SJO - ORD

Find Cheap Flights from San José to Chicago

1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
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
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Expert advice
Booking Insights
Flight Deals

Cheap Flights from San José to Chicago (SJO-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from San José to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals from San José to Chicago

Multiple Airlines Logo
SJO-ORD
2220 mimulti-stop
Multiple Airlines Logo
ORD-SJO
2220 mimulti-stop
Multiple Airlines
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Everything you should know

Our travellers' advice
AI-generated summary based on content written by travel experts
United's Economy Plus offers extra legroom on this route.
Take the CTA Blue Line from O'Hare to downtown Chicago.
Expert advice
Expert advice
Expert advice
Expert advice
When to book
2 weeks
in advance
Our data shows that travellers who book at least 2 weeks in advance save around 15% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
November
Cheapest • 10% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest return fare
Multiple Airlines
Mon 15/9
SJO - ORD • multi-stop
Cheapest one-way flight
Multiple Airlines
Mon 15/9
SJO - ORD • multi-stop
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KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Expert advice

Expert advice for your flight from San José to Chicago

 
Snippets provided in this section are AI-generated based on a summarisation of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
American Airlines

American Airlines' Main Cabin Extra includes early boarding and complimentary alcoholic drinks.


American Airlines offers high-speed Wi-Fi for purchase; T-Mobile customers may get complimentary access.

Read more about American Airlinesby Harriet Baskas
United Airlines

United's Economy Plus offers up to six inches more legroom than standard economy seats.


United's Wi-Fi offers free messaging; T-Mobile customers often get free streaming Wi-Fi.

Read more about United Airlinesby Stefanie Waldek
Airports
SJO

For a smooth departure, arrive early at SJO as security lines can vary. Enjoy free WiFi and self-check-in kiosks for convenience.

Read more about SJOby Mark Chesnut
ORD

Take the CTA Blue Line train from ORD to downtown Chicago in about 45 minutes, avoiding traffic delays common with driving.

Read more about ORDby Stefanie Waldek
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

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, 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.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

Stefanie Waldek

Stefanie Waldek

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 out at sea, likely en route to Antarctica or the Arctic.

Read more
Mark Chesnut

Mark Chesnut

Expert on SJO

Mark Chesnut

Mark Chesnut

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.

Read more
Booking Insights

KAYAK's insights & trends for San José to Chicago flights

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San José 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 to Chicago O'Hare Intl Airport is November, where tickets cost £315 (return) on average. On the other hand, the most expensive months are May and April, where the average cost of round-trip tickets is £381 and £380 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from San José 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 week.

To get a below average price on the flight from San José to Chicago O'Hare Intl Airport, you should book around 2 weeks before departure, which saves you about 15% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

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Good to know - Cheap tickets from San José to Chicago

Low seasonFebruary
Best time to beat the crowds (6% less expensive on average)
Most popular time to fly (7% more expensive 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?

    American Airlines, Air Canada, Iberia, 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 Boeing 737 MAX 8 is the aircraft model that flies most regularly on the San José to Chicago flight route.

  • 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.

Prefer to fly direct from San José to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from San José Juan Santamaria Intl to Chicago O'Hare Intl.
Find which airlines fly direct from San José Juan Santamaria Intl Airport to Chicago O'Hare Intl Airport, which days they fly and book direct flights.

Direct departures

San José Juan Santamaria Intl to Chicago O'Hare Intl

Monday

American Airlines

American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines

American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines

American Airlines

See more direct flights

Direct returns

Chicago O'Hare Intl to San José Juan Santamaria Intl

Monday

American Airlines

American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines

American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines

American Airlines

See more direct flights

Everything you need to know for your flight from San José to Chicago

Information on your arrival and departure airports

San José (SJO)
O'Hare Intl (ORD)

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