$82 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 5/17. 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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Best Puerto Rico Flight Deals from O'Hare Intl

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Aguadilla
Aguadilla1 stop$312
Ponce
Ponce1 stop$309
Culebra
Culebra2 stops$585
Mayagüez
Mayagüez1 stop$591
Aguadilla
Aguadilla1 stop$312
Ponce
Ponce1 stop$309
Culebra
Culebra2 stops$585
Mayagüez
Mayagüez1 stop$591

Cheap Flight Deals from O'Hare Intl to Puerto Rico (ORD-PR0)

 
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.

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

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from O'Hare Intl to Puerto Rico.
Discover the best prices for you by selecting your travel dates on KAYAK.
Spirit Airlines Logo
11:30 am - 5:16 pmORD-SJU
4h 46mnonstop
Spirit Airlines Logo
8:12 pm - 8:50 amSJU-ORD
13h 38m1 stop
$184Spirit Airlines
Find Deal
Sun, May 25 - Thu, May 29
Spirit Airlines Logo
8:17 am - 8:02 pmORD-SJU
10h 45m1 stop
Spirit Airlines Logo
8:12 pm - 8:50 amSJU-ORD
13h 38m1 stop
$186Spirit Airlines
Find Deal
Sun, Jun 1 - Fri, Jun 6
 Logo
4:35 pm - 12:54 amORD-SJU
7h 19m1 stop
 Logo
6:00 pm - 8:22 amSJU-ORD
15h 22m1 stop
Sat, May 17 - Wed, May 21
Frontier Logo
4:15 pm - 1:29 pmORD-SJU
20h 14m1 stop
Frontier Logo
3:56 am - 11:32 pmSJU-ORD
20h 36m1 stop
$270Frontier
Find Deal
Sun, May 11 - Fri, May 16
 Logo
11:30 am - 5:16 pmORD-SJU
4h 46mnonstop
 Logo
3:40 am - 12:36 amSJU-ORD
21h 56m1 stop
Tue, May 27 - Mon, Jun 2
Frontier Logo
4:15 pm - 2:51 amORD-SJU
9h 36m1 stop
Frontier Logo
2:34 pm - 11:32 pmSJU-ORD
9h 58m1 stop
$303Frontier
Find Deal
Sun, May 11 - Mon, May 12
JetBlue Logo
4:03 pm - 1:49 amORD-SJU
8h 46m1 stop
JetBlue Logo
8:00 am - 6:36 pmSJU-ORD
11h 36m1 stop
$333JetBlue
Find Deal
Tue, May 13 - Tue, May 20
JetBlue Logo
4:03 pm - 2:01 amORD-BQN
8h 58m1 stop
JetBlue Logo
5:05 am - 3:04 pmBQN-ORD
10h 59m1 stop
$371JetBlue
Find Deal
Sat, May 17 - Sun, May 25
United Airlines Logo
1:07 pm - 11:09 pmORD-BQN
9h 02m1 stop
United Airlines Logo
12:15 am - 7:33 amBQN-ORD
8h 18m1 stop
$485United Airlines
Find Deal
Wed, May 14 - Sat, May 17
United Airlines Logo
10:50 am - 11:09 pmORD-BQN
11h 19m2 stops
United Airlines Logo
12:15 am - 8:40 amBQN-ORD
9h 25m1 stop
$516United Airlines
Find Deal
Wed, May 14 - Sat, May 17
Useful Info

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago O'Hare Intl Airport to Puerto Rico.

The cheapest ticket to Puerto Rico from Chicago O'Hare Intl Airport found in the last 72 hours was to San Juan, at $231 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 $231.

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 August, when tickets cost $289 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $539 and $450 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 Tuesday and more expensive on a Thursday. 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 5 weeks before departure.


Good to know

Low seasonSeptember
High seasonDecember
Cheapest flight$82
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 17% 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.

  • 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 $298 on average. On average, there is no price difference when choosing to fly in the morning or the evening on this flight route. 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 $409.

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.

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.
8.0
DeltaOverall score based on 7936 reviews
7.9Comfort
8.2Boarding
7.3Food
8.5Crew
7.9Entertainment
Airline reviews

Our bag was lost so that made unnecessary chaos On our trip

6.0 GoodBarbara, Apr 2025JFK - FCO
Read more Delta reviews

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

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

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

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.

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

Good crew and safe. However, comfort and being nickeled-and-dimed are my issues. $75 each way for luggage is exhortation. The space to the next seat is so close you cannot open a laptop. The magazine rack doesn’t hold your items. Not a fan.

WiFi could have been a little more consistent - otherwise a phenomenal and positive experience. The 1000 mile giveaway was awesome!!!

Amazing flying experience, even in not the best of weather. The staff made us comfortable and the flight was actually pretty smooth.

Loved staff help @ kiosk, staff on airplane. Commitment to punctuality. I sat in a "blocked" row, where the middle seat had no passenger & loved it! I appreciate not having to pay for water, which I've experienced even on international flights. Only negative was how dirty the bathroom was for a 4.5 hrs flight. But I don't think flight attendants monitor this.

It wasn’t a bad flight just very uncomfortable seating wise.

Your employees need to learn how to talk to people as creations of Yah. We are not their children nor are we lower than them.

Helpful attendants at check-in is very good. The $70 charge for a checked bags I didn't care for.and the constant charges for picking a seat and faster check-in are too much. Please cut the prices by at least 50% would be fantastic!

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The worst flight of my life. Never will I fly frontier again

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

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