ORD - SJO

$166 Find Cheap Flights from Chicago O'Hare Airport to San José - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 25% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$407
Typical prices: $460-$714
Multiple Airlines
Tue 2/13Tue 2/20
ORD - SJO • 1 stop
Cheapest non-stop
$424
Typical prices: $460-$757
United Airlines
Mon 2/5Sat 2/10
ORD - SJO • Non-stop
Nonstop flights
You can fly direct with United Airlines. Average duration is 5h 14m
Direct flights
+1
Direct flights
+1
Avoid delays
Most punctual • 88% on-time
Best time • Fewest delays
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 7 weeks in advance save around 11% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 14% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $401 (round-trip)
Shortest trip • 8h 13m (one-way)
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to San José!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from O'Hare Intl to San José (ORD-SJO)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from O'Hare Intl to San José

Sat, Feb 13 - Sat, Feb 20
Multiple Airlines Logo
12:53 pm - 10:44 pmORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
9h 51m1 stop Guadalajara Miguel Hidal
Multiple Airlines Logo
3:00 pm - 11:13 amSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
20h 13m1 stop Guadalajara Miguel Hidal
$407Multiple Airlines
Thu, Feb 4 - Wed, Feb 10
United Airlines Logo
7:02 am - 12:15 pmORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
5h 13mnonstop
United Airlines Logo
1:25 pm - 6:57 pmSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
5h 32mnonstop
$424United Airlines
Wed, Feb 3 - Wed, Feb 17
Avianca Logo
10:30 pm - 8:50 amORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
10h 20m1 stop Bogotá El Dorado
Avianca Logo
1:50 am - 8:30 pmSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
18h 40m1 stop Bogotá El Dorado
$424Avianca
Wed, Jan 20 - Wed, Jan 27
Avianca Logo
10:30 pm - 8:50 amORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
10h 20m1 stop Bogotá El Dorado
Avianca Logo
9:30 am - 8:30 pmSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
11h 00m1 stop Bogotá El Dorado
$424Avianca
Sat, Feb 6 - Sat, Feb 13
Multiple Airlines Logo
12:53 pm - 10:44 pmORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
9h 51m1 stop Guadalajara Miguel Hidal
Multiple Airlines Logo
3:00 pm - 11:13 amSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
20h 13m1 stop Guadalajara Miguel Hidal
$424Multiple Airlines
Thu, Mar 4 - Tue, Mar 9
United Airlines Logo
7:02 am - 12:15 pmORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
5h 13mnonstop
United Airlines Logo
1:25 pm - 6:57 pmSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
5h 32mnonstop
$424United Airlines
Wed, Apr 7 - Wed, Apr 21
Copa Airlines Logo
3:13 pm - 1:44 pmORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
23h 31m1 stop Panama City Tocumen Intl
Copa Airlines Logo
2:20 pm - 12:44 amSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
9h 24m1 stop Panama City Tocumen Intl
$427Copa Airlines
Sat, Feb 13 - Tue, Feb 23
Copa Airlines Logo
2:13 pm - 7:04 amORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
16h 51m1 stop Panama City Tocumen Intl
Copa Airlines Logo
9:57 am - 12:11 amSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
14h 14m1 stop Panama City Tocumen Intl
$427Copa Airlines
Sat, Nov 28 - Fri, Dec 11
American Airlines Logo
5:19 am - 1:07 pmORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
7h 48m1 stop Charlotte Douglas
American Airlines Logo
6:07 am - 9:41 pmSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
15h 34m1 stop Miami
$439American Airlines
Mon, Dec 7 - Tue, Dec 22
American Airlines Logo
5:23 am - 12:37 pmORD  Chicago O'Hare Intl-SJO San José Juan Santamaria Intl
7h 14m1 stop Charlotte Douglas
American Airlines Logo
3:37 pm - 12:33 amSJO  San José Juan Santamaria Intl-ORD Chicago O'Hare Intl
8h 56m1 stop Miami
$439American Airlines
Booking Insights

Price, demand and travel trends for Chicago O'Hare Intl Airport to San José flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What's the cheapest day of the week to fly from Chicago O'Hare Intl Airport to San José?

Based on deals KAYAK users found in the last 12 months, Monday is the cheapest day of the week to fly from Chicago O'Hare Intl Airport to San José. It’s 10% cheaper than the average day, while Saturday is the most expensive, with prices 18% higher.

What’s the cheapest month to fly from Chicago O'Hare Intl Airport to San José?

•October is the cheapest month to fly from Chicago O'Hare Intl Airport to San José at $483 round-trip.
•December ($662) and March ($643) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 37% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Chicago O'Hare Intl Airport to San José the cheapest?

Flights from Chicago O'Hare Intl Airport to San José are cheapest 7 weeks before departure. Booking in this window typically costs about 11% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight from O'Hare Intl to San José

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

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 on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

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, USA TODAY, 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.

Mark Chesnut

Mark Chesnut

Expert on SJO

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.

Key details for Chicago O'Hare Intl Airport to San José flights

Low season

September

Cheapest flight

$166
Beat the crowds with an average 56% drop in travelers.
The most popular month to fly with an average 78% increase in travelers.
One-way flight from Chicago O'Hare Intl Airport to San José

When to book flights from O'Hare Intl to San José

Are your dates flexible? Find out the best times to travel from O'Hare Intl to San José based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago O'Hare Intl Airport to San José flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Chicago O'Hare Intl Airport to San José?

    These are the earliest and latest flight times available from Chicago O'Hare Intl Airport to San José:

    • Earliest: departs at 7:02 am and lands at 12:16 pm
    • Latest: departs at 7:30 am and lands at 12:44 pm.

    The flight takes about 5h 14m.

  • What cabin classes can I book on flights from Chicago O'Hare Intl Airport to San José?

    Four cabin classes are available on flights from Chicago O'Hare Intl Airport to San José:

    • Economy Class
    • Premium Economy Class
    • Business Class
    • First Class

    Prices vary by airline.

  • How long is a flight from Chicago O'Hare Intl Airport to San José?

    A nonstop flight from Chicago O'Hare Intl Airport to San José takes 5h 14m, covering 2,220 miles.

  • Do I need a passport to fly from Chicago O'Hare Intl Airport to San José?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • How much should I expect to pay for a Chicago O'Hare Intl Airport to San José flight?

    Round-trip flights from Chicago O'Hare Intl Airport to San José range from $460 to $714, with an average of $565 over the past 12 months. Anything below $460 counts as a good deal.

  • How expensive are last-minute Chicago O'Hare Intl Airport to San José flights?

    Last-minute fares on this route (booked within two weeks of departure) run 3% above the $565 route average. Book 7 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Chicago O'Hare Intl Airport to San José?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $401 round-trip via Monterrey Gen Mariano Escobedo (MTY), compared to $572 for nonstop.

  • What is the standard checked-bag allowance on flights from Chicago O'Hare Intl Airport to San José?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $35–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Chicago O'Hare Intl Airport to San José?

    The Boeing 737 MAX 8 family is used most often on this route, operated mainly by United Airlines and American Airlines. Other aircraft seen on the route include Canadair (Bombardier) Regional Jet 200 variants.

  • Have flight prices from Chicago O'Hare Intl Airport to San José changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $424 to $3,200. That means the highest observed fare was about 8x higher than the lowest one.

  • How are flight prices from Chicago O'Hare Intl Airport to San José looking right now?

    One-way fares from Chicago O'Hare Intl Airport to San José are currently higher than usual. Average one-way flight prices are about $336, which is 10% above the typical average for this route.

  • What car rental options are available at San José Juan Santamaria Intl Airport (SJO)?

    San José Juan Santamaria Intl Airport (SJO) hosts 5 major car rental companies, with daily rates averaging $30 for economy cars. Top options include:

    • Priceless
    • Avis
    • Budget
    • Routes Car & Truck Rentals
    • Payless

  • Which airports can I use when flying from Chicago O'Hare Intl Airport to San José?

    Flights from Chicago O'Hare Intl Airport to San José usually depart from Chicago O'Hare Intl (ORD) and arrive at San José Juan Santamaria Intl (SJO).

  • What time of day has the fewest delays on flights from Chicago O'Hare Intl Airport to San José?

    Morning flights have the fewest delays on this route, while afternoon departures tend to have the most.

  • At what point is a flight considered delayed from Chicago O'Hare Intl Airport to San José?

    A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Chicago O'Hare Intl Airport to San José route, 20% of flights were delayed in the past 3 months, with delays averaging 2h 29m.

  • Which airports do connecting flights from Chicago O'Hare Intl Airport to San José pass through?

    One-stop flights from Chicago O'Hare Intl Airport to San José most commonly connect through:

    • Panama City Tocumen Intl (PTY) - 28% of one-stop connections
    • Fort Lauderdale (FLL) - 19% of one-stop connections
    • Houston George Bush Intcntl (IAH) - 18% of one-stop connections
    • Miami (MIA) - 8% of one-stop connections

  • Can I save money by using flexible dates for flights from Chicago O'Hare Intl Airport to San José?

    Yes. Flexible dates can save you up to 24% on flights from Chicago O'Hare Intl Airport to San José. Monday is the cheapest departure day at $510 round-trip on average, while Saturday is the most expensive at $669, a difference of $159.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Chicago O'Hare Intl Airport to San José?

    Only United Airlines operates flights between Chicago O'Hare Intl Airport and San José.

  • How much time can I save by choosing a different layover airport from Chicago O'Hare Intl Airport to San José?

    Flying via Charlotte Douglas (CLT) gives the shortest average 1-stop total travel time at 8h 13m, compared with 8h 31m via Atlanta Hartsfield-Jackson (ATL) and 8h 33m via Guatemala City La Aurora (GUA).

  • What is the time difference between Chicago O'Hare Intl Airport and San José?

    San José is 1 hour behind Chicago O'Hare Intl Airport (Central Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in San José?

    Some of the most popular sights in San José are Parque Metropolitano La Sabana, Estadio Nacional de Costa Rica and Museo de Oro. These are among the most viewed places in San José on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Chicago O'Hare Intl Airport to San José flights?

    Among airlines operating Chicago O'Hare Intl Airport to San José flights:

    • United Airlines: offers extra legroom; offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Chicago O'Hare Intl Airport to San José flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • United Airlines: a cabin bag and a checked bag in Economy Class
    • Azul: a cabin bag and a checked bag in Business Class
    • Copa Airlines: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

  • 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.

Your guide to booking Chicago O'Hare Intl Airport to San José flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Monday departure and avoid flying on Saturday. On this route, Monday flights average $510, about $159 less than Saturday fares (24% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 7 weeks before you fly. On this route, that window historically saves about 11% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago O'Hare Intl Airport to San José trip for October. Fares historically average $483 round-trip in that month - typically $179 less than the most expensive month, which is December (based on the last 12 months).
  • For the best chance of arriving on time, fly with United Airlines. Over the past three months, 88% of United Airlines flights from Chicago O'Hare Intl Airport to San José arrived on time, slightly above the route average of 80%. When flights on this route arrive late, they're delayed by an average of 2h 29m, so choosing an airline with strong on-time performance can make a difference if you're on a tight schedule.
  • If you have the time, taking a 1-stop flight through Monterrey Gen Mariano Escobedo Airport (MTY) can be cheaper than flying direct. The cheapest layover option averages $401 round-trip on this route - about $171 less than direct flights (based on the last 12 months).
  • 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 O'Hare Airport 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

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

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

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

More options for your flight from O'Hare Intl to San José

Complete your trip to San José with a hotel stay or car rental