Cheap flights from Chicago to Puerto Rico from ₹ 10,318

Cheapest flight ticket found	₹ 10,318
Cheapest month to fly	August
Average flight time	4 hrs, 44 mins
Places to go	8
Most popular airline	American Airlines
Average flights per week	77

Cheapest time to fly from Chicago to Puerto Rico

Looking for the cheapest ticket prices to Puerto Rico from Chicago? We can help you pick the cheapest month to fly.

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Chicago to Puerto Rico flight deals

Looking for a cheap last-minute deal or the best return flight from Chicago to Puerto Rico? If you want to travel next month, return fares start from ₹ 14,140. Find the lowest prices on one-way and return flight tickets right here.

San Juan.₹ 10,298 per passenger.Departing Sun, 23 Aug, returning Tue, 25 Aug.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Sun, 23 Aug, arriving in San Juan Luis Munoz Marin.Inbound direct flight with Frontier Airlines departs from San Juan Luis Munoz Marin on Tue, 25 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From ₹ 10,298, select.

Aguadilla.₹ 33,651 per passenger.Departing Mon, 28 Sep, returning Mon, 5 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Mon, 28 Sep, arriving in Aguadilla.Inbound indirect flight with Frontier Airlines, departs from Aguadilla on Mon, 5 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From ₹ 33,651, select.

Ponce.₹ 36,270 per passenger.Departing Thu, 24 Sep, returning Thu, 1 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Thu, 24 Sep, arriving in Ponce.Inbound indirect flight with Frontier Airlines, departs from Ponce on Thu, 1 Oct, arriving in Chicago Rockford.Price includes taxes and charges.From ₹ 36,270, select.

Culebra.₹ 48,203 per passenger.Departing Sun, 27 Sep, returning Sun, 4 Oct.Return flight with Allegiant Air and Cape Air.Outbound indirect flight with Allegiant Air, departs from Chicago Rockford on Sun, 27 Sep, arriving in Culebra.Inbound indirect flight with Cape Air, departs from Culebra on Sun, 4 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From ₹ 48,203, select.

Vieques.₹ 59,063 per passenger.Departing Mon, 28 Sep, returning Mon, 5 Oct.Return flight with Frontier Airlines and Cape Air.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Mon, 28 Sep, arriving in Vieques.Inbound indirect flight with Cape Air, departs from Vieques on Mon, 5 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From ₹ 59,063, select.

Mayaguez.₹ 187,798 per passenger.Departing Mon, 14 Dec, returning Wed, 16 Dec.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Mon, 14 Dec, arriving in Mayaguez.Inbound indirect flight with United, departs from Mayaguez on Wed, 16 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From ₹ 187,798, select.

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Flights from Chicago to Puerto Rico FAQs

What is the cheapest flight to Puerto Rico from Chicago?

The cheapest flight from Chicago to Puerto Rico costs ₹ 10,318.

Explore the different prices of flights from Chicago to Puerto Rico and find the best option for you.

When is it the cheapest time to fly from Chicago to Puerto Rico?

The cheapest month to fly from Chicago to Puerto Rico is August. See if any of these flights in August suit you.

What is the cheapest Chicago to Puerto Rico flight route?

We've taken a look at the year ahead using our flights calendar. The cheapest flight route from Chicago to Puerto Rico is Chicago to San Juan Luis Munoz Marin. You can buy a ticket to fly this route from ₹ 10,318.

Take a look at Chicago to San Juan Luis Munoz Marin flights.

What is the cheapest airline that flies to Puerto Rico from Chicago?

Looking at the year ahead, the cheapest airline flying to Puerto Rico from Chicago is Frontier Airlines.

Explore flight ticket options today.

Cheapest flights to Puerto Rico from Chicago

How to find cheap flights from Chicago to Puerto Rico

Book a return flight from Chicago to Puerto Rico starting at ₹ 10,318, the cheapest price currently available.
That fare gets you from Chicago into San Juan Luis Munoz Marin in San Juan.
A one-way ticket starts at ₹ 5,158.
Flexible about where you land? Enter 'Puerto Rico' in the 'To' field to compare fares to different cities.
Puerto Rico is home to three international airports.
Widen your search by selecting 'Add nearby airports.' This will compare prices across the airports closest to both your departure and destination points, which could help you find a better deal.
Find the right flight at the right price by booking in advance. Leave it late and you might have to compromise on timing, airline or cost.
Easily track fare changes by setting up a Price Alert. If you haven't already, download the Skyscanner app to get updates instantly.

Best time to fly from Chicago to Puerto Rico

Catch a flight from Chicago to Puerto Rico in August and you'll be travelling at one of the cheapest times of the year.
In general, flying midweek is a practical way to keep costs down. Tuesdays and Wednesdays often mean cheaper fares.
June, July and August are the busiest months to travel to Puerto Rico. June tops the list, making it a great time to visit if you want to see things in full swing.
March, April and May are quieter months. March has the lowest demand from travellers and is a good choice if you want to keep things more relaxed.

Flights from Chicago to Puerto Rico: what to expect

When flying from Chicago, departures are available from Chicago O'Hare International Airport (ORD) or Chicago Midway Airport (MDW).
From Chicago, you can fly nonstop to at least one airport in Puerto Rico.
Roughly 28 direct flights operate each week between Chicago and destinations across Puerto Rico.
The main airlines flying this route include:
The most popular route from Chicago to Puerto Rico is to San Juan.
The average journey on this route takes around 4 hours 50 minutes.

Popular places to visit in Puerto Rico

San Juan

San Juan is a top destination for Chicago to Puerto Rico flights. Balneario El Escambron, La Garita del morro de san juan bahia and Beach San Juan are unmissable stops for first-time visitors.
You can travel to San Juan through San Juan Luis Munoz Marin Airport (SJU) or San Juan Isla Grande Airport (SIG).
Check out the lineup of hotels in San Juan and round out your trip with a stay that fits your budget and style.

Culebra

The biggest draws in Culebra include Playa Flamenco Beach, Bahía Flamenco and Tamarindo Beach.
The majority of flights arrive through Culebra Airport (CPX), the city's main airport.
The same magic that drives our flight search can also help you find the best-value stays around. Use it to compare availability and prices across hotels in Culebra.

Vieques

Drop by popular sights like Bahía Bioluminiscente, Black Sand Beach and Playa Blaydin while you're in Vieques.
You can reach the city through its main airport, Vieques Airport (VQS).
Find a deal on where you'll stay by browsing the list of hotels in Vieques.

Visiting Puerto Rico for the first time? Here's what you need to know

Entry rules can vary depending on your passport, length of stay and travel plans, so check well in advance. Airlines and official embassy sites will have the most recent advice on visas or any other documentation you may need.
Puerto Rico has a population of about 3.2 million. The capital city is San Juan.
Time is the same across this destination, with one standard time zone fixed at UTC-4.
Choose the season that suits how you like to explore, whether that's hotter, cooler or somewhere in between. August is one of the warmest months in Puerto Rico.
Plan your visit around March if you prefer cooler conditions.
January is usually the driest month, while September has the most rain.
The San Sebastián Street Festival, Casals Festival and the Puerto Rico Heineken JazzFest are among the biggest events here. Think about booking your Chicago to Puerto Rico flight around moments like these for a travel experience beyond the ordinary.

Complete your trip with hotels and a car rental

A cheap flight from Chicago to Puerto Rico gets you there. What comes next is planning the stay. Discover the best prices and exclusive rates for hotels in Puerto Rico. To travel when and where you want, also check out the range of car rental options in Puerto Rico.

Puerto Rico hotels and car hire

Did you know we can help you plan the rest of your trip from Chicago to Puerto Rico? Get exclusive deals and great rates for hotels and car hire in Puerto Rico.