Flying from Chicago to San Juan: what you need to know
Chicago has two main airports where you can kick off your trip. Explore your options for booking a flight from Chicago to San Juan flying out of O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW).
Luis Munoz Marin International Airport (SJU) is the primary point of entry to San Juan.
Take a direct Chicago to San Juan flight and you'll be flying for an average of 4 hours 45 minutes.
The timezone in San Juan is UTC-4, which is one hour ahead of Chicago.
With 22 weekly flights between the two airports, O'Hare International Airport (ORD) to Luis Munoz Marin International Airport (SJU) is the busiest route. Hop on the first flight from Chicago to San Juan with United Airlines at 07:20. If you'd like to make the most of your day before you fly, the last flight from ORD to SJU is with Spirit Airlines at 20:46.
Give yourself enough time to get on your Chicago to San Juan flight. Generally, it's best to arrive at least two hours before international departures and an hour ahead for domestic flights.
During popular months like August, you'll want to get to the airport earlier than usual. Plan to arrive two hours before domestic departures and four hours ahead of international flights when you travel during peak periods in general.
How to find the cheapest flights from Chicago to San Juan
The lowest price we've seen for a one-way ticket from Chicago to San Juan is RM270. For a return flight on this route, the best price is RM686. Depending on when and how early you book, these fares may change.
To snag cheap Chicago to San Juan flights, book your journey two months before your departure date.
May is the best month for nabbing a fantastic deal on a plane ticket from Chicago to San Juan. If you're looking to travel at a different time of year, the 'Whole month' tool will show you the lowest prices for every month.
There's no need to search every day to see if fares have dropped when you set up a Price Alert. We'll let you know the moment there's a better deal on cheap flights from Chicago to San Juan.
Tailor your trip using filters. Pick your departure and arrival times, airlines and total journey duration. You can also sort the results by 'Fastest,' 'Best' or 'Cheapest' Chicago to San Juan flights.
Flying from Chicago
O'Hare International Airport (ORD)
If you're after a direct flight from Chicago to San Juan, you can leave from O'Hare International Airport (ORD). Travel from ORD to Luis Munoz Marin International Airport (SJU) in one continuous trip.
Choose from a variety of airlines that offer direct Chicago to San Juan plane tickets out of ORD. Book your seat with one of these:
A stopover is the ideal opportunity to take a travel break — and possibly even visit a new city. When searching for Chicago to San Juan flights leaving from O'Hare International Airport, deselect the 'Direct flights only' box to see where you can stop along the way. Top options include:
Hartsfield-Jackson Atlanta International Airport (ATL)
Raleigh-Durham International Airport (RDU)
Punta Cana International Airport (PUJ)
Travelling from central Chicago to ORD takes around 55 minutes on public transport. If you ride-share, drive or get a cab, you'll cover the 26 kilometres in 35 minutes or so, depending on traffic.
Planning to catch an early flight from Chicago to San Juan? Avoid the stress of rushing to the terminal (and enjoy a little extra shut-eye) by choosing one of these stays close to O'Hare International Airport:
Of the flights that depart from O'Hare International Airport, 74.85% land on time at their destination.
You'll find ORD at 10000 West O'Hare.
Chicago Midway International Airport (MDW)
Rather fly from Chicago Midway International Airport (MDW)? This popular hub offers direct flights from Chicago to San Juan, seamlessly connecting to Luis Munoz Marin International Airport (SJU).
You can book a direct Chicago to San Juan plane ticket with Southwest Airlines. This is one of the leading airlines operating this route out of MDW.
Split up your Chicago to San Juan flight with a stop so you can stretch your legs or cross a new place off your list. Some popular stopovers between Chicago Midway International Airport and San Juan are:
Hartsfield-Jackson Atlanta International Airport (ATL)
Orlando International Airport (MCO)
Nashville International Airport (BNA)
Using public transport, you can travel from central Chicago to MDW in around 45 minutes. The terminal is roughly 14 kilometres away. Driving will take you about 20 minutes.
Want to treat yourself to an extra night away before catching your flight from Chicago to San Juan? Unwind in a hotel near Chicago Midway International Airport before your adventure officially begins. Stay at one of these accommodation options:
78% of flights out of Chicago Midway International Airport stick to their scheduled arrival time.
You'll find MDW at 5700 South Cicero.
Arriving in San Juan
Luis Munoz Marin International Airport (SJU)
The distance from Luis Munoz Marin International Airport (SJU) to central San Juan is roughly 11 kilometres. It'll take you around 10 minutes to reach the centre driving.
It usually takes 55 minutes to get there when travelling by public transport.
Book a hotel close to SJU if you have a late flight from Chicago to San Juan. Choose one of these accommodation options and skip the long transfer:
Grab a Luis Munoz Marin International Airport rental car and explore San Juan and beyond with your own wheels. Sixt, Ace Rent a Car and U-Save are top providers you can book with here.
For the best deal, book your vehicle from Luis Munoz Marin International Airport around two weeks ahead of your Chicago to San Juan flight.
Fernando Luis Ribas Dominicci Airport (SIG)
Fernando Luis Ribas Dominicci Airport (SIG) is about 6 kilometres from central San Juan. Once you've hopped off your flight from Chicago to San Juan, it'll take you approximately 15 minutes to reach the heart of the city in a ride-share or cab.
You can expect the trip to take about 1 hour on public transport.
Best time to go to San Juan
July is the most popular month for flights from Chicago to San Juan. To escape the crowds, go to San Juan in May.
Before locking in your Chicago to San Juan tickets, consider the type of weather you enjoy. September is the warmest month in San Juan, with temperatures ranging from 23ºC (73ºF) to 33ºC (91ºF).
If you like travelling in cooler conditions, search for a cheap flight from Chicago to San Juan in February when temperatures average between 20ºC (68ºF) and 28ºC (82ºF).
More about San Juan
When it comes to looking for somewhere to rest your head, you'll find the best places to stay in San Juan right here. Check out these hotels after locking in your flight from Chicago to San Juan:
There are so many things to explore in this city it can be hard to work out where to begin. Castillo San Felipe del Morro, La Garita del morro de san juan bahia and Fortaleza Street are leading attractions which should be on any good San Juan itinerary.
Explore more of Puerto Rico
Bayamon is just one of the many cities in Puerto Rico waiting to be explored once you've taken in the sights of San Juan. Around 10 kilometres to the west, top sights here include Plazoleta Ignacio Zorrilla, La Plaza de la Bomba Puertorriqueña, Monumento a los Trovadores and Parque Palm Court.
Around 11 kilometres east of San Juan, Carolina is another favourite stop in Puerto Rico. Experience this destination's highlights firsthand at Isla Verde Beach, Parque de Doble A Roberto Clemente Walker and Drone Zone Track.
