
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $242 (Kiwi.com) |
One-way from | $123 (Kiwi.com) |
Popular in | December |
Cheapest in | July |
Average price | $315 |
Good round-trip deal | $259 or less |
Good one-way deal | $141 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 3/11
9:05 pm-11:45 pm
Nonstop4h 40m
San Francisco
Wed 3/18
10:55 pm-9:20 am
1 stop8h 25m
ChicagoSan Francisco
ORD - SFO
ORDSFO
Chicago O'Hare Intl
Wed 2/25
6:25 am-9:27 am
Nonstop5h 02m
San Francisco
Mon 3/2
11:59 pm-6:19 am
Nonstop4h 20m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Sun 3/1
7:55 am-10:55 am
Nonstop5h 00m
San Francisco
Tue 3/10
5:40 am-11:40 am
Nonstop4h 00m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 4/15
9:00 pm-11:35 pm
Nonstop4h 35m
San Francisco
Fri 4/17
5:15 am-11:25 am
Nonstop4h 10m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 3/4
1:29 pm-6:36 pm
1 stop7h 07m
San Francisco
Mon 3/9
9:35 pm-9:56 am
1 stop10h 21m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Thu 4/30
1:23 pm-7:03 pm
1 stop7h 40m
San Francisco
Tue 5/5
12:06 pm-10:28 pm
1 stop8h 22m
ChicagoSan Francisco
ORD - SFO
ORDSFO
Chicago O'Hare Intl
Sun 3/1
5:37 pm-11:25 pm
1 stop7h 48m
San Francisco
Tue 3/3
10:00 pm-8:41 am
1 stop8h 41m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Sat 4/18
6:00 am-10:25 am
1 stop6h 25m
San Francisco
Tue 4/28
2:50 pm-11:20 pm
1 stop6h 30m
ChicagoSan Francisco
ORD - SFO
ORDSFO
Chicago O'Hare Intl
Tue 3/17
7:00 am-3:48 pm
1 stop10h 48m
San Francisco
Thu 3/19
6:35 am-7:02 pm
1 stop10h 27m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 3/4
8:10 am-1:45 pm
1 stop7h 35m
San Francisco
Sun 3/8
5:05 am-11:05 am
Nonstop4h 00m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | 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, October is the cheapest month in which you can book a flight from Chicago to San Francisco (average of $80). Flying from Chicago to San Francisco 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.
It’s optimal to fly from Chicago to San Francisco in the evening. By choosing this option you can save up to 19% 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 Tuesday afternoons when fares are most often at their lowest. Sunday afternoons 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 Friday (55 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (32 on average).
Denver (DEN) – chosen by Cheapflights users on 50% 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 Seattle (SEA) have the shortest average one-way travel time for 1-stop routes: 9h 08m.
Flights via Seattle (SEA) offer the fastest connection on this route, with an average layover time of 1h 40m.
About 21% of weekly flights between Chicago and San Francisco have experienced delays in the past year, with the average delay time being 172 minutes.
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Over the last year, United Airlines have had the lowest number of delays on this route, with just 19% of flights being delayed.
Entertainment
Comfort
Food
Overall
Boarding
Crew
Reviews
Anonymous,Jan 2026
STS - LAX
Entertainment
Comfort
Food
Overall
Boarding
Crew
Reviews
Anonymous,Jan 2026
STS - LAX
Entertainment
Comfort
Food
Overall
Boarding
Crew
Reviews
Anonymous,Jan 2026
STS - LAX
Entertainment
Comfort
Food
Overall
Boarding
Crew
Reviews
Anonymous,Jan 2026
STS - LAX
Entertainment
Comfort
Food
Overall
Boarding
Crew
Reviews
Anonymous,Jan 2026
STS - LAX
Entertainment
Comfort
Food
Overall
Boarding
Crew
Reviews
Anonymous,Jan 2026
STS - LAX
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$90 | Average$222 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$108 | Average$217 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$112 | Average$374 | FlexibilityNo cancel fee | On-time83% | |
| Cheapest$128 | Average$314 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$138 | Average$387 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$183 | Average$304 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$187 | Average$281 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$197 | Average$309 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$207 | Average$399 | FlexibilityNo cancel fee | On-time69% |