For early flights, BART offers a cost-efficient and fast connection from Oakland to San Francisco, avoiding potential bridge traffic delays.

Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $238 (KAYAK) |
One-way from | $120 (Southwest) |
Popular in | November |
Cheapest in | February |
Average price | $550 |
Good round-trip deal | $483 or less |
Good one-way deal | $203 or less |
Fly from
Fly to
Route
Depart
Return
Price
OaklandChicago
OAK - MDW
OAKMDW
Oakland
vie. 1/23
11:10 am-5:15 pm
Nonstop4h 05m
Chicago Midway
mar. 1/27
2:10 pm-7:50 pm
1 stop7h 40m
OaklandChicago
OAK - ORD
OAKORD
Oakland
mié. 12/3
2:31 pm-11:59 pm
1 stop7h 28m
Chicago O'Hare Intl
mar. 12/9
5:51 pm-11:59 pm
1 stop8h 08m
OaklandChicago
OAK - ORD
OAKORD
Oakland
sáb. 12/6
6:40 am-4:55 pm
1 stop8h 15m
Chicago O'Hare Intl
mar. 12/9
5:51 pm-11:59 pm
1 stop8h 08m
OaklandChicago
OAK - MDW
OAKMDW
Oakland
lun. 12/15
2:50 pm-10:55 pm
1 stop6h 05m
Chicago Midway
mar. 12/16
5:15 pm-9:45 pm
1 stop6h 30m
OaklandChicago
OAK - ORD
OAKORD
Oakland
mié. 12/3
5:55 am-4:57 pm
2 stops9h 02m
Chicago O'Hare Intl
lun. 12/8
7:40 pm-12:08 am
1 stop6h 28m
OaklandChicago
OAK - ORD
OAKORD
Oakland
mar. 12/9
4:50 pm-8:39 am
2 stops13h 49m
Chicago O'Hare Intl
sáb. 12/13
5:29 pm-10:00 pm
1 stop6h 31m
OaklandChicago
OAK - ORD
OAKORD
Oakland
mar. 12/9
5:55 am-4:57 pm
2 stops9h 02m
Chicago O'Hare Intl
dom. 12/14
7:20 am-11:50 am
1 stop6h 30m
OaklandChicago
OAK - MDW
OAKMDW
Oakland
mié. 12/3
5:55 am-6:18 pm
2 stops10h 23m
Chicago Midway
mar. 12/9
1:14 pm-12:08 am
2 stops12h 54m
OaklandChicago
OAK - MDW
OAKMDW
Oakland
mié. 12/3
5:55 am-6:18 pm
2 stops10h 23m
Chicago Midway
lun. 12/8
1:14 pm-12:08 am
2 stops12h 54m
OaklandChicago
OAK - MDW
OAKMDW
Oakland
sáb. 12/6
5:55 am-6:18 pm
2 stops10h 23m
Chicago Midway
lun. 12/8
1:14 pm-12:08 am
2 stops12h 54m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
The best time to book flights from Oakland, California to Chicago is 23 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, December is the cheapest month in which you can book a flight from Oakland, California to Chicago (average of $110). Flying from Oakland, California to Chicago in March is currently the most expensive (average of $194). 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 32% on airfare.
Travelers seeking maximum savings on their Oakland, California to Chicago flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Boarding
Overall
Comfort
Crew
Food
Entertainment
Reviews
Hannah,Aug 2025
SFO - SAN
Boarding
Overall
Comfort
Crew
Food
Entertainment
Reviews
Hannah,Aug 2025
SFO - SAN
Boarding
Overall
Comfort
Crew
Food
Entertainment
Reviews
Hannah,Aug 2025
SFO - SAN
Boarding
Overall
Comfort
Crew
Food
Entertainment
Reviews
Hannah,Aug 2025
SFO - SAN
Boarding
Overall
Comfort
Crew
Food
Entertainment
Reviews
Hannah,Aug 2025
SFO - SAN
Boarding
Overall
Comfort
Crew
Food
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$359 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$189 | Average$356 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$246 | Average$427 | FlexibilityNo cancel fee | On-time63% |