Cheap flights from Chicago to San José

Chicago FSS
CHI
Juan Santamaria
SJO

Flight deals from Chicago to San José

Below you can see the best deals on flights Chicago — San José for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 28 August, from AED 1,013.

Top 10 cheap flights from Chicago to San José

F9
AV
AV
 1,013

Chicago — San José

00:44—21:10
28 Aug 2026
21 h 26 m
2 stops
F9
AV
AV
 1,019

Chicago — San José

00:44—23:55
27 Aug 2026
24 h 11 m
2 stops
F9
AV
AV
 1,041

Chicago — San José

00:44—23:55
26 Aug 2026
24 h 11 m
2 stops
F9
CM
CM
 1,063

Chicago — San José

00:44—07:10
30 Aug 2026
31 h 26 m
2 stops
F9
Q6
 1,181

Chicago — San José

21:10—15:11
28 Aug 2026
19 h 1 m
1 stop
F9
Q6
 1,181

Chicago — San José

06:05—15:11
28 Aug 2026
34 h 6 m
1 stop
F9
CM
CM
 1,187

Chicago — San José

00:44—21:48
27 Aug 2026
22 h 4 m
2 stops
F9
CM
CM
 1,187

Chicago — San José

00:44—09:04
27 Aug 2026
33 h 20 m
2 stops
F9
CM
CM
 1,208

Chicago — San José

00:44—21:48
26 Aug 2026
22 h 4 m
2 stops
F9
F9
DL
DL
 1,212

Chicago — San José

14:41—11:49
29 Aug 2026
22 h 8 m
3 stops

Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the Chicago — San José flight

Looking for cheap flights from Chicago to San José? Compare fares from different airlines, check the flight schedule and travel time — and book your Chicago — San José ticket online at the best price.

The route has direct flights — around 4 flights per week, flights are operated by United Airlines, a nonstop flight takes about 6 h 51 min, the distance between the cities is around 3,557 km.

Planning your trip? You may find our San José travel guide, how to get from the airport into town and San José weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

Facts about this route

from AED 689Min. price
JanuaryCheapest
DecemberPeak season
YesDirect flights
3,557 kmDistance
6 h 51 minTravel time
1Airlines
4 / wkFlights

Flight ticket prices by day: Chicago — San José

Below is a calendar of the lowest flight ticket prices for Chicago — San José by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from AED 689 in January, and the most expensive are around AED 1,315 in December. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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Prices by month

Average one-way fares from Chicago to San José by month. Tickets are usually cheapest in October (around AED 830) and priciest in December (about AED 1,248) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
JanAED 1,141highMayAED 901lowSepAED 866low
FebAED 1,110mediumJunAED 968mediumOctAED 830low
MarAED 1,177highJulAED 1,039mediumNovAED 937medium
AprAED 1,075mediumAugAED 968mediumDecAED 1,248high

Some values are estimated based on seasonality.

When to fly

Weather in San José: it is warmest in April (up to 25 °C on average) and coolest in November (around 23 °C). The driest month is February.

Tickets are usually cheapest in January and most expensive in December. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · San José

Dry and wet days · San José

Wind speed and direction · San José

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How to get the best deal on a Chicago — San José ticket

  • Book ahead: fares for Chicago — San José are usually lower 3–8 weeks before departure than at the last minute.
  • Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
  • Chicago is served by more than one airport — compare fares and travel time to each before you book.
  • The cheapest month to fly to San José is usually January — plan your trip around it if your dates are flexible.
  • Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
  • Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
  • Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
  • Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Airlines

Flights on the Chicago — San José route are operated by 1 airline; United Airlines runs the most flights (around 100% of all flights). Compare carriers, flight shares and schedules below.

  • United AirlinesUA
    1x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight ORD → SJO1x/week
    100.0%Open →

Cities and airports on the Chicago — San José route

Flights Chicago — San José depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport and arrive at Juan Santamaria International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Arrival

San José

SJO
Costa Rica
About the cityHow to get thereWeatherAll about the country Costa Rica
Departure airports
Arrival airports

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Frequently asked questions about the Chicago — San José flight

How long is the flight from Chicago to San José?

A nonstop Chicago — San José flight takes about 6 h 51 min — the distance between the cities is around 3,557 km.

How far is it from Chicago to San José?

The distance from Chicago to San José is about 3,557 km, which a nonstop flight covers in around 6 h 51 min.

Are there direct flights from Chicago to San José?

Yes, there are nonstop flights Chicago — San José — around 4 flights per week.

Which airlines fly from Chicago to San José?

Airlines operating Chicago — San José include United Airlines. See the full list with schedules in the "Airlines" section on this page.

Which airports do Chicago — San José flights use?

Flights from Chicago depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport, and arrive at Juan Santamaria International Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Chicago to San José?

The price of a Chicago — San José ticket depends on your travel date, season and demand: it is usually cheapest to fly in January, and most expensive in December. Tickets typically cost between AED 689 and AED 1,315. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights Chicago — San José?

Flights Chicago — San José are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is January. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Chicago to San José?

To catch a low fare Chicago — San José, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually January.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

Where else you can fly from Chicago

See all
New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverLondonNashvilleIndianapolisSan DiegoMontrealMilwaukeeSt. LouisCharlottePhiladelphiaColumbusKansas CityMiamiPhoenixLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochester

Where else you can fly from San José

See all
Panama CitySan SalvadorBogotaMexico CityMiamiHoustonMedellínGuatemala CityOrlandoNew York CityDallasLos AngelesFort LauderdaleMadridCartagenaCancunQueposAtlantaTorontoCharlotteLimaSan FranciscoParisMontrealBuenos AiresNosaraWashington, D.C.Santo DomingoGuadalajaraSan JuanSao PauloFrankfurt am MainAmsterdamQuitoSan Pedro SulaMonterreyDenverGuayaquilManaguaPuerto Jimenez

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