For a quick departure, take the "L" train to ORD, avoiding Chicago traffic delays common with taxis or rideshares.

Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $158 (Kiwi.com) |
One-way from | $79 (Alaska Airlines) |
Popular in | March |
Cheapest in | October |
Average price | $333 |
Good round-trip deal | $194 or less |
Good one-way deal | $125 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Sat 1/24
7:10 am-9:40 am
Nonstop4h 30m
San Diego
Sun 1/25
2:11 pm-8:25 pm
Nonstop4h 14m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Sun 2/22
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
Sun 3/1
8:47 am-11:38 am
Nonstop4h 51m
San Diego
Sun 3/8
10:30 pm-4:29 am
Nonstop3h 59m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Thu 3/19
4:10 pm-6:55 pm
Nonstop4h 45m
San Diego
Tue 3/24
8:00 am-2:26 pm
Nonstop4h 26m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Wed 2/18
8:20 am-11:09 am
Nonstop4h 49m
San Diego
Fri 3/20
8:00 am-2:26 pm
Nonstop4h 26m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Sat 2/28
8:20 am-11:09 am
Nonstop4h 49m
San Diego
Mon 3/2
8:39 am-11:56 pm
1 stop13h 17m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Thu 2/5
3:44 pm-6:26 pm
Nonstop4h 42m
San Diego
Sun 2/8
5:10 pm-11:37 pm
Nonstop4h 27m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Mon 2/2
6:06 pm-10:07 am
1 stop18h 01m
San Diego
Wed 2/4
8:00 am-2:29 pm
Nonstop4h 29m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Tue 2/10
9:00 am-11:43 am
Nonstop4h 43m
San Diego
Thu 2/12
6:15 am-4:33 pm
1 stop8h 18m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Tue 1/20
4:25 pm-8:50 pm
1 stop6h 25m
San Diego
Mon 2/9
7:30 am-3:25 pm
1 stop5h 55m
| 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 Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
The price you pay for your flight from Chicago O'Hare Intl Airport to San Diego may vary depending on when you book. For the best chance of a lower fare, look to book 71 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to San Diego (average of $88). Flying from Chicago O'Hare Intl Airport to San Diego in May is currently the most expensive (average of $198). 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 Chicago O'Hare Intl Airport to San Diego at noon. By choosing this option you can save up to 29% on the cost of your flight, compared to a flight in the afternoon.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to San Diego flight should consider departing on Saturday at noon 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.
Boarding
Food
Entertainment
Overall
Comfort
Crew
Reviews
Georgana,Dec 2025
ORD - PDX
Boarding
Food
Entertainment
Overall
Comfort
Crew
Reviews
Georgana,Dec 2025
ORD - PDX
Boarding
Food
Entertainment
Overall
Comfort
Crew
Reviews
Georgana,Dec 2025
ORD - PDX
Boarding
Food
Entertainment
Overall
Comfort
Crew
Reviews
Georgana,Dec 2025
ORD - PDX
Boarding
Food
Entertainment
Overall
Comfort
Crew
Reviews
Georgana,Dec 2025
ORD - PDX
Boarding
Food
Entertainment
Overall
Comfort
Crew
Reviews
Georgana,Dec 2025
ORD - PDX
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$84 | Average$189 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$103 | Average$205 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$142 | Average$247 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$153 | Average$247 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$161 | Average$342 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$161 | Average$362 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$299 | FlexibilityNo cancel fee | On-timeN/A |