Flights from Windsor to Chicago

Cheapest flights from Windsor

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, Oct 15 - Sat, Oct 18

OAK

Oakland Intl.

ORD

O'Hare Intl.

$191 Roundtrip, found 3 days ago

$191

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Wed, Oct 15 from Oakland Intl. to O'Hare Intl., returning Sat, Oct 18, priced at $191 found 3 days ago

Fri, Oct 17 - Sat, Oct 18

OAK

Oakland Intl.

ORD

O'Hare Intl.

$198 Roundtrip, found 3 days ago

$198

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Fri, Oct 17 from Oakland Intl. to O'Hare Intl., returning Sat, Oct 18, priced at $198 found 3 days ago

Fri, Oct 17 - Sun, Oct 19

OAK

Oakland Intl.

ORD

O'Hare Intl.

$205 Roundtrip, found 3 days ago

$205

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Fri, Oct 17 from Oakland Intl. to O'Hare Intl., returning Sun, Oct 19, priced at $205 found 3 days ago

Wed, Oct 15 - Fri, Oct 17

OAK

Oakland Intl.

ORD

O'Hare Intl.

$246 Roundtrip, found 3 days ago

$246

Roundtrip

found 3 days ago

Select Hawaiian Airlines flight, departing Wed, Oct 15 from Oakland Intl. to O'Hare Intl., returning Fri, Oct 17, priced at $246 found 3 days ago

Thu, Oct 16 - Fri, Oct 17

OAK

Oakland Intl.

ORD

O'Hare Intl.

$256 Roundtrip, found 3 days ago

$256

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Thu, Oct 16 from Oakland Intl. to O'Hare Intl., returning Fri, Oct 17, priced at $256 found 3 days ago

Sun, Oct 19 - Tue, Oct 21

OAK

Oakland Intl.

ORD

O'Hare Intl.

$263 Roundtrip, found 3 days ago

$263

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Sun, Oct 19 from Oakland Intl. to O'Hare Intl., returning Tue, Oct 21, priced at $263 found 3 days ago

Mon, Oct 13 - Sat, Oct 18

OAK

Oakland Intl.

ORD

O'Hare Intl.

$285 Roundtrip, found 3 days ago

$285

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Mon, Oct 13 from Oakland Intl. to O'Hare Intl., returning Sat, Oct 18, priced at $285 found 3 days ago

Mon, Oct 13 - Thu, Oct 16

OAK

Oakland Intl.

ORD

O'Hare Intl.

$292 Roundtrip, found 3 days ago

$292

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Mon, Oct 13 from Oakland Intl. to O'Hare Intl., returning Thu, Oct 16, priced at $292 found 3 days ago

Thu, Oct 16 - Sun, Oct 19

OAK

Oakland Intl.

ORD

O'Hare Intl.

$298 Roundtrip, found 3 days ago

$298

Roundtrip

found 3 days ago

Select Alaska Airlines flight, departing Thu, Oct 16 from Oakland Intl. to O'Hare Intl., returning Sun, Oct 19, priced at $298 found 3 days ago

Mon, Oct 13 - Fri, Oct 17

OAK

Oakland Intl.

ORD

O'Hare Intl.

$301 Roundtrip, found 3 days ago

$301

Roundtrip

found 3 days ago

Select Hawaiian Airlines flight, departing Mon, Oct 13 from Oakland Intl. to O'Hare Intl., returning Fri, Oct 17, priced at $301 found 3 days ago

Thu, Oct 16 - Sun, Oct 19

OAK

Oakland Intl.

ORD

O'Hare Intl.

$312 Roundtrip, found 3 days ago

$312

Roundtrip

found 3 days ago

Select Alaska Airlines flight, departing Thu, Oct 16 from Oakland Intl. to O'Hare Intl., returning Sun, Oct 19, priced at $312 found 3 days ago

Thu, Oct 16 - Sun, Oct 19

OAK

Oakland Intl.

ORD

O'Hare Intl.

$348 Roundtrip, found 3 days ago

$348

Roundtrip

found 3 days ago

Select Alaska Airlines flight, departing Thu, Oct 16 from Oakland Intl. to O'Hare Intl., returning Sun, Oct 19, priced at $348 found 3 days ago

Thu, Oct 16 - Sun, Oct 19

OAK

Oakland Intl.

ORD

O'Hare Intl.

$351 Roundtrip, found 3 days ago

$351

Roundtrip

found 3 days ago

Select Alaska Airlines flight, departing Thu, Oct 16 from Oakland Intl. to O'Hare Intl., returning Sun, Oct 19, priced at $351 found 3 days ago

Thu, Oct 16 - Sun, Oct 19

OAK

Oakland Intl.

ORD

O'Hare Intl.

$354 Roundtrip, found 3 days ago

$354

Roundtrip

found 3 days ago

Select Alaska Airlines flight, departing Thu, Oct 16 from Oakland Intl. to O'Hare Intl., returning Sun, Oct 19, priced at $354 found 3 days ago

Thu, Oct 16 - Sun, Oct 19

OAK

Oakland Intl.

ORD

O'Hare Intl.

$356 Roundtrip, found 3 days ago

$356

Roundtrip

found 3 days ago

Select Alaska Airlines flight, departing Thu, Oct 16 from Oakland Intl. to O'Hare Intl., returning Sun, Oct 19, priced at $356 found 3 days ago

Thu, Oct 16 - Sun, Oct 19

OAK

Oakland Intl.

ORD

O'Hare Intl.

$368 Roundtrip, found 3 days ago

$368

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Thu, Oct 16 from Oakland Intl. to O'Hare Intl., returning Sun, Oct 19, priced at $368 found 3 days ago

Thu, Oct 16 - Sun, Oct 19

OAK

Oakland Intl.

ORD

O'Hare Intl.

$400 Roundtrip, found 3 days ago

$400

Roundtrip

found 3 days ago

Select Delta flight, departing Thu, Oct 16 from Oakland Intl. to O'Hare Intl., returning Sun, Oct 19, priced at $400 found 3 days ago

Thu, Oct 16 - Sun, Oct 19

OAK

Oakland Intl.

ORD

O'Hare Intl.

$404 Roundtrip, found 3 days ago

$404

Roundtrip

found 3 days ago

Select Alaska Airlines flight, departing Thu, Oct 16 from Oakland Intl. to O'Hare Intl., returning Sun, Oct 19, priced at $404 found 3 days ago

Thu, Oct 16 - Sun, Oct 19

OAK

Oakland Intl.

ORD

O'Hare Intl.

$407 Roundtrip, found 3 days ago

$407

Roundtrip

found 3 days ago

Select Alaska Airlines flight, departing Thu, Oct 16 from Oakland Intl. to O'Hare Intl., returning Sun, Oct 19, priced at $407 found 3 days ago

Thu, Oct 16 - Sun, Oct 19

OAK

Oakland Intl.

ORD

O'Hare Intl.

$416 Roundtrip, found 3 days ago

$416

Roundtrip

found 3 days ago

Select Alaska Airlines flight, departing Thu, Oct 16 from Oakland Intl. to O'Hare Intl., returning Sun, Oct 19, priced at $416 found 3 days ago