Find flights
Deals
When to book
FAQs & Tips
Airlines

Find cheap flights from Chicago O'Hare Airport to Puerto Rico from $88

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 8/20. 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
0 bags
Thu 6/27
Thu 7/4

Search hundreds of travel sites at once for deals on flights to Puerto Rico

In the last 7 days travelers have searched 42,816,550 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Best Puerto Rico Flight Deals

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

Aguadilla
Aguadilla1 stop$307
Ponce
Ponce1 stop$388

Good to know

Low season

September

High season

December

Cheapest flight

$88
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly with an average 58% 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 to Puerto Rico from Chicago O'Hare Airport 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 to Puerto Rico with an airline and back to Chicago O'Hare Airport 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 to Puerto Rico from Chicago O'Hare Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Puerto Rico

  • Morning departure is around 43% cheaper than an evening flight, on average*.
  • 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.
See more tips
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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 10502 reviews
8.6Crew
8.0Entertainment
8.2Boarding
7.9Comfort
7.4Food
Airline reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

10.0 ExcellentAnonymous, May 2024MSP - YVR
Read more about Delta reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Half the bathrooms assigned to economy were out of action

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

Standard flight experience, but there is only power at the seat to row 20 on the aircraft, on my initial check in it did not say that was the case

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight expected to leave at 6:40 pm ended leaving at 8:00 am the following day. I slept in a cold airport. Never again Spirit for me…

This was the return leg of my journey with Spirit Airlines. Despite its reputation, I found no issues as it got me from point A to B safely and without delay, especially with no mechanical delays, which is fantastic in my book! The staff, from ground crew to cabin crew, were all pleasant and hassle-free. The flight was smooth from takeoff to landing. I have absolutely no complaints about this no-frills airline!

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

My flight was cancelled!!! I had to spend 200.00 on another flight!!

The flight attendants were very personable, extremely friendly, and had a very good feeling of the energy around them not to mention they’re very funny and engaging. What made up for the discomfort of the seats and the fact that the plane sat for a long time on the Turmac. Not sure if the pilot was new, but the landing was very rough sort of like I was at a magic mountain theme park ride that was built in 1959

Didn’t happen. They stranded us in Orlando and had to book a flight on frontier to get to our destination.

Flight was delayed 2+ hours missed a concert because of it…

Flight left very close to original projected time. Paid for checked bag weight overage (my fault). Plane was literally brand new & this was its 2nd flight. Seats were alittle uncomfortable (I'm 5'11 * 175lbs and was alittle cramped, & brand new seats had little cushion). Food options were good. Main thing was flight took off & landed on time.

Flight left very close to original projected time. Plane was literally brand new & this was its 2nd flight. Seats were alittle uncomfortable (I'm 5'11 * 175lbs and was alittle cramped, & brand new seats had little cushion). Food options were good. Main thing was flight took off & landed on time.

I particularly did not have no problem with my backpack, but a few people in front of me did. The chairs were really uncomfortable. Unless is a super short flight for over a weekend I wouldn't take this airline.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

My experience with frontier staff at the Denver airport was absolutely horrible. The manager on duty was even worst if was the worst experience I have ever had, I have never been treated so poorly as a customer in my life! The staff was extremely rude, eye rolls and attitude and then refusal to help me at all. I wish I could never fly frontier again that’s how horrible it was!

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Plane could have been more on time. More leg room .

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

Check in online was easy. Seats aren’t very comfortable

Book cheap flights from Chicago to Puerto Rico

Recent round-trip flight deals

9/10Tue
1 stopSpirit Airlines
10h 30mORD-SJU
9/24Tue
1 stopSpirit Airlines
14h 36mSJU-ORD
$120
8/26Mon
1 stopSpirit Airlines
16h 53mORD-SJU
8/28Wed
nonstopSpirit Airlines
5h 14mSJU-ORD
$125
8/20Tue
1 stopSpirit Airlines
7h 38mORD-SJU
8/27Tue
nonstopSpirit Airlines
5h 14mSJU-ORD
$132
9/10Tue
nonstop
4h 55mORD-SJU
9/23Mon
1 stop
10h 08mSJU-ORD
$204
6/9Sun
1 stop
9h 19mORD-SJU
6/12Wed
1 stop
20h 04mSJU-ORD
$239
9/16Mon
1 stopFrontier
9h 19mORD-SJU
10/1Tue
1 stopFrontier
11h 21mSJU-ORD
$258
6/8Sat
1 stopFrontier
10h 49mORD-SJU
6/12Wed
1 stopFrontier
16h 10mSJU-ORD
$288
10/23Wed
1 stopUnited Airlines
9h 24mORD-BQN
10/29Tue
1 stopUnited Airlines
10h 34mBQN-ORD
$464
10/3Thu
1 stopUnited Airlines
9h 24mORD-BQN
10/7Mon
2 stopsUnited Airlines
15h 40mBQN-ORD
$517
6/10Mon
1 stopJetBlue
8h 08mORD-PSE
6/16Sun
1 stopJetBlue
7h 20mPSE-ORD
$633

Search by stops

Search by airline

Search by price

Recent one-way flight deals

8/20Tue
2 stopsSpirit Airlines
10h 54mORD-SJU
$88
8/21Wed
nonstopSpirit Airlines
4h 55mORD-SJU
$89
6/2Sun
1 stopAmerican Airlines
12h 45mORD-SJU
$132
6/4Tue
1 stopAmerican Airlines
7h 14mORD-SJU
$133
6/7Fri
1 stopFrontier
7h 01mORD-SJU
$139
6/8Sat
2 stopsFrontier
15h 40mORD-SJU
$144
8/2Fri
1 stopDelta
6h 19mORD-SJU
$201
8/1Thu
1 stopDelta
9h 44mORD-SJU
$256
6/2Sun
nonstopUnited Airlines
4h 50mORD-SJU
$302
6/10Mon
2 stopsUnited Airlines
27h 49mORD-BQN
$454

Search by stops

Search by airline

Search by price

Last minute flights from O'Hare Intl to Puerto Rico

Last minute flight, train and bus deals

5/30Thu
multi-stop
10h 46mORD-SJU
6/3Mon
multi-stop
13h 48mSJU-ORD
$211
6/2Sun
multi-stopSpirit Airlines
16h 14mORD-SJU
6/4Tue
nonstopSpirit Airlines
5h 10mSJU-ORD
$226
6/2Sun
multi-stopSpirit Airlines
16h 14mORD-SJU
6/15Sat
multi-stopSpirit Airlines
9h 10mSJU-ORD
$232
5/30Thu
multi-stop
10h 46mORD-SJU
6/4Tue
nonstop
5h 10mSJU-ORD
$234
5/30Thu
multi-stopAmerican Airlines
7h 45mORD-SJU
6/1Sat
multi-stopAmerican Airlines
15h 18mSJU-ORD
$266
6/2Sun
multi-stopFrontier
10h 46mORD-SJU
6/7Fri
multi-stopFrontier
14h 31mSJU-ORD
$288
5/31Fri
multi-stopFrontier
6h 53mORD-BQN
6/4Tue
multi-stopFrontier
23h 15mBQN-ORD
$303
5/31Fri
nonstopAmerican Airlines
4h 40mORD-SJU
6/3Mon
multi-stopAmerican Airlines
7h 04mSJU-ORD
$309
5/31Fri
nonstopUnited Airlines
4h 50mORD-SJU
6/1Sat
multi-stopUnited Airlines
8h 30mSJU-ORD
$420
5/31Fri
multi-stopUnited Airlines
7h 44mORD-BQN
6/4Tue
multi-stopUnited Airlines
10h 20mBQN-ORD
$884

Search by stops

Search by airline

Search by price

Chicago O'Hare Airport - Puerto Rico Flights

Departure:

Chicago O'Hare Airport (ORD)United States

Return flight deals:

Puerto Rico - Chicago O'Hare Airport

Cabin classes:

$783
$1,070
$906
$181