Skyscanner

Cheap Flights from Chicago (ORD) to San Jose (SJO)

Compare Chicago O'Hare International to San Jose Juan Santamaria flight deals

Find the cheapest month or even day of the year to fly to San Jose Juan Santamaria

Book the best San Jose Juan Santamaria fare with no extra fees

Flight deals from Chicago O'Hare International to San Jose Juan Santamaria

Looking for a cheap last-minute deal or the best return flight from Chicago O'Hare International to San Jose Juan Santamaria? Find the lowest prices on one-way and return tickets right here.
San Jose.$344 per passenger.Departing Thu, 10 Jul, returning Thu, 17 Jul.Return flight with Avianca.Outbound indirect flight with Avianca, departs from Chicago O'Hare International on Thu, 10 Jul, arriving in San Jose Juan Santamaria.Inbound indirect flight with Avianca, departs from San Jose Juan Santamaria on Thu, 17 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From $344, select.
San Jose.$413 per passenger.Departing Tue, 5 Aug, returning Wed, 6 Aug.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Tue, 5 Aug, arriving in San Jose Juan Santamaria.Inbound indirect flight with Spirit Airlines, departs from San Jose Juan Santamaria on Wed, 6 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From $413, select.
San Jose.$416 per passenger.Departing Tue, 29 Jul, returning Wed, 6 Aug.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Tue, 29 Jul, arriving in San Jose Juan Santamaria.Inbound indirect flight with Spirit Airlines, departs from San Jose Juan Santamaria on Wed, 6 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From $416, select.
San Jose.$438 per passenger.Departing Fri, 7 Nov, returning Sat, 22 Nov.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Fri, 7 Nov, arriving in San Jose Juan Santamaria.Inbound indirect flight with Viva, departs from San Jose Juan Santamaria on Sat, 22 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From $438, select.
San Jose.$446 per passenger.Departing Sun, 19 Oct, returning Sat, 8 Nov.Return flight with Spirit Airlines and Viva.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Sun, 19 Oct, arriving in San Jose Juan Santamaria.Inbound indirect flight with Viva, departs from San Jose Juan Santamaria on Sat, 8 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From $446, select.
San Jose.$479 per passenger.Departing Tue, 19 Aug, returning Tue, 9 Sep.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Tue, 19 Aug, arriving in San Jose Juan Santamaria.Inbound indirect flight with Spirit Airlines, departs from San Jose Juan Santamaria on Tue, 9 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From $479, select.
San Jose.$484 per passenger.Departing Tue, 9 Sep, returning Wed, 17 Sep.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Tue, 9 Sep, arriving in San Jose Juan Santamaria.Inbound indirect flight with Spirit Airlines, departs from San Jose Juan Santamaria on Wed, 17 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From $484, select.
San Jose.$510 per passenger.Departing Wed, 17 Sep, returning Tue, 7 Oct.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Wed, 17 Sep, arriving in San Jose Juan Santamaria.Inbound indirect flight with Spirit Airlines, departs from San Jose Juan Santamaria on Tue, 7 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From $510, select.

Find the cheapest month to fly from Chicago O'Hare International to San Jose Juan Santamaria

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago O'Hare International to San Jose Juan Santamaria flights are currently cheapest in July.
Jul
from $344
Aug
from $413
Sep
from $484
Oct
from $513
Nov
from $438
Dec
from $513
Jan
from $512
Feb
from $701
Mar
from $512
Apr
from $726
May
from $513
Jun
from $2,596

Direct flights from Chicago O'Hare International to San Jose Juan Santamaria

Chicago O'Hare International to San Jose Juan Santamaria: Alternative routes

Compare routes from Chicago O'Hare International to San Jose below. You may find an airport to fly into that's cheaper, faster, or easier than San Jose Juan Santamaria.

Chicago to San Jose: Flight information

The things to know before you go.
Cheapest flight found$344
Cheapest month to flyJuly
Average flight time5 hrs, 14 mins
Most popular airlineAmerican Airlines
Average flights per week12

Finding cheap flights from Chicago O'Hare International to San Jose Juan Santamaria: Frequently asked questions

The best price we found for a return flight from Chicago O'Hare International to San Jose Juan Santamaria is $344. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
5 hours and 14 minutes is the average flight time from Chicago O'Hare International to San Jose Juan Santamaria.
American Airlines and United fly direct from Chicago O'Hare International to San Jose Juan Santamaria.
As of July 2025, there are 12 flights per week flying from Chicago O'Hare International to San Jose Juan Santamaria.
The cheapest month to fly from Chicago O'Hare International to San Jose Juan Santamaria is usually July.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago O'Hare International Airport to San Jose Juan Santamaria Airport on Thursday, 10 July 2025.
Yes – the average flight time is 5 hours and 14 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to San Jose Juan Santamaria but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to San Jose is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Avianca and United offer the cheapest flight tickets to San Jose Juan Santamaria.

Flying from O'Hare International Airport (ORD) to Juan Santamaria International Airport (SJO): what you need to know

  • Jump on a direct flight from O'Hare International Airport to Juan Santamaria International Airport and you'll be in the air for an average of 5 hours 15 minutes.

  • The timezone in San Jose is UTC-6, which is one hour behind Chicago.

  • To ensure you get on your ORD to SJO flight, leave enough time for things like check-in and baggage drop. Arriving two hours before international departures and an hour before domestic flights is the standard rule.

  • During popular months such as August, you'll want to get to the airport earlier than usual. Plan to arrive two hours before a domestic departure and four hours ahead of international flights whenever you're travelling during a high season in general.

  • United Airlines offers direct flights from O'Hare International Airport to Juan Santamaria International Airport. Book with this popular carrier, then get ready to tick off the sights in San Jose — and maybe even more of Costa Rica if you have time.

  • Most passengers choose to travel with United Airlines on this route.

  • The most punctual carrier that offers ORD to SJO flights is United Airlines. Its services land without delay 77.78% of the time.

  • Think about adding a stopover when booking your ticket from O'Hare International Airport to Juan Santamaria International Airport. Just deselect 'Direct flights only' to break up your journey, or maybe even explore a new city along the way. Here are some options between ORD and SJO:

    • La Aurora International Airport

    • Hartsfield-Jackson Atlanta International Airport

    • Charlotte Douglas International Airport

How to find the cheapest flights from O'Hare International Airport (ORD) to Juan Santamaria International Airport (SJO)

  • Right now, $190 is the cheapest price we've found for a one-way O'Hare International Airport to Juan Santamaria International Airport flight. The best price for a return ticket is $344. Keep in mind that fares can change due to demand at the time of booking.

  • Get cheap tickets from ORD to SJO by booking at least six months ahead. According to our research, that's the sweet spot for picking up a bargain.

  • The cheapest month for flights from O'Hare International Airport to Juan Santamaria International Airport is May. Use the 'Whole month' tool to find the lowest airfares if you have a flexible travel schedule.

  • You won't have to check every day to find out if fares have gone down when you create a Price Alert. We'll update you the moment there's a new deal on cheap flights from ORD to SJO.

  • Tailor your flights using filters. Choose your ideal arrival and departure times, total journey duration and airlines. You can also sort your results by 'Best,' 'Fastest' or 'Cheapest' flights from O'Hare International Airport to Juan Santamaria International Airport.

Handy information about O'Hare International Airport (ORD)

  • You'll find ORD at 10000 West O'Hare.

  • When it comes to O'Hare International Airport's on-time performance, 74.85% of flights meet their scheduled arrival time.

  • Central Chicago to O'Hare International Airport is around 40 kilometres. Depending on traffic, it'll take you about 35 minutes to get there if you're ride-sharing, catching a cab or driving.

  • Expect a trip time of around 55 minutes on public transport.

  • Searching for a convenient hotel close to ORD? If you're boarding an early flight from O'Hare International Airport to Juan Santamaria International Airport, these stays will have you moments from your check-in counter:

Arriving at Juan Santamaria International Airport (SJO)

Getting from Juan Santamaria International Airport (SJO) to central San Jose

  • Juan Santamaria International Airport is approximately 18 kilometres from central San Jose. Driving there takes about 20 minutes.

  • Getting there by public transport takes around 2 hours 20 minutes.

When to fly to Juan Santamaria International Airport (SJO)

  • It's time to pick your travel dates for your flight from O'Hare International Airport to Juan Santamaria International Airport. July is the most popular month to head to San Jose. If you prefer a more low-key vibe, go in May.

  • Lock in your flight from O'Hare International Airport to Juan Santamaria International Airport for March if you'd like to go to San Jose during its warmest month. Expect temperatures of between 12ºC (54ºF) and 29ºC (84ºF).

  • If you like travelling in cooler conditions, look for a cheap ticket from ORD to SJO in January. Average temperatures are between 12ºC (54ºF) and 26ºC (79ºF) then.

Explore more of Costa Rica

  • Limon is just one of the many places in Costa Rica waiting to be discovered once you've taken in the sights of San Jose. Around 113 kilometres away to the east, its best attractions include Veragua Rainforest Park, Playa Bonita and Cruise Pier Puerto Limon.

  • If there's time to check out another corner of Costa Rica, head for Alajuela, roughly 18 kilometres north-west of San Jose. La Perla Park, Los Duendes Park and Finca El Soto are key reasons to visit.

Plan the rest of your trip from Chicago to San Jose

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.