American Airlines
Oneworld
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Costa Rica
Juan Santamaría International Airport (SJO)
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United States
O'Hare International Airport
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Scan through all non-stop flights from San José to Chicago. The full flight schedule below gives an overview of all non-stop flights from SJO to ORD, which includes the daily timetable of every operating airline for the upcoming 12 months.
Note: for airline-specific flight schedules, please scroll further down.
Known for its continental climate, Chicago features hot, humid summers with temperatures above 30°C (86°F) and cold, snowy winters that often drop below 0°C (32°F). This striking seasonal contrast offers travelers a variety of activities, from summer hiking to winter sports, ensuring year-round appeal.
The best time to visit Chicago is from March to November, covering spring, summer, and fall. While summer can be hot, it also sees slightly more rainfall than other seasons.
In total there are 2 airlines operating nonstop flights from San José SJO to Chicago ORD. This section gives an overview of the flight schedules and timetables of every airline with direct flights for this route.
Click an airline below to view their SJO ORD flight schedule.
Flights from SJO to ORD are operated 3 times a week, with an average of 1 flight per day. Departure times vary between 06:00 - 14:05. The earliest flight departs at 06:00, the last flight departs at 14:05. However, this depends on the date you are flying so please check with the full flight schedule above to see which departure times are available on your preferred date(s) of travel.
You can fly in Economy and Business Class. Premium Economy and First Class are not available on this route (at least not as a non-stop flight).
The fastest direct flight from San José to Chicago takes 5 hours and 29 minutes. The flight distance between San José and Chicago is 2,220 miles (or 3,573 km).
There are 2 airports in Chicago: O'Hare International Airport (ORD) and Midway International Airport (MDW).
There are 3 flights per week flying from San José to Chicago (as of April 2026).
5 hours and 29 minutes is the average flight time from San José to Chicago.
The distance from San José to Chicago is 2,220 miles (3,573 kilometers).
American Airlines and United Airlines are flying nonstop from San José to Chicago.
Oneworld and Star Alliance are flying nonstop from San José to Chicago.
You can fly non-stop in Economy and Business Class.
Aircraft types that fly from San José to Chicago:
The earliest flight departs at 06:00 from San José and arrives at 12:24 at Chicago.
The latest flight departs at 14:05 from San José and arrives at 19:35 at Chicago.
2,220 miles (3,573 km) · 5h 29m
06:00
12:24
American Airlines
Oneworld
AA 540
American Airlines
Boeing 737 MAX 8
Y
W
J
F
06:00
12:31
American Airlines
Oneworld
AA 2824
American Airlines
Boeing 737 MAX 8
Y
W
J
F
13:00
19:35
United Airlines
Star Alliance
UA 1952
United Airlines
Boeing 737 MAX 8
Y
W
J
F
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