Cheap flights from Chicago (CHI) to San José (SJO)

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The best prices from Chicago to San José Juan Santamaria Intl are usually found in September or May, booked 54 days in advance, depart on a Monday or Tuesday and return on a Tuesday

Home Costa Rica San José Cheap flights from Chicago to San José

How to find the cheapest flight from
Chicago (CHI) to San José (SJO)

All the information you need to plan the best CHI to SJO flight in 2021: compare Chicago to San José flight prices with the expected peak season, weather and rainfall in San José.
CHI - SJO
Price
$351 - $641
SJO
Temperature
64.4 - 69.8 °F
SJO
Precipitation
0 - 11.8 inches

Popular in

December

High demand for flights, 36% potential price rise

Cheapest in

September

Best time to find cheap flights, 15% potential price drop

Round-trip from

$351

From Chicago (CHI) to San José Juan Santamaria Intl

One-way from

$135

One-way flight from Chicago (CHI) to San José Juan Santamaria Intl

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest month to fly from Chicago to San José, San José Province?

The best pricing can be found in the month of September. Prices to San José, San José Province from Chicago average $413. You can even find prices in September for less than $413, as users have found deals to San José, San José Province from as low as $292. The month of December appears to be one of the more expensive times to travel to San José, San José Province from Chicago. Flying in the targeted month can save you up to 55%.

When is the cheapest time to fly from Chicago to San José, San José Province (CHI - SJO)?

One of the essential ways to save on airfare from Chicago to San José, San José Province is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 15% on airfare.

How far in advance should I book a flight from Chicago to San José, San José Province?

To save up to 22% on this flight, we recommend booking at least 53 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago to San José, San José Province from $403 1-2 weeks out and tickets from $497 for flights departing within the next 72 hours.

What is the cheapest day to fly round-trip from Chicago to San José, San José Province?

Users have found that leaving on a Sunday can be a cost-effective option. It’s possible to save up to 20% on your flight compared to booking on days when demand is much higher.

Cheap flights from Chicago to San José in December, January 2022

The best prices found for CHI to SJO flights for December, January
3 Dec - 5 Dec
$182pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJO
San José Juan Santamaria Intl
SJO
San José Juan Santamaria Intl
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
3 Dec - 5 Dec
$194pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJO
San José Juan Santamaria Intl
SJO
San José Juan Santamaria Intl
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
3 Dec - 5 Dec
$198pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJO
San José Juan Santamaria Intl
SJO
San José Juan Santamaria Intl
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl

Chicago to San José 2022 flight deals

Cheap flights to San José from Chicago found for this year
3 Dec - 5 Dec
$182pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJO
San José Juan Santamaria Intl
SJO
San José Juan Santamaria Intl
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
3 Dec - 5 Dec
$194pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJO
San José Juan Santamaria Intl
SJO
San José Juan Santamaria Intl
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
3 Dec - 5 Dec
$198pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJO
San José Juan Santamaria Intl
SJO
San José Juan Santamaria Intl
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl

Non-stop flights to San José from Chicago

Save time with Chicago to San José direct flight deals
25 Feb - 6 Mar
$467pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
SJO
San José Juan Santamaria Intl
SJO
San José Juan Santamaria Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
19 Apr - 24 Apr
$472pp
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
SJO
San José Juan Santamaria Intl
SJO
San José Juan Santamaria Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
11 Mar - 13 Mar
$509pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
SJO
San José Juan Santamaria Intl
SJO
San José Juan Santamaria Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to San José

Late deals on round-trip flights to San José from Chicago, departing today and this week
9 Dec - 20 Dec
$198pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJO
San José Juan Santamaria Intl
SJO
San José Juan Santamaria Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
12 Dec - 19 Dec
$199pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJO
San José Juan Santamaria Intl
SJO
San José Juan Santamaria Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
9 Dec - 21 Dec
$205pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
SJO
San José Juan Santamaria Intl
SJO
San José Juan Santamaria Intl
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl

One-way flights to Juan Santamaria Intl from Chicago

The cheapest one-way flights from Chicago to San José
6:30 am - 4:58 am
Multiple Airlines
3 Stops
22h 28m
ORD - SJO
Multiple Airlines
$135
Kiwi.com
6:04 pm - 8:37 am
Frontier
2 Stops
38h 33m
ORD - SJO
Frontier
$141
Kiwi.com
12:25 am - 7:52 am
Spirit Airlines
1 Stop
7h 27m
ORD - SJO
Spirit Airlines
$144
mytrip.com

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Chicago</span> to <span class="emphasized">San José</span> flights.

Flight FAQs

From Chicago to San José

What airport do you fly into for flights to San José from Chicago?

Located just 8.8 mi from the city center, San José Juan Santamaria Intl is the airport most travelers will use when flying to San José from Chicago. Booking flights from Chicago to Juan Santamaria Intl (SJO) should be relatively easy as there are 0 daily inbound flights from Chicago from 11 different airlines.

Which airlines flying from Chicago to San José Juan Santamaria Intl have flexible cancellations due to COVID-19?

Some of our airline partners flying from Chicago to San José Juan Santamaria Intl have new flexible policies in place due to COVID-19. United Airlines, Copa Airlines, and Spirit Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like United Airlines with this kind of flexibility.

Can I find flights from Chicago to San José, San José Province for under $200 on Cheapflights?

Yes, there are multiple flights from Chicago to San José, San José Province for under $200. The cheapest flight booked recently is on Multiple Airlines for just $199, but on average you can expect to pay $217.

Are there nonstop flights from Chicago to San José, San José Province for under $500 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to San José, San José Province under $500. A good price for a nonstop flight from Chicago to San José, San José Province is less than $675.

Are there last-minute flights available from Chicago to San José, San José Province for under $200?

There are currently 20+ open flights from Chicago to San José, San José Province within the next 7 days for less than $200.

What are the cheapest airlines flying from Chicago to San José, San José Province round-trip?

Currently priced at $207, Spirit Airlines will fly you from Chicago to San José, San José Province and back. In addition to Spirit Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on Frontier for as low as $234. Spirit Airlines is currently priced 49% below the average price you’ll pay for this route.

What are the cheapest airlines to fly from Chicago to San José, San José Province one-way?

The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $64. However, be on the lookout for offers from Spirit Airlines and JetBlue, as they are both options that can get you from Chicago to San José, San José Province for a low price.

What are the cheapest flights from Chicago to San José, San José Province?

The cheapest flight price from Chicago to San José, San José Province is $90. On average you can expect to pay $517. The most popular route, (Chicago O'Hare Intl - San José Juan Santamaria Intl), can usually be booked for $202.

What are the most popular airlines that fly from Chicago to San José, San José Province?

Consider Interjet, Major Airline or American Airlines when booking your flight. These represent the most popular airlines when flying from Chicago to San José, San José Province.

Related searches

Flights to San José (SJO) from Chicago
Flights to Chicago Flights to San José Flights from Chicago

COVID Restrictions

View COVID Travel Restrictions for San José (SJO)

Do I need a COVID test to fly to San José from Chicago?

Information is based on travel restrictions from Chicago to San José Juan Santamaria Intl

Most visitors from Chicago can enter San José Juan Santamaria Intl 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 San José Juan Santamaria Intl.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering San José Juan Santamaria Intl.

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.


Do I need a test to fly back to Chicago from San José?

Returning to Chicago from San José Juan Santamaria Intl

COVID-19 testing requirements
Visitors from San José Juan Santamaria Intl must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from San José Juan Santamaria Intl are not required to quarantine after entering Chicago.

Hide COVID Travel Restrictions for San José (SJO)

Alternative routes for Chicago to San José

See prices for flight routes from nearby airports that may be better suited for you.
Moline Quad-City to Liberia from $372 pp
Bloomington Bloomington-Normal to San José Juan Santamaria Intl from $784 pp

Destination information for San José

Things to know before you go - useful duration and weather info for your trip from Chicago to San José.
Today's exchange rate
$1 = ₡616.10
Average temperature for December in San José
82.4 °F
Avg rainfall for December in San José
1.7 ″

Airports servicing Chicago

O'Hare Intl (ORD)
Midway (MDW)
Rockford (RFD)

Airports servicing San José

San José (SJO)

Top 10 airlines flying from Chicago to San José Juan Santamaria Intl

The chart below displays the airlines Cheapflights users traveling from Chicago to San José choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
JetBlue 		$148 $337 No cancel fee 62%
Spirit Airlines 		$179 $394 No cancel fee 65%
United Airlines 		$203 $549 No cancel fee 69%
Interjet 		$262 $393 No cancel fee 68%

We couldn't confirm the COVID-19 safety measures taken by Interjet. Please check directly on their website for additional information.
Air Canada 		$271 $505 No cancel fee 67%
Copa Airlines 		$292 $418 No cancel fee 70%
Delta 		$325 $645 No cancel fee N/A
Avianca 		$326 $692 No cancel fee 71%
American Airlines 		$328 $563 No cancel fee 71%
Aeromexico 		$421 $644 No cancel fee N/A

Popular flight searches

Check out other popular destinations found by fellow travelers in 2021.

Hourly flight availability from Chicago to San José

See what time of day planes typically take off from Chicago towards San José.
Afternoon Noon to 6 PM 100% of CHI to SJO departures
Early morning Midnight to 6 AM 0% of CHI to SJO departures
Morning 6 AM to noon 0% of CHI to SJO departures
Evening 6 PM to midnight 0% of CHI to SJO departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Chicago to San José
See how many times per day planes take to the skies headed from Chicago to San José.
Sunday
0 flights
Monday
0 flights
Tuesday
1 daily flight
Wednesday
0 flights
Thursday
1 daily flight
Friday
0 flights
Saturday
1 daily flight
Home Costa Rica San José Cheap flights from Chicago to San José