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

Find cheap airline tickets from Chicago to Oakland by date

  • any
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • October 2020
  • November 2020
  • any
  • December 2019
  • January 2020
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  • price
  • month of departure
  • month of return
$275
Frontier Airlines outward: Apr 22, 2020
1:05p ORD » 9:57p SFO
Frontier Airlines 1 stop (8h52m)
Alaska Airlines inbound: Apr 28, 2020
5:10a SJC » 12:45a ORD
Alaska Airlines 1 stop (19h35m)
$275
Frontier Airlines outward: Apr 22, 2020
1:05p ORD » 9:57p SFO
Frontier Airlines 1 stop (8h52m)
Alaska Airlines inbound: Apr 28, 2020
5:10a SJC » 12:45a ORD
Alaska Airlines 1 stop (19h35m)
$280
American Airlines outward: Dec 13, 2019
10:14p ORD » 3:02a SFO
American Airlines direct (4h48m)
United Airlines inbound: Jan 6, 2020
8:10a SFO » 12:08p ORD
United Airlines direct (3h58m)
$308
American Airlines outward: Dec 13, 2019
10:14p ORD » 3:02a SFO
American Airlines direct (4h48m)
United Airlines inbound: Jan 5, 2020
8:59a SFO » 1:00p ORD
United Airlines direct (4h01m)
Return
Departure
Find the cheapest Chicago Oakland flight by browsing the dates below to find alternative flight prices found in the last days. To launch a flight search for Chicago - Oakland with these new dates, click on an offer. Want to depart from another city? Choose:

Airlines operating flights from Chicago to Oakland

  • any
  • December 2019
  • January 2020
  • February 2020
  • March 2020
  • April 2020
  • May 2020
  • June 2020
  • July 2020
  • August 2020
  • September 2020
  • October 2020
  • November 2020
  • all
  • Spirit Airlines
Spirit Airlines
outbound: Jan 24, 2020
Spirit Airlines 1 stop
return: Jan 27, 2020
Spirit Airlines 1 stop

Travel tips for flights Chicago - Oakland

Average flight duration: 4h23m (direct flight)

  • Arrival city:
  • Oakland, USA
  • Airport(s):
  • Oakland International Airport (OAK)
  • Local time:
  • Dec 5, 2019 6:42 PM, GMT-8
  • Weather:
  • min. 50ºF, max. 60ºF
  • Departure city:
  • Chicago, USA
  • Airport(s):
  • Midway International Airport (MDW)
  • O'Hare International Airport (ORD)
  • Local time:
  • Dec 5, 2019 8:42 PM, GMT-6
  • Weather:
  • min. 33ºF, max. 39ºF