San Juan to Chicago Flight Tickets
Compare the best flight deals from San Juan to Chicago
About San Juan - Chicago Flights
Find the best prices for flights between San Juan (United States) and Chicago (United States) on Tripuck. We compare prices from hundreds of airlines to offer you the best options.
San Juan has 2 airports, while Chicago has 6 airports. Compare flights between all airports to find the best deal.
Cheapest Months for San Juan - Chicago Flights
Best month to fly
September 2026 - 2.843 ₺
September 2026
2.843 ₺
Direct
CheapestOctober 2026
4.738 ₺
Direct
November 2026
4.975 ₺
1 stops
August 2026
7.166 ₺
1 stops
January 2027
22.328 ₺
1 stops
| Ay | Flight Type | Price |
|---|---|---|
| September 2026Cheapest | Direct | 2.843 ₺ |
| October 2026 | Direct | 4.738 ₺ |
| November 2026 | 1 stops | 4.975 ₺ |
| August 2026 | 1 stops | 7.166 ₺ |
| January 2027 | 1 stops | 22.328 ₺ |
Prices may change. Based on recent searches.
Popular San Juan - Chicago Flights
San Juan - Chicago
Chicago - San Juan
Airlines on San Juan - Chicago Route
| Havayolu | Uçuş Tipi | Fiyat |
|---|---|---|
| Frontier Airlines | Direct | 2.843 ₺ |
San Juan Airports
Chicago Airports
Alternative Routes
Alternative Routes from San Juan
San Juan - Chicago Flight Summary
Cheaper tickets are usually available on weekdays and with early bookings.
San Juan and Chicago - Airport Transportation
Luis Munoz Marin International Airport (SJU)
How to Get to the Airport
Bus (AMA – T5 Line, From City to Airport): To reach the airport from the city center (especially from the Old San Juan/Viejo San Juan area) using public transportation, you can use the T5 bus line. The T5 departs from Old San Juan and proceeds along the Condado – Isla Verde route towards the airport; you can board the bus from the main stops in Old San Juan. The journey from Old San Juan to the airport takes 35–50 minutes depending on traffic, and from Condado to the airport, it generally takes about 20–30 minutes. The T5 line operates approximately every 20–30 minutes from the city center to the airport.
Taxi (From City to Airport): You can hail street taxis in San Juan city center (Old San Juan, Condado, Isla Verde, and hotel areas) or request a taxi from the hotel reception. The journey from Old San Juan or Condado to the airport typically takes 20–30 minutes depending on traffic.
Car Rental: You can rent a car from car rental offices in the city center to go to the airport. Transportation from the city to the airport with the rented car takes approximately 20–30 minutes depending on traffic.
Uber: You can use the Uber app to go from San Juan city center to the airport. The vehicle you call through the app will typically get you to the airport in 15–30 minutes depending on traffic.
Regional Bus Lines: Quite a few regional bus lines operate from the city center to the airport. However, the exact routes and frequency of these lines may vary, so we recommend paying attention to current information.
O'Hare International Airport (ORD)
From Airport to City Center
Metro/Train: The CTA Blue Line Train is the most convenient option for transportation from O'Hare International Airport to downtown Chicago. The airport station is directly connected to Terminals 1, 2, and 3. Access from Terminal 5 is possible via a free shuttle train. The journey takes approximately 40-45 minutes. Services operate 24 hours a day, with trains running every 5-10 minutes during peak hours.
Bus (CTA and Private Shuttles): Buses connecting O'Hare Terminals 1, 2, 3, and 5 operate routes to downtown. The journey time varies between 45-60 minutes depending on traffic conditions. Services run every 15-30 minutes and generally operate from 5:00 AM to 11:45 PM.
Taxi: Official taxi stands at O'Hare are located at each terminal exit and provide direct transportation to downtown. The journey time varies between 30-60 minutes depending on traffic. Taxi services are available 24 hours a day.
Airport App-Based Rides (Uber/Lyft): Apps like Uber and Lyft operate in designated pickup areas at O'Hare. Journey time and cost can vary based on traffic and demand.
Car Rental: Various car rental companies are available at the airport. Car rental options can be arranged at offices located at terminal exits or at rental centers accessible via shuttle services.