Midway Intl.

$309 Roundtrip, found 2 days ago

$309

Roundtrip

found 2 days ago

Select Porter Airlines flight, departing Sun, Jul 27 from Pierre Elliott Trudeau Intl. to Midway Intl., returning Mon, Jul 28, priced at $309 found 2 days ago

Fri, Jul 25 - Sun, Jul 27

YUL

Pierre Elliott Trudeau Intl.

ORD

O'Hare Intl.

$311 Roundtrip, found 2 days ago

$311

Roundtrip

found 2 days ago

Select Air Canada flight, departing Fri, Jul 25 from Pierre Elliott Trudeau Intl. to O'Hare Intl., returning Sun, Jul 27, priced at $311 found 2 days ago

Fri, Jul 25 - Sun, Jul 27

YUL

Pierre Elliott Trudeau Intl.

ORD

O'Hare Intl.

$311 Roundtrip, found 2 days ago

$311

Roundtrip

found 2 days ago

Select United flight, departing Fri, Jul 25 from Pierre Elliott Trudeau Intl. to O'Hare Intl., returning Sun, Jul 27, priced at $311 found 2 days ago

Fri, Jul 25 - Sun, Jul 27

YUL

Pierre Elliott Trudeau Intl.

ORD

O'Hare Intl.

$313 Roundtrip, found 2 days ago

$313

Roundtrip

found 2 days ago

Select Air Canada flight, departing Fri, Jul 25 from Pierre Elliott Trudeau Intl. to O'Hare Intl., returning Sun, Jul 27, priced at $313 found 2 days ago

Fri, Jul 25 - Sun, Jul 27

YUL

Pierre Elliott Trudeau Intl.

ORD

O'Hare Intl.

$313 Roundtrip, found 2 days ago

$313

Roundtrip

found 2 days ago

Select United flight, departing Fri, Jul 25 from Pierre Elliott Trudeau Intl. to O'Hare Intl., returning Sun, Jul 27, priced at $313 found 2 days ago

Fri, Jul 25 - Sun, Jul 27

YUL

Pierre Elliott Trudeau Intl.

ORD

O'Hare Intl.

$381 Roundtrip, found 2 days ago

$381

Roundtrip

found 2 days ago

Select American Airlines flight, departing Fri, Jul 25 from Pierre Elliott Trudeau Intl. to O'Hare Intl., returning Sun, Jul 27, priced at $381 found 2 days ago

Fri, Jul 25 - Sun, Jul 27

YUL

Pierre Elliott Trudeau Intl.

ORD

O'Hare Intl.

$472 Roundtrip, found 2 days ago

$472

Roundtrip

found 2 days ago

Select WestJet flight, departing Fri, Jul 25 from Pierre Elliott Trudeau Intl. to O'Hare Intl., returning Sun, Jul 27, priced at $472 found 2 days ago