
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $179 (Kiwi.com) |
One-way from | $80 (Frontier) |
Popular in | March |
Cheapest in | October |
Average price | $367 |
Good round-trip deal | $265 or less |
Good one-way deal | $125 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Mon 4/27
1:35 pm-1:29 pm
1 stop25h 54m
San Diego
Fri 5/1
7:00 am-9:37 pm
1 stop12h 37m
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Sat 5/2
6:15 am-8:30 am
Nonstop4h 15m
San Diego
Wed 5/6
10:40 am-4:35 pm
Nonstop3h 55m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Tue 4/14
12:55 pm-5:16 pm
1 stop6h 21m
San Diego
Tue 4/28
6:20 am-12:34 pm
Nonstop4h 14m
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Sat 4/18
5:21 pm-11:25 pm
1 stop8h 04m
San Diego
Tue 4/21
6:15 am-5:58 pm
1 stop9h 43m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Tue 4/14
6:25 am-10:43 am
1 stop6h 18m
San Diego
Tue 5/5
10:30 pm-8:40 am
1 stop8h 10m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Sat 4/25
3:05 pm-11:25 pm
2 stops10h 20m
San Diego
Wed 4/29
12:45 pm-10:55 pm
2 stops8h 10m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Fri 4/17
7:59 pm-10:41 pm
Nonstop4h 42m
San Diego
Sat 4/18
12:37 pm-7:02 pm
Nonstop4h 25m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Mon 4/13
8:20 am-11:02 am
Nonstop4h 42m
San Diego
Sat 5/2
7:03 am-1:13 pm
Nonstop4h 10m
ChicagoSan Diego
MDW - SAN
MDWSAN
Chicago Midway
Wed 5/6
6:45 am-9:00 am
Nonstop4h 15m
San Diego
Mon 5/11
10:40 pm-4:35 am
Nonstop3h 55m
ChicagoSan Diego
ORD - SAN
ORDSAN
Chicago O'Hare Intl
Tue 4/14
10:30 am-6:25 pm
2 stops9h 55m
San Diego
Wed 4/29
7:25 am-6:50 pm
2 stops9h 25m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
Booking 80 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, April is the cheapest month in which you can book a flight from Chicago to San Diego (average of $67). Flying from Chicago to San Diego in March is currently the most expensive (average of $167). 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 evening. If you’re flexible enough to do this you can expect to save up to 23% on your trip compared to booking a flight at noon.
Travelers seeking maximum savings on their Chicago to San Diego flight should consider departing on Saturday at noon when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from CHI to SAN are scheduled on a Friday (45 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (21 on average).
Entertainment
Food
Comfort
Boarding
Crew
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Food
Comfort
Boarding
Crew
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Food
Comfort
Boarding
Crew
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Food
Comfort
Boarding
Crew
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Food
Comfort
Boarding
Crew
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Food
Comfort
Boarding
Crew
Overall
Reviews
Dominic,Mar 2026
MCO - SMF
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$84 | Average$184 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$97 | Average$255 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$138 | Average$240 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$146 | Average$279 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$157 | Average$310 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$157 | Average$282 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$167 | Average$358 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$177 | Average$343 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$237 | Average$297 | FlexibilityNo cancel fee | On-timeN/A |