Costa Rica

Cheap flights from Chicago (CHI) to Costa Rica

How far in advance should I book a flight from Chicago to Costa Rica?

Find a great deal and save up to 22% by booking at least 53 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 $403.

What is the cheapest month to fly from Chicago to Costa Rica?

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 $292.

When is the cheapest time to fly from Chicago to Costa Rica (CHI - CR)?

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.

Cheap flights from Chicago to Costa Rica in January, February 2022

The best prices found for CHI to Costa Rica flights for January, February
Jan 25 - Feb 1
ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

7h 44m
SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

10h 01m
$173

Spirit Airlines

View Deal

Deal found 18/1/22

Jan 29 - Feb 6
ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

7h 44m
SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

9h 36m
$180

Multiple Airlines

View Deal

Deal found 19/1/22

Feb 8 - Feb 16
ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

7h 44m
SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

10h 47m
$184

Spirit Airlines

View Deal

Deal found 19/1/22

Chicago to Costa Rica 2022 flight deals

Cheap flights to Costa Rica from Chicago found for this year
Mar 23 - Mar 29
ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

7h 03m
SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

10h 50m
$173

Spirit Airlines

View Deal

Deal found 17/1/22

Mar 15 - Mar 29
ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

7h 03m
SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

10h 50m
$174

Spirit Airlines

View Deal

Deal found 18/1/22

Mar 1 - Mar 15
ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

7h 28m
SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

10h 50m
$175

Spirit Airlines

View Deal

Deal found 17/1/22

Non-stop flights to Costa Rica from Chicago

Save time with Chicago to Costa Rica direct flight deals
Apr 16 - Apr 20
ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

Nonstop

5h 09m
SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

Nonstop

5h 25m
$468

American Airlines

View Deal

Deal found 19/1/22

Apr 14 - Apr 20
ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

Nonstop

5h 09m
SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

Nonstop

5h 25m
$472

American Airlines

View Deal

Deal found 19/1/22

Apr 16 - Apr 24
ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

Nonstop

5h 09m
SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

Nonstop

5h 25m
$474

American Airlines

View Deal

Deal found 18/1/22

Last minute flights from Chicago to Costa Rica

Late deals on return flights to Costa Rica from Chicago, departing today and this week
Jan 25 - Feb 1
ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

7h 44m
SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

10h 01m
$173

Spirit Airlines

View Deal

Deal found 18/1/22

Jan 29 - Feb 6
ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

7h 44m
SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

9h 36m
$180

Multiple Airlines

View Deal

Deal found 19/1/22

Jan 29 - Feb 17
ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

7h 44m
SJO

San José Juan Santamaria Intl

ORD

Chicago O'Hare Intl

1 stop

9h 35m
$185

Multiple Airlines

View Deal

Deal found 17/1/22

One-way flights to Costa Rica from Chicago

The cheapest one-way flights from Chicago to Costa Rica
Mar 16
ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

7h 03m
$65

Spirit Airlines

View Deal

Deal found 17/1/22

Feb 2
ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

7h 44m
$67

Spirit Airlines

View Deal

Deal found 18/1/22

Mar 28
ORD

Chicago O'Hare Intl

SJO

San José Juan Santamaria Intl

1 stop

16h 20m
$73

Spirit Airlines

View Deal

Deal found 17/1/22

Related info for your journey

Useful info, stats and facts about Chicago to Costa Rica flights.

Which airlines flying from Chicago to Costa Rica have flexible cancellations due to COVID-19?

United Airlines, Copa Airlines, and Spirit Airlines are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

Can I find flights from Chicago to Costa Rica for under $200 on Cheapflights?

Yes, there are multiple flights from Chicago to Costa Rica for under $200. The cheapest flight booked recently is on Spirit Airlines for just $173, but on average you can expect to pay $186.

Are there nonstop flights from Chicago to Costa Rica for under $500 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Costa Rica under $500. A good price for a nonstop flight from Chicago to Costa Rica is less than $656.

Are there last-minute flights available from Chicago to Costa Rica for under $200?

There are currently 20+ open flights from Chicago to Costa Rica within the next 7 days for less than $200.

What are the most popular routes from Chicago to Costa Rica?

While some choose either Chicago Midway - San José Juan Santamaria Intl or Chicago O'Hare Intl - Liberia, Chicago O'Hare Intl - San José Juan Santamaria Intl is the most popular route from Chicago to Costa Rica.

What are the most popular airlines that fly from Chicago to Costa Rica?

Interjet, Major Airline and American Airlines are the most popular airlines when flying from Chicago to Costa Rica.

What are the cheapest flights from Chicago to Costa Rica?

While on average a flight from Chicago to Costa Rica is generally $517, our data shows the cheapest flight currently is $90. When looking at the most popular route, (Chicago O'Hare Intl - San José Juan Santamaria Intl), you can expect to pay $174 for that flight.

Can I fly to Costa Rica from Chicago right now?

Information is based on travel restrictions from Chicago to Costa Rica

Most visitors from Chicago can enter Costa Rica without restrictions.

COVID-19 testing requirements
Visitors from Chicago are not required to present a negative COVID-19 PCR test or antigen result upon entering Costa Rica.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Costa Rica.

Documents
Epidemiological Health Pass Form - The Health Pass can only be completed within 72 hours of arriving in the country. One form must be completed per person, including minors, without exception.

Health Insurance - Tourists may get an insurance from Costa Rican insurance companies that are registered and authorized by the General Superintendence of Insurance of Costa Rica.


Can I fly back to Chicago from Costa Rica?

Returning to Chicago from Costa Rica

COVID-19 testing requirements
Visitors from Costa Rica must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Chicago.

Quarantine requirements
Visitors from Costa Rica are not required to quarantine after entering Chicago.

Destination points for flights from Chicago to Costa Rica

Select to see more specific information for flights from Chicago to all places in Costa Rica

Top 10 airlines flying from Chicago to Costa Rica

The chart below displays the airlines Cheapflights users traveling from Chicago to Costa Rica choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
JetBlue
Cheapest$148
Average$337
FlexibilityNo cancel fee
On-time62%
COVID-19 safety
Spirit Airlines
Cheapest$179
Average$394
FlexibilityNo cancel fee
On-time65%
COVID-19 safety
United Airlines
Cheapest$203
Average$685
FlexibilityNo cancel fee
On-time69%
COVID-19 safety
Interjet
Cheapest$262
Average$393
FlexibilityNo cancel fee
On-time68%
COVID-19 safety
Air Canada
Cheapest$271
Average$563
FlexibilityNo cancel fee
On-time67%
COVID-19 safety
American Airlines
Cheapest$276
Average$595
FlexibilityNo cancel fee
On-time71%
COVID-19 safety
Delta
Cheapest$283
Average$700
FlexibilityNo cancel fee
On-timeN/A
COVID-19 safety
Copa Airlines
Cheapest$292
Average$410
FlexibilityNo cancel fee
On-time70%
COVID-19 safety
Avianca
Cheapest$326
Average$692
FlexibilityNo cancel fee
On-time71%
COVID-19 safety
Aeromexico
Cheapest$421
Average$644
FlexibilityNo cancel fee
On-timeN/A
COVID-19 safety

Hourly flight availability from Chicago to Costa Rica

See what time of day planes typically take off from Chicago to Costa Rica
0%of flight departuresEarly morningMidnight to 6 am
50%of flight departuresMorning6 am to noon
50%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM