
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $236 (Alaska Airlines) |
One-way from | $91 (Priceline) |
Popular in | December |
Cheapest in | July |
Average price | $449 |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoOakland
MDW - OAK
MDWOAK
Chicago Midway
Sat 1/17
7:40 pm-10:35 pm
Nonstop4h 55m
Oakland
Sat 1/24
5:55 am-12:00 pm
Nonstop4h 05m
ChicagoOakland
ORD - OAK
ORDOAK
Chicago O'Hare Intl
Sat 2/14
3:54 pm-10:49 pm
1 stop8h 55m
Oakland
Wed 2/18
6:15 am-4:33 pm
1 stop8h 18m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Sat 1/10
4:05 pm-8:35 pm
1 stop6h 30m
San Francisco
Sat 1/17
5:10 am-6:30 pm
2 stops11h 20m
ChicagoSan Francisco
ORD - SFO
ORDSFO
Chicago O'Hare Intl
Wed 3/11
3:54 pm-10:56 pm
1 stop9h 02m
San Francisco
Mon 3/16
8:42 am-11:56 pm
1 stop13h 14m
ChicagoSan Francisco
ORD - SFO
ORDSFO
Chicago O'Hare Intl
Thu 1/29
8:00 am-2:00 pm
1 stop8h 00m
San Francisco
Mon 2/2
7:40 pm-5:10 pm
1 stop19h 30m
ChicagoSan Francisco
ORD - SFO
ORDSFO
Chicago O'Hare Intl
Thu 1/29
3:35 pm-9:58 pm
1 stop8h 23m
San Francisco
Fri 1/30
9:00 am-11:50 pm
1 stop12h 50m
ChicagoSan Francisco
ORD - SFO
ORDSFO
Chicago O'Hare Intl
Mon 3/9
5:29 pm-11:59 pm
1 stop8h 30m
San Francisco
Mon 3/16
7:28 pm-2:11 pm
1 stop16h 43m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Wed 2/25
7:00 am-8:00 pm
1 stop15h 00m
San Jose
Thu 2/26
10:16 am-4:33 pm
1 stop28h 17m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Sat 1/31
8:00 am-2:42 pm
1 stop8h 42m
San Jose
Thu 2/5
6:15 am-5:10 pm
1 stop8h 55m
ChicagoSan Jose
ORD - SJC
ORDSJC
Chicago O'Hare Intl
Wed 1/21
8:00 am-2:42 pm
1 stop8h 42m
San Jose
Sat 1/24
11:00 am-11:50 pm
1 stop10h 50m
Currently, October is the cheapest month in which you can book a flight from Chicago to San Francisco Bay Area (average of $80). Flying from Chicago to San Francisco Bay Area in November is currently the most expensive (average of $207). 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.
A simple way to save on the total cost of your ticket is to fly from Chicago to San Francisco Bay Area at noon. If you’re flexible enough to do this you can expect to save up to 23% on your trip compared to booking a flight in the morning.
Travelers seeking maximum savings on their Chicago to San Francisco Bay Area flight should consider departing on Thursday mornings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from CHI to zzXIH are scheduled on a Saturday (72 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (39 on average).
Entertainment
Food
Crew
Overall
Comfort
Boarding
Reviews
Georgana,Dec 2025
ORD - PDX
Entertainment
Food
Crew
Overall
Comfort
Boarding
Reviews
Georgana,Dec 2025
ORD - PDX
Entertainment
Food
Crew
Overall
Comfort
Boarding
Reviews
Georgana,Dec 2025
ORD - PDX
Entertainment
Food
Crew
Overall
Comfort
Boarding
Reviews
Georgana,Dec 2025
ORD - PDX
Entertainment
Food
Crew
Overall
Comfort
Boarding
Reviews
Georgana,Dec 2025
ORD - PDX
Entertainment
Food
Crew
Overall
Comfort
Boarding
Reviews
Georgana,Dec 2025
ORD - PDX
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$80 | Average$224 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$83 | Average$212 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$108 | Average$382 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$112 | Average$375 | FlexibilityNo cancel fee | On-time83% | |
| Cheapest$138 | Average$437 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$159 | Average$350 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$183 | Average$427 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$187 | Average$316 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$197 | Average$571 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$203 | Average$429 | FlexibilityNo cancel fee | On-time69% |