Travelling from Chicago to San Juan: what you need to know
There are a couple of main airports you can start your journey from in Chicago. Check out your options leaving from O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW) when reserving your flight from Chicago to San Juan.
Come in for landing at San Juan's major arrival point, Luis Munoz Marin International Airport (SJU).
Take a direct Chicago to San Juan flight and you'll be travelling for an average of 4 hours 45 minutes.
San Juan is one hour ahead of Chicago and follows the UTC-4 timezone.
O'Hare International Airport (ORD) to Luis Munoz Marin International Airport (SJU) is the most popular route that connects these two cities. There are 22 weekly departures to choose from. If you prefer a later start to the day, the last flight from Chicago to San Juan is with Spirit Airlines at 22:26. Opt for the first ORD to SJU departure with United Airlines at 07:40 to maximise your time in San Juan.
Leave plenty of time to catch your Chicago to San Juan flight. As a rule of thumb, arrive two hours before international departures and an hour ahead for domestic flights.
If you're getting away during a popular month like August, arrive at the terminal even earlier. It's smart to arrive up to four hours before international flights and two hours ahead of domestic departures. Expect lines to be longer during high seasons like Thanksgiving, Christmas and New Year.
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 R 1,725. For a return flight on this route, the best price is R 3,849. 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)
Take off from O'Hare International Airport (ORD) on a nonstop flight from Chicago to San Juan. From ORD, you can fly directly into Luis Munoz Marin International Airport (SJU).
Popular airlines that offer direct Chicago to San Juan plane tickets departing from ORD include:
A stopover is the perfect opportunity to break up your journey — and perhaps even explore a different city. When searching for Chicago to San Juan flights departing from O'Hare International Airport, uncheck the 'Direct flights only' box to see where you can stop along the way. Here are some options to consider:
Hartsfield-Jackson Atlanta International Airport (ATL)
Raleigh-Durham International Airport (RDU)
Punta Cana International Airport (PUJ)
ORD is about 26 kilometres from central Chicago. If you're ride-sharing, catching a cab or driving from the centre, it'll take 35 minutes or so to get there, depending on traffic. If you're using public transport, expect the journey time to be around 55 minutes.
Searching for a convenient hotel near O'Hare International Airport? If you've booked an early flight from Chicago to San Juan, these accommodation options will have you sleeping moments from your departure gate:
Of the departures 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)
Prefer to take off from Chicago Midway International Airport (MDW)? This hub offers nonstop flights from Chicago to San Juan, seamlessly connecting to Luis Munoz Marin International Airport (SJU).
From MDW, you can book a direct Chicago to San Juan plane ticket with Southwest Airlines.
Get the most out of your holiday with a stopover on your Chicago to San Juan flight. Visit friends or family or tick a new city off your list. Whatever you'd like to do, check out these stops between Chicago Midway International Airport and San Juan:
Hartsfield-Jackson Atlanta International Airport (ATL)
Nashville International Airport (BNA)
Orlando International Airport (MCO)
Using public transport, you can travel from central Chicago to MDW in around 45 minutes. The airport is roughly 14 kilometres away. Driving will take you about 20 minutes.
Want to enjoy an extra night away before boarding your flight from Chicago to San Juan? Check in to a hotel near Chicago Midway International Airport before your break officially starts. Consider one of these stays:
Chicago Midway International Airport has an on-time performance of 77.88%. This figure shows how often flights that depart from this airport land on schedule.
MDW is located at 5700 South Cicero.
Arriving in San Juan
Luis Munoz Marin International Airport (SJU)
Luis Munoz Marin International Airport (SJU) to central San Juan takes around 10 minutes by car. The centre is roughly 6 kilometres away.
If you're using public transport, expect a journey time of about 55 minutes.
Book a hotel near SJU if you have a late flight from Chicago to San Juan. Select one of these options and skip the long transfer:
Get on the fast track to adventure by picking up a Luis Munoz Marin International Airport rental car. Grab a set of wheels from Sixt, Ace Rent a Car or U-Save to explore San Juan and beyond.
To get the best deal, reserve your ride from Luis Munoz Marin International Airport around two weeks in advance of your Chicago to San Juan flight.
Fernando Luis Ribas Dominicci Airport (SIG)
Fernando Luis Ribas Dominicci Airport (SIG) is about 6 kilometres from the centre of San Juan. Following your flight from Chicago to San Juan, it'll take you approximately 15 minutes to reach the heart of the city in a cab or ride-share.
If you choose to travel on public transport, you'll get to the city centre in 1 hour or so.
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 lay your head, you'll find the top stays in San Juan right here. Browse these hotels as soon as you've locked in your flight from Chicago to San Juan:
All great adventures should include a little sightseeing. Castillo San Felipe del Morro, La Garita del morro de san juan bahia and Fortaleza Street are essential stops on your 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.
