
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to San Francisco (SFO). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $287 (Cheapflightsfares) |
One-way from | $149 (Southwest) |
Popular in | June |
Cheapest in | September |
Average price | $431 |
Good round-trip deal | $360 or less |
Good one-way deal | $212 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoSan Francisco
MDW Chicago Midway - SFO San Francisco
MDWSFO
Chicago Midway
Wed 12/2
9:05 pm-11:55 pm
Nonstop4h 50m
San Francisco
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoSan Francisco
ORD Chicago O'Hare Intl - SFO San Francisco
ORDSFO
Chicago O'Hare Intl
Mon 2/15
4:45 pm-7:43 pm
Nonstop4h 58m
San Francisco
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoSan Francisco
MDW Chicago Midway - SFO San Francisco
MDWSFO
Chicago Midway
Mon 12/21
10:25 pm-1:20 am
Nonstop4h 55m
San Francisco
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoSan Francisco
MDW Chicago Midway - SFO San Francisco
MDWSFO
Chicago Midway
Thu 12/3
9:05 pm-11:55 pm
Nonstop4h 50m
San Francisco
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoSan Francisco
RFD Chicago Greater Rockford - SFO San Francisco
RFDSFO
Chicago Greater Rockford
Sun 12/6
12:47 pm-8:08 pm
2 stops33h 21m
San Francisco
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoSan Francisco
RFD Chicago Greater Rockford - SFO San Francisco
RFDSFO
Chicago Greater Rockford
Wed 12/2
4:01 pm-1:15 pm
1 stop23h 14m
San Francisco
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoSan Francisco
ORD Chicago O'Hare Intl - SFO San Francisco
ORDSFO
Chicago O'Hare Intl
Wed 12/23
10:00 pm-1:08 am
Nonstop5h 08m
San Francisco
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoSan Francisco
MDW Chicago Midway - SFO San Francisco
MDWSFO
Chicago Midway
Sat 1/16
10:47 am-5:24 pm
1 stop8h 37m
San Francisco
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoSan Francisco
MDW Chicago Midway - SFO San Francisco
MDWSFO
Chicago Midway
Wed 12/2
6:00 am-12:47 pm
1 stop8h 47m
San Francisco
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoSan Francisco
MDW Chicago Midway - SFO San Francisco
MDWSFO
Chicago Midway
Wed 11/25
5:13 pm-11:58 pm
1 stop8h 45m
San Francisco
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
Everything you need to know about your flight from Chicago to San Francisco
Overall
Boarding
Food
Crew
Comfort
Entertainment
Reviews
Sarah,Aug 2024
MDW - AUS
Overall
Boarding
Food
Crew
Comfort
Entertainment
Reviews
Sarah,Aug 2024
MDW - AUS
Overall
Boarding
Food
Crew
Comfort
Entertainment
Reviews
Sarah,Aug 2024
MDW - AUS
Overall
Boarding
Food
Crew
Comfort
Entertainment
Reviews
Sarah,Aug 2024
MDW - AUS
Overall
Boarding
Food
Crew
Comfort
Entertainment
Reviews
Sarah,Aug 2024
MDW - AUS
Overall
Boarding
Food
Crew
Comfort
Entertainment
Reviews
Sarah,Aug 2024
MDW - AUS
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.
Find useful and relevant information for your journey from Chicago to San Francisco. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$110 | Average$274 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$162 | Average$334 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$205 | Average$330 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$237 | Average$411 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$243 | Average$325 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$255 | Average$516 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$257 | Average$392 | FlexibilityNo cancel fee | On-time63% |