
| Most accurate provider | CheapOair 3 stars | 
|---|---|
| Most trusted provider | CheapOair 3 stars | 
| Round-trip from | $158 (eDestinos) | 
| One-way from | $71 (Frontier) | 
| Popular in | January | 
| Cheapest in | September | 
| Average price | $452 | 
| Good round-trip deal | $272 or less | 
Fly from
Fly to
Route
Depart
Return
Price
San DiegoChicago
SAN - ORD
SANORD
San Diego
Tue 3/3
8:05 am-1:59 pm
Nonstop3h 54m
Chicago O'Hare Intl
Wed 3/4
9:00 am-11:25 am
Nonstop4h 25m
San DiegoChicago
SAN - ORD
SANORD
San Diego
Fri 1/16
8:00 am-2:29 pm
Nonstop4h 29m
Chicago O'Hare Intl
Wed 1/21
3:49 pm-6:31 pm
Nonstop4h 42m
San DiegoChicago
SAN - ORD
SANORD
San Diego
Mon 11/24
5:31 pm-11:32 pm
Nonstop4h 01m
Chicago O'Hare Intl
Wed 11/26
3:51 pm-6:15 pm
Nonstop4h 24m
San DiegoChicago
SAN - ORD
SANORD
San Diego
Tue 3/3
5:25 pm-5:04 am
1 stop9h 39m
Chicago O'Hare Intl
Wed 3/4
9:00 am-11:25 am
Nonstop4h 25m
San DiegoChicago
SAN - ORD
SANORD
San Diego
Tue 12/30
5:31 pm-11:59 pm
Nonstop4h 28m
Chicago O'Hare Intl
Tue 1/6
8:00 am-4:31 pm
1 stop10h 31m
San DiegoChicago
SAN - ORD
SANORD
San Diego
Fri 11/21
5:21 pm-11:30 pm
Nonstop4h 09m
Chicago O'Hare Intl
Mon 11/24
4:20 pm-6:50 pm
Nonstop4h 30m
San DiegoChicago
SAN - ORD
SANORD
San Diego
Tue 11/18
1:41 pm-7:55 pm
Nonstop4h 14m
Chicago O'Hare Intl
Thu 11/20
2:54 pm-5:19 pm
Nonstop4h 25m
San DiegoChicago
SAN - ORD
SANORD
San Diego
Sat 11/22
5:31 pm-11:32 pm
Nonstop4h 01m
Chicago O'Hare Intl
Wed 12/3
3:05 pm-5:33 pm
Nonstop4h 28m
San DiegoChicago
SAN - ORD
SANORD
San Diego
Wed 12/3
5:53 pm-11:50 pm
Nonstop3h 57m
Chicago O'Hare Intl
Sun 12/7
6:00 am-12:47 pm
1 stop8h 47m
San DiegoChicago
SAN - ORD
SANORD
San Diego
Sat 2/14
8:50 pm-1:04 pm
1 stop14h 14m
Chicago O'Hare Intl
Tue 2/17
9:00 am-11:25 am
Nonstop4h 25m
Currently, July is the cheapest month in which you can book a flight from San Diego to Wisconsin (average of $122). Flying from San Diego to Wisconsin in January is currently the most expensive (average of $279). 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.
When flying from San Diego to Wisconsin, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 47% versus a flight at noon.
Travelers seeking maximum savings on their San Diego to Wisconsin flight should consider departing on Thursday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Crew
Comfort
Food
Entertainment
Boarding
Overall
Reviews
Walter,Aug 2025
OAK - SAN
Crew
Comfort
Food
Entertainment
Boarding
Overall
Reviews
Walter,Aug 2025
OAK - SAN
Crew
Comfort
Food
Entertainment
Boarding
Overall
Reviews
Walter,Aug 2025
OAK - SAN
Crew
Comfort
Food
Entertainment
Boarding
Overall
Reviews
Walter,Aug 2025
OAK - SAN
Crew
Comfort
Food
Entertainment
Boarding
Overall
Reviews
Walter,Aug 2025
OAK - SAN
Crew
Comfort
Food
Entertainment
Boarding
Overall
Reviews
Walter,Aug 2025
OAK - SAN
| Airline | Cheapest | Average | Flexibility | On-time | 
|---|---|---|---|---|
| Cheapest$119 | Average$305 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$168 | Average$257 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$256 | Average$459 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$256 | Average$473 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$441 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$269 | Average$470 | FlexibilityNo cancel fee | On-time71% |