$88 Find Cheap Flights from Chicago 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 Chicago to Puerto Rico departing on 5/8. 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

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

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

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

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

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

Flight Deals
Booking Insights
Flight Deals

Book Cheap Chicago 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 Chicago 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 Chicago to Puerto Rico

Fri, May 8 - Fri, May 15
Frontier Logo
5:30 pm - 9:07 am
ORD
-
PSE
14h 37m
1 stop
Frontier Logo
9:47 am - 11:13 pm
PSE
-
ORD
14h 26m
1 stop
$186Frontier
Fri, May 15 - Sat, May 23
Frontier Logo
5:30 pm - 2:02 am
ORD
-
BQN
7h 32m
1 stop
Frontier Logo
4:28 pm - 11:13 pm
BQN
-
ORD
7h 45m
1 stop
$196Frontier
Sun, May 3 - Wed, May 6
Frontier Logo
6:00 am - 2:01 am
ORD
-
SJU
19h 01m
1 stop
Frontier Logo
6:41 pm - 9:37 am
SJU
-
ORD
15h 56m
1 stop
$205Frontier
Mon, Apr 6 - Thu, Apr 9
Frontier Logo
1:19 pm - 12:25 am
ORD
-
SJU
10h 06m
1 stop
Frontier Logo
4:33 pm - 11:36 pm
SJU
-
ORD
8h 03m
1 stop
$206Frontier
Thu, Apr 16 - Thu, Apr 23
Frontier Logo
7:38 am - 2:01 am
ORD
-
SJU
17h 23m
1 stop
Frontier Logo
11:30 am - 11:59 pm
SJU
-
ORD
13h 29m
1 stop
$207Frontier
Fri, Apr 10 - Sun, Apr 12
Multiple Airlines Logo
11:55 am - 12:25 am
ORD
-
SJU
11h 30m
1 stop
Multiple Airlines Logo
1:29 am - 5:45 am
SJU
-
ORD
5h 16mnonstop
$208Multiple Airlines
Thu, Apr 30 - Mon, May 4
Frontier Logo
3:52 pm - 5:59 pm
ORD
-
SJU
25h 07m
1 stop
Frontier Logo
6:00 am - 11:55 pm
SJU
-
ORD
18h 55m
1 stop
$209Frontier
Thu, Apr 16 - Mon, Apr 20
Frontier Logo
2:20 pm - 12:29 am
ORD
-
SJU
9h 09m
1 stop
Frontier Logo
3:37 pm - 11:06 pm
SJU
-
ORD
8h 29m
1 stop
$211Frontier
Mon, Apr 13 - Thu, Apr 16
Frontier Logo
5:30 am - 1:26 pm
MDW
-
SJU
6h 56m
1 stop
Frontier Logo
3:03 pm - 10:19 pm
SJU
-
MDW
8h 16m
1 stop
$211Frontier
Mon, Apr 6 - Tue, Apr 14
Spirit Airlines Logo
8:56 pm - 2:29 am
ORD
-
SJU
4h 33mnonstop
Spirit Airlines Logo
7:54 pm - 9:36 am
SJU
-
ORD
14h 42m
1 stop
$214Spirit Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Puerto Rico flights

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

What is the cheapest Chicago 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 found in the last 72 hours was to San Juan, at $198 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 $198.

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

The average price for all round-trip flights from Chicago 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 $372 on average. Morning departures are around 11% 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 $486.

Can I save money by flying with a layover from Chicago 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 $349 on average.

What is the cheapest month to fly from Chicago 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 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 to Puerto Rico is October, when tickets cost $348 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $541 and $447 respectively.

What’s the cheapest day of the week to fly from Chicago to Puerto Rico?

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

For Chicago to Puerto Rico, Monday is the cheapest day to fly on average and Friday is the most expensive. Flying from Puerto Rico back to Chicago, the best deals are generally found on Friday, with Sunday being the most expensive.

How far in advance should I book a flight from Chicago 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 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 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 seasonOctober
Cheapest flight$88
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Chicago O'Hare Airport to Aguadilla

FAQs - booking Puerto Rico flights

  • Are there direct flights from Chicago to Puerto Rico?

    Yes, American Airlines and United Airlines offer direct flights from Chicago O’Hare International Airport (ORD) to San Juan International Airport (SJU) on the island of Puerto Rico. It is also convenient to connect from San Juan to other major destinations in Puerto Rico, such as Vieques (VQS) by way of SJU, or to transfer to San Juan’s Isla Grande airport (SIG) for connections to cities like Ceiba (NRR). Airlines such as Spirit or Frontier offer such itineraries.

  • What are the passport and visa requirements for entering Puerto Rico from Chicago?

    Although Puerto Rico is not one of the 50 states, it is a territory of the United States, and, therefore, citizens of the US are not required to present a passport when traveling to Puerto Rico from Chicago. They may, however, need to show photo ID when boarding their flight in Illinois, as with any domestic flight. Likewise, visas are not required for US citizens visiting the island; however, non-US citizens that fly into the United States, such as to Puerto Rico, may require passports or visas, depending on their port of entry, national origin, and reason for visiting.

  • Is there public transportation available from San Juan International Airport to the city center?

    Yes, you can take the bus into town by heading to the departures level of Terminals A, D, and E. From there, you can take the bus into Old San Juan, to the Convention Center, or even to the Isla Verde district on bus D53 or T5. There are also taxis available from outside the Baggage Claim areas of Terminals B and C, which can take you to any address in the city.

  • Which airport in Puerto Rico should I fly to from Chicago to enjoy a beach vacation?

    Puerto Rico offers visitors seeking a beach vacation a number of beautiful options. For example, visit Black Sand Beach or Mosquito Bay by booking a flight to Vieques Airport (VQS). You could also visit Flamenco Beach by flying into Culebra Airport (CPX). United Airlines offers flights to both of these destinations from Chicago. Of course, you can also experience Condado Beach or the many sights around the Bay of San Juan by flying into San Juan’s airport (SJU). Jet Blue and American Airlines offer cheap flights from Chicago to San Juan.

  • How does KAYAK find such low prices on flights from Chicago 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 to Puerto Rico.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago 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 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 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 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 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

  • You can easily book flights from Chicago O’Hare International Airport to Puerto Rico on a number of airline carriers, such as United Airlines, American Airlines, Frontier, or even Spirit.
  • Flights from Chicago to Puerto Rico’s capital city San Juan will land at Luis Marín Airport (SJU) in Carolina. It’s easy to connect from here to other destinations, such as Ceiba (NRR).
  • Connecting flights from Chicago to Puerto Rico sometimes include transferring between San Juan’s SJU airport and downtown's Isla Grande (SIG) airport. Simply use the Zone 5 shuttle outside the terminals.
  • Traveling with children from Chicago to Puerto Rico? You can comfortably pass the time waiting for your flight at the Family Lounge located in Terminal 2. Mothers' rooms are also available in every terminal.
  • If you’re flying into San Juan from Chicago, arrive looking your best by taking advantage of the shoeshine stations located in Terminals A, C, and D of the SJU airport.
  • San Juan International Airport offers travelers arriving from Chicago baggage service options, including a free porter service and paid baggage storage to make your trip easier.

Reviews of the top 5 airlines serving from Chicago to Puerto Rico

 
Need help choosing which airline to fly with from Chicago 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 9500 reviews
7.7Boarding
8.1Crew
6.6Food
7.1Entertainment
7.3Comfort
Airline reviews

Awful. No counter attendants. No dinner offered due to delays.

2.0 MediocreD, Mar 2026
ORD - CAE
Read more United Airlines reviews

Awful. No counter attendants. No dinner offered due to delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

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.

Absolutely horrible. Flight was delayed 4 hours and they had no clue what was going on.

Onboard functioning wide-variety entertainment on a budget and having an open pantry is nice. Seats are not comfortable but go provide plenty of legroom for a 6'2" 260lbs man.

Even though the weather made a lot of flights become cancelled Jet Blue made the flight that was supposed to leave at 9 pm and we left at 12:15 am and I was so grateful- Thanks to the Senior Jet Blue Staff who made those decisions

Worst customer service ever experienced on the planet, dirty plane, no communication, and severe delays

Flight cancelled 2 hours prior to boarding. No explanation. No refunds.

Delayed by 1.5 hours. Terrible apologies, half hearted at best. It will be a LONG time until i book w Jet Blue again. Very disappointed.

My check in was stressful. I somehow lost my seat from my original booking, the plane showed no availability/no seat when it was time to check-in. I called and was instructed to try to get a seat at the airport. I asked if it was a full flight and the travel agent said the site showed some seating but was not able to secure one for me. Why not? On my way to the airport the app finally revealed one available seat towards the back of the aircraft that I was able to book. It ended up being an overbooked flight, so glad I wasn't stuck.

Flights with JetBlue from San Diego to Boston are a miserable experience. The flight was delayed about 1.5 hours due to “weather” supposedly but the flights for other airlines left on time so it just have been some kind of weather that only affects JetBlue. I had a small carry on - purse. The crew stored it in a bin 2 rows down from me because they were using the bin next to my seat for other people’s stuff. The TV screen in the emergency row seats does not work. It just was awful from start to finish. When we landed, we had to sit inside the plane for a very long time because the plane had to be moved to a different gate.

They made me check my bag and I didn't need to as there was overhead space available. I paid for a seat towards the front of the plane and it didn't recline. I requested a refund and they declined to give me one.

I have to congratulate Kayak (and Dylan the Chatdeal agent) because because when we decided extended our trip in Florida by two days, there were many direct flights oprions back to Boston available on the Friday we wanted to fly on the JetBlue website, but once I canceled the original JetBlue flight on their website, those direct return options disappeared immediatley! I think it's a game JetBlue plays. . Luckily, I checked Kayak and they had a direct flight that wasn't appearing on JetBlue's website and so I booked it, and we were able to fly home direct through the Kayak booking when JetBlue was offering nothing (even though I have been a True Blue member for 20 years, and also am a Mosaic member). So much for loyalty- their algorithm for booking is like a shell game. JetBlue used to be a good company but now they're worse than anyone. Also I was originally booked this trip to Florida, two months before the departure date, I booked the trip on JetBlue's website and then after the payment part, they said there was a problem and that I needed to do the booking again, so when I immediately went to rebook , the price had gone up 30%! I called them and it sounded like they had heard this so many times before and the guy told me to check back in 10 minutes and the price would be back to where it was when I was booking- it but it never was. How could the price go up 30% in one minute two months before the flight???? They're playing a game with their customers. Anyways, I booked a cheaper flight then at a less convenient time. So fast forward two months the night before the 7 AM flight, they sent me an email at midnight when I was sleeping to let me know that my flight at 7 AM had been canceled. The only thing they offered was a flight that night from from a different airport (Providence) to a different airport in Florida (West Palm Beach) or a flight two days later. No compensation, nothing. They couldn't of tried to get another plane to the Boston airport? They had all night to do it. I passed on their ridiculous options and flew with Delta and it was a great experience. Of course, I had to pay a lot more booking on the same day, but JetBlue doesn't care. I put in a lengthy complaint with the agent who assured me someone would get back to me by email within three days and I haven't heard a thing. JetBlue used to be a good company but now they're among the worst. The only thing they still have is decent legroom, but the corporate bean counters will probably start taking that away too.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

They cancelled our flight. 2 hours before we were supposed to take off and offered us nothing! We got our money back and that was it. No other flight to get to our cruise no working with another airline or with us to get there. Terrible customer service, no apology.

Not enough crew members so we had to wait for more to arrive and they could never give us updates timing. Not even water for free on board. Bare bones airplane- there wasn’t even a seat back pocket to put things into. Spirit is cheap for a reason but this was dismal

We get stuck in the plane when landed during 45min and no communication from the crew People were listening to their phone and music out loud and nobody told them anything I definitely want stop booking spirit flight it is a disaster

The staff were very helpful. Definitely the stars of my experience. The seats were very uncomfortable.

Good: It was cheap and they got us to our destination safely. Not so Good: Gates experience with many, many nauseatingly (almost) threatening announcements about bags size and how much they were going to charge us if our bag was too big, even to the point of having a gate agent roaming around through the passengers eyeballing bags size and making people go check their bags in the sizers.

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

Checking in at desk in Chicago was horrible. Person was not friendly never smiled and said my flight was not paid for so I had to give another credit card. Then it ended up that I was charged twice. Then after arriving at my destination had to wait on the phone a long time to speak to a person to fix the double charge! Thank goodness the flight was perfect.

Flight was delayed for 12 h. They should stop overlooking flights.

My flight was at 11:34am at February 4th don’t know the names of the crew, but they were the best, My first great flight. Loved it 😊🥰 Thank you!!

All of our flights were canceled, though every other airline was flying out and in

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

Everything you need to know for your flight from Chicago to Puerto Rico

Cabin class types available on flights to Puerto Rico

Cabin classes available on flights to Puerto Rico. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.