$114 Find Cheap Flights from Chicago O'Hare Airport to Puerto Rico - Compare and Save

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 9/4. 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.
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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$352
Ponce
Ponce1 stop$347
Culebra
Culebra1 stop$668
Mayagüez
Mayagüez2 stops$493
Aguadilla
Aguadilla1 stop$352
Ponce
Ponce1 stop$347
Culebra
Culebra1 stop$668
Mayagüez
Mayagüez2 stops$493

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

Wed, Aug 26 - Sun, Aug 30
United Airlines Logo
5:00 am - 1:45 pm
ORD
-
SJU
7h 45m
1 stop
United Airlines Logo
3:56 pm - 8:05 pm
SJU
-
ORD
5h 09mnonstop
$254United Airlines
Tue, Aug 18 - Mon, Aug 24
Frontier Logo
12:29 am - 6:26 am
ORD
-
SJU
4h 57mnonstop
Frontier Logo
6:11 pm - 10:26 pm
SJU
-
ORD
5h 15mnonstop
$255Frontier
Sat, Aug 15 - Sat, Aug 29
American Airlines Logo
11:40 am - 10:24 pm
ORD
-
SJU
9h 44m
1 stop
American Airlines Logo
10:33 am - 12:35 am
SJU
-
ORD
15h 02m
1 stop
$256American Airlines
Thu, Aug 27 - Thu, Sep 3
American Airlines Logo
5:20 pm - 11:15 pm
ORD
-
SJU
4h 55mnonstop
American Airlines Logo
1:38 pm - 12:35 am
SJU
-
ORD
11h 57m
1 stop
$257American Airlines
Sat, Aug 8 - Tue, Aug 18
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
Frontier Logo
6:11 pm - 10:26 pm
SJU
-
ORD
5h 15mnonstop
$258Frontier
Wed, Aug 26 - Sat, Aug 29
Frontier Logo
12:29 am - 6:26 am
ORD
-
SJU
4h 57mnonstop
Frontier Logo
6:11 pm - 10:26 pm
SJU
-
ORD
5h 15mnonstop
$259Frontier
Thu, Aug 27 - Thu, Sep 3
American Airlines Logo
7:30 am - 11:59 pm
ORD
-
SJU
15h 29m
1 stop
American Airlines Logo
1:38 pm - 12:35 am
SJU
-
ORD
11h 57m
1 stop
$261American Airlines
Thu, Aug 27 - Sun, Aug 30
United Airlines Logo
8:55 am - 2:44 pm
ORD
-
SJU
4h 49mnonstop
United Airlines Logo
3:56 pm - 8:05 pm
SJU
-
ORD
5h 09mnonstop
$264United Airlines
Tue, Jul 21 - Tue, Jul 28
JetBlue Logo
2:35 pm - 11:59 pm
ORD
-
PSE
8h 24m
1 stop
JetBlue Logo
5:01 am - 1:39 pm
PSE
-
ORD
9h 38m
1 stop
$347JetBlue
Wed, Aug 12 - Wed, Aug 19
JetBlue Logo
2:35 pm - 12:33 am
ORD
-
BQN
8h 58m
1 stop
JetBlue Logo
5:01 am - 1:39 pm
BQN
-
ORD
9h 38m
1 stop
$352JetBlue
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 5 days was to San Juan, at $267 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 5 days was $267.

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

The average price for all round-trip flights from Chicago O'Hare Intl Airport to Puerto Rico depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Puerto Rico is generally at night, when round-trip flights cost $390 on average. Morning departures are around 15% 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 $528.

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 $456, 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 September, when tickets cost $113 (return) on average. On the other hand, the most expensive months are August and November, when the average cost of round-trip tickets is $887 and $549 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 Thursday, and avoid Sundays 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 9 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$114
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Chicago O'Hare Airport to San Juan

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.

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.
7.9
SouthwestOverall score based on 4235 reviews
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

Smooth travel. Immediate update prior flight delay so I can arrange myself properly without too rush.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

My pillow had a shoe print on it, when I asked if I can have another pillow, I was told “I’m sorry but it is one pillow per guest, do YOU want to turn it inside out” to which I responded , no thanks I will go without. This is generally not ok, but For the price tag I paid flying business this is absolutely unacceptable. Hopefully American Airlines can update their accommodations to bedding that is not tossed on the ground and stepped on, or at least have a couple of extra pillows in hand, incase someone had decided to step on the pillows for what ever reason

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Our flight was cancelled while we are on our way to the airport. So, no notice. We were rescheduled to another airline with a 2 hour later takeoff and so arrived at our destination on time. We pre-paid American Airlines $190 to upgrade our seats. No refund. So no use for AA or Kayak.

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

I like everything. Blythe at DCA is the absolute best!

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

They lost my luggage and refuse to help. Terrible airline. I've never experienced worse customer service in my life. Pretty much just told me too bad that I lost all my luggage, not caring that I am stuck in Europe for 2 weeks with absolutely nothing.

You should have had Wifi to make it much enjoyable.

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

The flight was delayed after already taxiing from the gate due to a malfunction. After 3 hours we were told the flight was canceled. The next flight available was Sunday. My daughter and I stayed overnight in the airport due to this issue. I was given a $12 meal voucher. Unacceptable

Whole experience was poor. Delayed 2 hours. Lied about the delays. Was all jet blues fault and tried to blame on air traffic control. Sent out other let trips and wouldn't allow people to switch aircraft.

My bag was not loaded on my flight. it was not communicated to me until i was waiting for my bag at my destination. there was no confirmation of when my bag was arriving and no way to track it.

Nice plane, clean, wifi available and movies. All the flight attendants were courteous.

The gate attendant in Boston had a high raspy voice and spoke much too fast to be understood. Not pleasant.

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

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

Information on your arrival and departure airports