Flights from San Jose to Chicago – Direct & connecting routes
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SJO to ORD – All flight route options from Juan Santamaria International, Costa Rica to Chicago O Hare International, Illinois, USA. These routes are operated by 10 airlines. Fly non-stop with United Airlines or American Airlines, or choose from 14 different stopover flights. The shortest flight time is 5 hours and 30 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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San Jose to Chicago flights
There are over 16 airlines and as many as 221 flights every week to this destination. You can fly non-stop to Chicago (ORD) from San Jose (SJO) with United Airlines or American Airlines but if a stopover option suits you better you can choose to fly via Charlotte, Panama City or any other of the 14 alternatives with connectiing airports.
San Jose to Chicago with United Airlines
United Airlines has non-stop every Saturday or Sunday at 13:00, 13:05 or 14:05. You can also take a connecting flight via Dulles or Houston. United Airlines is a Star Alliance member.
With Southwest Airlines
If you fly from San Jose with Southwest Airlines you will do a stopover in Orlando, MCO before reaching Chicago. This flight trip will take 8 hours and 10 minutes and you can fly every day of the week except Mondays with departures at 8:00 am, 12 noon or 1:00 pm.
Distance & flight times: Juan Santamaria International to Chicago O'Hare
The shortest flight time between SJO and ORD is 5 hours and 30 minutes.
Via | Total flight time | Layover time | Distance |
---|---|---|---|
Direct | 5h 30m | - | 2233 miles (3593 km) |
CLT Charlotte | 8h 27m | 2h 5m | 2366 miles (3807 km) |
PTY Panama City | 8h 32m | 1h 53m | 2681 miles (4314 km) |
IAD Dulles | 9h 13m | 1h 55m | 2645 miles (4256 km) |
MIA Miami | 9h 33m | 4h 27m | 2332 miles (3752 km) |
ATL Atlanta | 9h 36m | 3h 22m | 2252 miles (3623 km) |
MEX Mexico City | 9h 46m | 2h 54m | 2891 miles (4652 km) |
SAL San Salvador | 10h 0m | 4h 0m | 2391 miles (3847 km) |
DFW Dallas | 10h 4m | 3h 1m | 2596 miles (4177 km) |
FLL Fort Lauderdale | 10h 17m | 3h 5m | 2338 miles (3762 km) |
YYZ Toronto | 10h 27m | 3h 4m | 2794 miles (4496 km) |
IAH Houston | 10h 45m | 3h 47m | 2495 miles (4014 km) |
MCO Orlando | 10h 55m | 4h 24m | 2305 miles (3709 km) |
GUA Guatemala City | 11h 0m | 4h 48m | 2444 miles (3932 km) |
CUN Cancun | 12h 45m | 1h 40m | 2243 miles (3609 km) |


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From San Jose to USA
Below is a list of other destinations to USA from Juan Santamaria International with either direct flights or 1 stop connections.
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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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CLT Charlotte Direct
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LAX Los Angeles Direct
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IAH Houston Direct
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EWR New York Direct
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MSP Minneapolis
From Costa Rica to Chicago
We have found another destination to USA from Juan Santamaria International as well.
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LIR Guanacaste Direct