Find flights
Deals
Insights
When to book
FAQs & Tips
Direct Flights

ORD - SJO

£313 Find cheap flights from Chicago to San José

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to San José departing on 20/7. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Tue 2/7
Tue 9/7

Search hundreds of travel sites at once for deals on flights to San José

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San José, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San José, as well as popular online travel agencies
In the last 7 days, travellers have searched 41,909,192 times on KAYAK, and here's why:

Save 28% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Chicago to San José (ORD-SJO)

 
These are the cheapest deals for flights from Chicago to San José currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent return flight deals from Chicago to San José

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to San José.

Recent one-way flight deals from Chicago to San José

Only flying one-way? Below are some of the best one-way flight deals from Chicago to San José found on KAYAK recently.

Recent last-minute flight deals from Chicago to San José

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Chicago to San José.

Recent direct flight deals from Chicago to San José

The latest deals for direct flights from Chicago to San José so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Chicago to San José

Find recent round-trip train or bus tickets from Chicago to San José.

All round-trip flight deals to San José

The cheapest plane tickets to San José found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
06:54 - 18:50ORD-SJO
12h 56m2 stops
02:04 - 23:59SJO-ORD
20h 55m2 stops
Thu, 5 Sep - Mon, 9 Sep
07:27 - 23:15ORD-SJO
16h 48m2 stops
02:04 - 23:59SJO-ORD
20h 55m2 stops
Tue, 10 Sep - Mon, 16 Sep
09:05 - 20:44ORD-SJO
12h 39m1 stop
21:44 - 08:14SJO-ORD
9h 30m1 stop
£399JetBlue
Find Deal
Fri, 4 Oct - Sun, 13 Oct
07:54 - 18:51ORD-SJO
11h 57m1 stop
05:50 - 23:21SJO-ORD
17h 31m1 stop
£461Copa Airlines
Find Deal
Fri, 1 Nov - Fri, 8 Nov
06:54 - 15:48ORD-SJO
8h 54m1 stop
18:05 - 12:16SJO-ORD
18h 11m1 stop
£483Copa Airlines
Find Deal
Fri, 8 Nov - Sat, 23 Nov
17:55 - 07:30ORD-SJO
13h 35m2 stops
07:00 - 16:35SJO-ORD
9h 35m1 stop
£490Delta
Find Deal
Sat, 16 Nov - Sat, 23 Nov
07:35 - 12:56ORD-SJO
5h 21mdirect
14:05 - 19:30SJO-ORD
5h 25mdirect
£538United Airlines
Find Deal
Sat, 9 Nov - Sat, 16 Nov
14:10 - 06:25ORD-SJO
16h 15m1 stop
14:05 - 19:30SJO-ORD
5h 25mdirect
£541United Airlines
Find Deal
Fri, 8 Nov - Sat, 23 Nov
11:19 - 21:08ORD-SJO
9h 49m1 stop
07:00 - 21:04SJO-ORD
14h 04m1 stop
£542Delta
Find Deal
Tue, 26 Nov - Mon, 2 Dec
10:35 - 21:56ORD-SJO
12h 21m1 stop
23:56 - 17:43SJO-ORD
16h 47m1 stop
£690JetBlue
Find Deal
Sat, 29 Jun - Sat, 6 Jul
07:41 - 11:55ORD-SJO
5h 14mdirect
£313United Airlines
Find Deal
Sat, 20 Jul
01:55 - 12:09ORD-SJO
11h 14m1 stop
£352Aeromexico
Find Deal
Thu, 3 Oct
01:55 - 04:32ORD-SJO
27h 37m1 stop
£403Aeromexico
Find Deal
Sat, 20 Jul
01:55 - 23:43ORD-SJO
22h 48m1 stop
£450Aeromexico
Find Deal
Sun, 18 Aug
02:01 - 04:47ORD-SJO
27h 46m1 stop
£462Aeromexico
Find Deal
Wed, 19 Jun
02:01 - 04:47ORD-SJO
27h 46m1 stop
£473Aeromexico
Find Deal
Thu, 20 Jun
02:01 - 23:43ORD-SJO
22h 42m1 stop
£538Aeromexico
Find Deal
Fri, 21 Jun
02:01 - 12:09ORD-SJO
11h 08m1 stop
£544Aeromexico
Find Deal
Fri, 28 Jun
00:59 - 20:00ORD-SJO
44h 01m2 stops
£586Alaska Airlines
Find Deal
Mon, 24 Jun
11:55 - 21:56ORD-SJO
34h 01m3 stops
£1,532Turkish Airlines
Find Deal
Sun, 3 Nov
14:10 - 11:54ORD-SJO
22h 44m2 stops
07:42 - 05:18SJO-ORD
20h 36m1 stop
£1,032Aeromexico
Find Deal
Mon, 3 Jun - Mon, 10 Jun
07:47 - 11:54ORD-SJO
29h 07m1 stop
07:42 - 05:18SJO-ORD
20h 36m1 stop
£1,039Aeromexico
Find Deal
Mon, 3 Jun - Mon, 10 Jun
02:01 - 11:54ORD-SJO
10h 53m1 stop
07:42 - 23:58SJO-ORD
15h 16m1 stop
£1,051Aeromexico
Find Deal
Wed, 5 Jun - Sun, 9 Jun
21:20 - 20:00ORD-SJO
23h 40m2 stops
00:33 - 04:40SJO-ORD
27h 07m3 stops
£1,094Alaska Airlines
Find Deal
Tue, 4 Jun - Wed, 5 Jun
17:28 - 20:00ORD-SJO
27h 32m3 stops
00:33 - 04:40SJO-ORD
27h 07m3 stops
£1,108Alaska Airlines
Find Deal
Tue, 4 Jun - Wed, 5 Jun
14:10 - 11:54ORD-SJO
22h 44m2 stops
07:42 - 12:25SJO-ORD
27h 43m2 stops
£1,110Aeromexico
Find Deal
Mon, 3 Jun - Mon, 10 Jun
02:01 - 23:59ORD-SJO
22h 58m1 stop
07:42 - 14:32SJO-ORD
29h 50m1 stop
£1,258Aeromexico
Find Deal
Wed, 5 Jun - Sat, 8 Jun
07:35 - 12:56ORD-SJO
5h 21mdirect
14:05 - 19:30SJO-ORD
5h 25mdirect
£538United Airlines
Find Deal
Sat, 9 Nov - Sat, 16 Nov
07:41 - 11:55ORD-SJO
5h 14mdirect
13:00 - 19:28SJO-ORD
5h 28mdirect
£590United Airlines
Find Deal
Sat, 27 Jul - Sat, 3 Aug
07:41 - 11:55ORD-SJO
5h 14mdirect
13:00 - 19:28SJO-ORD
5h 28mdirect
£621United Airlines
Find Deal
Sat, 3 Aug - Sat, 10 Aug
07:41 - 11:55ORD-SJO
5h 14mdirect
13:00 - 19:28SJO-ORD
5h 28mdirect
£698United Airlines
Find Deal
Sat, 15 Jun - Sat, 22 Jun
07:41 - 11:55ORD-SJO
5h 14mdirect
13:00 - 19:28SJO-ORD
5h 28mdirect
£840United Airlines
Find Deal
Sat, 15 Jun - Sat, 22 Jun
07:35 - 12:56ORD-SJO
5h 21mdirect
14:05 - 19:30SJO-ORD
5h 25mdirect
£1,460United Airlines
Find Deal
Sat, 23 Nov - Sat, 30 Nov

Flights from Chicago to San José - Travel Insights & Trends

Get data-powered insights and trends into flights from Chicago to San José to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago to San José?

The average price of all flights from Chicago O'Hare Intl Airport to San José, San José Province clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to San José on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Chicago to San José. For your return ticket, we recommend flying on a Monday and avoiding Thursdays for the best deals.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to San José, San José Province?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago O'Hare Intl Airport to San José, San José Province, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago O'Hare Intl Airport to San José, San José Province is August, where tickets cost £333 on average. On the other hand, the most expensive months are December and March, where the average cost of tickets is £586 and £560 respectively.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to San José, San José Province?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago O'Hare Intl Airport to San José, San José Province, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago O'Hare Intl Airport to San José, San José Province, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 33 days before departure.

Which airlines provide the cheapest flights from Chicago to San José?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 3 days, United Airlines offered the best one-way deal for that route, at £313. KAYAK users also found Chicago to San José return flights on JetBlue from £399 and on Copa Airlines from £461.

How many flights are there between Chicago O'Hare Intl Airport and San José, San José Province per day?

There is a maximum of 1 direct flight a day that takes off from Chicago O'Hare Intl Airport and lands in San José, San José Province, with an average flight time of 5h 14m. The most common departure time is 07:00 and most flights take off in the morning. Each week, there are 1 flights.

How long does a flight from Chicago to San José take?

The average direct flight takes 5h 14m, covering a distance of 2,220 miles.

What’s the earliest departure time from Chicago to San José?

Early birds can take the earliest flight from Chicago O'Hare Intl Airport at 07:41 and will be landing in San José, San José Province at 11:55.

What’s the latest departure time from Chicago to San José?

If you prefer to fly at night, the latest flight from Chicago O'Hare Intl Airport to San José, San José Province jets off at 07:41 and lands at 11:55.

Good to know - Cheap tickets from Chicago to San José

Low season

October

High season

December

Cheapest flight

£313
Best time to beat the crowds (15% less expensive on average)
Most popular time to fly (32% more expensive on average)
Flight from Chicago to San José

When to book flights from Chicago to San José

Are your dates flexible? Find out the best times to travel from Chicago to San José based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to San José flights

  • What is the luggage allowance on Aeromexico flights from Chicago O'Hare Airport to San José?

    For flights from Chicago O'Hare Airport to San José with Aeromexico, the maximum weight allowance is 55 pounds for all regular and Premiere fares and the maximum linear dimension limit is 62 inches. Passengers may bring one carry-on bag of up to 22 lbs plus one personal item. Fees apply for oversize and overweight luggage and will depend on the fare type and flight route.

  • How do I get from San Jose Airport (SJO) to the city center?

    The bus is the most affordable way to get to the city center. The bus stop is located just outside the airport terminal. Take the Alajuela-San Jose bus and get off at the last stop, which is in the center of San Jose. The trip takes around 45 minutes. Taxis are also available at the airport and can bring you directly to your destination in the city center.

  • What seat selection options are available on Avianca flights from Chicago O'Hare Airport to San José?

    Avianca offers various seat selection options on flights from Chicago O'Hare Airport to San José. Passengers can choose seats from the available standard seating options at no additional cost during the check-in process. Avianca also offers preferred seats for an additional fee. These seats are typically located in the front rows of the cabin or have extra legroom.

  • What services are offered by Copa Airlines to economy class passengers on flights from Chicago O'Hare Airport to San Jose?

    Copa Airlines offers a variety of services to economy class passengers on its flights from Chicago O'Hare Airport to San José. Economy class passengers can enjoy Copa Airlines' in-flight entertainment system, which includes movies, TV shows, and music. Passengers in economy class also receive complimentary meals and drinks on all Copa Airlines flights.

  • What is the cheapest flight from Chicago O'Hare Intl Airport to San José, San José Province?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to San José, San José Province was £399 for a one-way ticket and £423 for a return.

  • Which airports will I be using when flying from Chicago to San José?

    Chicago and San José are both served by 1 main airport. You will leave Chicago from Chicago O'Hare Intl and will be arriving at San José Juan Santamaria Intl.

  • Which aircraft models fly most regularly from Chicago to San José?

    The Airbus A320-100/200 is the aircraft model that flies most regularly on the Chicago to San José flight route.

  • Which airline alliances offer flights from Chicago to San José?

    Star Alliance is the only airline alliance operating flights between Chicago and San José.

  • On which days can I fly direct from Chicago to San José?

    You can catch a direct flight from Chicago to San José on Saturday.

  • How does KAYAK find such low prices on flights from Chicago to San José?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to San José.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to San José?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San José from Chicago is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to San José?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly to San José with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to San José?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to San José from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

KAYAK’s top tips for finding a cheap flight from Chicago O'Hare Intl Airport to San José, San José Province

  • US citizens require a valid visa to enter Costa Rica, including for flights from Chicago O'Hare International Airport (ORD) to San José (SJO). The type of visa needed depends on the purpose of travel, and there are several options such as tourist visas, work visas, and student visas.
  • Spirit Airlines assists passengers who require a wheelchair to get to and from their gate or assistance in boarding and disembarking the aircraft. The airline also offers special seating options for passengers with reduced mobility on flights from Chicago O'Hare Airport to San José, including seats with movable armrests and bulkhead seats.
  • Air Canada allows pets to travel in the cabin or as checked baggage on flights from Chicago O'Hare Airport to San José. For pets traveling in the cabin, only dogs and cats are permitted and the pet carrier will count as one of the traveler's carry-on items. For pets traveling as checked baggage, Air Canada only accepts cats and dogs, and they must be at least 12 weeks old.
  • JetBlue offers early boarding for families with children under the age of 2 and one accompanying adult on flights from Chicago O'Hare Airport to San José. This allows families to get settled on the plane before other passengers.
  • Frontier Airlines operates flights from Chicago O'Hare Airport to San José with fuel-efficient aircraft equipped with advanced technology and optimized performance capabilities to reduce carbon emissions.
See more tips

Prefer to fly direct from Chicago to San José?

Find which airlines fly direct from O'Hare Intl to Juan Santamaria Intl, which days they fly and book direct flights.

Direct departures

Chicago O'Hare Intl to San José Juan Santamaria Intl

Saturday

United Airlines

United Airlines

See more direct flights

Direct returns

San José Juan Santamaria Intl to Chicago O'Hare Intl

Saturday

United Airlines

United Airlines

See more direct flights
See more direct flights

Book cheap flights from Chicago to San José

Cheapest flights to San José from Chicago found in 2024

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to San José found on KAYAK in the last 72 hours.
20/7Sat
directUnited Airlines
5h 14mORD-SJO
£313
3/10Thu
1 stopAeromexico
11h 14mORD-SJO
£352
20/7Sat
1 stopAeromexico
27h 37mORD-SJO
£403
18/8Sun
1 stopAeromexico
22h 48mORD-SJO
£450
19/6Wed
1 stopAeromexico
27h 46mORD-SJO
£462
20/6Thu
1 stopAeromexico
27h 46mORD-SJO
£473
21/6Fri
1 stopAeromexico
22h 42mORD-SJO
£538
28/6Fri
1 stopAeromexico
11h 08mORD-SJO
£544
24/6Mon
2 stopsAlaska Airlines
44h 01mORD-SJO
£586
3/11Sun
3 stopsTurkish Airlines
34h 01mORD-SJO
£1,532

Search by stops

Search by airline

Search by price

Last minute flights from Chicago to San José

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to San José that are departing in the next 10 days.
3/6Mon
multi-stopAeromexico
22h 44mORD-SJO
10/6Mon
multi-stopAeromexico
20h 36mSJO-ORD
£1,032
3/6Mon
multi-stopAeromexico
29h 07mORD-SJO
10/6Mon
multi-stopAeromexico
20h 36mSJO-ORD
£1,039
5/6Wed
multi-stopAeromexico
10h 53mORD-SJO
9/6Sun
multi-stopAeromexico
15h 16mSJO-ORD
£1,051
4/6Tue
multi-stopAlaska Airlines
23h 40mORD-SJO
5/6Wed
multi-stopAlaska Airlines
27h 07mSJO-ORD
£1,094
4/6Tue
multi-stopAlaska Airlines
27h 32mORD-SJO
5/6Wed
multi-stopAlaska Airlines
27h 07mSJO-ORD
£1,108
3/6Mon
multi-stopAeromexico
22h 44mORD-SJO
10/6Mon
multi-stopAeromexico
27h 43mSJO-ORD
£1,110
5/6Wed
multi-stopAeromexico
22h 58mORD-SJO
8/6Sat
multi-stopAeromexico
29h 50mSJO-ORD
£1,258

Search by stops

Search by airline

Search by price

Chicago - San José Flights

Departure:

Chicago (ORD)United States

Destination:

San José (SJO)Costa Rica

Return flight deals:

San José - Chicago

Cabin classes:

Browse origins:

  • Flights » 
  • Chicago O'Hare Airport

Browse destinations:

  • Flights » 
  • Worldwide » 
  • San José