Flights from Chicago to Windsor

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.

Tue, Jul 15 - Tue, Jul 22

ORD

O'Hare Intl.

OAK

Oakland Intl.

$175 Roundtrip, found 1 day ago

$175

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Jul 15 from O'Hare Intl. to Oakland Intl., returning Tue, Jul 22, priced at $175 found 1 day ago

Sat, Jul 12 - Tue, Jul 22

ORD

O'Hare Intl.

OAK

Oakland Intl.

$182 Roundtrip, found 1 day ago

$182

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, Jul 12 from O'Hare Intl. to Oakland Intl., returning Tue, Jul 22, priced at $182 found 1 day ago

Sat, Jul 12 - Sat, Jul 19

ORD

O'Hare Intl.

OAK

Oakland Intl.

$189 Roundtrip, found 1 day ago

$189

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, Jul 12 from O'Hare Intl. to Oakland Intl., returning Sat, Jul 19, priced at $189 found 1 day ago

Wed, Jul 9 - Wed, Jul 16

ORD

O'Hare Intl.

OAK

Oakland Intl.

$201 Roundtrip, found 1 day ago

$201

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Jul 9 from O'Hare Intl. to Oakland Intl., returning Wed, Jul 16, priced at $201 found 1 day ago

Tue, Jul 15 - Mon, Jul 21

ORD

O'Hare Intl.

OAK

Oakland Intl.

$208 Roundtrip, found 1 day ago

$208

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Jul 15 from O'Hare Intl. to Oakland Intl., returning Mon, Jul 21, priced at $208 found 1 day ago

Fri, Jul 11 - Wed, Jul 16

ORD

O'Hare Intl.

OAK

Oakland Intl.

$209 Roundtrip, found 1 day ago

$209

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Fri, Jul 11 from O'Hare Intl. to Oakland Intl., returning Wed, Jul 16, priced at $209 found 1 day ago

Sun, Jul 13 - Tue, Jul 22

ORD

O'Hare Intl.

OAK

Oakland Intl.

$213 Roundtrip, found 1 day ago

$213

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sun, Jul 13 from O'Hare Intl. to Oakland Intl., returning Tue, Jul 22, priced at $213 found 1 day ago

Wed, Jul 9 - Mon, Jul 14

ORD

O'Hare Intl.

OAK

Oakland Intl.

$215 Roundtrip, found 1 day ago

$215

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Jul 9 from O'Hare Intl. to Oakland Intl., returning Mon, Jul 14, priced at $215 found 1 day ago

Sun, Jul 13 - Sat, Jul 19

ORD

O'Hare Intl.

OAK

Oakland Intl.

$220 Roundtrip, found 1 day ago

$220

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sun, Jul 13 from O'Hare Intl. to Oakland Intl., returning Sat, Jul 19, priced at $220 found 1 day ago

Mon, Jul 7 - Wed, Jul 16

ORD

O'Hare Intl.

OAK

Oakland Intl.

$221 Roundtrip, found 1 day ago

$221

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Mon, Jul 7 from O'Hare Intl. to Oakland Intl., returning Wed, Jul 16, priced at $221 found 1 day ago

Fri, Jul 11 - Mon, Jul 14

ORD

O'Hare Intl.

OAK

Oakland Intl.

$223 Roundtrip, found 1 day ago

$223

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Fri, Jul 11 from O'Hare Intl. to Oakland Intl., returning Mon, Jul 14, priced at $223 found 1 day ago

Wed, Jul 9 - Sat, Jul 12

ORD

O'Hare Intl.

OAK

Oakland Intl.

$225 Roundtrip, found 1 day ago

$225

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Jul 9 from O'Hare Intl. to Oakland Intl., returning Sat, Jul 12, priced at $225 found 1 day ago

Fri, Jul 18 - Tue, Jul 22

ORD

O'Hare Intl.

OAK

Oakland Intl.

$227 Roundtrip, found 1 day ago

$227

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Fri, Jul 18 from O'Hare Intl. to Oakland Intl., returning Tue, Jul 22, priced at $227 found 1 day ago

Tue, Jul 8 - Mon, Jul 14

ORD

O'Hare Intl.

OAK

Oakland Intl.

$229 Roundtrip, found 1 day ago

$229

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Jul 8 from O'Hare Intl. to Oakland Intl., returning Mon, Jul 14, priced at $229 found 1 day ago

Fri, Jul 18 - Sat, Jul 19

ORD

O'Hare Intl.

OAK

Oakland Intl.

$234 Roundtrip, found 1 day ago

$234

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Fri, Jul 18 from O'Hare Intl. to Oakland Intl., returning Sat, Jul 19, priced at $234 found 1 day ago

Tue, Jul 1 - Fri, Jul 4

ORD

O'Hare Intl.

OAK

Oakland Intl.

$277 Roundtrip, found 1 day ago

$277

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Jul 1 from O'Hare Intl. to Oakland Intl., returning Fri, Jul 4, priced at $277 found 1 day ago

Tue, Oct 28 - Tue, Nov 4

ORD

O'Hare Intl.

STS

Sonoma County

$295 Roundtrip, found 1 day ago

$295

Roundtrip

found 1 day ago

Select Hawaiian Airlines flight, departing Tue, Oct 28 from O'Hare Intl. to Sonoma County, returning Tue, Nov 4, priced at $295 found 1 day ago

Tue, Oct 28 - Thu, Nov 6

ORD

O'Hare Intl.

STS

Sonoma County

$353 Roundtrip, found 1 day ago

$353

Roundtrip

found 1 day ago

Select Alaska Airlines flight, departing Tue, Oct 28 from O'Hare Intl. to Sonoma County, returning Thu, Nov 6, priced at $353 found 1 day ago

Fri, Oct 31 - Tue, Nov 4

ORD

O'Hare Intl.

STS

Sonoma County

$381 Roundtrip, found 1 day ago

$381

Roundtrip

found 1 day ago

Select American Airlines flight, departing Fri, Oct 31 from O'Hare Intl. to Sonoma County, returning Tue, Nov 4, priced at $381 found 1 day ago

Tue, Jul 1 - Sat, Jul 5

MDW

Midway Intl.

OAK

Oakland Intl.

$429 Roundtrip, found 1 day ago

$429

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Jul 1 from Midway Intl. to Oakland Intl., returning Sat, Jul 5, priced at $429 found 1 day ago