Chicago to San Juan Flight Tickets
Compare the best flight deals from Chicago to San Juan
About Chicago - San Juan Flights
Find the best prices for flights between Chicago (United States) and San Juan (United States) on Tripuck. We compare prices from hundreds of airlines to offer you the best options.
Chicago has 6 airports, while San Juan has 2 airports. Compare flights between all airports to find the best deal.
Cheapest Months for Chicago - San Juan Flights
Best month to fly
September 2026 - 3.055 ₺
September 2026
3.055 ₺
Direct
CheapestNovember 2026
5.401 ₺
1 stops
| Ay | Flight Type | Price |
|---|---|---|
| September 2026Cheapest | Direct | 3.055 ₺ |
| November 2026 | 1 stops | 5.401 ₺ |
Prices may change. Based on recent searches.
Popular Chicago - San Juan Flights
Chicago - San Juan
San Juan - Chicago
Airlines on Chicago - San Juan Route
| Havayolu | Uçuş Tipi | Fiyat |
|---|---|---|
| Frontier Airlines | Direct | 3.055 ₺ |
Chicago Airports
San Juan Airports
Alternative Routes
Alternative Routes from Chicago
Chicago - San Juan Flight Summary
Cheaper tickets are usually available on weekdays and with early bookings.
Chicago and San Juan - Airport Transportation
O'Hare International Airport (ORD)
How to Get to the Airport
Metro/Train: You can reach the airport in 40-45 minutes by taking the CTA Blue Line train from downtown Chicago. Services run every 5-15 minutes and operate 24 hours a day.
Bus: You can reach the airport by taking buses departing from downtown bus stops (e.g., around Union Station). The journey takes approximately 45-60 minutes, with buses departing every 15-30 minutes.
Taxi: Transportation from downtown Chicago to O'Hare by taxi is possible. The journey takes 30-60 minutes depending on traffic, and taxis operate 24 hours a day.
Airport App-Based Rides (Uber/Lyft): You can reach O'Hare from downtown via Uber or Lyft. You can request a ride through the app and board at designated pickup points.
Car Rental: You can reach the airport by renting a car from rental offices located in the city center. Information on rental procedures can be obtained from rental offices at the airport.
Luis Munoz Marin International Airport (SJU)
From Airport to City Center
Bus (AMA – T5 and other lines): The T5 bus line departs near Terminal A of the airport and heads towards Old San Juan (Viejo San Juan) via Isla Verde – Condado. The journey to Old San Juan takes approximately 35–50 minutes depending on traffic; areas like Condado can generally be reached within 25–35 minutes. The T5 line operates approximately every 20–30 minutes throughout the day and provides service from early morning to late evening (e.g., 05:00–21:00).
Taxi (Official Airport Taxi Service): Official taxi stands are located just outside the terminal doors in front of the arrivals exits. A taxi ride to the Isla Verde/Condado area typically takes 10–20 minutes, and to Old San Juan, it takes about 20–30 minutes depending on traffic.
Car Rental: There are offices of many international car rental companies at the airport. By renting a car from the airport, you can easily reach your desired destinations. Remember to have the necessary documents for car rental with you.
Uber: App-based vehicles like Uber also operate within the airport. Transportation to the city center with Uber typically takes 15–30 minutes depending on traffic. You can quickly arrange transportation by making a reservation through the app.
Limousine: Private limousine services are also available at the airport. If you are looking for a special travel experience, you can ensure comfortable transportation by renting a limousine.