Find a great deal and save up to 29% by booking at least 34 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago to Costa Rica within the next two weeks, with the cheapest ticket starting at $349.
Flights from Chicago to Costa Rica lean towards being more expensive in December. Prices are generally better when you fly from Chicago to Costa Rica in August, with the cheapest ticket starting at $288.
When flying from Chicago to Costa Rica, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$198 - $402
Route
Depart
Return
Price
Chicago O'Hare IntlSan José Juan Santamaria Intl
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Wed 9/4
1 stop7h 32m
San José Juan Santamaria Intl
Tue 9/10
1 stop10h 28m
Chicago O'Hare IntlSan José Juan Santamaria Intl
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Tue 8/20
1 stop6h 35m
San José Juan Santamaria Intl
Tue 8/27
1 stop10h 28m
Chicago O'Hare IntlSan José Juan Santamaria Intl
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Fri 5/31
1 stop18h 50m
San José Juan Santamaria Intl
Tue 6/4
1 stop9h 57m
Chicago O'Hare IntlSan José Juan Santamaria Intl
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Sat 6/1
1 stop22h 51m
San José Juan Santamaria Intl
Wed 6/5
1 stop8h 02m
Chicago O'Hare IntlSan José Juan Santamaria Intl
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Wed 9/4
1 stop7h 32m
San José Juan Santamaria Intl
Sun 9/8
1 stop22h 28m
Chicago O'Hare IntlSan José Juan Santamaria Intl
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Wed 9/4
1 stop7h 32m
San José Juan Santamaria Intl
Sun 9/8
3 stops30h 10m
Chicago O'Hare IntlSan José Juan Santamaria Intl
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Wed 8/7
1 stop18h 10m
San José Juan Santamaria Intl
Wed 8/21
Nonstop7h 55m
Chicago MidwaySan José Juan Santamaria Intl
MDW - SJO
MDWSJO
Chicago Midway
Wed 9/4
1 stop11h 41m
San José Juan Santamaria Intl
Thu 9/12
1 stop10h 09m
Chicago O'Hare IntlSan José Juan Santamaria Intl
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Sat 9/14
1 stop12h 39m
San José Juan Santamaria Intl
Fri 9/20
1 stop9h 30m
No data available for this route at this time. Please check back soon.
Entertainment
Boarding
Comfort
Crew
Food
Overall
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Entertainment
Boarding
Comfort
Crew
Food
Overall
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Entertainment
Boarding
Comfort
Crew
Food
Overall
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Entertainment
Boarding
Comfort
Crew
Food
Overall
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Entertainment
Boarding
Comfort
Crew
Food
Overall
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Entertainment
Boarding
Comfort
Crew
Food
Overall
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
0%of flight departures | Early morningMidnight to 6 am |
---|---|
100%of flight departures | Morning6 am to noon |
0%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |
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