ORD - SJO

£115 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 17/11. 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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Flight 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

Wed, 8 Oct - Mon, 13 Oct
Copa Airlines Logo
07:59 - 16:34ORD-SJO
9h 35m1 stop
Copa Airlines Logo
17:55 - 13:41SJO-ORD
18h 46m1 stop
£241Copa Airlines
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Sat, 8 Nov - Tue, 18 Nov
American Airlines Logo
17:13 - 22:13ORD-SJO
5h 00mdirect
American Airlines Logo
06:00 - 11:29SJO-ORD
5h 29mdirect
£242American Airlines
Find Deal
Sat, 1 Nov - Wed, 5 Nov
Copa Airlines Logo
15:07 - 07:33ORD-SJO
17h 26m1 stop
Copa Airlines Logo
04:08 - 12:46SJO-ORD
8h 38m1 stop
£244Copa Airlines
Find Deal
Thu, 4 Dec - Mon, 15 Dec
Delta Logo
05:32 - 22:12ORD-SJO
16h 40m1 stop
Delta Logo
07:00 - 21:53SJO-ORD
14h 53m1 stop
£253Delta
Find Deal
Tue, 18 Nov - Mon, 24 Nov
Delta Logo
06:45 - 22:07ORD-SJO
15h 22m2 stops
Delta Logo
07:00 - 20:29SJO-ORD
13h 29m2 stops
£256Delta
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Sat, 21 Feb - Sun, 1 Mar
Logo
13:35 - 00:50ORD-SJO
11h 15m1 stop
Logo
09:00 - 12:30SJO-ORD
27h 30m1 stop
£261
Find Deal
Wed, 19 Nov - Tue, 25 Nov
Southwest Logo
06:05 - 20:30ORD-SJO
14h 25m2 stops
Southwest Logo
09:00 - 21:50SJO-ORD
12h 50m1 stop
£300Southwest
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Tue, 6 Jan - Wed, 14 Jan
Southwest Logo
06:05 - 12:50ORD-SJO
6h 45m1 stop
Southwest Logo
13:45 - 21:50SJO-ORD
8h 05m1 stop
£338Southwest
Find Deal
Thu, 1 Jan - Sat, 31 Jan
United Airlines Logo
07:39 - 12:56ORD-SJO
5h 17mdirect
United Airlines Logo
14:05 - 19:35SJO-ORD
5h 30mdirect
£339United Airlines
Find Deal
Mon, 5 Jan - Thu, 22 Jan
United Airlines Logo
11:35 - 20:39ORD-SJO
9h 04m1 stop
United Airlines Logo
14:05 - 19:35SJO-ORD
5h 30mdirect
£343United Airlines
Find Deal

Everything you should know

Our travellers' advice
AI-generated summary based on content written by travel experts
United's Premier Access eases check-in at O'Hare.
Pre-arrange transportation at SJO for a smooth arrival.
Expert advice
Expert advice
Expert advice
Expert advice
When to book
3 weeks
in advance
Our data shows that travellers who book at least 3 weeks in advance save around 31% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
October
Cheapest • 32% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest return fare
£241
Overall average: £285
Copa Airlines
Wed 8/10Mon 13/10
ORD - SJO • 1 stop
Cheapest direct flights
£242
Typical prices: £368-565
American Airlines
Sat 8/11Tue 18/11
ORD - SJO • Direct
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KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to San José!
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.
Airlines
American Airlines

American's Flagship Lounges provide upgraded seating and meals, enhancing the premium travel experience.


American's Main Cabin Extra offers early boarding and complimentary drinks, enhancing comfort on longer flights.

Read more about American Airlinesby Harriet Baskas
United Airlines

United's Premier Access offers priority check-in and boarding, ideal for international travel convenience.


United's Polaris Lounge offers a luxurious experience with seated meals, perfect for premium travelers.

Read more about United Airlinesby Stefanie Waldek
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
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, The Points Guy, and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and 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
Booking Insights

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 October, where tickets cost £285 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is £563 and £503 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 3 weeks before departure, which saves you about 31% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Find deals

Good to know - Cheap tickets from Chicago to San José

Low seasonSeptember
Cheapest flight£115
Best time to beat the crowds (20% less expensive on average)
Most popular time to fly (19% 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 £156 for a one-way ticket and £328 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?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Chicago and San José, with Star Alliance being the most commonly used for this route.

  • 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?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago O'Hare Intl to San José Juan Santamaria Intl.
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

Monday

American Airlines

American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines

American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines

American Airlines

See more direct flights

Direct returns

San José Juan Santamaria Intl to Chicago O'Hare Intl

Monday

American Airlines

American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines

American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines

American Airlines

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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