$123 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 8/12. 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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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

Sat, Aug 15 - Fri, Aug 28
American Airlines Logo
4:59 pm - 10:54 pm
ORD
-
SJU
4h 55mnonstop
American Airlines Logo
12:55 am - 5:00 am
SJU
-
ORD
5h 05mnonstop
$257American Airlines
Tue, Aug 18 - Mon, Aug 24
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
Frontier Logo
8:57 pm - 11:08 pm
SJU
-
ORD
27h 11m
1 stop
$258Frontier
Tue, Aug 4 - Thu, Aug 13
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
Frontier Logo
7:14 pm - 11:27 pm
SJU
-
ORD
5h 13mnonstop
$259Frontier
Tue, Aug 4 - Fri, Aug 7
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
Frontier Logo
7:14 pm - 11:27 pm
SJU
-
ORD
5h 13mnonstop
$260Frontier
Sat, Aug 15 - Fri, Aug 28
American Airlines Logo
6:59 am - 9:55 pm
ORD
-
SJU
13h 56m
1 stop
American Airlines Logo
12:55 am - 5:00 am
SJU
-
ORD
5h 05mnonstop
$262American Airlines
Fri, Aug 21 - Tue, Aug 25
Southwest Logo
1:00 pm - 10:50 pm
MDW
-
SJU
8h 50m
2 stops
Southwest Logo
5:15 am - 12:05 pm
SJU
-
MDW
7h 50m
2 stops
$286Southwest
Fri, Sep 4 - Sun, Sep 13
Southwest Logo
7:50 pm - 9:25 am
MDW
-
SJU
12h 35m
1 stop
Southwest Logo
5:00 am - 11:45 am
SJU
-
MDW
7h 45m
1 stop
$291Southwest
Thu, Aug 27 - Tue, Sep 1
JetBlue Logo
7:00 am - 12:33 am
ORD
-
BQN
16h 33m
1 stop
JetBlue Logo
2:30 pm - 11:44 pm
BQN
-
ORD
10h 14m
1 stop
$349JetBlue
Wed, Aug 12 - Wed, Aug 19
JetBlue Logo
2:35 pm - 12:33 am
ORD
-
BQN
8h 58m
1 stop
JetBlue Logo
2:30 pm - 11:44 pm
BQN
-
ORD
10h 14m
1 stop
$359JetBlue
Mon, Aug 24 - Wed, Aug 26
United Airlines Logo
8:55 am - 5:21 pm
ORD
-
CPX
7h 26m
1 stop
United Airlines Logo
10:48 am - 11:22 pm
CPX
-
ORD
13h 34m
2 stops
$1,558United 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 5 days was to San Juan, at $255 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 $255.

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 $388 on average. Morning departures are around 13% 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 $527.

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.

No, with an average price for the route of $423, prices are generally cheapest when you fly direct.

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 April, when tickets cost $315 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $635 and $537 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 Thursday, 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$123
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 22% increase in price.
Flight from Chicago O'Hare Airport to San Juan

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.
7.9
SouthwestOverall score based on 4242 reviews
8.0Comfort
7.0Food
8.1Boarding
7.5Entertainment
8.6Crew
Airline reviews

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

2.0 MediocreIrene, Jun 2026
DEN - SFO
Read more Southwest reviews

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

It was just okay, no frills, basic transportation with no luxury. No screens on the seats, no water or drinks on a short flight. Full flight but at least it was on time.

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

Over a 3 hour flight. The turbulence was almost imperceptible except for 2 short periods which were not bad and over quickly. The attendants claimed "Safety first" and sat looking at their phones for 3 hours with no drink or snack service. This isn't the first time with Southwest. I thinkit may be there new plan of operation. Oh, and it was June 18, Southwest's Birthday which offered free drinks. NOT.

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

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.

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

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.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

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.

The flight was delayed 14 hours and communication was very poor. No one seemed to know what was happening and the gate agent was trying to help people for several flights. She was by herself trying to help 100s of people.

Domestic flights are good. Just stay away from international travel

Flight left 2 hours late with no explanation as to the delay

The aircraft was fine, it’s was just the service. The flight got canceled several times and that was very inconvenient for my 69 years old mom.

My checked in luggage cost was $59, almost ticket price. The first 13 rows were empty, but fly attendant did not alow women with little boy change her middle sit, sweet boy was crying, I am so sorry for mother and passengers. At the end of the flight the cabin became impossible cold. Only good was timing of departure and early landing, but it suppose to be normal.

Seamless flight, didn’t feel like five hours at all very smooth ride. Watched two good movies didn’t even realize I was on a plane. The staff were extremely nice and helpful.

I tried to book a flight with Jet Blue. Your third party company hijacked my attempt with a website that looked like I was booking with Jet Blue. I realized it when I paid. I tried to cancel and was told by a man in India that there were no refunds. $735 stolen, Thanks Kayak!

It was inexplicably canceled and we are stuck in LA, haven't gotten home and it has been an inconvenience having lost work (on unpaid leave for my husband).

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!

Crew was kind of grumpy and there was no beverage service at all. Sodas were $4. Disappointing.

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!!!

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.