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 | $162 (Kiwi.com) |
One-way from | $79 (Southwest) |
Popular in | March |
Cheapest in | October |
Average price | $243 |
Good round-trip deal | $193 or less |
Good one-way deal | $99 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Sat 2/21
7:10 am-9:52 am
Nonstop4h 42m
San Diego
Wed 2/25
7:50 pm-5:03 am
1 stop7h 13m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Wed 1/7
7:15 am-11:50 am
1 stop6h 35m
San Diego
Tue 1/13
1:00 pm-10:35 pm
1 stop7h 35m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Mon 11/17
2:54 pm-5:19 pm
Nonstop4h 25m
San Diego
Mon 11/24
5:31 pm-11:32 pm
Nonstop4h 01m
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Fri 11/21
11:15 am-1:35 pm
Nonstop4h 20m
San Diego
Mon 11/24
4:15 pm-12:05 am
1 stop5h 50m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Tue 12/30
1:00 pm-3:33 pm
Nonstop4h 33m
San Diego
Tue 1/6
7:00 am-1:13 pm
Nonstop4h 13m
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Sat 11/15
7:30 pm-9:50 pm
Nonstop4h 20m
San Diego
Wed 11/19
5:00 pm-10:55 pm
Nonstop3h 55m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Sat 1/17
3:49 pm-6:31 pm
Nonstop4h 42m
San Diego
Wed 1/21
7:58 pm-1:10 pm
1 stop15h 12m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Sat 1/31
8:00 am-3:29 pm
1 stop9h 29m
San Diego
Sat 2/7
8:00 am-2:29 pm
Nonstop4h 29m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Wed 1/7
8:00 am-3:29 pm
1 stop9h 29m
San Diego
Tue 1/13
8:00 am-2:29 pm
Nonstop4h 29m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Tue 11/25
8:49 pm-11:13 pm
Nonstop4h 24m
San Diego
Wed 11/26
1:43 pm-7:53 pm
Nonstop4h 10m
| 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 Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy- | Trust Score*1 star |
Booking 85 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 16% 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.
Comfort
Food
Entertainment
Boarding
Overall
Crew
Reviews
Hannah,Aug 2025
SFO - SAN
Comfort
Food
Entertainment
Boarding
Overall
Crew
Reviews
Hannah,Aug 2025
SFO - SAN
Comfort
Food
Entertainment
Boarding
Overall
Crew
Reviews
Hannah,Aug 2025
SFO - SAN
Comfort
Food
Entertainment
Boarding
Overall
Crew
Reviews
Hannah,Aug 2025
SFO - SAN
Comfort
Food
Entertainment
Boarding
Overall
Crew
Reviews
Hannah,Aug 2025
SFO - SAN
Comfort
Food
Entertainment
Boarding
Overall
Crew
Reviews
Hannah,Aug 2025
SFO - SAN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$87 | Average$202 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$104 | Average$205 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$142 | Average$229 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$165 | Average$373 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$168 | Average$237 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$176 | Average$440 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$195 | Average$458 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$223 | Average$330 | FlexibilityNo cancel fee | On-timeN/A |