
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $304 (Kiwi.com) |
One-way from | $132 (Kiwi.com) |
Popular in | January |
Cheapest in | August |
Average price | $503 |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Fri 1/30
6:00 am-1:00 pm
1 stop7h 00m
San José Juan Santamaria Intl
Sat 2/7
7:00 am-10:26 pm
1 stop15h 26m
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Wed 1/28
9:55 am-7:30 pm
2 stops9h 35m
San José Juan Santamaria Intl
Wed 2/4
9:40 am-10:55 pm
1 stop13h 15m
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sat 2/7
9:34 am-10:15 pm
2 stops12h 41m
San José Juan Santamaria Intl
Tue 2/10
2:31 pm-10:26 pm
1 stop7h 55m
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Thu 1/29
8:55 am-7:30 pm
1 stop10h 35m
San José Juan Santamaria Intl
Tue 2/3
9:40 am-10:55 pm
1 stop13h 15m
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sat 1/3
6:00 am-9:55 pm
1 stop15h 55m
San José Juan Santamaria Intl
Thu 1/15
7:00 am-10:09 pm
1 stop15h 09m
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Thu 1/29
9:34 am-10:15 pm
2 stops12h 41m
San José Juan Santamaria Intl
Tue 2/3
7:00 am-10:26 pm
1 stop15h 26m
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Wed 12/10
10:15 am-8:30 pm
1 stop10h 15m
San José Juan Santamaria Intl
Sat 12/13
2:15 pm-10:35 pm
1 stop8h 20m
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sun 2/1
5:55 am-7:30 pm
1 stop13h 35m
San José Juan Santamaria Intl
Sun 2/8
9:40 am-10:55 pm
1 stop13h 15m
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sat 1/24
1:00 pm-7:30 pm
1 stop6h 30m
San José Juan Santamaria Intl
Fri 1/30
9:40 am-10:55 pm
1 stop13h 15m
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Mon 1/12
2:47 pm-3:30 pm
1 stop24h 43m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
About 100% of weekly flights between Chicago and San José have experienced delays in the past year, with the average delay time being 97 minutes.
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
Overall
Boarding
Crew
Entertainment
Comfort
Food
Reviews
Mike,Aug 2025
OKC - AUS
Overall
Boarding
Crew
Entertainment
Comfort
Food
Reviews
Mike,Aug 2025
OKC - AUS
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$394 | Average$594 | FlexibilityNo cancel fee | On-time63% |