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ORD - SJO

£203 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 29/8. 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
Sat 15/6
Sat 22/6

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 42,211,976 times on KAYAK, and here's why:

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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
10:00 - 23:15ORD-SJO
14h 15m2 stops
05:10 - 20:32SJO-ORD
14h 22m2 stops
Mon, 12 Aug - Sat, 24 Aug
07:32 - 23:15ORD-SJO
16h 43m2 stops
05:10 - 09:00SJO-ORD
26h 50m2 stops
Tue, 6 Aug - Thu, 15 Aug
10:00 - 23:15ORD-SJO
14h 15m2 stops
05:10 - 08:25SJO-ORD
26h 15m2 stops
Mon, 12 Aug - Mon, 19 Aug
09:05 - 20:44ORD-SJO
12h 39m1 stop
21:44 - 08:14SJO-ORD
9h 30m1 stop
£363JetBlue
Find Deal
Fri, 20 Sep - Fri, 4 Oct
09:05 - 20:44ORD-SJO
12h 39m1 stop
21:44 - 08:14SJO-ORD
9h 30m1 stop
£366JetBlue
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Fri, 20 Sep - Thu, 3 Oct
06:56 - 15:59ORD-SJO
9h 03m1 stop
08:07 - 23:21SJO-ORD
15h 14m1 stop
£486Copa Airlines
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Sat, 9 Nov - Sat, 16 Nov
07:35 - 12:56ORD-SJO
5h 21mdirect
14:05 - 19:30SJO-ORD
5h 25mdirect
£541United Airlines
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Sat, 9 Nov - Sat, 16 Nov
10:35 - 20:39ORD-SJO
10h 04m1 stop
14:05 - 19:30SJO-ORD
5h 25mdirect
£544United Airlines
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Sat, 9 Nov - Sat, 16 Nov
08:45 - 20:13ORD-SJO
12h 28m2 stops
07:00 - 20:58SJO-ORD
12h 58m2 stops
£697Delta
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Wed, 29 May - Tue, 11 Jun
07:10 - 20:27ORD-SJO
14h 17m2 stops
07:00 - 21:03SJO-ORD
13h 03m2 stops
£783Delta
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Sat, 15 Jun - Sat, 22 Jun
09:17 - 23:15ORD-SJO
14h 58m2 stops
Thu, 29 Aug
10:00 - 23:15ORD-SJO
14h 15m2 stops
Mon, 14 Oct
01:55 - 23:36ORD-SJO
22h 41m1 stop
£350Aeromexico
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Mon, 26 Aug
01:55 - 11:48ORD-SJO
10h 53m1 stop
£397Aeromexico
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Sun, 13 Oct
02:01 - 23:59ORD-SJO
22h 58m1 stop
£401Aeromexico
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Wed, 5 Jun
02:01 - 23:59ORD-SJO
22h 58m1 stop
£467Aeromexico
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Tue, 4 Jun
02:01 - 23:59ORD-SJO
22h 58m1 stop
£470Aeromexico
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Tue, 4 Jun
01:55 - 12:09ORD-SJO
11h 14m1 stop
£485Aeromexico
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Fri, 12 Jul
00:45 - 20:00ORD-SJO
44h 15m2 stops
£931Alaska Airlines
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Sat, 8 Jun
20:30 - 22:04ORD-SJO
50h 34m3 stops
£2,583Turkish Airlines
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Wed, 10 Jul
19:07 - 09:21ORD-SJO
15h 14m1 stop
09:36 - 23:29SJO-ORD
12h 53m1 stop
£422Spirit Airlines
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Sat, 18 May - Tue, 21 May
06:00 - 18:50ORD-SJO
13h 50m2 stops
06:10 - 14:49SJO-ORD
31h 39m2 stops
Sat, 18 May - Fri, 24 May
06:00 - 18:50ORD-SJO
13h 50m2 stops
02:04 - 19:33SJO-ORD
40h 29m2 stops
Sat, 18 May - Thu, 23 May
06:10 - 12:47ORD-SJO
7h 37m1 stop
00:59 - 17:40SJO-ORD
15h 41m1 stop
£466Spirit Airlines
Find Deal
Sat, 18 May - Mon, 20 May
06:10 - 12:47ORD-SJO
7h 37m1 stop
00:59 - 19:45SJO-ORD
17h 46m2 stops
£495Spirit Airlines
Find Deal
Sat, 18 May - Mon, 20 May
06:10 - 12:47ORD-SJO
7h 37m1 stop
10:11 - 06:30SJO-ORD
19h 19m2 stops
£592Spirit Airlines
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Sat, 18 May - Tue, 21 May
02:01 - 11:48ORD-SJO
10h 47m1 stop
07:36 - 12:16SJO-ORD
27h 40m2 stops
£1,080Aeromexico
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Sun, 19 May - Sun, 26 May
02:01 - 11:48ORD-SJO
10h 47m1 stop
13:36 - 00:10SJO-ORD
9h 34m1 stop
£1,081Aeromexico
Find Deal
Sat, 18 May - Sun, 4 Aug
02:01 - 11:48ORD-SJO
10h 47m1 stop
13:17 - 12:16SJO-ORD
21h 59m2 stops
£1,088Aeromexico
Find Deal
Fri, 17 May - Tue, 21 May
02:01 - 11:48ORD-SJO
10h 47m1 stop
13:17 - 05:18SJO-ORD
15h 01m1 stop
£1,112Aeromexico
Find Deal
Sun, 19 May - Sun, 26 May
07:35 - 12:56ORD-SJO
5h 21mdirect
14:05 - 19:30SJO-ORD
5h 25mdirect
£541United Airlines
Find Deal
Sat, 9 Nov - Sat, 16 Nov
07:41 - 11:55ORD-SJO
5h 14mdirect
13:00 - 19:28SJO-ORD
5h 28mdirect
£660United Airlines
Find Deal
Sat, 3 Aug - Sat, 10 Aug
07:41 - 11:55ORD-SJO
5h 14mdirect
13:00 - 19:28SJO-ORD
5h 28mdirect
£686United Airlines
Find Deal
Sat, 15 Jun - Sat, 22 Jun

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 £334 on average. On the other hand, the most expensive months are December and March, where the average cost of tickets is £590 and £562 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 5 days 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, Aeromexico offered the best one-way deal for that route, at £350. KAYAK users also found Chicago to San José return flights on JetBlue from £363 and on Copa Airlines from £486.

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

£203
Best time to beat the crowds (21% 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 £257 for a one-way ticket and £394 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.
29/8Thu
2 stops
14h 58mORD-SJO
£203
14/10Mon
2 stops
14h 15mORD-SJO
£224
26/8Mon
1 stopAeromexico
22h 41mORD-SJO
£350
13/10Sun
1 stopAeromexico
10h 53mORD-SJO
£397
5/6Wed
1 stopAeromexico
22h 58mORD-SJO
£401
4/6Tue
1 stopAeromexico
22h 58mORD-SJO
£467
4/6Tue
1 stopAeromexico
22h 58mORD-SJO
£470
12/7Fri
1 stopAeromexico
11h 14mORD-SJO
£485
8/6Sat
2 stopsAlaska Airlines
44h 15mORD-SJO
£931
10/7Wed
3 stopsTurkish Airlines
50h 34mORD-SJO
£2,583

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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.
18/5Sat
multi-stopSpirit Airlines
15h 14mORD-SJO
21/5Tue
multi-stopSpirit Airlines
12h 53mSJO-ORD
£422
18/5Sat
multi-stop
13h 50mORD-SJO
24/5Fri
multi-stop
31h 39mSJO-ORD
£464
18/5Sat
multi-stop
13h 50mORD-SJO
23/5Thu
multi-stop
40h 29mSJO-ORD
£465
18/5Sat
multi-stopSpirit Airlines
7h 37mORD-SJO
20/5Mon
multi-stopSpirit Airlines
15h 41mSJO-ORD
£466
18/5Sat
multi-stopSpirit Airlines
7h 37mORD-SJO
20/5Mon
multi-stopSpirit Airlines
17h 46mSJO-ORD
£495
18/5Sat
multi-stopSpirit Airlines
7h 37mORD-SJO
21/5Tue
multi-stopSpirit Airlines
19h 19mSJO-ORD
£592
19/5Sun
multi-stopAeromexico
10h 47mORD-SJO
26/5Sun
multi-stopAeromexico
27h 40mSJO-ORD
£1,080
18/5Sat
multi-stopAeromexico
10h 47mORD-SJO
4/8Sun
multi-stopAeromexico
9h 34mSJO-ORD
£1,081
17/5Fri
multi-stopAeromexico
10h 47mORD-SJO
21/5Tue
multi-stopAeromexico
21h 59mSJO-ORD
£1,088
19/5Sun
multi-stopAeromexico
10h 47mORD-SJO
26/5Sun
multi-stopAeromexico
15h 01mSJO-ORD
£1,112

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Chicago - San José Flights

Departure:

Chicago (undefined)United States

Destination:

San José (SJO)Costa Rica

Return flight deals:

San José - Chicago

Cabin classes:

Browse origins:

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  • Chicago O'Hare Airport

Browse destinations:

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  • San José