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Flights San José — Chicago

San Jose
SJO
Chicago
CHI

Cheap flights San José — Chicago

Below you can see the best deals on flights San José — Chicago 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 24 August, from AED 902.

Top 10 cheap flights San José — Chicago

Direct flights San José — Chicago

Direct flight options for San José — Chicago with no stopovers on upcoming dates. A direct flight is faster and more convenient — especially when travelling with luggage or children.

The fastest direct flight takes around 4 h 57 min.

Top 10 direct flights San José — Chicago

About the San José — Chicago flight

On this page, you can find and purchase flight tickets for the San Jose — Chicago route. The distance between the cities is 3,557 km, and flights on this route operate approximately once a week.

The primary carrier for this route is United Airlines (UA). Ticket prices are dynamic; therefore, we recommend using the low-fare calendar and price chart to find the best deals. You can also find information on how to get to the airport in San Jose and how to get from the airport to Chicago on our website.

Flight ticket prices by day: San José — Chicago

Below is a calendar of the lowest flight ticket prices for San José — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from AED 884 in b, and the most expensive are around AED 1,717 in u. 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

San José → Chicago, average one-way price

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
JanAED 1,637mediumMayAED 1,416lowSepAED 1,372low
FebAED 1,372lowJunAED 1,593mediumOctAED 1,327low
MarAED 1,726highJulAED 1,903highNovAED 1,504medium
AprAED 1,327lowAugAED 1,549mediumDecAED 1,947high

Some values are estimated based on seasonality.

When to fly

The warmest month in Chicago is July, with average temperatures reaching 26.5°C, while January remains the coldest month with temperatures as low as -5°C. Rainfall peaks in May (126.06 mm), and the driest weather typically occurs in November.

The most affordable flight prices are recorded in November, when tickets are available AED 884. The most expensive period to travel on this route is April, when the cost increases AED 1,717.

The best time to fly is considered to be August or September: these months offer pleasant weather (around 23-26°C) while prices remain at a moderate level — AED 902. We recommend avoiding April if your goal is to maximize your savings.

Temperature · Chicago

Dry and wet days · Chicago

Wind speed and direction · Chicago

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

  • Use the low-fare calendar: Since flights between these cities operate only about once a week, ticket prices can change drastically depending on the chosen date.
  • Check United Airlines' baggage allowance: On flights from Costa Rica to the USA, rules for carry-on and checked luggage may differ from domestic rates, so it is best to verify them before paying.
  • Book in advance for November: This is the most budget-friendly month for flying, with deals starting AED 884 if you purchase your ticket several weeks before departure.
  • Monitor the price chart: The tool on this page will help you catch the moment when the price for this 3,557 km route is at its lowest.

Airlines

Flights between San Jose and Chicago are operated by United Airlines (UA). Since there is approximately one flight per week on this route, United is the primary carrier. You can view the detailed schedule, including departure and arrival times, in the interactive list below to choose the most convenient option for your trip.

  • United Airlines
    United AirlinesUA
    1x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight SJO → ORD1x/week
      Duration
      5h 35m
      Days
      MTWTFSS
    100.0%Open →

Cities and airports on the San José — Chicago route

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

Departure

San José

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

Chicago

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

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Frequently asked questions about the San José — Chicago flight

How long is the flight from San Jose to Chicago?

The average flight time for a direct flight over a distance of 3,557 km is about 4 hours and 15 minutes; however, the exact duration depends on weather conditions and the chosen airline.

Which airlines fly this route?

The main carrier on the San Jose — Chicago route is United Airlines (UA).

Are there direct flights?

Yes, direct flights are available, but their frequency is limited to approximately one departure per week. Please check the schedule on this page for the current availability of direct flights on specific dates.

How much is the cheapest ticket?

Flight prices change constantly depending on the season and demand. You can find the current lowest price for your dates in the low-fare calendar above.

Which airport does the flight arrive at?

Flights from San Jose typically arrive at Chicago's international airports (O'Hare or Midway), depending on the airline's operations.

Do I need a visa for this trip?

Since Chicago is in the USA, citizens of most countries (including Russia) require a valid US visa to cross the border.

Where else you can fly from San José

Panama CitySan SalvadorBogotaMexico CityMiamiHoustonMedellínGuatemala CityOrlandoNew York CityDallasLos AngelesFort LauderdaleCartagenaMadridCancunAtlantaQueposTorontoCharlotteLimaParisSan FranciscoMontrealBuenos AiresNosaraWashington, D.C.GuadalajaraSanto DomingoAmsterdamFrankfurt am MainSao PauloSan JuanDenverMonterreySan Pedro SulaQuitoGuayaquilManaguaPuerto Jimenez

Where else you can fly from Chicago

New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonHoustonOrlandoDenverLondonPhiladelphiaMiamiPhoenixLas VegasSan FranciscoTampaFort LauderdaleMexico CitySanta AnaParisColumbiaFrankfurt am MainHonoluluMunichIstanbulMyrtle BeachBarcelonaAthensWarsaw
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