
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $150 (Cheapflightsfares) |
One-way from | $79 (United Airlines) |
Popular in | December |
Cheapest in | September |
Average price | $354 |
Good round-trip deal | $256 or less |
Good one-way deal | $125 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Tue 4/28
8:20 pm-10:59 pm
Nonstop4h 39m
San Diego
Sun 5/3
8:45 pm-5:06 am
1 stop6h 21m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Thu 4/23
7:59 pm-10:42 pm
Nonstop4h 43m
San Diego
Wed 4/29
10:51 am-11:59 pm
1 stop11h 08m
ChicagoLas Vegas
MDW - LAS
MDWLAS
Chicago Midway
Sat 5/9
6:25 pm-8:20 pm
Nonstop3h 55m
Las Vegas Harry Reid Intl
Tue 5/12
3:05 pm-8:40 pm
Nonstop3h 35m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Tue 5/19
8:46 am-11:25 am
Nonstop4h 39m
San Diego
Fri 5/22
4:41 pm-11:01 pm
Nonstop4h 20m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Fri 4/3
4:15 pm-11:20 pm
2 stops9h 05m
San Diego
Wed 4/8
4:25 pm-11:55 pm
1 stop5h 30m
ChicagoLas Vegas
MDW - LAS
MDWLAS
Chicago Midway
Wed 4/29
4:00 pm-8:00 pm
1 stop6h 00m
Las Vegas Harry Reid Intl
Sat 5/2
5:45 am-11:15 am
Nonstop3h 30m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Fri 5/1
8:50 am-11:30 am
Nonstop4h 40m
San Diego
Mon 5/4
7:35 pm-6:40 am
1 stop9h 05m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Fri 5/8
2:30 pm-8:02 pm
1 stop7h 32m
San Diego
Sun 5/10
7:00 am-1:12 pm
Nonstop4h 12m
ChicagoLos Angeles
MDW - LAX
MDWLAX
Chicago Midway
Sat 4/25
6:55 am-12:10 pm
1 stop7h 15m
Los Angeles Los Angeles
Sat 5/2
5:40 am-11:40 am
Nonstop4h 00m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Wed 4/15
10:30 am-5:45 pm
2 stops9h 15m
San Diego
Sun 4/19
10:40 pm-12:50 pm
1 stop12h 10m
Currently, April is the cheapest month in which you can book a flight from Chicago to California (average of $67). Flying from Chicago to California in March is currently the most expensive (average of $166). 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.
When flying from Chicago to California, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 20% versus a flight at noon.
Travelers seeking maximum savings on their Chicago to California flight should consider departing on Monday evenings when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from CHI to USCA are scheduled on a Friday (111 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (84 on average).
Food
Overall
Entertainment
Comfort
Crew
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Reviews
Walter,Aug 2025
OAK - SAN
Food
Overall
Entertainment
Comfort
Crew
Boarding
Reviews
Walter,Aug 2025
OAK - SAN
Food
Overall
Entertainment
Comfort
Crew
Boarding
Reviews
Walter,Aug 2025
OAK - SAN
Food
Overall
Entertainment
Comfort
Crew
Boarding
Reviews
Walter,Aug 2025
OAK - SAN
Food
Overall
Entertainment
Comfort
Crew
Boarding
Reviews
Walter,Aug 2025
OAK - SAN
Food
Overall
Entertainment
Comfort
Crew
Boarding
Reviews
Walter,Aug 2025
OAK - SAN
When you're looking to get out of Chicago for a few days or weeks, a California vacation could be just what you need. The state has some of the nation's best outdoor areas, including national parks, hiking trails and beaches, giving you the opportunity to enjoy that fantastic California weather. If you want to visit another big city like Chicago, Los Angeles and San Francisco are two of the best options, or you can check out one of California's charming smaller towns. There are plenty of daily direct flights from Chicago to California, and it only takes about four hours.
Which direct flight route between Chicago and California is cheapest?
There's no single route between Chicago and California that's consistently the cheapest, as it depends on the airline deals available. Since O'Hare International Airport and Los Angeles International Airport are the two options with the most flights available, that route sometimes has the cheapest routes. The best way to book your flight is to first figure out which part of California you want to visit and then look for deals to that area.
Most travelers visit California either to check out one of its cities or focus on one of its theme parks, such as Disneyland in Anaheim or Universal Studios in Los Angeles. If you go during the summer, make sure you spend an afternoon at one of the state's many beautiful beaches, which include Coronado in San Diego and El Matador in Malibu. Since California is known for having delicious fresh fruits and vegetables, you may also want to stop by a farmers market while you're there.
There's always plenty to do when you go on a California vacation. Use our smart search engine to find yourself the cheapest flights from Chicago to California.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$69 | Average$198 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$80 | Average$236 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$108 | Average$228 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$112 | Average$374 | FlexibilityNo cancel fee | On-time83% | |
| Cheapest$128 | Average$338 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$138 | Average$438 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$139 | Average$380 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$147 | Average$315 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$156 | Average$378 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$157 | Average$411 | FlexibilityNo cancel fee | On-time69% |