For a quick snack, grab Garrett Popcorn near gate B8, a Chicago favorite, perfect before your flight.

Most accurate provider | Mytrip 3 stars |
|---|---|
Most trusted provider | Mytrip 3 stars |
Round-trip from | $157 (Southwest) |
One-way from | $79 (Southwest) |
Popular in | March |
Cheapest in | October |
Average price | $298 |
Good round-trip deal | $205 or less |
Good one-way deal | $121 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Sat 2/21
3:07 pm-5:52 pm
Nonstop4h 45m
San Diego
Sat 2/28
8:35 am-2:58 pm
Nonstop4h 23m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Sat 1/17
1:00 pm-3:36 pm
Nonstop4h 36m
San Diego
Wed 1/21
7:00 am-1:13 pm
Nonstop4h 13m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Tue 1/13
2:40 pm-8:49 pm
1 stop8h 09m
San Diego
Tue 1/20
2:11 pm-8:25 pm
Nonstop4h 14m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Mon 2/23
3:07 pm-5:52 pm
Nonstop4h 45m
San Diego
Tue 3/3
8:35 am-2:58 pm
Nonstop4h 23m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Wed 2/25
8:20 am-11:09 am
Nonstop4h 49m
San Diego
Fri 2/27
5:42 pm-11:59 pm
Nonstop4h 17m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Thu 1/15
7:10 am-9:40 am
Nonstop4h 30m
San Diego
Sun 1/18
4:47 pm-10:59 pm
Nonstop4h 12m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Thu 1/15
9:00 am-11:43 am
Nonstop4h 43m
San Diego
Sun 1/18
8:00 am-2:29 pm
Nonstop4h 29m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Sun 2/22
8:20 am-11:09 am
Nonstop4h 49m
San Diego
Tue 3/3
8:35 am-2:58 pm
Nonstop4h 23m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Thu 2/19
3:07 pm-5:52 pm
Nonstop4h 45m
San Diego
Sat 2/21
5:42 pm-11:59 pm
Nonstop4h 17m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Fri 2/20
3:07 pm-5:52 pm
Nonstop4h 45m
San Diego
Tue 2/24
5:42 pm-11:59 pm
Nonstop4h 17m
| 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 Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars |
Booking 48 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to San Diego. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Currently, September is the cheapest month in which you can book a flight from Chicago to San Diego (average of $88). Flying from Chicago to San Diego in May is currently the most expensive (average of $197). 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.
A simple way to save on the total cost of your ticket is to fly from Chicago to San Diego in the morning. If you’re flexible enough to do this you can expect to save up to 13% on your trip compared to booking a flight in the afternoon.
Travelers seeking maximum savings on their Chicago to San Diego flight should consider departing on Tuesday mornings when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Food
Overall
Boarding
Entertainment
Crew
Comfort
Reviews
Hannah,Aug 2025
SFO - SAN
Food
Overall
Boarding
Entertainment
Crew
Comfort
Reviews
Hannah,Aug 2025
SFO - SAN
Food
Overall
Boarding
Entertainment
Crew
Comfort
Reviews
Hannah,Aug 2025
SFO - SAN
Food
Overall
Boarding
Entertainment
Crew
Comfort
Reviews
Hannah,Aug 2025
SFO - SAN
Food
Overall
Boarding
Entertainment
Crew
Comfort
Reviews
Hannah,Aug 2025
SFO - SAN
Food
Overall
Boarding
Entertainment
Crew
Comfort
Reviews
Hannah,Aug 2025
SFO - SAN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$84 | Average$189 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$103 | Average$215 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$141 | Average$238 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$161 | Average$347 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$163 | Average$372 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$168 | Average$247 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$177 | Average$392 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$256 | Average$312 | FlexibilityNo cancel fee | On-timeN/A |