$253 Cheap United flights San José (SJO) to Chicago (ORD)

View $253 flight on Sat, Jul 12, 2025Opens in a new window

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$253 Cheap United flights San José (SJO) to Chicago (ORD)

Prices were available within the past 7 days and start at $253 for one-way flights and $464 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Thu, Jan 22 - Mon, Jan 26
SJO
San José
ORD
Chicago
$464 Roundtrip, found 1 hour ago
$464
Roundtrip
found 1 hour ago
Select United flight, departing Thu, Jan 22 from San José to Chicago, returning Mon, Jan 26, priced at $464 found 1 hour ago
Flights from San José (SJO) to Chicago (ORD)
Origin airport
Juan Santamaría Intl.
Destination airport
O'Hare Intl.
Airlines serving
Aeromexico, Air Canada, American Airlines, Copa, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Spirit Airlines, United, avianca
Popular airline
avianca
Distance
2220 mi
Average flight time
7 hours 37 mins

Frequently asked questions

How much is a United Airlines flight from Juan Santamaria Intl. Airport (SJO) to O'Hare Intl. Airport (ORD)?
Apply the "Price (lowest to highest)" filter on Expedia to look for cheap United Airlines return flights from $464 from SJO to ORD. Affordable one-way fares from $253 are also on offer.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly from SJO to ORD with United Airlines?
United Airlines flights to Chicago tend to be cheaper in the off-peak months of January and February. Whether you're after a round-trip or one-way ticket, you could find a better deal then.
What is the cheapest time to book flights from Juan Santamaria Intl. Airport (SJO) to O'Hare Intl. Airport (ORD) with United Airlines?
Landing the best United Airlines deals from SJO to ORD often comes down to timing. You can save 17% on international flights when you book 18 to 29 days before takeoff instead of four to five months ahead. Better yet, you can pocket 17% on average by buying your fare on a Sunday compared to a Friday, which is usually the most expensive day to book.* It's smart to kick off your flight search about one month before your departure date.*Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC's global airline sales database.
Does United Airlines fly nonstop from Juan Santamaria Intl. Airport (SJO) to O'Hare Intl. Airport (ORD)?
United Airlines has direct flights from Juan Santamaria Intl. Airport (SJO) to O'Hare Intl. Airport (ORD), with 2 departures each week. Just apply the "Nonstop" and "Airline" filters during your search on Expedia to show all direct United Airlines flights to ORD.
How long does it take to fly from SJO to ORD with United Airlines?
It takes around 5h 25m to travel nonstop from Juan Santamaria Intl. Airport (SJO) to O'Hare Intl. Airport (ORD) with United Airlines.
What is the earliest United Airlines flight from SJO to ORD?
The first flight from SJO to ORD with United Airlines leaves at 2:05PM UTC-6. You'll touch down at 7:30PM UTC-6. The final United Airlines flight of the day leaves at 2:05PM UTC-6 and arrives at 7:30PM UTC-6. With around 20% fewer cancellations for departures before noon, starting your travel day early is typically the wisest option.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports does United Airlines fly into in Chicago?
O'Hare Intl. Airport (ORD) is the main Chicago gateway for United Airlines flights from Juan Santamaria Intl. Airport (SJO).
Why fly with United Airlines from SJO to ORD?
A rewarding loyalty program and the ability to collect points through United Mileage Plus are the start of the reasons to travel from SJO to ORD with United Airlines. Plus, when you join our One Key™ program, you can earn OneKeyCash™* on top of United Airlines's loyalty program earnings. It's yours to use wherever your next trip takes you.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
What type of plane does United Airlines fly from Juan Santamaria Intl. Airport (SJO) to O'Hare Intl. Airport (ORD)?
You'll probably travel on a Boeing 737 MAX 8 for your United Airlines flight from Juan Santamaria Intl. Airport (SJO) to O'Hare Intl. Airport (ORD). However, you may be switched to a different aircraft if there's an operational need.
Can I change or cancel my United Airlines flight from Juan Santamaria Intl. Airport (SJO) to O'Hare Intl. Airport (ORD)?
Changes are typically free within 24 hours of booking, but your airline may charge a fee after that time. For further information about modifying your flights, head to your "Trips," select your flight and click on "Manage Booking." If you want the freedom to adjust your plans without additional charges, tick the "No cancel fee" or "Changes included" filter when planning your next getaway.

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