For early flights, BART offers a cost-efficient and fast connection from Oakland to San Francisco, avoiding potential bridge traffic delays.
Most accurate provider | FlightHub 3 stars |
---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $298 (Southwest) |
One-way from | $111 (SmartFares) |
Popular in | November |
Cheapest in | February |
Average price | $381 |
Good round-trip deal | $382 or less |
Good one-way deal | $239 or less |
Fly from
Fly to
Route
Depart
Return
Price
OaklandChicago
OAK - ORD
OAKORD
Oakland
Sat 11/22
7:59 pm-5:01 am
1 stop7h 02m
Chicago O'Hare Intl
Wed 12/3
8:00 am-10:41 am
1 stop28h 41m
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Fri 10/24
11:35 am-8:25 pm
1 stop6h 50m
Chicago Midway
Wed 10/29
9:20 am-3:15 pm
2 stops7h 55m
OaklandChicago
OAK - ORD
OAKORD
Oakland
Fri 10/24
10:10 am-9:30 pm
1 stop9h 20m
Chicago O'Hare Intl
Wed 10/29
7:00 am-2:30 pm
2 stops9h 30m
OaklandChicago
OAK - ORD
OAKORD
Oakland
Mon 2/23
6:45 pm-1:04 pm
1 stop16h 19m
Chicago O'Hare Intl
Sat 2/28
2:00 pm-11:38 pm
1 stop11h 38m
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Thu 11/6
12:25 pm-9:10 pm
1 stop6h 45m
Chicago Midway
Sun 11/9
6:05 am-11:15 am
1 stop7h 10m
OaklandChicago
OAK - ORD
OAKORD
Oakland
Wed 11/26
5:15 am-2:45 pm
1 stop7h 30m
Chicago O'Hare Intl
Tue 12/2
7:15 am-1:00 pm
1 stop7h 45m
OaklandChicago
OAK - ORD
OAKORD
Oakland
Mon 10/27
12:45 pm-10:20 pm
2 stops7h 35m
Chicago O'Hare Intl
Mon 11/3
2:15 pm-8:35 pm
1 stop8h 20m
OaklandChicago
OAK - ORD
OAKORD
Oakland
Tue 11/4
9:48 am-9:40 pm
2 stops9h 52m
Chicago O'Hare Intl
Thu 11/6
3:25 pm-11:59 pm
1 stop10h 34m
OaklandChicago
OAK - ORD
OAKORD
Oakland
Sat 11/1
5:55 am-1:56 pm
1 stop6h 01m
Chicago O'Hare Intl
Fri 11/7
7:36 pm-11:53 pm
1 stop6h 17m
OaklandChicago
OAK - ORD
OAKORD
Oakland
Fri 11/28
5:55 am-1:44 pm
1 stop5h 49m
Chicago O'Hare Intl
Wed 12/3
7:40 pm-12:08 am
1 stop6h 28m
Provider | Price Accuracy | Trust Score* |
---|---|---|
Price Accuracy2 stars | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*3 stars | |
Price Accuracy2 stars | Trust Score*1 star | |
Price Accuracy1 star | Trust Score*3 stars |
The best time to book flights from Oakland, California to Chicago is 19 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 at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 38% 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
Food
Overall
Crew
Boarding
Entertainment
Reviews
Hannah,Aug 2025
SFO - SAN
Comfort
Food
Overall
Crew
Boarding
Entertainment
Reviews
Hannah,Aug 2025
SFO - SAN
Comfort
Food
Overall
Crew
Boarding
Entertainment
Reviews
Hannah,Aug 2025
SFO - SAN
Comfort
Food
Overall
Crew
Boarding
Entertainment
Reviews
Hannah,Aug 2025
SFO - SAN
Comfort
Food
Overall
Crew
Boarding
Entertainment
Reviews
Hannah,Aug 2025
SFO - SAN
Comfort
Food
Overall
Crew
Boarding
Entertainment
Reviews
Hannah,Aug 2025
SFO - SAN
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$108 | Average$220 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$163 | Average$287 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$189 | Average$356 | FlexibilityNo cancel fee | On-time75% | |
Cheapest$242 | Average$417 | FlexibilityNo cancel fee | On-time63% |