
Popular airlines from Juan Santamaria Intl. Airport (SJO) to Chicago O'Hare Intl. Airport (ORD)
- Avianca
Avianca
- Air Canada
Air Canada
- Aeromexico
Aeromexico
- JetBlue Airways
JetBlue Airways
- Spirit Airlines
Spirit Airlines
- Copa
Copa
- United
United
- Be in the knowGet alerts if flight prices drop or rise*
- Book smarterSave up to 30% on select hotels after you book a flight*
Cheap Flights from San José to Chicago (SJO-ORD)
Prices were available within the past 7 days and start at RM1,107 for one-way flights and RM1,953 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, 23 Feb - Sun, 1 Mar
SJO
San José
ORD
Chicago
RM1,953 Return, found 1 day ago
RM1,953
Return
found 1 day ago

Mon, 23 Feb - Sun, 1 Mar
SJO
San José
ORD
Chicago
RM1,955 Return, found 1 day ago
RM1,955
Return
found 1 day ago

Mon, 23 Feb - Sun, 1 Mar
SJO
San José
ORD
Chicago
RM1,999 Return, found 1 day ago
RM1,999
Return
found 1 day ago

Mon, 23 Feb - Sun, 1 Mar
SJO
San José
ORD
Chicago
RM2,021 Return, found 1 day ago
RM2,021
Return
found 1 day ago

Mon, 23 Feb - Sun, 1 Mar
SJO
San José
ORD
Chicago
RM2,057 Return, found 1 day ago
RM2,057
Return
found 1 day ago

Mon, 23 Feb - Sun, 1 Mar
SJO
San José
ORD
Chicago
RM2,065 Return, found 1 day ago
RM2,065
Return
found 1 day ago

Mon, 23 Feb - Sun, 1 Mar
SJO
San José
ORD
Chicago
RM2,100 Return, found 1 day ago
RM2,100
Return
found 1 day ago

Mon, 23 Feb - Sun, 1 Mar
SJO
San José
ORD
Chicago
RM2,340 Return, found 1 day ago
RM2,340
Return
found 1 day ago

Mon, 23 Feb - Sun, 1 Mar
SJO
San José
ORD
Chicago
RM2,500 Return, found 1 day ago
RM2,500
Return
found 1 day ago

Mon, 23 Feb - Sun, 1 Mar
SJO
San José
ORD
Chicago
RM2,763 Return, found 1 day ago
RM2,763
Return
found 1 day ago
Find the cheapest month to fly from San José (SJO) to Chicago (ORD)
October is typically the cheapest month to fly
From RM 705 - RM 1,603 per traveller.
Origin airport | Juan Santamaría Intl. |
|---|---|
Destination airport | O'Hare Intl. |
Airlines serving | Aeromexico, Air Canada, American Airlines, Copa, Delta, United, avianca |
Return price | RM1,953 |
Distance | 3553 km |
Average flight time | 5 hours 29 mins |
Perfect flights from San José to Chicago
Your Journey from San José to Chicago
Start your unforgettable journey with Expedia. Our broad selection of flights from San José to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
Choosing Your Ideal Flight
With Expedia, you have access to a wide range of airlines, including avianca, Air Canada, Delta, Copa, United, Aeromexico, American Airlines. Our selection of flights from Juan Santamaría Intl. to O'Hare Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
Maximizing Value with San José to Chicago Flights
Experience the joy of finding cheap flights from Juan Santamaría Intl. to O'Hare Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from RM1,107 and roundtrip prices from RM1,953*.
Pre-Flight Essentials
Ensure a smooth journey from San José to Chicago with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
Experience the Vibrant Chicago
Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
Added Convenience on Your San José to Chicago Flight
Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from San José to Chicago.
Beyond the Flight – Exploring Chicago
With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
Book Your Flight from San José to Chicago with Confidence
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from San José to Chicago with confidence. Book your travel arrangements with Expedia today.
*Note: Prices may vary based on availability and are subject to change.
Explore a world of travel with Expedia
Top Routes from San José
Top Routes to Chicago
- Los Angeles to Chicago (LAX - ORD)
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- New York to Chicago (LGA - ORD)
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*Available to Expedia members.