- Be in the knowGet alerts if flight prices drop or rise*
- Book smarterSave up to 30% on select hotels after you book a flight*
Plan, book, fly with confidence
Cheap Flights from Chicago to Windsor (CHI-OAK)
Prices were available within the past 7 days and start at $77 for one-way flights and $137 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Jun 25 - Wed, Sep 25
ORD
Chicago
OAK
Oakland
$137 Roundtrip, found 2 days ago
$137
Roundtrip
found 2 days ago
Tue, Jun 25 - Wed, Sep 25
ORD
Chicago
OAK
Oakland
$148 Roundtrip, found 2 days ago
$148
Roundtrip
found 2 days ago
Tue, Aug 27 - Tue, Sep 10
ORD
Chicago
OAK
Oakland
$154 Roundtrip, found 6 hours ago
$154
Roundtrip
found 6 hours ago
Wed, Aug 21 - Wed, Aug 28
ORD
Chicago
OAK
Oakland
$163 Roundtrip, found 10 hours ago
$163
Roundtrip
found 10 hours ago
Tue, Aug 27 - Tue, Sep 10
ORD
Chicago
OAK
Oakland
$165 Roundtrip, found 6 hours ago
$165
Roundtrip
found 6 hours ago
Tue, Oct 1 - Tue, Oct 15
ORD
Chicago
OAK
Oakland
$182 Roundtrip, found 11 hours ago
$182
Roundtrip
found 11 hours ago
*Available to One Key members.