Take off on cheap flights from Oakland to Chicago, your adventure starts now!

Find cheap airline tickets from Oakland to Chicago by date

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  • month of departure
  • month of return
$225
Spirit Airlines outward: Sep 29, 2022
2:30p OAK » 3:43a ORD
Spirit Airlines 1 stop (13h13m)
Spirit Airlines inbound: Oct 4, 2022
4:38a ORD » 4:30p OAK
Spirit Airlines 1 stop (11h52m)
$225
Spirit Airlines outward: Sep 29, 2022
2:30p OAK » 3:43a ORD
Spirit Airlines 1 stop (13h13m)
Spirit Airlines inbound: Oct 4, 2022
4:38a ORD » 4:30p OAK
Spirit Airlines 1 stop (11h52m)
$334
Unknown Company outward: Jul 3, 2022
11:22p OAK » 1:03p MDW
Unknown Company 1 stop (13h41m)
Frontier Airlines inbound: Jul 9, 2022
2:22a MDW » 4:36p OAK
Frontier Airlines 1 stop (14h14m)
$358
Unknown Company outward: Jul 3, 2022
6:10a OAK » 1:03p MDW
Unknown Company 1 stop (6h53m)
Frontier Airlines inbound: Jul 9, 2022
2:22a MDW » 4:36p OAK
Frontier Airlines 1 stop (14h14m)
$413
Unknown Company outward: Jul 2, 2022
7:10a OAK » 1:03p MDW
Unknown Company 1 stop (29h53m)
Unknown Company inbound: Jul 10, 2022
2:22a MDW » 4:56p OAK
Unknown Company 1 stop (14h34m)
$425
Unknown Company outward: Jul 2, 2022
7:10a OAK » 1:03p MDW
Unknown Company 1 stop (29h53m)
Unknown Company inbound: Jul 17, 2022
2:22a MDW » 4:56p OAK
Unknown Company 1 stop (14h34m)
$517
Unknown Company outward: Jul 2, 2022
1:13a OAK » 2:50p MDW
Unknown Company 1 stop (13h37m)
Unknown Company inbound: Jul 17, 2022
4:29a ORD » 4:56p OAK
Unknown Company 1 stop (12h27m)
$582
Spirit Airlines outward: Jul 2, 2022
7:10a OAK » 6:58a ORD
Spirit Airlines 1 stop (23h48m)
Spirit Airlines inbound: Jul 17, 2022
4:30a ORD » 9:05a OAK
Spirit Airlines direct (4h35m)
Return
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Airlines operating flights from Oakland to Chicago

  • any
  • June 2022
  • July 2022
  • August 2022
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  • all
  • Spirit Airlines
Spirit Airlines
outbound: Sep 29, 2022
Spirit Airlines 1 stop
return: Oct 3, 2022
Spirit Airlines 1 stop

Travel tips for flights Oakland - Chicago

Average flight duration: 16h23m (flight with stopovers)

  • Arrival city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Jun 30, 2022 11:56 AM, GMT-5
  • Weather:
  • min. 68ºF, max. 82ºF
  • Departure city:
  • Oakland, USA
  • Airport(s):
  • Oakland International Airport (OAK)
  • Local time:
  • Jun 30, 2022 9:56 AM, GMT-7
  • Weather:
  • min. 54ºF, max. 67ºF