Round-trip from | $286 (Priceline) |
---|---|
One-way from | $83 (Priceline) |
Popular in | December |
Cheapest in | July |
Average price | $449 |
Good round-trip deal | $511 or less |
Good one-way deal | $207 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Thu 8/21
8:47 pm-11:12 am
2 stops15h 25m
San José Juan Santamaria Intl
Sat 8/23
12:18 pm-7:42 pm
2 stops30h 24m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Sat 8/2
5:01 am-12:31 pm
1 stop8h 30m
San José Juan Santamaria Intl
Sat 8/9
1:47 pm-11:29 pm
1 stop8h 42m
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sun 8/24
5:45 am-11:35 am
1 stop6h 50m
San José Juan Santamaria Intl
Wed 8/27
1:40 pm-11:20 pm
1 stop8h 40m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Wed 7/9
6:00 am-10:05 pm
1 stop17h 05m
San José Juan Santamaria Intl
Fri 7/11
11:59 pm-10:59 am
1 stop10h 00m
ChicagoSan José
ORD - SJO
ORDSJO
Chicago O'Hare Intl
Mon 8/25
5:05 am-11:12 am
1 stop7h 07m
San José Juan Santamaria Intl
Fri 8/29
4:13 pm-11:05 am
1 stop17h 52m
ChicagoSan José
MDW - SJO
MDWSJO
Chicago Midway
Sat 8/16
9:12 pm-10:32 am
1 stop14h 20m
San José Juan Santamaria Intl
Sat 8/23
12:18 pm-1:56 pm
2 stops24h 38m
ChicagoLiberia
ORD - LIR
ORDLIR
Chicago O'Hare Intl
Tue 8/12
5:45 am-12:00 pm
1 stop7h 15m
Liberia
Thu 8/21
1:25 pm-11:56 pm
1 stop9h 31m
ChicagoLiberia
ORD - LIR
ORDLIR
Chicago O'Hare Intl
Tue 8/12
8:41 pm-11:25 am
2 stops15h 44m
Liberia
Fri 8/22
12:30 pm-10:59 pm
1 stop9h 29m
ChicagoLiberia
ORD - LIR
ORDLIR
Chicago O'Hare Intl
Sun 8/10
7:52 am-11:53 am
Nonstop5h 01m
Liberia
Sat 8/16
1:03 pm-7:28 pm
Nonstop5h 25m
ChicagoLiberia
MDW - LIR
MDWLIR
Chicago Midway
Sun 7/27
5:15 am-11:35 am
1 stop7h 20m
Liberia
Sat 8/2
11:50 am-11:00 pm
1 stop10h 10m
Currently, September is the cheapest month in which you can book a flight from Chicago to Costa Rica (average of $398). Flying from Chicago to Costa Rica in March is currently the most expensive (average of $555). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
When flying from Chicago to Costa Rica, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 30% versus a flight in the morning.
Travelers seeking maximum savings on their Chicago to Costa Rica flight should consider departing on Friday afternoons when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Comfort
Food
Overall
Crew
Entertainment
Boarding
Reviews
Surinder,May 2025
SEA - YYZ
Comfort
Food
Overall
Crew
Entertainment
Boarding
Reviews
Surinder,May 2025
SEA - YYZ
Comfort
Food
Overall
Crew
Entertainment
Boarding
Reviews
Surinder,May 2025
SEA - YYZ
Comfort
Food
Overall
Crew
Entertainment
Boarding
Reviews
Surinder,May 2025
SEA - YYZ
Comfort
Food
Overall
Crew
Entertainment
Boarding
Reviews
Surinder,May 2025
SEA - YYZ
Comfort
Food
Overall
Crew
Entertainment
Boarding
Reviews
Surinder,May 2025
SEA - YYZ
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$274 | Average$449 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$317 | Average$459 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$345 | Average$635 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$367 | Average$608 | FlexibilityNo cancel fee | On-time70% | |
Cheapest$438 | Average$726 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$444 | Average$717 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$477 | Average$661 | FlexibilityNo cancel fee | On-time63% | |
Cheapest$480 | Average$808 | FlexibilityNo cancel fee | On-time69% |