Find a great deal and save up to 15% by booking at least 52 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 $478.
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 September, with the cheapest ticket starting at $228.
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
$194 - $310
Route
Depart
Return
Price
Chicago O'Hare IntlSan José Juan Santamaria Intl
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Do 5/30
1 stop7h 23m
San José Juan Santamaria Intl
Mo 6/3
1 stop27h 03m
Chicago O'Hare IntlSan José Juan Santamaria Intl
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Di 5/28
1 stop17h 52m
San José Juan Santamaria Intl
Mo 6/3
1 stop14h 36m
Chicago O'Hare IntlSan José Juan Santamaria Intl
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Mi 5/29
1 stop7h 23m
San José Juan Santamaria Intl
Mo 6/10
1 stop15h 41m
Chicago O'Hare IntlSan José Juan Santamaria Intl
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Mi 5/29
1 stop7h 23m
San José Juan Santamaria Intl
Do 6/6
1 stop11h 23m
Chicago O'Hare IntlSan José Juan Santamaria Intl
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Mi 5/22
1 stop18h 50m
San José Juan Santamaria Intl
Mi 5/29
1 stop9h 57m
Chicago O'Hare IntlSan José Juan Santamaria Intl
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Di 5/14
1 stop7h 23m
San José Juan Santamaria Intl
Fr 5/24
1 stop7h 56m
Chicago MidwaySan José Juan Santamaria Intl
MDW - SJO
MDWSJO
Chicago Midway
Fr 5/10
2 stops36h 30m
San José Juan Santamaria Intl
Fr 5/17
1 stop26h 45m
Chicago MidwaySan José Juan Santamaria Intl
MDW - SJO
MDWSJO
Chicago Midway
Sa 5/11
1 stop16h 55m
San José Juan Santamaria Intl
Fr 5/17
2 stops19h 37m
Chicago MidwaySan José Juan Santamaria Intl
MDW - SJO
MDWSJO
Chicago Midway
Mi 6/5
1 stop19h 23m
San José Juan Santamaria Intl
So 6/9
1 stop28h 11m
No data available for this route at this time. Please check back soon.
Crew
Entertainment
Overall
Comfort
Boarding
Food
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Crew
Entertainment
Overall
Comfort
Boarding
Food
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Crew
Entertainment
Overall
Comfort
Boarding
Food
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Crew
Entertainment
Overall
Comfort
Boarding
Food
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Crew
Entertainment
Overall
Comfort
Boarding
Food
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
Crew
Entertainment
Overall
Comfort
Boarding
Food
Reviews
Paid a lot for our exit row seats and they weren’t that roomy.
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