
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | Priceline 3 stars |
Round-trip from | $269 (Frontier) |
One-way from | $169 (Kiwi.com) |
Popular in | December |
Cheapest in | August |
Average price | $727 |
Fly from
Fly to
Route
Depart
Return
Price
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Wed 1/14
7:00 am-10:07 pm
1 stop15h 07m
Chicago Midway
Wed 1/21
9:32 am-10:15 pm
2 stops12h 43m
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 2/5
7:00 am-5:29 pm
1 stop10h 29m
Chicago Midway
Sun 2/22
12:46 pm-10:02 pm
1 stop9h 16m
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 2/19
2:25 pm-10:42 pm
1 stop8h 17m
Chicago Midway
Wed 2/25
9:34 am-10:02 pm
2 stops12h 28m
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Wed 1/21
2:31 pm-10:22 pm
1 stop7h 51m
Chicago Midway
Sat 1/24
6:25 am-2:29 pm
1 stop8h 04m
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Wed 2/18
9:40 am-10:55 pm
1 stop13h 15m
Chicago Midway
Wed 2/25
9:55 am-7:30 pm
2 stops9h 35m
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Tue 4/21
1:25 pm-12:30 pm
2 stops22h 05m
Chicago Midway
Tue 4/28
6:00 am-12:04 pm
1 stop7h 04m
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Mon 12/22
7:00 am-8:49 am
2 stops25h 49m
Chicago Midway
Sat 1/3
6:00 am-9:55 pm
1 stop15h 55m
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Thu 12/25
7:00 am-10:22 pm
1 stop15h 22m
Chicago Midway
Tue 1/6
9:32 am-10:15 pm
2 stops12h 43m
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Mon 12/29
7:00 am-10:22 pm
1 stop15h 22m
Chicago Midway
Tue 1/6
6:45 am-10:15 pm
1 stop15h 30m
San JoséChicago
SJO - MDW
SJOMDW
San José Juan Santamaria Intl
Wed 2/25
12:35 pm-2:26 pm
1 stop25h 51m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars |
About 0% of weekly flights between San José and Chicago have experienced delays in the past year, with the average delay time being 0 minutes.
Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
Food
Boarding
Comfort
Overall
Entertainment
Crew
Reviews
Thomas,Dec 2025
SEA - DEN
Food
Boarding
Comfort
Overall
Entertainment
Crew
Reviews
Thomas,Dec 2025
SEA - DEN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$463 | Average$523 | FlexibilityNo cancel fee | On-time63% |