ORD → SJU
Compare one-way, round-trip and flight + hotel packages from Chicago to San Juan, a nonstop flight of about 4h 40m, with fares from around 265. Nonstop fares seen from Frontier.
Chicago to San Juan is an international route covering about 2,073 miles, arriving at Luis Munoz Marin International Airport (SJU) in Puerto Rico. Peak travel season in San Juan runs December–April (warm, dry and sunny), while June–October is usually the quietest and best-value time to visit. Nonstop fares we've tracked on this route come from Frontier.
| Departing from | O'Hare International Airport (ORD) |
|---|---|
| Arriving at | Luis Munoz Marin International Airport (SJU) |
| Distance | 2,073 miles (3,338 km) |
| Nonstop flight time | About 4h 40m |
| Nonstop airlines seen | Frontier |
| Round-trip fares from | $265 (estimate) |
| Cheapest months | February, September, January |
| Peak season in San Juan | December–April |
| Cheapest hotel months in San Juan | June–October |
| Best time to book | 2 to 6 months ahead |
| Route info updated | October 16, 2026 |
December–April
Warm, dry and sunny
May & November
Hot with passing showers
June–October
Humid, rainy, hurricane season
| Month | Fares from |
|---|---|
| January | $305 |
| February | $265 |
| March | $320 |
| April | $335 |
| May | $310 |
| June | $380 |
| July | $420 |
| August | $340 |
| September | $280 |
| October | $325 |
| November | $315 |
| December | $415 |
Nonstop fares we've tracked on this route come from Frontier. Ducoffs.com compares full-service and low-cost airlines flying between Chicago and San Juan 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 January. For the best selection, book about 2 to 6 months before departure and stay flexible by a day or two.
Chicago and San Juan are about 2,073 miles apart. A nonstop flight takes roughly 4h 40m; 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 January 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 Juan are about 2,073 miles apart. A nonstop flight takes roughly 4h 40m, while connecting itineraries usually add 2 to 5 hours depending on the layover.
Recent nonstop fares we've tracked on this route come from Frontier. Schedules change by season, so your live search shows every airline flying your dates.
Hotel rates in San Juan are usually lowest in June–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 Luis Munoz Marin International Airport (SJU). 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