Flights from Chicago to Winnipeg

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, Aug 17 - Thu, Aug 28

ORD

O'Hare Intl.

YWG

Winnipeg James Armstrong Richardson Intl.

$414 Roundtrip, found 3 days ago

$414

Roundtrip

found 3 days ago

Select United flight, departing Sun, Aug 17 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Thu, Aug 28, priced at $414 found 3 days ago

Sun, Aug 17 - Thu, Aug 28

ORD

O'Hare Intl.

YWG

Winnipeg James Armstrong Richardson Intl.

$417 Roundtrip, found 3 days ago

$417

Roundtrip

found 3 days ago

Select Air Canada flight, departing Sun, Aug 17 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Thu, Aug 28, priced at $417 found 3 days ago

Sun, Aug 17 - Wed, Aug 27

ORD

O'Hare Intl.

YWG

Winnipeg James Armstrong Richardson Intl.

$419 Roundtrip, found 3 days ago

$419

Roundtrip

found 3 days ago

Select Air Canada flight, departing Sun, Aug 17 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Aug 27, priced at $419 found 3 days ago

Sun, Aug 17 - Thu, Aug 28

ORD

O'Hare Intl.

YWG

Winnipeg James Armstrong Richardson Intl.

$450 Roundtrip, found 3 days ago

$450

Roundtrip

found 3 days ago

Select Air Canada flight, departing Sun, Aug 17 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Thu, Aug 28, priced at $450 found 3 days ago

Sun, Aug 17 - Thu, Aug 28

ORD

O'Hare Intl.

YWG

Winnipeg James Armstrong Richardson Intl.

$450 Roundtrip, found 3 days ago

$450

Roundtrip

found 3 days ago

Select Air Canada flight, departing Sun, Aug 17 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Thu, Aug 28, priced at $450 found 3 days ago

Sun, Aug 17 - Thu, Aug 28

ORD

O'Hare Intl.

YWG

Winnipeg James Armstrong Richardson Intl.

$451 Roundtrip, found 3 days ago

$451

Roundtrip

found 3 days ago

Select United flight, departing Sun, Aug 17 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Thu, Aug 28, priced at $451 found 3 days ago

Sun, Aug 17 - Wed, Aug 27

ORD

O'Hare Intl.

YWG

Winnipeg James Armstrong Richardson Intl.

$452 Roundtrip, found 3 days ago

$452

Roundtrip

found 3 days ago

Select Air Canada flight, departing Sun, Aug 17 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Aug 27, priced at $452 found 3 days ago

Sun, Aug 17 - Thu, Aug 28

ORD

O'Hare Intl.

YWG

Winnipeg James Armstrong Richardson Intl.

$455 Roundtrip, found 3 days ago

$455

Roundtrip

found 3 days ago

Select Air Canada flight, departing Sun, Aug 17 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Thu, Aug 28, priced at $455 found 3 days ago

Sun, Aug 17 - Wed, Aug 27

ORD

O'Hare Intl.

YWG

Winnipeg James Armstrong Richardson Intl.

$457 Roundtrip, found 3 days ago

$457

Roundtrip

found 3 days ago

Select Air Canada flight, departing Sun, Aug 17 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Aug 27, priced at $457 found 3 days ago

Sat, Aug 16 - Tue, Aug 26

ORD

O'Hare Intl.

YWG

Winnipeg James Armstrong Richardson Intl.

$458 Roundtrip, found 3 days ago

$458

Roundtrip

found 3 days ago

Select United flight, departing Sat, Aug 16 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Tue, Aug 26, priced at $458 found 3 days ago

Sat, Aug 16 - Wed, Aug 27

ORD

O'Hare Intl.

YWG

Winnipeg James Armstrong Richardson Intl.

$464 Roundtrip, found 3 days ago

$464

Roundtrip

found 3 days ago

Select United flight, departing Sat, Aug 16 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Aug 27, priced at $464 found 3 days ago

Wed, Aug 20 - Wed, Aug 27

ORD

O'Hare Intl.

YWG

Winnipeg James Armstrong Richardson Intl.

$469 Roundtrip, found 3 days ago

$469

Roundtrip

found 3 days ago

Select Air Canada flight, departing Wed, Aug 20 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Aug 27, priced at $469 found 3 days ago

Sun, Aug 17 - Wed, Aug 27

ORD

O'Hare Intl.

YWG

Winnipeg James Armstrong Richardson Intl.

$470 Roundtrip, found 3 days ago

$470

Roundtrip

found 3 days ago

Select United flight, departing Sun, Aug 17 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Aug 27, priced at $470 found 3 days ago

Sun, Aug 17 - Wed, Aug 27

ORD

O'Hare Intl.

YWG

Winnipeg James Armstrong Richardson Intl.

$474 Roundtrip, found 3 days ago

$474

Roundtrip

found 3 days ago

Select United flight, departing Sun, Aug 17 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Aug 27, priced at $474 found 3 days ago

Sun, Aug 17 - Wed, Aug 27

ORD

O'Hare Intl.

YWG

Winnipeg James Armstrong Richardson Intl.

$475 Roundtrip, found 3 days ago

$475

Roundtrip

found 3 days ago

Select Air Canada flight, departing Sun, Aug 17 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Aug 27, priced at $475 found 3 days ago

Sun, Aug 17 - Wed, Aug 27

ORD

O'Hare Intl.

YWG

Winnipeg James Armstrong Richardson Intl.

$479 Roundtrip, found 3 days ago

$479

Roundtrip

found 3 days ago

Select Air Canada flight, departing Sun, Aug 17 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Aug 27, priced at $479 found 3 days ago

Sun, Aug 17 - Thu, Aug 28

ORD

O'Hare Intl.

YWG

Winnipeg James Armstrong Richardson Intl.

$488 Roundtrip, found 3 days ago

$488

Roundtrip

found 3 days ago

Select Air Canada flight, departing Sun, Aug 17 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Thu, Aug 28, priced at $488 found 3 days ago

Sun, Aug 17 - Wed, Aug 27

ORD

O'Hare Intl.

YWG

Winnipeg James Armstrong Richardson Intl.

$490 Roundtrip, found 3 days ago

$490

Roundtrip

found 3 days ago

Select Air Canada flight, departing Sun, Aug 17 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Wed, Aug 27, priced at $490 found 3 days ago

Sun, Aug 17 - Thu, Aug 28

ORD

O'Hare Intl.

YWG

Winnipeg James Armstrong Richardson Intl.

$507 Roundtrip, found 3 days ago

$507

Roundtrip

found 3 days ago

Select Delta flight, departing Sun, Aug 17 from O'Hare Intl. to Winnipeg James Armstrong Richardson Intl., returning Thu, Aug 28, priced at $507 found 3 days ago

Sun, Aug 17 - Tue, Aug 26

MDW

Midway Intl.

YWG

Winnipeg James Armstrong Richardson Intl.

$1,056 Roundtrip, found 3 days ago

$1,056

Roundtrip

found 3 days ago

Select WestJet flight, departing Sun, Aug 17 from Midway Intl. to Winnipeg James Armstrong Richardson Intl., returning Tue, Aug 26, priced at $1,056 found 3 days ago