
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $164 (Kiwi.com) |
One-way from | $79 (Kiwi.com) |
Popular in | April |
Cheapest in | October |
Average price | $267 |
Good round-trip deal | $282 or less |
Good one-way deal | $147 or less |
Fly from
Fly to
Route
Depart
Return
Price
San DiegoChicago
SAN - ORD
SANORD
San Diego
jue. 4/9
10:30 pm-4:35 am
Nonstop4h 05m
Chicago O'Hare Intl
jue. 4/16
8:20 pm-10:59 pm
Nonstop4h 39m
San DiegoChicago
SAN - MDW
SANMDW
San Diego
vie. 4/17
7:10 am-1:05 pm
Nonstop3h 55m
Chicago Midway
lun. 4/20
5:25 pm-7:45 pm
Nonstop4h 20m
San DiegoChicago
SAN - ORD
SANORD
San Diego
jue. 4/16
4:49 pm-10:59 pm
Nonstop4h 10m
Chicago O'Hare Intl
lun. 4/20
8:20 pm-10:59 pm
Nonstop4h 39m
San DiegoChicago
SAN - MDW
SANMDW
San Diego
mar. 5/5
9:00 pm-5:45 am
1 stop6h 45m
Chicago Midway
mar. 5/12
6:45 am-9:00 am
Nonstop4h 15m
San DiegoChicago
SAN - MDW
SANMDW
San Diego
dom. 5/10
10:40 pm-4:35 am
Nonstop3h 55m
Chicago Midway
mié. 5/13
10:05 am-3:00 pm
1 stop6h 55m
San DiegoChicago
SAN - ORD
SANORD
San Diego
mié. 4/8
12:40 pm-9:20 pm
1 stop6h 40m
Chicago O'Hare Intl
dom. 4/12
7:00 am-9:40 am
Nonstop4h 40m
San DiegoChicago
SAN - MDW
SANMDW
San Diego
sáb. 3/14
10:40 pm-4:35 am
Nonstop3h 55m
Chicago Midway
lun. 3/16
8:55 pm-11:25 pm
Nonstop4h 30m
San DiegoChicago
SAN - MDW
SANMDW
San Diego
vie. 4/10
3:35 pm-11:40 pm
1 stop6h 05m
Chicago Midway
vie. 4/17
8:45 pm-11:10 pm
Nonstop4h 25m
San DiegoChicago
SAN - ORD
SANORD
San Diego
vie. 3/13
10:30 pm-8:30 am
1 stop8h 00m
Chicago O'Hare Intl
lun. 3/16
5:40 pm-10:59 pm
1 stop7h 19m
San DiegoChicago
SAN - MDW
SANMDW
San Diego
mar. 4/7
10:10 pm-8:53 am
1 stop8h 43m
Chicago Midway
mié. 4/8
7:20 pm-11:40 pm
1 stop6h 20m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 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 | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
The price you pay for your flight from San Diego to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 35 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Currently, April is the cheapest month in which you can book a flight from San Diego to Chicago (average of $98). Flying from San Diego to Chicago in May is currently the most expensive (average of $177). 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 San Diego to Chicago in the afternoon. By choosing this option you can save up to 31% on the cost of your flight, compared to a flight in the morning.
Travelers seeking maximum savings on their San Diego to Chicago flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from SAN to CHI are scheduled on a Monday (34 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (23 on average).
About 9% of weekly flights between San Diego and Chicago have experienced delays in the past year, with the average delay time being 172 minutes.
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
Monday 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 7% of flights being delayed.
Boarding
Overall
Comfort
Entertainment
Food
Crew
Reviews
Anonymous,Jan 2026
STS - LAX
Boarding
Overall
Comfort
Entertainment
Food
Crew
Reviews
Anonymous,Jan 2026
STS - LAX
Boarding
Overall
Comfort
Entertainment
Food
Crew
Reviews
Anonymous,Jan 2026
STS - LAX
Boarding
Overall
Comfort
Entertainment
Food
Crew
Reviews
Anonymous,Jan 2026
STS - LAX
Boarding
Overall
Comfort
Entertainment
Food
Crew
Reviews
Anonymous,Jan 2026
STS - LAX
Boarding
Overall
Comfort
Entertainment
Food
Crew
Reviews
Anonymous,Jan 2026
STS - LAX
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$98 | Average$182 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$109 | Average$213 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$139 | Average$197 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$139 | Average$266 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$158 | Average$333 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$171 | Average$369 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$205 | Average$362 | FlexibilityNo cancel fee | On-time63% |