
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $241 (Southwest) |
One-way from | $125 (Expedia) |
Popular in | December |
Cheapest in | October |
Average price | $431 |
Good round-trip deal | $283 or less |
Good one-way deal | $158 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Sat 2/14
4:40 pm-9:55 pm
1 stop7h 15m
San Francisco
Tue 2/17
6:25 am-12:25 pm
Nonstop4h 00m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Sat 3/14
9:40 pm-12:20 am
Nonstop4h 40m
San Francisco
Sat 3/21
5:15 am-11:10 am
Nonstop3h 55m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 3/4
10:49 am-5:48 pm
1 stop8h 59m
San Francisco
Mon 3/9
9:35 pm-9:56 am
1 stop10h 21m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Mon 4/6
1:10 pm-7:07 pm
1 stop7h 57m
San Francisco
Wed 4/15
10:35 pm-9:56 am
1 stop9h 21m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 3/4
4:10 pm-9:50 pm
1 stop7h 40m
San Francisco
Wed 3/11
11:25 pm-5:30 am
Nonstop4h 05m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Sat 3/21
9:40 pm-12:20 am
Nonstop4h 40m
San Francisco
Mon 3/23
11:25 pm-5:30 am
Nonstop4h 05m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Wed 3/18
5:45 am-11:45 am
1 stop8h 00m
San Francisco
Wed 3/25
5:55 am-4:10 pm
2 stops8h 15m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Tue 3/31
7:05 am-1:50 pm
1 stop8h 45m
San Francisco
Mon 4/13
11:25 pm-5:40 am
Nonstop4h 15m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Thu 4/23
9:45 pm-12:20 am
Nonstop4h 35m
San Francisco
Wed 4/29
7:40 pm-4:35 am
1 stop6h 55m
ChicagoSan Francisco
MDW - SFO
MDWSFO
Chicago Midway
Sat 2/28
2:05 pm-10:05 pm
2 stops10h 00m
San Francisco
Sat 3/7
5:00 am-5:40 pm
2 stops10h 40m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | 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 $332). 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 evening. Doing so could potentially save you 29% on the flight price compared to flying at noon, which is usually more expensive.
Travelers seeking maximum savings on their Chicago Midway Airport 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.
About 25% of weekly flights between Chicago and San Francisco have experienced delays in the past year, with the average delay time being 132 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.
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 25% of flights being delayed.
Comfort
Food
Boarding
Crew
Overall
Entertainment
Reviews
Walter,Aug 2025
OAK - SAN
Comfort
Food
Boarding
Crew
Overall
Entertainment
Reviews
Walter,Aug 2025
OAK - SAN
Comfort
Food
Boarding
Crew
Overall
Entertainment
Reviews
Walter,Aug 2025
OAK - SAN
Comfort
Food
Boarding
Crew
Overall
Entertainment
Reviews
Walter,Aug 2025
OAK - SAN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$90 | Average$217 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$217 | Average$418 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$217 | Average$442 | FlexibilityNo cancel fee | On-time63% |