Round-trip from | $198 (Booking.com) |
---|---|
One-way from | $62 (FlightHub) |
Popular in | April |
Cheapest in | September |
Average price | $324 |
Good round-trip deal | $417 or less |
Good one-way deal | $228 or less |
Fly from
Fly to
Route
Depart
Return
Price
OaklandChicago
OAK - ORD
OAKORD
Oakland
Thu 7/24
2:38 pm-6:03 am
2 stops13h 25m
Chicago O'Hare Intl
Tue 7/29
3:18 pm-11:33 pm
1 stop10h 15m
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Sun 8/10
5:50 am-11:55 am
Nonstop4h 05m
Chicago Midway
Sat 8/16
3:25 pm-5:55 pm
Nonstop4h 30m
OaklandChicago
OAK - ORD
OAKORD
Oakland
Thu 8/7
6:00 am-2:13 pm
1 stop6h 13m
Chicago O'Hare Intl
Sun 8/10
9:56 pm-12:27 pm
2 stops16h 31m
OaklandChicago
OAK - RFD
OAKRFD
Oakland
Thu 9/4
6:00 am-6:52 pm
1 stop10h 52m
Chicago Greater Rockford
Sun 9/7
9:16 pm-7:03 am
1 stop11h 47m
OaklandChicago
OAK - ORD
OAKORD
Oakland
Fri 8/22
7:07 pm-5:00 am
1 stop7h 53m
Chicago O'Hare Intl
Tue 8/26
8:00 am-1:36 pm
1 stop7h 36m
OaklandChicago
OAK - ORD
OAKORD
Oakland
Sun 7/27
6:05 am-4:45 pm
1 stop8h 40m
Chicago O'Hare Intl
Sat 8/9
6:15 am-12:25 pm
1 stop8h 10m
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Tue 9/30
5:05 pm-9:40 am
2 stops14h 35m
Chicago Midway
Sat 10/4
1:43 pm-10:48 pm
2 stops11h 05m
OaklandChicago
OAK - ORD
OAKORD
Oakland
Sat 8/9
6:00 am-2:13 pm
1 stop6h 13m
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Sun 8/31
8:15 am-2:20 pm
Nonstop4h 05m
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Fri 9/26
6:00 am-8:52 pm
1 stop12h 52m
The best time to book flights from Oakland, California to Chicago is 47 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Currently, August is the cheapest month in which you can book a flight from Oakland, California to Chicago (average of $245). Flying from Oakland, California to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
One of the essential ways to save on airfare from Oakland, California to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 44% on airfare.
Travelers seeking maximum savings on their Oakland, California to Chicago flight should consider departing on Saturday afternoons when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Comfort
Entertainment
Overall
Crew
Food
Boarding
Reviews
James,Apr 2025
LAX - SFO
Comfort
Entertainment
Overall
Crew
Food
Boarding
Reviews
James,Apr 2025
LAX - SFO
Comfort
Entertainment
Overall
Crew
Food
Boarding
Reviews
James,Apr 2025
LAX - SFO
Comfort
Entertainment
Overall
Crew
Food
Boarding
Reviews
James,Apr 2025
LAX - SFO
Comfort
Entertainment
Overall
Crew
Food
Boarding
Reviews
James,Apr 2025
LAX - SFO
Comfort
Entertainment
Overall
Crew
Food
Boarding
Reviews
James,Apr 2025
LAX - SFO
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$104 | Average$257 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$138 | Average$356 | FlexibilityNo cancel fee | On-time75% | |
Cheapest$163 | Average$279 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$236 | Average$360 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$263 | Average$413 | FlexibilityNo cancel fee | On-time63% |