Airlines with flights from San Jose to Chicago

There are 9 airlines with scheduled flights between SJO and ORD. United is the only airline with non-stop flights from Juan Santamaria International to Chicago O'Hare and the flight time is 5 hours and 30 minutes.

Change direction

Choose airline

Direct

$United Airlines from {( $airportFrom->city_name }} to Chicago$

Non-stop

5h 30min

Via Miami

7h 57min

Via Atlanta

7h 59min

Via Houston

8h 6min

Via Panama City

8h 12min

Via Orlando

8h 25min

Via Dallas

8h 31min

Via Fort Lauderdale

8h 47min

Via Toronto

8h 48min

Via Charlotte

8h 54min

Via Dulles

9h 8min

Via Mexico City

9h 28min

NEW

Via Guatemala City

7h 20min

Via San Salvador

9h 50min

Schedules

Non-stop with United Airlines

Total flight time: 5 hours and 30 minutes
Chicago is a United Airlines hub (Largest hub ).

1 flight per week
Boeing 737MAX 8 Passenger
First class available

SJO

Direct

ORD

Flight

Mon

Jun 15

Tue

Jun 16

Wed

Jun 17

Thu

Jun 18

Fri

Jun 19

Sat

Jun 20

Sun

Jun 21

UA1952

----

13:00

----

SHOW RETURN SCHEDULE

CLOSE RETURN SCHEDULE

CHECK PRICES FOR SJO - ORD

The timetable & schedule information was updated at 2026-04-21

Via Miami with American Airlines

Total flight time: 7h 57m - 11h 53m.
One World Alliance
Chicago is a American Airlines hub.

114 flights per week

SJO

Via MIA

ORD

Flight

Mon

Jun 15

Tue

Jun 16

Wed

Jun 17

Thu

Jun 18

Fri

Jun 19

Sat

Jun 20

Sun

Jun 21

AA498
AA2247

06:00

07:00

06:00

AA1600
AA1881

12:50

----

12:50

AA1788
AA2323

15:08

SHOW RETURN SCHEDULE

CLOSE RETURN SCHEDULE

CHECK PRICES FOR SJO - ORD

The timetable & schedule information was updated at 2026-04-21

Via Atlanta with Delta Air Lines

Total flight time: 7h 59m - 9h 48m.
Sky Team Alliance

39 flights per week

SJO

Via ATL

ORD

Flight

Mon

Jun 15

Tue

Jun 16

Wed

Jun 17

Thu

Jun 18

Fri

Jun 19

Sat

Jun 20

Sun

Jun 21

DL1756
DL1139