Economy fares · CHI to SJO
Lowest fare in our last check: $928 per person, round trip · checked Nov 8, 2026. Fares change and are confirmed when you book.
Photo of Chicago, where this route departs: Chicago skyline at sunrise reflected in Lake Michigan. Daniel Schwen, CC BY-SA 4.0, via Wikimedia Commons, cropped; the crop is shared under the same licence.
Distance
2,221 mi
ORD to SJO, straight line
Nonstop
Not seen
in our Nov 8 check
Airline seen
1
United Airlines
Fare checks
4
since Sep 27, 2026, latest Nov 8
Avianca operates flights between Chicago and San Jose. Reviewing different stopover times and routing options helps you find a price and schedule that works for your trip to Costa Rica.
From 10 real fares found in our latest check. Prices are per person and can change.
10 real fares from our latest check, cheapest first. Prices are per person and can change until ticketed.
United Airlines
1 stop · 11h · Wed, Dec 23
United Airlines
1 stop · 11h 40m · Wed, Dec 23
United Airlines
1 stop · 11h 49m · Wed, Dec 23
United Airlines
1 stop · 11h · Wed, Dec 23
United Airlines
1 stop · 11h 40m · Wed, Dec 23
Avianca offers service on this route. Every option currently found involves 1 stop. Total journey times vary significantly depending on the layover, with some flights taking 10h 20m and others extending to 17h 50m or 26h 0m. Comparing these schedules helps clarify how your time on the ground between flights impacts the final price.
Fares on this route fluctuate across the winter months. Recent data shows prices climbing from late autumn into December and January, before dropping noticeably in February. Checking the live fares shown above for different dates in your travel window can help you locate these shifts in price.
Flexibility with your departure and return dates is a reliable way to improve the price you pay. Since all current options involve connections, comparing long layovers against faster transits can also reveal different price tiers. Booking well in advance of the winter travel season allows you to monitor how prices change over time.
We are not currently seeing any nonstop flights from Chicago to San Jose. The available flights all require 1 stop. Because of the required connection, the total travel time can be as short as 10h 20m or stretch out to 26h 0m. Always review the layover city and the waiting time before you finalize your booking.
ASAirspace provides live fare search without adding booking fees. If you need help comparing the options between Chicago and Costa Rica, our advisors are available on the phone to talk you through the current schedules. You can compare different layover times and airlines to make an informed choice.
Avianca operates flights on this route. You can view their current pricing and schedules in the live fares shown above.
Recent flight searches show no nonstop options. All the flights we are currently seeing require 1 stop.
The total journey time depends on your connection. Our latest data shows 1 stop flights taking 10h 20m, 17h 50m, or up to 26h 0m depending on the length of the layover.
Pricing varies across the year. Over the upcoming winter season, fares peak in January and drop down again in February. Check the live fares shown above to see current prices for your specific travel dates.
Booking several months ahead gives you the best chance to track fare trends. Start comparing options early, especially if you plan to travel during the busy December and January period.
The time of year, how far ahead you book, and your willingness to accept a longer layover all impact the price. Flights with a 26h 0m total duration might differ in cost from a faster 10h 20m journey.
Baggage policies vary by ticket type. Check the airline's baggage allowance before booking, as basic economy fares often charge extra for checked bags.
Booking a return flight can sometimes offer better overall value and simplifies your travel plans. Compare the live fares for both one-way and return options to see which suits your schedule.
