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  1. Flights
  2. Puerto Rico
  3. San Juan
  4. Chicago - San Juan

Book cheap flights from Chicago to San Juan from $246

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Discover the cheapest flights from Chicago to San Juan
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Fri, 14 Aug - Sun, 16 Aug
American Airlines
American AirlinesDirect
CHI - SJU
Frontier Airlines
Frontier Airlines1 stop
SJU - CHI
557$
552$
Prime price per passenger
Fri, 14 Aug
American Airlines
American AirlinesDirect
CHI - SJU
246$
Prime price per passenger
The prices shown on this page were available within the last 20 days for the specified periods and should not be considered the final price offered. Please note that availability and prices are subject to change.

Cheapest time to fly from Chicago to San Juan

If you’re planning to fly this route soon, keep in mind that the lowest fares are usually available in the middle of July. Take advantage of this per
week: 13 July - 19 July
Flights from just $304
$304
JuneJulyAugustSeptember
Distance: 3307 kms
Chicago airports
San Juan airports
Luis Munoz Marin International (SJU)How far from city centre: 11 kms

Get the Best Deals on Flights from Chicago to San Juan

Discover the best last-minute airfares and cheap prices from Chicago to San Juan with Opodo Australia. Avoid overspending on flight tickets and start planning your perfect getaway. Opodo offers a hassle-free booking experience, providing access to top airline carriers and the most competitive prices.


Find the best flights that fit your needs

When do you want to depart from Chicago? Adjust your travel dates and explore a wide range of options to San Juan. With Opodo, you can find the perfect flight from our extensive selection, ensuring a seamless and enjoyable trip. Compare prices, flight durations, and amenities to choose the best option that suits your needs.


Book all in one place

But wait, there's more! Enhance your travel experience by booking a hotel and renting a car along with your flight. It's easier and often cheaper to book everything together. Choose the best offer from Chicago to San Juan and get ready for an incredible journey. Enjoy your holiday, and remember to fasten your seatbelt. We’re ready for takeoff!

Frequently asked questions about flights from Chicago to San Juan

How long does the flight take to go from Chicago to San Juan?
The total flight time between Chicago and San Juan is of around 4 h and 53 m on average, considering an average distance of 3,307.41 km, for both direct and indirect flights for the route (which may have 1 or more stops in other cities in between).
On average, how much is the price of a flight from Chicago to San Juan?
When you fly from Chicago to San Juan the average price is $416. However, this price depends on many other factors such as seasonality or how far in advance the route has been booked.
How can I find cheap flights from Chicago to San Juan at Opodo?
The cheapest price for a flight from Chicago to San Juan is $246. At Opodo we use different machine learned based methodologies to find our costumers the best option available, considering airline combinations, stopovers and direct flights as well as different criteria for inbound and outbound journeys.
When is the best time to book a flight from Chicago to San Juan?
The most popular months to book a trip from Chicago to San Juan are February, June and December, based on the searches of our customers.
When is the best time to travel from Chicago to San Juan?
The best time of the year to go to San Juan when flying from Chicago depends on several preference factors like climate, seasonality and, of course, price. When it comes to popularity, December is the top 1º month to fly to San Juan from Chicago in terms of searches from our customer, followed by June and August. If you prefer to avoid high peaks of turism, however, and escape a crowded period, February, October and January are the months with less volume of searchs for the route Chicago - San Juan.
Which are the airlines with flights from Chicago to San Juan?

Airlines with direct flights departing from Chicago to San Juan are:

  • American Airlines.

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