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.
AV
1 stop · 26h · Fri, Nov 6
AV
1 stop · 26h · Fri, Nov 6
AV
1 stop · 17h 50m · Fri, Nov 6
AV
1 stop · 17h 50m · Fri, Nov 6
AV
1 stop · 10h 20m · Fri, Nov 6
Lowest fare we found for each month we checked. Based on real searches, not a forecast.
Cheapest month found: Feb 2027 from $483
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.
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