
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $331 (CheapOair) |
One-way from | $154 (Trip.com) |
Popular in | July |
Cheapest in | January |
Average price | $525 |
Fly from
Fly to
Route
Depart
Return
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 5/7
1:00 pm-9:54 am
2 stops19h 54m
Chicago O'Hare Intl
Sun 5/10
5:05 am-11:45 am
1 stop7h 40m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Fri 7/10
2:20 am-12:40 am
1 stop21h 20m
Chicago O'Hare Intl
Fri 7/17
1:30 am-1:15 am
1 stop24h 45m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 5/30
1:00 pm-7:35 pm
Nonstop5h 35m
Chicago O'Hare Intl
Sun 6/14
6:30 am-10:39 pm
1 stop17h 09m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 5/30
1:00 pm-7:35 pm
Nonstop5h 35m
Chicago O'Hare Intl
Tue 6/9
9:21 pm-10:11 am
1 stop13h 50m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sun 6/14
10:05 am-4:00 am
1 stop16h 55m
Chicago O'Hare Intl
Mon 6/22
3:21 pm-9:06 am
1 stop18h 45m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Wed 6/3
5:57 pm-2:06 pm
1 stop19h 09m
Chicago O'Hare Intl
Thu 6/11
3:21 pm-7:12 am
1 stop16h 51m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Mon 7/13
5:55 pm-1:57 pm
1 stop19h 02m
Chicago O'Hare Intl
Sun 7/19
3:21 pm-7:26 am
1 stop17h 05m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Thu 5/21
4:10 am-2:06 pm
1 stop8h 56m
Chicago O'Hare Intl
Mon 6/1
8:02 am-7:01 pm
1 stop11h 59m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sun 6/14
10:05 am-4:00 am
1 stop16h 55m
Chicago O'Hare Intl
Thu 6/18
3:21 pm-9:06 am
1 stop18h 45m
San JoséChicago
SJO - ORD
SJOORD
San José Juan Santamaria Intl
Sat 5/16
6:19 pm-2:06 pm
1 stop18h 47m
Chicago O'Hare Intl
Sat 5/30
3:21 pm-9:06 am
1 stop18h 45m
Currently, May is the cheapest month in which you can book a flight from San José to Wisconsin (average of $256). Flying from San José to Wisconsin in October is currently the most expensive (average of $520). 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.
Overall
Crew
Entertainment
Boarding
Food
Comfort
Reviews
Anonymous,Apr 2026
DFW - EWR
Overall
Crew
Entertainment
Boarding
Food
Comfort
Reviews
Anonymous,Apr 2026
DFW - EWR
Overall
Crew
Entertainment
Boarding
Food
Comfort
Reviews
Anonymous,Apr 2026
DFW - EWR
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$399 | Average$554 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$458 | Average$537 | FlexibilityNo cancel fee | On-time69% |