Flights from Chicago to San Jose – Direct & connecting routes
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ORD to SJO – All flight route options from Chicago O Hare International, Illinois, USA to Juan Santamaria International, Costa Rica. These routes are operated by 10 airlines. Fly non-stop with American Airlines or United Airlines, or choose from 15 different stopover flights. The shortest flight time is 5 hours and 12 minutes. See the full flight schedule and time table, including departure times, airlines and stopover details to find the best option for you.
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Chicago to San Jose flights
There are over 17 airlines and as many as 235 flights every week to this destination. You can fly non-stop to San Jose (SJO) from Chicago (ORD) with United Airlines or American Airlines but if a stopover option suits you better you can choose to fly via Orlando, San Salvador or any other of the 15 alternatives with connectiing airports.
Chicago to San Jose with United Airlines
United Airlines has non-stop every Saturday or Sunday at 07:39 or 07:41. You also have the option to do a transit flight via Houston. United Airlines is a Star Alliance member.
With Southwest Airlines
If you fly from Chicago with Southwest Airlines you will do a stopover in Orlando, MCO before reaching San Jose. This flight trip will take 7 hours and 10 minutes and you can fly every day of the week except Mondays and Tuesday with departures at 06:00 or 06:05.
Distance & flight times: Chicago O'Hare to Juan Santamaria International
The shortest flight time between ORD and SJO is 5 hours and 17 minutes.
Via | Total flight time | Layover time | Distance |
---|---|---|---|
Direct | 5h 17m | - | 2233 miles (3593 km) |
MCO Orlando | 7h 10m | 1h 45m | 2305 miles (3709 km) |
SAL San Salvador | 7h 10m | 1h 20m | 2391 miles (3847 km) |
FLL Fort Lauderdale | 7h 13m | 1h 15m | 2338 miles (3762 km) |
ATL Atlanta | 7h 23m | 46m | 2252 miles (3623 km) |
GUA Guatemala City | 8h 30m | 2h 35m | 2444 miles (3932 km) |
CLT Charlotte | 8h 45m | 56m | 2366 miles (3807 km) |
MIA Miami | 9h 0m | 58m | 2332 miles (3752 km) |
PTY Panama City | 9h 3m | 3h 5m | 2681 miles (4314 km) |
DFW Dallas | 9h 36m | 1h 42m | 2596 miles (4177 km) |
IAH Houston | 10h 42m | 1h 2m | 2495 miles (4014 km) |
IAD Dulles | 10h 42m | 3h 52m | 2669 miles (4294 km) |
MEX Mexico City | 11h 8m | 1h 15m | 2891 miles (4652 km) |
YYZ Toronto | 11h 55m | 4h 59m | 2794 miles (4496 km) |
DCA Washington | 13h 22m | - | - |
CUN Cancun | 15h 55m | 1h 56m | 2243 miles (3609 km) |


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From Chicago to Costa Rica
We have found another destination to Costa Rica from Chicago O Hare International as well.
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LIR Guanacaste Direct
From USA to San Jose
Below is a list of other cities in USA with flights to San Jose with either non-stop or connecting flights.
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DFW Dallas Direct
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ATL Atlanta Direct
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DEN Denver Direct
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JFK New York Direct
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MIA Miami Direct
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LAX Los Angeles Direct
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CLT Charlotte Direct
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IAH Houston Direct
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EWR New York Direct
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MSP Minneapolis