Skip to main content
Beginning of main content

SJO (San Jose) to ORD (Chicago) Flights $295.89

Search over 321,000 hotels worldwide and 400 airlines worldwide.
Secure incredible value with Expedia's Price Guarantee.
No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheap SJO to ORD Flights

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.



Interesting Facts About Flights from San Jose to Chicago (SJO to ORD)

Question : What's the expected flight time for SJO to ORD?
Answer : The average flight duration between SJO and ORD is five hours and 30 minutes.

Question : How many departure times are there on a given day?
Answer : Depending on the day of the week, the number of flight times will change, but on average there are two. That is the same number of choices as the average route departing Costa Rica.

Question : Will you do what it takes to get the absolute cheapest flight?
Answer : The best day to fly on a budget this month is Tuesday. Flexibility is paramount when booking travel plans in order to keep travel costs down.

Question : Is the price you found a good deal?
Answer : Ranging anywhere from $279 to $2,532, prices for SJO to ORD do change a lot more than the majority of routes from Costa Rica. Prices tend to be lower the further out you book.

Question : Looking for the cheapest flight over the next 30 days?
Answer : Since low prices are preferred, look at Jul 12th. As of Jun 19th, it's showing the cheapest ticket sales at $362. That is 37% below the average price for this route, so you can spend that extra cash on a fun experience in Chicago.

Question : Which airline is offering the cheapest flight from SJO to ORD?
Answer : AVIANCA is the leader in keeping costs down for their passengers over the next three months. Fares are being booked at just $279, which is quite a deal when compared to the high-end bookings of $2,532.

Question : What is the shortest flight from SJO to ORD?
Answer : United Airlines can get you there in five hours and 30 minutes. For example, if you were to leave San Jose at 11:45 PM CST, you would arrive in Chicago at 5:15 AM CDT.