
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $289 (Cheapflightsfares) |
One-way from | $133 (Trip.com) |
Popular in | March |
Cheapest in | September |
Average price | $437 |
Good round-trip deal | $385 or less |
Good one-way deal | $205 or less |
Fly from
Fly to
Route
Depart
Return
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Sat 7/11
4:21 pm-10:59 pm
Nonstop4h 38m
Chicago O'Hare Intl
Tue 7/14
9:35 pm-12:32 am
Nonstop4h 57m
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Mon 6/8
7:45 pm-4:40 am
1 stop6h 55m
Chicago Midway
Tue 6/16
6:55 pm-11:25 pm
1 stop6h 30m
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Mon 6/1
5:05 am-11:29 am
Nonstop4h 24m
Chicago O'Hare Intl
Fri 6/5
4:30 pm-7:24 pm
Nonstop4h 54m
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Wed 6/3
2:50 pm-11:20 pm
1 stop6h 30m
Chicago Midway
Sat 6/6
8:50 pm-11:30 pm
Nonstop4h 40m
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Tue 7/7
2:27 pm-9:01 pm
Nonstop4h 34m
Chicago O'Hare Intl
Sun 7/12
6:10 am-8:47 am
Nonstop4h 37m
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Wed 6/17
11:30 pm-5:53 am
Nonstop4h 23m
Chicago O'Hare Intl
Mon 6/22
10:30 am-1:14 pm
Nonstop4h 44m
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Mon 6/29
2:15 pm-12:10 am
2 stops7h 55m
Chicago Midway
Wed 7/8
5:05 am-9:45 am
1 stop6h 40m
San FranciscoChicago
SFO - RFD
SFORFD
San Francisco
Wed 7/22
10:56 pm-12:24 pm
1 stop11h 28m
Chicago Greater Rockford
Mon 7/27
9:13 pm-4:06 pm
1 stop20h 53m
San FranciscoChicago
SFO - MDW
SFOMDW
San Francisco
Wed 6/24
3:35 pm-12:05 am
1 stop6h 30m
Chicago Midway
Mon 6/29
9:30 pm-12:10 am
Nonstop4h 40m
San FranciscoChicago
SFO - ORD
SFOORD
San Francisco
Tue 7/14
12:50 am-7:16 am
Nonstop4h 26m
Chicago O'Hare Intl
Wed 7/29
7:30 am-10:19 am
Nonstop4h 49m
| 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 Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
The best time to book flights from San Francisco to Chicago is 66 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Currently, September is the cheapest month in which you can book a flight from San Francisco to Chicago (average of $288). Flying from San Francisco to Chicago in January is currently the most expensive (average of $1,094). 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.
One of the essential ways to save on airfare from San Francisco to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 20% on airfare.
Travelers seeking maximum savings on their San Francisco to Chicago flight should consider departing on Saturday afternoons when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from SFO to CHI are scheduled on a Wednesday (93 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (72 on average).
Las Vegas (LAS) – chosen by Cheapflights users on 40% of 1-stop itineraries from San Francisco to Chicago on Cheapflights.
Denver (DEN) is the most affordable 1-stop option, with an average round-trip price of $153.
Flights via San Diego (SAN) have the shortest average one-way travel time for 1-stop routes: 7h 01m.
Flights via San Diego (SAN) offer the fastest connection on this route, with an average layover time of 0h 57m.
About 10% of weekly flights between San Francisco and Chicago have experienced delays in the past year, with the average delay time being 183 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, American Airlines have had the lowest number of delays on this route, with just 10% of flights being delayed.
Food
Overall
Crew
Boarding
Entertainment
Comfort
Reviews
Franzi,Mar 2026
SFO - PDX
Food
Overall
Crew
Boarding
Entertainment
Comfort
Reviews
Franzi,Mar 2026
SFO - PDX
Food
Overall
Crew
Boarding
Entertainment
Comfort
Reviews
Franzi,Mar 2026
SFO - PDX
Food
Overall
Crew
Boarding
Entertainment
Comfort
Reviews
Franzi,Mar 2026
SFO - PDX
Food
Overall
Crew
Boarding
Entertainment
Comfort
Reviews
Franzi,Mar 2026
SFO - PDX
Food
Overall
Crew
Boarding
Entertainment
Comfort
Reviews
Franzi,Mar 2026
SFO - PDX
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$222 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$122 | Average$383 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$130 | Average$268 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$133 | Average$452 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$179 | Average$330 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$185 | Average$347 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$199 | Average$377 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$224 | Average$321 | FlexibilityNo cancel fee | On-time62% |