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SJO - ORD

Find cheap flights from San José to Chicago

1 adult
0 bags
Sat 1/6
Sat 8/6

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These are the airlines KAYAK users have selected most often from within our search results in flight searches from San José to Chicago, 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 San José to Chicago, as well as popular online travel agencies
In the last 7 days, travellers have searched 43,740,974 times on KAYAK, and here's why:

Save 28% or moreCompare multiple travel sites with one search.

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Flights from San José to Chicago - Travel Insights & Trends

Get data-powered insights and trends into flights from San José to Chicago to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from San José to Chicago?

The average price of all flights from San José, San José Province to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from San José to Chicago, look for departures on Mondays and avoid leaving on a Thursday, as it's usually the priciest day. When flying back from Chicago, Monday is the cheapest day to fly and Saturday is the most expensive.

What is the cheapest month to fly from San José, San José Province to Chicago O'Hare Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from San José, San José Province to Chicago O'Hare Intl Airport, 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 San José, San José Province to Chicago O'Hare Intl Airport is September, where tickets cost £222 on average. On the other hand, the most expensive months are March and July, where the average cost of tickets is £490 and £478 respectively.

How far in advance should I book a flight from San José, San José Province to Chicago O'Hare Intl Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from San José, San José Province to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from San José, San José Province to Chicago O'Hare Intl Airport, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 53 days before departure.

How many flights are there between San José, San José Province and Chicago O'Hare Intl Airport per day?

There is a maximum of 1 direct flight a day that takes off from San José, San José Province and lands in Chicago O'Hare Intl Airport, with an average flight time of 5h 28m. The most common departure time is 13:00 and most flights take off in the afternoon. Each week, there are 1 flights.

Which cabin class options are there for flights between San José, San José Province and Chicago O'Hare Intl Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

What’s the earliest departure time from San José to Chicago?

Early birds can take the earliest flight from San José, San José Province at 13:00 and will be landing in Chicago O'Hare Intl Airport at 19:28.

What’s the latest departure time from San José to Chicago?

If you prefer to fly at night, the latest flight from San José, San José Province to Chicago O'Hare Intl Airport jets off at 13:00 and lands at 19:28.

Good to know - Cheap tickets from San José to Chicago

Low season

February

High season

September
Best time to beat the crowds (14% less expensive on average)
Most popular time to fly and prices are also 47% lower on average.

When to book flights from San José to Chicago

Are your dates flexible? Find out the best times to travel from San José to Chicago 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 San José to Chicago flights

  • Which airlines offer Wi-Fi service onboard planes from San José to Chicago?

    Lufthansa, Delta, and Alaska Airlines offer inflight Wi-Fi service on the San José to Chicago flight route.

  • Which aircraft models fly most regularly from San José to Chicago?

    The Airbus A350-900 is the aircraft model that flies most regularly on the San José to Chicago flight route.

  • Which airline alliances offer flights from San José to Chicago?

    Star Alliance is the only airline alliance operating flights between San José and Chicago.

  • On which days can I fly direct from San José to Chicago?

    You can catch a direct flight from San José to Chicago on Saturday.

  • How does KAYAK find such low prices on flights from San José to Chicago?

    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 San José to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San José to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from San José 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 San José to Chicago?

    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 Chicago with an airline and back to San José with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from San José to Chicago?

    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 Chicago from San José up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly direct from San José to Chicago?

Find which airlines fly direct from Juan Santamaria Intl to O'Hare Intl, which days they fly and book direct flights.

Direct departures

San José Juan Santamaria Intl to Chicago O'Hare Intl

Saturday

United Airlines

United Airlines

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Direct returns

Chicago O'Hare Intl to San José Juan Santamaria Intl

Saturday

United Airlines

United Airlines

See more direct flights
See more direct flights

Book cheap flights from San José to Chicago

One-way flight deals

directUnited Airlines
5h 28mSJO-ORD

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San José - Chicago Flights

Departure:

San José (SJO)Costa Rica

Destination:

Chicago (ORD)United States

Return flight deals:

Chicago - San José

Cabin classes:

£623

Browse origins:

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  • San José

Browse destinations:

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  • Chicago O'Hare Airport