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 | $227 (Southwest) |
One-way from | $109 (Southwest) |
Popular in | December |
Cheapest in | February |
Average price | $624 |
Good round-trip deal | $386 or less |
Good one-way deal | $179 or less |
Fly from
Fly to
Route
Depart
Return
Price
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Tue 1/20
11:10 am-5:15 pm
Nonstop4h 05m
Chicago Midway
Sat 1/24
7:40 pm-10:35 pm
Nonstop4h 55m
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Sat 2/14
6:40 am-12:45 pm
Nonstop4h 05m
Chicago Midway
Tue 2/17
7:55 am-12:35 pm
1 stop6h 40m
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Sat 1/10
5:55 am-12:00 pm
Nonstop4h 05m
Chicago Midway
Sat 1/17
8:35 am-2:25 pm
1 stop7h 50m
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Tue 2/3
11:10 am-5:15 pm
Nonstop4h 05m
Chicago Midway
Wed 2/11
5:35 pm-10:15 pm
1 stop6h 40m
OaklandChicago
OAK - ORD
OAKORD
Oakland
Tue 1/13
11:43 am-11:50 pm
1 stop10h 07m
Chicago O'Hare Intl
Tue 1/20
2:06 pm-9:46 am
1 stop21h 40m
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Tue 1/20
11:10 am-5:15 pm
Nonstop4h 05m
Chicago Midway
Fri 1/23
2:10 pm-9:45 pm
1 stop9h 35m
OaklandChicago
OAK - ORD
OAKORD
Oakland
Tue 1/20
8:10 am-11:50 pm
1 stop13h 40m
Chicago O'Hare Intl
Fri 1/23
8:00 am-8:40 pm
1 stop14h 40m
OaklandChicago
OAK - ORD
OAKORD
Oakland
Wed 1/28
5:55 am-1:38 pm
1 stop5h 43m
Chicago O'Hare Intl
Tue 2/3
6:40 pm-11:53 pm
1 stop7h 13m
OaklandChicago
OAK - ORD
OAKORD
Oakland
Tue 1/20
8:10 am-11:50 pm
1 stop13h 40m
Chicago O'Hare Intl
Sat 1/24
8:00 am-9:46 am
2 stops27h 46m
OaklandChicago
OAK - ORD
OAKORD
Oakland
Sat 2/14
5:31 pm-2:05 pm
1 stop18h 34m
Chicago O'Hare Intl
Wed 2/18
3:54 pm-9:24 am
2 stops19h 30m
| 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 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 $107). Flying from Oakland, California to Chicago in November is currently the most expensive (average of $210). 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 42% 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.
Crew
Food
Overall
Comfort
Boarding
Entertainment
Reviews
Art,Dec 2025
SAN - OGG
Crew
Food
Overall
Comfort
Boarding
Entertainment
Reviews
Art,Dec 2025
SAN - OGG
Crew
Food
Overall
Comfort
Boarding
Entertainment
Reviews
Art,Dec 2025
SAN - OGG
Crew
Food
Overall
Comfort
Boarding
Entertainment
Reviews
Art,Dec 2025
SAN - OGG
Crew
Food
Overall
Comfort
Boarding
Entertainment
Reviews
Art,Dec 2025
SAN - OGG
Crew
Food
Overall
Comfort
Boarding
Entertainment
Reviews
Art,Dec 2025
SAN - OGG
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$222 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$163 | Average$329 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$189 | Average$527 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$246 | Average$419 | FlexibilityNo cancel fee | On-time63% |