$91 Find Cheap Flights from Chicago O'Hare Airport to Puerto Rico

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to Puerto Rico departing on 1/15. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from O'Hare Intl to Puerto Rico

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Aguadilla
Aguadilla1 stop$211
Mayagüez
Mayagüez1 stop$395
Aguadilla
Aguadilla1 stop$211
Mayagüez
Mayagüez1 stop$395

Book Cheap O'Hare Intl to Puerto Rico Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl to Puerto Rico that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from O'Hare Intl to Puerto Rico

Sat, Mar 7 - Thu, Mar 12
Frontier Logo
5:08 pm - 8:55 am
ORD
-
PSE
13h 47m1 stop
Frontier Logo
10:50 am - 12:29 am
PSE
-
ORD
14h 39m1 stop
$180Frontier
Fri, Jan 9 - Mon, Jan 12
Multiple Airlines Logo
12:17 pm - 6:49 pm
ORD
-
SJU
4h 32mnonstop
Multiple Airlines Logo
10:47 pm - 8:18 am
SJU
-
ORD
11h 31m1 stop
$199Multiple Airlines
Sat, Jan 17 - Sat, Jan 24
Frontier Logo
3:49 pm - 11:20 am
ORD
-
PSE
17h 31m1 stop
Frontier Logo
1:50 pm - 11:11 am
PSE
-
ORD
23h 21m1 stop
$200Frontier
Tue, Jan 6 - Sat, Jan 10
Frontier Logo
2:26 pm - 12:05 am
ORD
-
SJU
7h 39m1 stop
Frontier Logo
9:19 pm - 3:28 pm
SJU
-
ORD
20h 09m1 stop
$200Frontier
Mon, Jan 12 - Tue, Jan 20
JetBlue Logo
6:45 am - 6:05 pm
ORD
-
SJU
9h 20m1 stop
JetBlue Logo
11:06 am - 7:36 pm
SJU
-
ORD
10h 30m1 stop
$201JetBlue
Thu, Feb 19 - Tue, Feb 24
Frontier Logo
1:54 pm - 2:25 am
ORD
-
SJU
10h 31m1 stop
Frontier Logo
3:53 am - 3:52 pm
SJU
-
ORD
13h 59m1 stop
$202Frontier
Wed, Jan 7 - Sun, Jan 11
Frontier Logo
5:29 pm - 9:08 am
ORD
-
SJU
13h 39m1 stop
Frontier Logo
6:30 am - 3:28 pm
SJU
-
ORD
10h 58m1 stop
$203Frontier
Thu, Feb 5 - Wed, Feb 11
JetBlue Logo
9:40 am - 7:23 pm
ORD
-
SJU
7h 43m1 stop
JetBlue Logo
11:15 am - 7:45 pm
SJU
-
ORD
10h 30m1 stop
$205JetBlue
Sun, Jun 7 - Sun, Jun 14
United Airlines Logo
6:03 pm - 3:49 pm
ORD
-
MAZ
20h 46m1 stop
United Airlines Logo
1:25 pm - 11:55 am
MAZ
-
ORD
23h 30m1 stop
$1,026United Airlines
Sun, Jun 7 - Sun, Jun 14
United Airlines Logo
6:03 pm - 3:49 pm
ORD
-
MAZ
20h 46m1 stop
United Airlines Logo
1:25 pm - 9:25 am
MAZ
-
ORD
21h 00m2 stops
$1,030United Airlines
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Puerto Rico flights

Get data-powered insights and trends into flights from O'Hare Intl to Puerto Rico to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago O'Hare Intl Airport to Puerto Rico flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Puerto Rico from Chicago O'Hare Intl Airport found in the last 72 hours was to San Juan, at $190 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $190.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Puerto Rico?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $439, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Puerto Rico?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Puerto Rico, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Puerto Rico is April, when tickets cost $339 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $548 and $448 respectively.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Puerto Rico?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Puerto Rico clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Puerto Rico on a Monday and more expensive on a Friday. On your return trip to Chicago O'Hare Airport, you should consider flying back on a Friday, and avoid Mondays for better deals.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Puerto Rico?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to Puerto Rico, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to Puerto Rico, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$91
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 19% increase in price.
Flight from Chicago to Ponce

FAQs - booking Puerto Rico flights

  • Is it worth it to book a flight that requires me to change airports or check in again during a layover?

    It depends. If the ticket in question fits your budget and your schedule, it is worth considering. The one thing you need to make sure of, however, is that you have enough time and money to do what is required . Collecting your baggage and going through security again or changing airports in New York City (NYC) can be time-consuming. Also, crossing NYC to a different airport could get expensive.

  • Does ORD have a play area for kids?

    Yes, in the Family Lounge in Terminal 2 of ORD. This lounge features a place for kids to play, room to park a stroller, seating with charging stations for parents, and live entertainment at certain times throughout the year, especially holidays.

  • What can I do to pass the time at ORD while I am waiting for my flight to Puerto Rico?

    You can watch planes take off and land as you get yourself something to eat. In Terminal 1, you can see the planes from certain seats in the Berghoff Cafe and the Food Court. In Terminal 3, you can watch the planes from Chili's, too.

  • Does ORD have an on-site hotel?

    Yes. If you want to stay near ORD the night before your flight to Puerto Rico, consider booking the Hilton Chicago O'Hare Airport, which is located in Terminal 2 of ORD. This accommodation offers rooms with king size beds, family suites, business doubles, wheelchair accessible rooms, and allergy-free rooms.

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport to Puerto Rico?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago O'Hare Airport to Puerto Rico.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago O'Hare Airport to Puerto Rico?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago O'Hare Airport to Puerto Rico is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago O'Hare Airport to Puerto Rico?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago O'Hare Airport to Puerto Rico with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago O'Hare Airport to Puerto Rico?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago O'Hare Airport to Puerto Rico up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Puerto Rico?

    The cheapest time of day to fly to Puerto Rico is generally at night, when round-trip flights cost $318 on average. Morning departures are around 12% more expensive than evening flights, on average. The most expensive time of day to fly to Puerto Rico is generally in the morning, which is peak travel time and where the average cost of a ticket is $447.

Top tips for finding cheap flights to Puerto Rico

  • Serving as a hub for American and United Airlines, the Chicago O'Hare International Airport (ORD) is the larger of two major airports serving the Chicago metropolitan area. When searching for flights from ORD to Puerto Rico on KAYAK, you will find many options.
  • When you fly from ORD to the popular San Juan, you'll be landing at the Luis Muñoz Marín International Airport (SJU). Airline such as Delta, Spirit, American, United, Frontier, and Southwest offer flights from ORD to SJU that stop once in cities such as Baltimore, Orlando, Punta Cana, and Philadelphia. American, United, and Spirit are among the airlines that offer flights from ORD to SJU with two stops.
  • When you fly from ORD to Ponce, a city along the southern shores of Puerto Rico, you will be landing at the Mercedita International Airport (PSE). Spirit is one airline that offers flights from ORD to PSE with one stop, usually in Orlando, and two stops, usually in Miami, Fort Lauderdale, or Houston paired with Orlando.
  • The Rafael Hernández Marín International Airport (BQN) serves Aquadilla, a coastal city in the northwestern corner of Puerto Rico. Airlines such as Spirit, Frontier, and United fly from Chicago O'Hare to BQN with one stop, which is often in New York, Orlando, or Fort Lauderdale. United, Spirit, and United paired with Delta are among the airlines that offer flights with two stops.
  • Puerto Rico is comprised of 143 islands, but only three of them are inhabited. If you want to fly to Isla de Culebra, one of the smaller inhabited islands, you will be landing at the Aeropuerto Benjamín Rivera Noriega (CPX). United Airlines paired with Cape Air offers a flight from ORD to CPX with one stop in San Juan. United and Spirit offer flights with two or three stops.

Reviews of the top 5 airlines serving from O'Hare Intl to Puerto Rico

 
Need help choosing which airline to fly with from O'Hare Intl to Puerto Rico? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9095 reviews
7.3Comfort
8.1Crew
7.7Boarding
6.6Food
7.1Entertainment
Airline reviews

The movies offered were great. Staff were very pleasant and very efficient.

10.0 ExcellentAnonymous, Dec 2025
ORD - HND
Read more United Airlines reviews

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

Checking In on JetBlue site was impossible. It hung up on REAL ID. Even my Global Entry did not help. Luckily, on Kayak site it was a breeze. Entire flight the temperature was COLD! Otherwise the crew was great!

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

There was a fowl odour coming from the lavatory the entire flight

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

No internet on a flight over three hours in this age is criminal. Staff inattentive and dismissive

Cancelled my flight and the earliest that they are willing give me for the next flight which was 3 days later on a weekday. Only accommodation they are willing to give was $30 airline credit that will expire in 1 year

Flight was canceled, huge lines to get baggage returned. Most other airlines had delays but not widespread cancellations like Spirit.

never ever fly spirit airlines you will be screwed in the end

No Tumberlence smooth flight. Try to change the menu on Snacks.

It was a good an early bird pleasant and quiet

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

The spirit flight was on time. The airplane itself was surprisingly very nice. We had great seats. Seems like there's more room. Only complaint is that I didn't get a full refund for my mistakenly buying the baggage twice.

The flight times got delayed multiple times due to weather which is understandable, but later the time got prepared 30min. Made to the flight barely but got stressed too much.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

Not clean and was told I would get a great seat and it was not great at all

Flight got delayed for 5 hours no good explanation was offered ;(

Horrible. I would never fly Frontier again. The booking process is tricky at best, but fraudulent in my opinion. Frontier customer service did nothing to rectify my purchase -- I ended up paying more than double what I could have gotten from other airlines and nearly triple what I thought I was buying from Frontier. Their booking practices are unfair to the consumer.

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

Better than expected. Staff were friendly and nice on both flights.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Everything you need to know for your flight from O'Hare Intl to Puerto Rico

Information on your arrival and departure airports