Plan to arrive at SAN at least two hours early, especially during peak times, to avoid stress from traffic congestion.

Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $154 (Kiwi.com) |
One-way from | $84 (United Airlines) |
Popular in | March |
Cheapest in | October |
Average price | $304 |
Good round-trip deal | $313 or less |
Good one-way deal | $168 or less |
Fly from
Fly to
Route
Depart
Return
Price
San DiegoChicago
SAN - ORD
SANORD
San Diego
mié. 2/18
8:35 am-2:58 pm
Nonstop4h 23m
Chicago O'Hare Intl
mié. 2/25
8:20 am-11:09 am
Nonstop4h 49m
San DiegoChicago
SAN - ORD
SANORD
San Diego
mié. 1/14
5:10 pm-11:37 pm
Nonstop4h 27m
Chicago O'Hare Intl
dom. 1/18
3:44 pm-6:26 pm
Nonstop4h 42m
San DiegoChicago
SAN - ORD
SANORD
San Diego
sáb. 2/14
8:35 am-2:58 pm
Nonstop4h 23m
Chicago O'Hare Intl
mar. 2/17
3:07 pm-5:52 pm
Nonstop4h 45m
San DiegoChicago
SAN - ORD
SANORD
San Diego
sáb. 1/17
8:00 am-2:29 pm
Nonstop4h 29m
Chicago O'Hare Intl
mié. 1/21
3:44 pm-6:26 pm
Nonstop4h 42m
San DiegoChicago
SAN - ORD
SANORD
San Diego
mié. 3/4
5:42 pm-11:59 pm
Nonstop4h 17m
Chicago O'Hare Intl
mié. 3/11
7:40 am-10:29 am
Nonstop4h 49m
San DiegoChicago
SAN - ORD
SANORD
San Diego
lun. 1/12
8:00 am-2:29 pm
Nonstop4h 29m
Chicago O'Hare Intl
mar. 1/13
3:44 pm-6:26 pm
Nonstop4h 42m
San DiegoChicago
SAN - ORD
SANORD
San Diego
jue. 1/15
5:10 pm-11:37 pm
Nonstop4h 27m
Chicago O'Hare Intl
dom. 1/18
9:00 am-11:43 am
Nonstop4h 43m
San DiegoChicago
SAN - ORD
SANORD
San Diego
lun. 1/12
8:00 am-2:29 pm
Nonstop4h 29m
Chicago O'Hare Intl
sáb. 1/17
3:44 pm-6:26 pm
Nonstop4h 42m
San DiegoChicago
SAN - ORD
SANORD
San Diego
mar. 1/20
8:00 am-2:29 pm
Nonstop4h 29m
Chicago O'Hare Intl
lun. 1/26
9:00 am-11:43 am
Nonstop4h 43m
San DiegoChicago
SAN - ORD
SANORD
San Diego
mié. 1/21
8:00 am-2:29 pm
Nonstop4h 29m
Chicago O'Hare Intl
lun. 1/26
3:44 pm-6:26 pm
Nonstop4h 42m
| 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 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*3 stars |
To ensure you get the cheapest price possible for a flight from San Diego to Chicago O'Hare Intl Airport, you should look to book at least 72 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Currently, February is the cheapest month in which you can book a flight from San Diego to Chicago O'Hare Intl Airport (average of $91). Flying from San Diego to Chicago O'Hare Intl Airport in May is currently the most expensive (average of $179). 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 typically best to fly out from San Diego to Chicago O'Hare Intl Airport in the afternoon. Doing so could potentially save you 47% on the flight price compared to flying in the morning, which is usually more expensive.
Travelers seeking maximum savings on their San Diego to Chicago O'Hare Intl Airport 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.
About 9% of weekly flights between San Diego and Chicago have experienced delays in the past year, with the average delay time being 171 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
Crew
Comfort
Food
Overall
Entertainment
Reviews
Art,Dec 2025
SAN - OGG
Boarding
Crew
Comfort
Food
Overall
Entertainment
Reviews
Art,Dec 2025
SAN - OGG
Boarding
Crew
Comfort
Food
Overall
Entertainment
Reviews
Art,Dec 2025
SAN - OGG
Boarding
Crew
Comfort
Food
Overall
Entertainment
Reviews
Art,Dec 2025
SAN - OGG
Boarding
Crew
Comfort
Food
Overall
Entertainment
Reviews
Art,Dec 2025
SAN - OGG
Boarding
Crew
Comfort
Food
Overall
Entertainment
Reviews
Art,Dec 2025
SAN - OGG
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$99 | Average$181 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$119 | Average$197 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$139 | Average$262 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$139 | Average$197 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$166 | Average$354 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$178 | Average$387 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$368 | FlexibilityNo cancel fee | On-timeN/A |