Cheap Flights from Chicago to San Juan Starting at $111

The Chicago — San Juan route is served by a wide range of airlines: 4 in total, including Spirit Airlines, United Airlines, Frontier Airlines, and American Airlines. Competition among carriers gives passengers the opportunity to find tickets at attractive fares — with prices starting from $111. Our service helps compare all available offers within seconds and choose the most convenient option. You can filter flights by price, departure time, or baggage rules to make your trip as comfortable as possible. With so many airlines, there’s always a chance to catch special promotions and save.

Chicago is served by two main airports with distinct roles. O’Hare International (ORD) is the city’s primary international hub and a major connecting point for full-service carriers such as United and American, so fares can be competitive for long-haul and connecting itineraries. It sits about 17–20 miles northwest of downtown; the Blue Line ‘L’ takes roughly 45–50 minutes and fares are typically in the local transit range, while taxis or rideshares can take 30–60 minutes depending on traffic and cost more. Midway (MDW) is a smaller, more budget-leaning airport about 10 miles southwest, often favored by low-cost and leisure carriers; travel to downtown usually takes 20–35 minutes by CTA Orange Line or 25–40 minutes by road. O’Hare offers extensive international routes and many amenities but can be busier and involve longer security or connection times; Midway can be quicker to navigate and cheaper on short domestic flights but has fewer long-haul options.

Luis Muñoz Marín International Airport (SJU) is San Juan’s primary international gateway and typically functions as the island’s main hub for both legacy carriers and regional airlines, handling most long-haul and nonstop flights. Located about 8 miles (roughly 15–30 minutes) east of Old San Juan, it’s reachable by taxi, ride-hail or shared van services; expect fares generally to fall in the moderate range depending on time and vehicle. Ground transit includes private shuttles and car rentals; public buses are available but can be slower. Advantages include frequent connections and full-service facilities; downsides can be crowds and occasional traffic into the city during peak times. Fernando Luis Ribas Dominicci Airport (Isla Grande, SIG) is a smaller, centrally located airport serving mainly regional, private and commuter flights, often used for short hops and general aviation rather than major international routes. Sitting within San Juan’s Isleta de San Juan, it’s typically only a few minutes from downtown—reachable by taxi or local cab services with short travel times and modest fares. The airport is convenient for business travelers or private flyers but offers limited commercial options and fewer amenities compared with the larger international airport. Its compact size can mean quicker check-ins but fewer flight choices.

We carefully collect statistics on the search and pricing of airlines and, based on these data, we make an assumption about future prices. Thus, you can better understand which season is the cheapest to fly from Chicago to San Juan