United's Polaris Lounges offer showers, daybeds, and dining for premium passengers.
Basic Economy on United allows a personal item but no carry-on bags.
Most accurate provider | FlightHub 3 stars |
---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $214 (Booking.com) |
One-way from | $105 (Frontier) |
Popular in | December |
Cheapest in | July |
Average price | $299 |
Good round-trip deal | $298 or less |
Good one-way deal | $165 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 12/3
12:05 pm-5:25 pm
1 stop7h 20m
San Francisco
Tue 12/9
6:10 am-12:15 pm
Nonstop4h 05m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Tue 11/11
10:47 am-6:14 pm
1 stop9h 27m
San Francisco
Wed 11/12
7:15 am-4:39 pm
1 stop7h 24m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 11/19
5:34 pm-12:13 am
1 stop8h 39m
San Francisco
Wed 12/3
10:45 pm-8:54 am
1 stop8h 09m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 11/12
6:00 am-12:30 pm
1 stop8h 30m
San Francisco
Wed 11/19
7:15 am-4:39 pm
1 stop7h 24m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 10/22
1:08 pm-5:51 pm
1 stop6h 43m
San Francisco
Tue 10/28
12:35 am-8:55 am
1 stop6h 20m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Tue 10/21
5:30 pm-11:05 pm
2 stops7h 35m
San Francisco
Tue 10/28
6:30 am-12:35 pm
Nonstop4h 05m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Thu 10/23
12:55 pm-3:25 pm
Nonstop4h 30m
San Francisco
Wed 10/29
1:05 pm-11:35 pm
1 stop8h 30m
ChicagoSan Francisco
ORD - SFO
ORDSFO
Chicago O'Hare Intl
Mon 10/20
7:59 pm-9:06 am
1 stop15h 07m
San Francisco
Wed 10/22
10:26 am-11:59 pm
1 stop11h 33m
ChicagoSan Francisco
ORD - SFO
ORDSFO
Chicago O'Hare Intl
Mon 10/27
7:10 am-9:55 am
Nonstop4h 45m
San Francisco
Mon 11/3
11:44 pm-6:02 am
Nonstop4h 18m
ChicagoSan Francisco
ORD - SFO
ORDSFO
Chicago O'Hare Intl
Mon 11/24
8:20 am-10:42 pm
1 stop16h 22m
San Francisco
Tue 12/2
7:00 am-11:50 pm
1 stop14h 50m
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 Accuracy- | Trust Score*3 stars | |
Price Accuracy2 stars | Trust Score*1 star | |
Price Accuracy3 stars | Trust Score*3 stars |
To ensure you get the cheapest price possible for a flight from Chicago to San Francisco, you should look to book at least 83 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Currently, January is the cheapest month in which you can book a flight from Chicago to San Francisco (average of $276). Flying from Chicago to San Francisco in June is currently the most expensive (average of $357). 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.
It’s optimal to fly from Chicago to San Francisco in the evening. By choosing this option you can save up to 21% on the cost of your flight, compared to a flight in the afternoon.
Travelers seeking maximum savings on their Chicago to San Francisco flight should consider departing on Wednesday evenings 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 SFO are scheduled on a Monday (96 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (52 on average).
Denver (DEN) – chosen by Cheapflights users on 75% of 1-stop itineraries from Chicago to San Francisco on Cheapflights.
Atlanta (ATL) is the most affordable 1-stop option, with an average round-trip price of $177.
Flights via Denver (DEN) have the shortest average one-way travel time for 1-stop routes: 7h 24m.
Flights via Seattle (SEA) offer the fastest connection on this route, with an average layover time of 1h 40m.
Crew
Overall
Comfort
Food
Boarding
Entertainment
Reviews
Hannah,Aug 2025
SFO - SAN
Crew
Overall
Comfort
Food
Boarding
Entertainment
Reviews
Hannah,Aug 2025
SFO - SAN
Crew
Overall
Comfort
Food
Boarding
Entertainment
Reviews
Hannah,Aug 2025
SFO - SAN
Crew
Overall
Comfort
Food
Boarding
Entertainment
Reviews
Hannah,Aug 2025
SFO - SAN
Crew
Overall
Comfort
Food
Boarding
Entertainment
Reviews
Hannah,Aug 2025
SFO - SAN
Crew
Overall
Comfort
Food
Boarding
Entertainment
Reviews
Hannah,Aug 2025
SFO - SAN
Dozens of flights are waiting to carry you from the freeways and skyscrapers of Chicago to the fishing piers and historic neighborhoods of San Francisco. A major metropolis along the California coastline, the Bay Area is famous for its maritime atmosphere and architectural marvels such as the Ferry Building Marketplace and the Legion of Honor. Browse direct flights between these two major travel hubs to find a cheap flight to match your travel schedule.
The moment you leave the Windy City behind and step onto the hilly streets San Francisco, the historic Bay Area instantly transports you to a world of cable cars and charming wharfs. Trade the trains of Chicago for the ferries and whale-watching bay cruises of this California city, and enjoy milder winter months with temperatures hovering in the 60's F. Before saying goodbye to the Golden Gate Bridge, don't forget to tour Alcatraz Island and enjoy the catch of the day at one of the bay-side seafood shacks.
The Golden Gate Bridge is just a short flight away, so what's stopping you? Try out our smart search engine to find great flight deals and start planning your San Francisco adventure.
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$108 | Average$217 | FlexibilityNo cancel fee | On-time85% | |
Cheapest$112 | Average$335 | FlexibilityNo cancel fee | On-time83% | |
Cheapest$123 | Average$272 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$128 | Average$320 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$180 | Average$380 | FlexibilityNo cancel fee | On-time63% | |
Cheapest$188 | Average$285 | FlexibilityNo cancel fee | On-time75% | |
Cheapest$197 | Average$304 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$200 | Average$392 | FlexibilityNo cancel fee | On-time69% |