Travelling from Chicago to San Juan: what you need to know
Chicago is home to two main airports that could be the jumping-off point for your adventure. Explore your options for reserving a flight from Chicago to San Juan departing from O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW).
Disembark at San Juan's primary gateway, Luis Munoz Marin International Airport (SJU).
The average length of a direct flight from Chicago to San Juan is 4 hours 40 minutes. San Juan's timezone is UTC-4, which makes San Juan 1 hour ahead of Chicago.
The busiest route for flights from Chicago to San Juan is from O'Hare International Airport (ORD) to Luis Munoz Marin International Airport (SJU). There are 25 weekly services between these two airports. If you'd like to get going first thing, the earliest flight from ORD to SJU is the 07:40 United Airlines service. If you prefer travelling later, the last departure is at 22:26 with Spirit Airlines.
Give yourself enough time to get on your flight from Chicago to San Juan. Generally, it's best to arrive at least two hours before international departures and an hour ahead for domestic flights.
You'll likely experience longer lines in popular months like August and other peak periods. Arriving up to four hours ahead of an international flight and two hours for a domestic departure is a good idea.
You won't need a visa for Puerto Rico if you have a passport from United States and are travelling for tourism purposes. Visa and travel documentation requirements are subject to change. So before reserving your cheap flights from Chicago to San Juan, be sure to check with your airline and your destination country's local consulate or embassy for the latest information.
Flying from Chicago
O'Hare International Airport (ORD)
If you're searching for a direct flight from Chicago to San Juan, you can board one at O'Hare International Airport (ORD). Get from ORD to Luis Munoz Marin International Airport (SJU) in one continuous trip.
Top carriers that offer direct flights from Chicago to San Juan out of ORD include:
A stopover is the ideal opportunity to break up your journey — and perhaps even explore another city. When searching for flights from Chicago to San Juan leaving from O'Hare International Airport, uncheck the 'Direct flights only' box to see where you can visit along the way. Top options include:
Punta Cana International Airport (PUJ)
Hartsfield-Jackson Atlanta International Airport (ATL)
Raleigh-Durham International Airport (RDU)
Located around 40 kilometres from central Chicago, ORD can be reached in approximately 35 minutes by car (depending on traffic). The journey by public transport takes roughly 54 minutes.
Searching for a handy hotel near O'Hare International Airport? If you're boarding an early flight from Chicago to San Juan, these accommodation options will have you moments from check-in:
Chicago Midway International Airport (MDW)
Break up your flight from Chicago to San Juan with a stop so you can freshen up or tick another place off your list. Popular stopovers between O'Hare International Airport and San Juan include:
Punta Cana International Airport (PUJ)
Hartsfield-Jackson Atlanta International Airport (ATL)
Raleigh-Durham International Airport (RDU)
Using public transport, you can travel from central Chicago to MDW in about 46 minutes. The airport is roughly 19 kilometres away, and getting there by car takes approximately 21 minutes.
You're going on holiday, so why not enjoy an extra night away from home? Think about staying at one of these accommodation options near Chicago Midway International Airport the day before your flight from Chicago to San Juan:
Arriving in San Juan
Luis Munoz Marin International Airport (SJU)
Luis Munoz Marin International Airport (SJU) to central San Juan takes about 11 minutes by car. It's approximately 8 kilometres away.
It takes roughly 56 minutes when travelling by public transport.
The last thing you want is a long journey to your hotel if you're getting in late on a flight from Chicago to San Juan. Stay at one of these accommodation options near SJU instead:
Fernando Luis Ribas Dominicci Airport (SIG)
Central San Juan is located around 8 kilometres from Fernando Luis Ribas Dominicci Airport (SIG). Once your flight from Chicago to San Juan has landed and you've made your way through the terminal, expect a drive of about 14 minutes.
You can also travel by public transport, which will take roughly 58 minutes.
Hang the 'Do not disturb' sign on your door and rest at a hotel close to SIG. Here are a few options where you can settle in after your flight from Chicago to San Juan:
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 $121. For a return flight on this route, the best price is $292. Depending on when and how early you book, these fares could change.
Book 9 months before you want to fly. After crunching the numbers on our calendar, this is how far you'll want to book ahead to secure cheap tickets from Chicago to San Juan.
Schedule your trip for May. That's the cheapest month for flight tickets from Chicago to San Juan. If your travel dates are flexible, use the 'Whole month' tool to find the lowest price across each month.
Create a Price Alert for cheap tickets from Chicago to San Juan. You don't need to check back in every day to see if prices have fallen. We'll notify you as soon as there's a change in price.
Use filters to tailor your flights from Chicago to San Juan. Pick your preferred arrival and departure times, number of stops and airlines. Or sort your results by 'Cheapest' to find the best deals.
Best time to go to San Juan
July is the most popular month for flights from Chicago to San Juan. To steer clear of the crowds, head to San Juan in May.
The warmest month in San Juan is September, with temperatures ranging between 23ºC and 33ºC. Book your flights from Chicago to San Juan in this month if you like this kind of weather.
February has average temperatures of between 20ºC and 28ºC. Search for cheap tickets from Chicago to San Juan sometime around then if you want to travel when it's cooler.
More about San Juan
Start your San Juan trip right by choosing the ideal place to stay. Once you've booked your flight from Chicago to San Juan, explore our selection of accommodation options including:
There are so many things to explore in this city it can be tricky to work out where to begin. Castillo San Felipe del Morro, La Garita del morro de san juan bahia and Fortaleza Street are highlights which should feature on any well-planned San Juan itinerary.
Complete your San Juan trip with a car rental
Finding you a cheap flight from Chicago to San Juan isn't the only trick up our sleeve. Check out our car rentals in San Juan and explore the city on your own terms. We search for deals from trusted car rental companies and put them all in one place. Instantly compare rates and then book with no fees.
