Plan to arrive at least two hours before your flight from SAN to avoid stress, especially during peak traffic times.

Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $154 (Kiwi.com) |
One-way from | $81 (Trip.com) |
Popular in | April |
Cheapest in | October |
Average price | $292 |
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 - MDW
SANMDW
San Diego
Mon 1/12
6:25 am-12:25 pm
Nonstop4h 00m
Chicago Midway
Sat 1/17
7:40 pm-10:10 pm
Nonstop4h 30m
San DiegoChicago
SAN - ORD
SANORD
San Diego
Wed 2/18
8:35 am-2:58 pm
Nonstop4h 23m
Chicago O'Hare Intl
Wed 2/25
8:20 am-11:09 am
Nonstop4h 49m
San DiegoChicago
SAN - ORD
SANORD
San Diego
Wed 1/14
5:10 pm-11:37 pm
Nonstop4h 27m
Chicago O'Hare Intl
Sun 1/18
3:44 pm-6:26 pm
Nonstop4h 42m
San DiegoChicago
SAN - ORD
SANORD
San Diego
Sat 2/14
8:35 am-2:58 pm
Nonstop4h 23m
Chicago O'Hare Intl
Tue 2/17
3:07 pm-5:52 pm
Nonstop4h 45m
San DiegoChicago
SAN - ORD
SANORD
San Diego
Sat 1/17
8:00 am-2:29 pm
Nonstop4h 29m
Chicago O'Hare Intl
Wed 1/21
3:44 pm-6:26 pm
Nonstop4h 42m
San DiegoChicago
SAN - ORD
SANORD
San Diego
Wed 3/4
5:42 pm-11:59 pm
Nonstop4h 17m
Chicago O'Hare Intl
Wed 3/11
7:40 am-10:29 am
Nonstop4h 49m
San DiegoChicago
SAN - ORD
SANORD
San Diego
Mon 1/12
8:00 am-2:29 pm
Nonstop4h 29m
Chicago O'Hare Intl
Tue 1/13
3:44 pm-6:26 pm
Nonstop4h 42m
San DiegoChicago
SAN - ORD
SANORD
San Diego
Thu 1/15
5:10 pm-11:37 pm
Nonstop4h 27m
Chicago O'Hare Intl
Sun 1/18
9:00 am-11:43 am
Nonstop4h 43m
San DiegoChicago
SAN - ORD
SANORD
San Diego
Mon 1/12
8:00 am-2:29 pm
Nonstop4h 29m
Chicago O'Hare Intl
Sat 1/17
3:44 pm-6:26 pm
Nonstop4h 42m
San DiegoChicago
SAN - ORD
SANORD
San Diego
Tue 1/20
8:00 am-2:29 pm
Nonstop4h 29m
Chicago O'Hare Intl
Mon 1/26
9:00 am-11:43 am
Nonstop4h 43m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| 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 44 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Currently, February is the cheapest month in which you can book a flight from San Diego to Chicago (average of $91). Flying from San Diego to Chicago in May is currently the most expensive (average of $176). 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 33% on the cost of your flight, compared to a flight in the evening.
Travelers seeking maximum savings on their San Diego to Chicago flight should consider departing on Friday evenings 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 (42 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (24 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 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.
Crew
Entertainment
Food
Boarding
Overall
Comfort
Reviews
Art,Dec 2025
SAN - OGG
Crew
Entertainment
Food
Boarding
Overall
Comfort
Reviews
Art,Dec 2025
SAN - OGG
Crew
Entertainment
Food
Boarding
Overall
Comfort
Reviews
Art,Dec 2025
SAN - OGG
Crew
Entertainment
Food
Boarding
Overall
Comfort
Reviews
Art,Dec 2025
SAN - OGG
Crew
Entertainment
Food
Boarding
Overall
Comfort
Reviews
Art,Dec 2025
SAN - OGG
Crew
Entertainment
Food
Boarding
Overall
Comfort
Reviews
Art,Dec 2025
SAN - OGG
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$99 | Average$181 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$110 | Average$214 | 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$205 | Average$389 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$256 | Average$368 | FlexibilityNo cancel fee | On-timeN/A |