Cheap Flights from San Juan to Chicago Starting at $63

Looking for cheap flights from San Juan to Chicago? Look no further! Our air ticket search website offers the best deals for your travel needs. Discover the vibrant city of Chicago without breaking the bank. Whether you're planning a weekend getaway or a longer trip, we've got you covered. With our user-friendly search engine, finding the most affordable flights has never been easier. Explore famous landmarks like the Navy Pier or indulge in deep-dish pizza in the Windy City. Don't miss out on the stunning views from the Willis Tower Skydeck or the cultural attractions at Millennium Park. Start your adventure now by booking your affordable flight from San Juan to Chicago with us. Travel smart, travel with us!

More than 6 airlines operate flights from San Juan to Chicago, including Southwest Airlines, Spirit Airlines, United Airlines, American Airlines, JetBlue Airways, and Frontier Airlines. This is a popular route, so passengers can choose tickets based on budget and preferences. Ticket prices start from $63, and our service lets you instantly compare all options. The variety of offers simplifies planning: you can choose budget fares or more comfortable options with baggage included or extra services. We help you find the best deals so your trip is cost-efficient.

Looking for direct flights from San Juan, Puerto Rico to Chicago, United States? Good news! There are direct flight options available for this route. Traveling directly from sunny San Juan to the vibrant city of Chicago has never been easier. Enjoy a hassle-free journey with no layovers or transfers, allowing you to maximize your time and experience both the tropical beauty of Puerto Rico and the bustling charm of the Windy City. Book your air tickets now and immerse yourself in the diverse cultures, delicious cuisines, and iconic attractions of these two incredible destinations. For those seeking alternative routes with transfers, you can consider connecting flights via major hubs such as Miami or Atlanta. Discover the best travel options to create unforgettable memories on your journey from San Juan to Chicago.

San Juan, Puerto Rico boasts two major airports, each with its own advantages and drawbacks for travelers looking to depart. Luis Muñoz Marín International Airport, located just a few miles from downtown, offers convenience and minimal commute time. With a wide range of prestigious airlines using it as a hub, travelers can find competitive prices and abundant flight options. However, its popularity also means potentially longer security lines and crowded terminals. On the other hand, if you're willing to explore further afield, Rafael Hernández Airport in Aguadilla offers a quieter, less hectic experience. While it may require additional travel time and possible transportation costs, it provides a more relaxed atmosphere with shorter queues. While the flight options may be slightly limited, airlines such as JetBlue and Spirit Airlines still use this airport, ensuring reasonable fares. Whether you prioritize convenience or a calmer departure experience, San Juan's airports have you covered. Compare ticket prices on our airfare search website to find the best deal for your flight!

Chicago is served by two main airports that cater to travelers arriving in the city. O'Hare International Airport, one of the busiest airports worldwide, offers excellent connectivity and a wide range of airlines, including prestigious carriers like United Airlines and American Airlines. Although getting to O'Hare from the city center can take some time, it is well connected by public transportation, making it a convenient and affordable choice for most travelers. On the other hand, Midway International Airport presents a more compact and time-efficient option. Despite handling fewer airlines, it is a hub for budget carriers like Southwest Airlines. Travelers arriving at Midway can quickly reach downtown Chicago via affordable and efficient public transport, saving both time and money. It is essential to consider your flight options and preferred airlines when choosing between the two airports. O'Hare, with its extensive flight network and hub status for prestigious airlines, may be a more desirable choice for those seeking a wider range of connections and a more luxurious travel experience. However, Midway's easy accessibility and cost-effective options make it an attractive alternative for budget-conscious travelers. By comparing the benefits and downsides of each airport, you can make an informed decision based on your travel preferences. Whether you prioritize convenience, price, or airline options, both O'Hare International Airport and Midway International Airport ensure a smooth and enjoyable entry into Chicago. Fly hassle-free and experience the vibrant Windy City!

The distance between San Juan and Chicago is 3305km (2049 miles). There are 30 direct flights from San Juan to Chicago. The time difference between San Juan and Chicago is 2h. Flights from San Juan begin at 8:10 AM. The latest flight from San Juan departs at 8:45 PM

The cost of a one-way flight from San Juan to Chicago ranges from $63 (March 2026) to $103 (February 2026). On average, the ticket price is about $83–$103.