$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 2/18. 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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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$201
Mayagüez
Mayagüez2 stops$1,668
Aguadilla
Aguadilla1 stop$201
Mayagüez
Mayagüez2 stops$1,668

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

Sun, Feb 8 - Thu, Feb 12
Multiple Airlines Logo
5:15 am - 3:35 pm
ORD
-
SJU
8h 20m
1 stop
Multiple Airlines Logo
4:11 pm - 10:39 pm
SJU
-
ORD
8h 28m
1 stop
$185Multiple Airlines
Tue, Mar 3 - Sat, Mar 7
Spirit Airlines Logo
12:17 pm - 6:49 pm
ORD
-
SJU
4h 32mnonstop
Spirit Airlines Logo
12:32 pm - 3:48 pm
SJU
-
ORD
5h 16mnonstop
$186Spirit Airlines
Tue, Feb 24 - Thu, Mar 5
Spirit Airlines Logo
7:00 am - 3:31 pm
ORD
-
SJU
6h 31m
1 stop
Spirit Airlines Logo
12:32 pm - 3:48 pm
SJU
-
ORD
5h 16mnonstop
$187Spirit Airlines
Tue, Feb 24 - Fri, Mar 6
Multiple Airlines Logo
7:00 am - 3:31 pm
ORD
-
SJU
6h 31m
1 stop
Multiple Airlines Logo
6:50 pm - 9:53 am
SJU
-
ORD
17h 03m
1 stop
$188Multiple Airlines
Tue, Feb 24 - Fri, Feb 27
Spirit Airlines Logo
7:00 am - 3:31 pm
ORD
-
SJU
6h 31m
1 stop
Spirit Airlines Logo
12:32 pm - 3:48 pm
SJU
-
ORD
5h 16mnonstop
$189Spirit Airlines
Mon, Feb 23 - Tue, Feb 24
JetBlue Logo
10:00 am - 10:53 pm
ORD
-
SJU
10h 53m
1 stop
JetBlue Logo
5:10 am - 11:59 am
SJU
-
ORD
8h 49m
1 stop
$191JetBlue
Wed, Mar 4 - Tue, Mar 10
Frontier Logo
8:30 am - 2:57 am
ORD
-
BQN
16h 27m
1 stop
Frontier Logo
2:42 am - 3:38 pm
BQN
-
ORD
13h 56m
1 stop
$201Frontier
Thu, May 14 - Sun, May 17
Frontier Logo
10:25 am - 10:36 am
ORD
-
PSE
23h 11m
1 stop
Frontier Logo
11:36 am - 2:17 pm
PSE
-
ORD
27h 41m
1 stop
$217Frontier
Mon, Mar 9 - Wed, Mar 18
United Airlines Logo
1:06 pm - 4:13 pm
ORD
-
CPX
26h 07m
2 stops
United Airlines Logo
10:30 am - 2:33 pm
CPX
-
ORD
29h 03m
2 stops
$1,056United Airlines
Fri, Jun 5 - Tue, Jun 16
United Airlines Logo
8:49 am - 5:21 pm
ORD
-
CPX
7h 32m
1 stop
United Airlines Logo
10:48 am - 12:10 am
CPX
-
ORD
14h 22m
2 stops
$1,558United 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 $176 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 $176.

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $364 on average.

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 $340 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $521 and $447 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 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 2 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$91
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from Chicago O'Hare Airport to Aguadilla

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 $329 on average. Morning departures are around 10% more expensive than evening flights, on average. The most expensive time of day to fly to Puerto Rico is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $466.

Top tips for finding cheap flights to Puerto Rico

  • Looking for a cheap flight? 25% of our users found tickets from Chicago O'Hare Airport to the following destinations at these prices or less: San Juan $128 one-way - $303 round-trip
  • 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 9215 reviews
6.6Food
7.3Comfort
7.7Boarding
8.1Crew
7.1Entertainment
Airline reviews

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

8.0 ExcellentAnonymous, Jan 2026
ORD - TPA
Read more United Airlines reviews

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

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.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

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.

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

Horribly rude check in at airport, worst in 25 years of flying. All over a simple issue they could have googled to resolve.

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

Flight was fine, price was good but food onboard was abysmal. I was on there for breakfast and lunch and dinner 845am EST to 845pm GMT and all I got was a yoghurt parfait, fruit and a piece of cake. Later snacks included an ice-cream brownie and a pizza twist. I was hungry by the time I landed and the airport amenities were closed. Not happy.

1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready

Good. No issues except a slight delay. Crew came in late.

Not a pleasant experience, service was poor. Didn't like it

It was good. I prefer JB over other airlines.I just wish we had headphones for the films, but other than that - good.

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!

it was terrible. flight was cancelled hours before the flight without a given reason and no other booking available .

Spirit Airlines has a reputation for being a terrible, cheap airline, this is why. I took a gamble on them, having never flown with them before, and the flight got cancelled. First they delayed the flight about 4 times before finally canceling it because a flight attendant didn’t show up to work that day. That’s so stupid. When I asked a ticketing agent she said that’s “company policy”. A company policy that inconveniences hundreds of passengers because a single flight attendant didn’t show is ridiculous and inefficient. I will never, ever try flying Spirit Airlines again.

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.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Plane and crew on board were fine. Everything else was terrible.

The third party booking with cheapflightsfares was awful. Kayak should NOT partner with them. They sold me a bundle including seat selection and carry-on, but did not book the carry-ons with Frontier, so I’m out of pocket for $414 more while I await resolution.

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

Information on your arrival and departure airports