ORD → SJO
Compare one-way, round-trip and flight + hotel packages from Chicago to San Jose, a nonstop flight of about 5h, with fares from around 265.
Chicago to San Jose is an international route covering about 2,220 miles, arriving at Juan Santamaria International Airport (SJO) in Costa Rica. Peak travel season in San Jose runs December–April (dry and sunny), while July–October is usually the quietest and best-value time to visit. The cheapest fares we've tracked on this route include at least one stop.
| Departing from | O'Hare International Airport (ORD) |
|---|---|
| Arriving at | Juan Santamaria International Airport (SJO) |
| Distance | 2,220 miles (3,575 km) |
| Nonstop flight time | About 5h |
| Nonstop airlines seen | None in recent fares, expect 1 stop |
| Round-trip fares from | $265 (estimate) |
| Cheapest months | February, September, April |
| Peak season in San Jose | December–April |
| Cheapest hotel months in San Jose | July–October |
| Best time to book | 2 to 6 months ahead |
| Route info updated | October 16, 2026 |
December–April
Dry and sunny
May–June & November
Green, short afternoon rains
July–October
Rainy green season
| Month | Fares from |
|---|---|
| January | $325 |
| February | $265 |
| March | $330 |
| April | $315 |
| May | $340 |
| June | $430 |
| July | $415 |
| August | $380 |
| September | $275 |
| October | $330 |
| November | $340 |
| December | $390 |
The cheapest fares we've tracked on this route include at least one stop. Ducoffs.com compares full-service and low-cost airlines flying between Chicago and San Jose in a single search, including nonstop and one-stop options, so you can weigh price against total travel time.
Fares on this route tend to be lowest in February, September, and April. For the best selection, book about 2 to 6 months before departure and stay flexible by a day or two.
Chicago and San Jose are about 2,220 miles apart. A nonstop flight takes roughly 5h; connecting itineraries usually add 2 to 5 hours.
The best way to secure budget rates is by comparing multiple airlines simultaneously and checking flexible dates. Ducoffs.com scans available partner networks to bring you real-time pricing options.
Based on typical seasonal demand, February, September, and April tend to offer the lowest fares on this route, with estimated round-trip prices starting around $265. Live prices change daily, so run a search for your exact dates.
Chicago and San Jose are about 2,220 miles apart. A nonstop flight takes roughly 5h, while connecting itineraries usually add 2 to 5 hours depending on the layover.
The cheapest fares we've tracked recently on this route include at least one stop. Your live search shows any nonstop options available for your dates.
Hotel rates in San Jose are usually lowest in July–October, when demand is quieter, and highest during peak season (December–April). Booking your flight and hotel together can save up to 30%.
This route arrives at Juan Santamaria International Airport (SJO). Your search results also show nearby airports when they offer a cheaper or faster option.
For this route, booking about 2 to 6 months before departure usually gives the best balance of price and seat selection. Mid-week departures are often cheaper than weekend flights.
Yes. Bundling your travel components can save you up to 30% compared to booking flights and hotels separately, as airlines and properties offer exclusive package discounts.
Ducoffs.com