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
$220 - $530
Route
Depart
Return
Price
Chicago O'Hare IntlSan José Juan Santamaria Intl
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Tue 5/7
1 stop16h 45m
San José Juan Santamaria Intl
Wed 5/22
1 stop13h 12m
Chicago O'Hare IntlSan José Juan Santamaria Intl
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Tue 4/9
1 stop16h 40m
San José Juan Santamaria Intl
Wed 4/10
1 stop9h 24m
Chicago O'Hare IntlSan José Juan Santamaria Intl
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Tue 4/9
1 stop7h 27m
San José Juan Santamaria Intl
Tue 4/16
1 stop7h 47m
Chicago MidwaySan José Juan Santamaria Intl
MDW - SJO
MDWSJO
Chicago Midway
Sat 4/13
1 stop16h 45m
San José Juan Santamaria Intl
Tue 4/16
1 stop12h 45m
Chicago MidwaySan José Juan Santamaria Intl
MDW - SJO
MDWSJO
Chicago Midway
Wed 4/24
1 stop26h 11m
San José Juan Santamaria Intl
Thu 5/2
1 stop11h 06m
Chicago MidwaySan José Juan Santamaria Intl
MDW - SJO
MDWSJO
Chicago Midway
Tue 4/16
1 stop16h 20m
San José Juan Santamaria Intl
Tue 4/23
1 stop12h 45m
Chicago MidwaySan José Juan Santamaria Intl
MDW - SJO
MDWSJO
Chicago Midway
Sat 5/4
1 stop26h 26m
San José Juan Santamaria Intl
Thu 5/9
1 stop11h 06m
Chicago O'Hare IntlSan José Juan Santamaria Intl
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Wed 8/14
Nonstop6h 45m
San José Juan Santamaria Intl
Sun 8/18
Nonstop7h 55m
Chicago O'Hare IntlLiberia
ORD - LIR
ORDLIR
Chicago O'Hare Intl
Sat 4/20
2 stops31h 46m
Liberia
Thu 4/25
2 stops25h 10m
Entertainment
Boarding
Crew
Food
Overall
Comfort
Reviews
This is trivial however, I was in row 11B there aren’t any windows in that row. I enjoy being able to look out the window.
Entertainment
Boarding
Crew
Food
Overall
Comfort
Reviews
This is trivial however, I was in row 11B there aren’t any windows in that row. I enjoy being able to look out the window.
Entertainment
Boarding
Crew
Food
Overall
Comfort
Reviews
This is trivial however, I was in row 11B there aren’t any windows in that row. I enjoy being able to look out the window.
Entertainment
Boarding
Crew
Food
Overall
Comfort
Reviews
This is trivial however, I was in row 11B there aren’t any windows in that row. I enjoy being able to look out the window.
Entertainment
Boarding
Crew
Food
Overall
Comfort
Reviews
This is trivial however, I was in row 11B there aren’t any windows in that row. I enjoy being able to look out the window.
Entertainment
Boarding
Crew
Food
Overall
Comfort
Reviews
This is trivial however, I was in row 11B there aren’t any windows in that row. I enjoy being able to look out the window.
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 |
Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Chicago to Costa Rica. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.
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