
Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $249 (Southwest) |
One-way from | $129 (Kiwi.com) |
Popular in | December |
Cheapest in | October |
Average price | $390 |
Good round-trip deal | $309 or less |
Good one-way deal | $249 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Sat 12/6
2:45 pm-8:20 pm
1 stop7h 35m
San Francisco
Sat 12/13
10:10 am-4:10 pm
Nonstop4h 00m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Sat 12/6
9:29 am-2:23 pm
1 stop6h 54m
San Francisco
Sat 12/13
6:00 am-3:44 pm
1 stop7h 44m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 12/17
1:50 pm-8:28 pm
1 stop8h 38m
San Francisco
Wed 1/7
11:46 am-10:09 pm
1 stop8h 23m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Mon 12/8
1:14 pm-10:31 pm
2 stops11h 17m
San Francisco
Sun 12/14
12:30 am-9:19 am
1 stop6h 49m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Thu 11/27
8:15 am-11:00 am
Nonstop4h 45m
San Francisco
Wed 12/3
6:10 am-12:15 pm
Nonstop4h 05m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 12/10
8:15 am-11:00 am
Nonstop4h 45m
San Francisco
Sat 12/13
5:30 am-4:30 pm
2 stops9h 00m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Tue 12/9
8:35 am-2:40 pm
2 stops8h 05m
San Francisco
Tue 12/16
10:35 am-8:55 pm
1 stop8h 20m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Mon 1/19
10:46 am-7:45 pm
1 stop10h 59m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Fri 1/16
8:15 am-11:15 am
Nonstop5h 00m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Sun 12/14
8:20 am-11:05 am
Nonstop4h 45m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars |
Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to San Francisco (average of $145). Flying from Chicago Midway Airport to San Francisco in November is currently the most expensive (average of $307). 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 typically best to fly out from Chicago Midway Airport to San Francisco in the morning. Doing so could potentially save you 23% on the flight price compared to flying at noon, which is usually more expensive.
About 21% of weekly flights between Chicago and San Francisco have experienced delays in the past year, with the average delay time being 137 minutes.
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
Saturday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.
Over the last year, Southwest have had the lowest number of delays on this route, with just 21% of flights being delayed.
Entertainment
Crew
Overall
Comfort
Boarding
Food
Reviews
Walter,Aug 2025
OAK - SAN
Entertainment
Crew
Overall
Comfort
Boarding
Food
Reviews
Walter,Aug 2025
OAK - SAN
Entertainment
Crew
Overall
Comfort
Boarding
Food
Reviews
Walter,Aug 2025
OAK - SAN
Entertainment
Crew
Overall
Comfort
Boarding
Food
Reviews
Walter,Aug 2025
OAK - SAN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$90 | Average$313 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$217 | Average$418 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$227 | Average$457 | FlexibilityNo cancel fee | On-time63% |