Flights from Chicago to Kenwood

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.

Wed, Sep 3 - Tue, Sep 9

ORD

O'Hare Intl.

OAK

Oakland Intl.

$185 Roundtrip, found 5 days ago

$185

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Wed, Sep 3 from O'Hare Intl. to Oakland Intl., returning Tue, Sep 9, priced at $185 found 5 days ago

Thu, Sep 4 - Mon, Sep 8

ORD

O'Hare Intl.

OAK

Oakland Intl.

$186 Roundtrip, found 5 days ago

$186

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Thu, Sep 4 from O'Hare Intl. to Oakland Intl., returning Mon, Sep 8, priced at $186 found 5 days ago

Tue, Sep 2 - Tue, Sep 9

ORD

O'Hare Intl.

OAK

Oakland Intl.

$192 Roundtrip, found 5 days ago

$192

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Tue, Sep 2 from O'Hare Intl. to Oakland Intl., returning Tue, Sep 9, priced at $192 found 5 days ago

Thu, Sep 4 - Mon, Sep 8

ORD

O'Hare Intl.

OAK

Oakland Intl.

$197 Roundtrip, found 5 days ago

$197

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Thu, Sep 4 from O'Hare Intl. to Oakland Intl., returning Mon, Sep 8, priced at $197 found 5 days ago

Tue, Sep 2 - Fri, Sep 5

ORD

O'Hare Intl.

OAK

Oakland Intl.

$199 Roundtrip, found 5 days ago

$199

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Tue, Sep 2 from O'Hare Intl. to Oakland Intl., returning Fri, Sep 5, priced at $199 found 5 days ago

Thu, Sep 4 - Mon, Sep 8

ORD

O'Hare Intl.

OAK

Oakland Intl.

$204 Roundtrip, found 5 days ago

$204

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Thu, Sep 4 from O'Hare Intl. to Oakland Intl., returning Mon, Sep 8, priced at $204 found 5 days ago

Fri, Sep 5 - Sat, Sep 6

ORD

O'Hare Intl.

OAK

Oakland Intl.

$204 Roundtrip, found 5 days ago

$204

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Fri, Sep 5 from O'Hare Intl. to Oakland Intl., returning Sat, Sep 6, priced at $204 found 5 days ago

Thu, Sep 4 - Mon, Sep 8

ORD

O'Hare Intl.

OAK

Oakland Intl.

$214 Roundtrip, found 5 days ago

$214

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Thu, Sep 4 from O'Hare Intl. to Oakland Intl., returning Mon, Sep 8, priced at $214 found 5 days ago

Thu, Sep 4 - Mon, Sep 8

ORD

O'Hare Intl.

OAK

Oakland Intl.

$220 Roundtrip, found 5 days ago

$220

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Thu, Sep 4 from O'Hare Intl. to Oakland Intl., returning Mon, Sep 8, priced at $220 found 5 days ago

Thu, Sep 4 - Mon, Sep 8

ORD

O'Hare Intl.

OAK

Oakland Intl.

$225 Roundtrip, found 5 days ago

$225

Roundtrip

found 5 days ago

Select Delta flight, departing Thu, Sep 4 from O'Hare Intl. to Oakland Intl., returning Mon, Sep 8, priced at $225 found 5 days ago

Thu, Sep 4 - Mon, Sep 8

ORD

O'Hare Intl.

OAK

Oakland Intl.

$227 Roundtrip, found 5 days ago

$227

Roundtrip

found 5 days ago

Select Alaska Airlines flight, departing Thu, Sep 4 from O'Hare Intl. to Oakland Intl., returning Mon, Sep 8, priced at $227 found 5 days ago

Thu, Sep 4 - Mon, Sep 8

ORD

O'Hare Intl.

OAK

Oakland Intl.

$232 Roundtrip, found 5 days ago

$232

Roundtrip

found 5 days ago

Select Alaska Airlines flight, departing Thu, Sep 4 from O'Hare Intl. to Oakland Intl., returning Mon, Sep 8, priced at $232 found 5 days ago

Thu, Sep 4 - Mon, Sep 8

ORD

O'Hare Intl.

OAK

Oakland Intl.

$235 Roundtrip, found 5 days ago

$235

Roundtrip

found 5 days ago

Select Alaska Airlines flight, departing Thu, Sep 4 from O'Hare Intl. to Oakland Intl., returning Mon, Sep 8, priced at $235 found 5 days ago

Thu, Sep 4 - Mon, Sep 8

ORD

O'Hare Intl.

OAK

Oakland Intl.

$239 Roundtrip, found 5 days ago

$239

Roundtrip

found 5 days ago

Select Delta flight, departing Thu, Sep 4 from O'Hare Intl. to Oakland Intl., returning Mon, Sep 8, priced at $239 found 5 days ago

Sat, Aug 2 - Sat, Aug 9

ORD

O'Hare Intl.

OAK

Oakland Intl.

$239 Roundtrip, found 1 day ago

$239

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, Aug 2 from O'Hare Intl. to Oakland Intl., returning Sat, Aug 9, priced at $239 found 1 day ago

Thu, Sep 4 - Mon, Sep 8

ORD

O'Hare Intl.

OAK

Oakland Intl.

$242 Roundtrip, found 5 days ago

$242

Roundtrip

found 5 days ago

Select Alaska Airlines flight, departing Thu, Sep 4 from O'Hare Intl. to Oakland Intl., returning Mon, Sep 8, priced at $242 found 5 days ago

Thu, Sep 4 - Mon, Sep 8

ORD

O'Hare Intl.

OAK

Oakland Intl.

$247 Roundtrip, found 5 days ago

$247

Roundtrip

found 5 days ago

Select Alaska Airlines flight, departing Thu, Sep 4 from O'Hare Intl. to Oakland Intl., returning Mon, Sep 8, priced at $247 found 5 days ago

Sat, Aug 2 - Sat, Aug 9

ORD

O'Hare Intl.

OAK

Oakland Intl.

$253 Roundtrip, found 1 day ago

$253

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, Aug 2 from O'Hare Intl. to Oakland Intl., returning Sat, Aug 9, priced at $253 found 1 day ago

Mon, Sep 1 - Tue, Sep 9

ORD

O'Hare Intl.

OAK

Oakland Intl.

$254 Roundtrip, found 5 days ago

$254

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Mon, Sep 1 from O'Hare Intl. to Oakland Intl., returning Tue, Sep 9, priced at $254 found 5 days ago

Thu, Sep 4 - Mon, Sep 8

ORD

O'Hare Intl.

OAK

Oakland Intl.

$261 Roundtrip, found 5 days ago

$261

Roundtrip

found 5 days ago

Select Alaska Airlines flight, departing Thu, Sep 4 from O'Hare Intl. to Oakland Intl., returning Mon, Sep 8, priced at $261 found 5 days ago