ORD - SJO

£98 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 30/8. 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
1 adult, Economy

KAYAK searches 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
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Flights Deals

Cheap Flights from Chicago to San José (ORD-SJO)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from Chicago to San José that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals from Chicago to San José

Tue, 16 Sep - Fri, 26 Sep
Copa Airlines Logo
07:54 - 21:53ORD-SJO
14h 59m1 stop
Copa Airlines Logo
10:05 - 00:22SJO-ORD
13h 17m1 stop
£228Copa Airlines
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Tue, 11 Nov - Thu, 13 Nov
Copa Airlines Logo
06:56 - 18:56ORD-SJO
12h 00m1 stop
Copa Airlines Logo
04:13 - 12:22SJO-ORD
8h 09m1 stop
£239Copa Airlines
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Wed, 16 Jul - Tue, 22 Jul
Logo
08:09 - 22:40ORD-SJO
15h 31m1 stop
Logo
05:05 - 16:05SJO-ORD
10h 00m1 stop
£254
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Sat, 26 Jul - Sat, 2 Aug
Logo
05:05 - 11:11ORD-SJO
7h 06m1 stop
Logo
13:47 - 10:25SJO-ORD
19h 38m1 stop
£279
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Sun, 27 Jul - Sun, 3 Aug
Spirit Airlines Logo
08:50 - 11:11ORD-SJO
27h 21m3 stops
Spirit Airlines Logo
11:24 - 15:31SJO-ORD
27h 07m1 stop
£291Spirit Airlines
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Sun, 27 Jul - Sun, 3 Aug
Spirit Airlines Logo
08:50 - 11:11ORD-SJO
27h 21m3 stops
Spirit Airlines Logo
11:24 - 07:50SJO-ORD
19h 26m2 stops
£292Spirit Airlines
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Sat, 26 Jul - Sat, 2 Aug
Avianca Logo
17:25 - 07:40ORD-SJO
15h 15m2 stops
Avianca Logo
16:20 - 14:25SJO-ORD
21h 05m1 stop
£314Avianca
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Sat, 5 Jul - Thu, 10 Jul
United Airlines Logo
07:41 - 11:55ORD-SJO
5h 14mdirect
United Airlines Logo
11:13 - 00:15SJO-ORD
12h 02m1 stop
£332United Airlines
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Sat, 19 Jul - Thu, 24 Jul
Avianca Logo
17:25 - 23:35ORD-SJO
7h 10m1 stop
Avianca Logo
16:20 - 14:25SJO-ORD
21h 05m1 stop
£339Avianca
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Wed, 23 Jul - Sat, 2 Aug
United Airlines Logo
21:50 - 10:11ORD-SJO
13h 21m1 stop
United Airlines Logo
13:00 - 19:34SJO-ORD
5h 34mdirect
£342United Airlines
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Expert advice

Expert advice for your flight from Chicago to San José

 
Snippets provided in this section are AI-generated based on a summarisation of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
ORD

Security lines at ORD can exceed 30 minutes during peak times. Arrive early to avoid delays, especially for international flights.

Read more about ORDby Stefanie Waldek
SJO

For a smooth arrival at SJO, pre-arrange ground transportation through your hotel to avoid long waits and ensure a hassle-free transfer.

Read more about SJOby Mark Chesnut
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on ORD

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or out at sea, likely en route to Antarctica or the Arctic.

Read more
Mark Chesnut

Mark Chesnut

Expert on SJO

Mark Chesnut

Mark Chesnut

Mark Chesnut is a travel writer and public speaker with more than 30 years of experience. The 2019 winner of the NLGJA Excellence in Travel Writing Award, Mark is the author of the book “Prepare for Departure” and has covered air travel for multiple top consumer and trade media outlets.

Read more
Useful Info

KAYAK's insights & trends for Chicago to San José flights

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to San José, 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 is August, where tickets cost £318 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is £566 and £514 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to San José, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to San José, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

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Good to know - Cheap tickets from Chicago to San José

Low seasonSeptember
High seasonMarch
Cheapest flight£98
Best time to beat the crowds (6% less expensive on average)
Most popular time to fly (16% 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?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to San José was £133 for a one-way ticket and £310 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 airlines offer Wi-Fi service onboard planes from Chicago to San José?

    Only American Airlines offers inflight Wi-Fi service on the Chicago to San José flight route.

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

    The Boeing 737 MAX 8 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, and Sunday.

  • 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.

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

  • 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.

Prefer to fly direct from Chicago to San José?

Find which airlines fly direct from Chicago O'Hare Intl Airport to San José Juan Santamaria Intl Airport, 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

Sunday

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

Sunday

United Airlines

United Airlines

See more direct flights
See more direct flights

Everything you need to know for your flight from Chicago to San José

Information on your arrival and departure airports

Chicago (ORD)
San José (SJO)

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