Flight tickets from Chicago O'Hare International to San Juan

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Flight deals from Chicago O'Hare International to San Juan

Looking for a cheap last-minute deal or the best return flight from Chicago O'Hare International Airport to San Juan? If you want to travel next month, return fares start from ₹ 38,066. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago O'Hare International to San Juan

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago O'Hare International to San Juan flights are currently cheapest in August.

Direct flights from Chicago O'Hare International to San Juan

Chicago to San Juan: Flight information

The things to know before you go.
Cheapest flight found₹ 7,596
Cheapest month to flyAugust
Average flight time4 hrs, 46 mins
Most popular airlineAmerican Airlines
Average flights per week73

Finding cheap flights from Chicago O'Hare International to San Juan: Frequently asked questions

There are 6 airports in San Juan: San Juan Isla Grande, San Juan Luis Munoz Marin, Roosevelt Roads, Ponce, Vieques, and Culebra.
The best price we found for a return flight from Chicago O'Hare International to San Juan is ₹ 20,644. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
4 hours and 46 minutes is the average flight time from Chicago O'Hare International to San Juan.
American Airlines, Alaska Airlines and Qatar Airways fly direct from Chicago O'Hare International to San Juan.
As of May 2026, there are 73 flights per week flying from Chicago O'Hare International to San Juan.
The cheapest month to fly from Chicago O'Hare International to San Juan is usually August.
If you're flying from Chicago O'Hare International Airport, the cheapest airport near San Juan is San Juan Luis Munoz Marin – which is 11.3 km away from the centre of San Juan. We've found flights into this airport from ₹ 20,644.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago O'Hare International Airport to San Juan on Monday, 31 August 2026.
Yes – the average flight time is 4 hours and 46 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to San Juan but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to San Juan is around 40 days in advance, so don’t leave your flight to the last minute.
In May, the average temperature is usually around 27°C. August is typically the warmest month in San Juan, when it usually averages around 29°C. You can expect the least rain in February. The coldest month is January, with temperatures averaging 23°C. The rainiest month is September.
Currently, Frontier Airlines offers the cheapest flight tickets to San Juan.

Flying from Chicago O'Hare International Airport (ORD) to San Juan: what you need to know

  • Expect to be travelling for 5 hours 20 minutes. On average, that's the duration of a direct flight from Chicago O'Hare International Airport to San Juan.

  • The timezone in San Juan is UTC-4. The city is two hours ahead of Chicago, where Chicago O'Hare International Airport is located.

  • The most popular flight route is from Chicago O'Hare International Airport (ORD) to Luis Munoz Marin International Airport (SJU). You can choose from 25 services between these airports every week.

  • For stress-free travel, arrive at the airport two hours ahead of international flights and one hour before domestic departures. This ensures you have enough time to board your ORD to San Juan flight.

  • Flying during a peak month such as July? Public holidays and other popular periods can lead to longer queues at security. Play things extra safe and get there up to four hours before international flights and two hours before a domestic departure.

  • You can book a direct Chicago O'Hare International Airport to San Juan ticket. Start your trip at ORD and land at Luis Munoz Marin International Airport (SJU).

  • You'll have your choice of airlines offering direct flights from Chicago O'Hare International Airport to San Juan. Book your seat with one of these:

  • Stopovers are the ideal opportunity to break up your journey and maybe even tick off a new city. When browsing for plane tickets from ORD to San Juan, uncheck the 'Direct flights only' box to see where you can stop along the way. Some popular options include:

    • Atlanta Hartsfield-Jackson International Airport (ATL)

    • Raleigh-Durham International Airport (RDU)

    • Punta Cana International Airport (PUJ)

  • Located around 26 kilometres from the centre of Chicago, ORD can be reached in about 30 minutes by car. Travelling on public transport takes roughly 45 minutes.

  • Want an easy start to your trip? Stay near ORD. Whether you're taking an early flight from Chicago O'Hare International Airport to San Juan or don't want departure day to feel hectic, these hotels are just the thing:

  • 70% of flights departing from Chicago O'Hare International Airport touch down at their destination on schedule.

  • ORD is located at 10000 West O'Hare.

How to find the cheapest flights from Chicago O'Hare International Airport (ORD) to San Juan

  • The lowest price we've found for a one-way Chicago O'Hare International Airport to San Juan flight is ₹ 7,596. The cheapest price for a return flight is ₹ 20,579. Keep in mind fares may change due to availability at the time of booking.

  • Don't leave things to the last minute. You're more likely to land cheap flights from ORD to San Juan if you book in advance. Airlines often offer some excellent early bird deals.

  • The 'Whole month' tool will show you the cheapest tickets from Chicago O'Hare International Airport to San Juan across each month. It's an easy way to snap up a bargain if your dates are flexible.

  • Cut down on the time spent looking for cheap flights from ORD to San Juan by creating a Price Alert. You'll receive an email or push notification on the app when a new low fare is offered.

  • Select your preferred departure and arrival times, number of stops and airlines with our filters. Then, sort the results for your flight from Chicago O'Hare International Airport to San Juan by 'Fastest,' 'Best' or 'Cheapest.'

Airports in San Juan

Luis Munoz Marin International Airport (SJU)

  • Luis Munoz Marin International Airport (SJU) is around 11 kilometres from the centre of San Juan. If you're grabbing a taxi or a ride-share, the drive takes roughly 20 minutes.

  • If you're travelling on public transport, expect a journey time of around 1 hour.

  • Consider staying in a hotel close to SJU if you have a late flight from Chicago O'Hare International Airport to San Juan. Choose one of these options and make your arrival easier:

  • Reserving your ride from Luis Munoz Marin International Airport around two weeks before your flight from ORD to San Juan can help you get the best possible rate.

Best time to go to San Juan

  • March is the most popular month for flights from Chicago O'Hare International Airport to San Juan. To steer clear of the crowds, plan your trip to San Juan in December.

  • Book a Chicago O'Hare International Airport to San Juan plane ticket with a departure in August to explore the city during its warmest month. Expect temperatures to range from 24ºC to 32ºC.

  • Look for cheap tickets from ORD to San Juan in February if you'd rather travel during cooler conditions. Temperatures are at their lowest then, ranging between 21ºC and 28ºC on average.

More about San Juan

  • Once you've booked your flight from Chicago O'Hare International Airport to San Juan, find a hotel that offers both comfort and a great location. Make one of these options your base for exploring San Juan:

  • All great journeys should include some sightseeing. Esperanza Beach, Balneario El Escambron and Escambron Green are essential stops on your San Juan itinerary.

Explore more of Puerto Rico

  • Aguadilla is just one of the many cities in Puerto Rico waiting to be discovered once you've taken in the sights of San Juan. Around 113 kilometres away to the west, its top attractions include Silla Aguadilla, Bridges Surf Beach and Playa Rompe Olas.

  • Around 105 kilometres west of San Juan, Isabela is another favourite stop in Puerto Rico. Experience major highlights starting with Playa montones, Shore Island Beach and Guajataca Forest Reserve.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.