$65 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 9/28. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Best Puerto Rico Flight Deals from Chicago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Aguadilla
Aguadilla1 stop$244
Aguadilla
Aguadilla1 stop$244

Cheap Flights from Chicago to Puerto Rico

 
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

Mon, Sep 8 - Fri, Sep 26
Frontier Logo
5:10 am - 2:11 pmORD-SJU
8h 01m1 stop
Frontier Logo
7:15 am - 3:50 pmSJU-ORD
9h 35m1 stop
$143Frontier
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Thu, Oct 2 - Sun, Oct 5
Frontier Logo
5:10 am - 2:11 pmORD-SJU
8h 01m1 stop
Frontier Logo
3:16 pm - 12:10 amSJU-ORD
9h 54m1 stop
$153Frontier
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Fri, Aug 1 - Wed, Aug 6
 Logo
5:01 am - 2:18 pmORD-SJU
8h 17m1 stop
 Logo
4:43 pm - 7:04 amSJU-ORD
15h 21m1 stop
Thu, Jul 31 - Fri, Aug 1
 Logo
5:01 am - 2:18 pmORD-SJU
8h 17m1 stop
 Logo
6:00 am - 10:16 amSJU-ORD
5h 16mnonstop
Sun, Jul 20 - Sat, Aug 2
Spirit Airlines Logo
5:05 am - 9:09 pmORD-SJU
15h 04m1 stop
Spirit Airlines Logo
4:30 pm - 7:04 amSJU-ORD
15h 34m1 stop
$196Spirit Airlines
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Tue, Jul 22 - Thu, Aug 7
Spirit Airlines Logo
4:36 pm - 1:35 amORD-SJU
7h 59m1 stop
Spirit Airlines Logo
3:50 pm - 7:04 amSJU-ORD
16h 14m1 stop
$203Spirit Airlines
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Thu, Jul 31 - Mon, Aug 4
JetBlue Logo
12:06 pm - 12:19 amORD-PSE
11h 13m1 stop
JetBlue Logo
1:59 am - 11:18 amPSE-ORD
10h 19m1 stop
$397JetBlue
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Sat, Aug 16 - Fri, Aug 22
JetBlue Logo
12:20 pm - 12:43 amORD-PSE
11h 23m1 stop
JetBlue Logo
1:59 am - 11:18 amPSE-ORD
10h 19m1 stop
$405JetBlue
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Wed, Sep 3 - Tue, Sep 9
United Airlines Logo
7:17 am - 11:09 pmORD-BQN
14h 52m2 stops
United Airlines Logo
12:15 am - 9:38 amBQN-ORD
10h 23m1 stop
$474United Airlines
Find Deal
Wed, Oct 1 - Tue, Oct 7
United Airlines Logo
2:20 pm - 11:09 pmORD-BQN
7h 49m1 stop
United Airlines Logo
12:15 am - 9:53 amBQN-ORD
34h 38m2 stops
$492United Airlines
Find Deal
Useful Info

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?

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

The cheapest ticket to Puerto Rico from Chicago found in the last 72 hours was to San Juan, at $208 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 $208.

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 2 stops layover the cheapest option at $249 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 September, when tickets cost $303 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $566 and $424 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 Sunday is the most expensive. Flying from Puerto Rico back to Chicago, the best deals are generally found on Friday, with Monday 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 7 weeks before departure.


Good to know

Low seasonSeptember
High seasonMarch
Cheapest flight$65
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly and prices are also 10% lower on average.
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.

  • 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 $300 on average. Morning departures are around 4% 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 $438.

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.
8.0
SouthwestOverall score based on 4272 reviews
7.0Food
8.0Comfort
7.6Entertainment
8.6Crew
8.2Boarding
Airline reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

4.0 OkayTraci, Jun 2025OAK - SEA
Read more Southwest reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

Flights delayed by 4-6 hours. Boarding was a mess and unclear. Bags were not at arrival airport and had never even been put on the plane. No idea when I’ll get them. Don’t fly into Denver!

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

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

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

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

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

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

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

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

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

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

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

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

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

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

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.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

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

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

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

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

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

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

My flight was delayed by two hours which made it so that I would miss my layover flight. I stood in line for customer service for over an hour and when I reached the agent she told me to scan a QR code and it'll give me options. I wasn't offered any help, guidance or compensation, only told that I have options but that I had to figure it all out myself. I was refunded part of the trip and had to buy an expensive same day ticket from another airline in order to get home. I will never fly Frontier again.

We were delayed three times ,and that destroyed my plans, and reservations

Very bad! No good service delayed my second connection flight

The confirmation # CK8GNW and my name was not recognized/in Frontier system. I was able to check in on Frintier app so i went to the Frontier ticket agent, at time they told me that my name/ confirmation did not show up as a purchased ticket. I had to purchase a new ticket that cost $289.00 one way.

Flight was late. Missed connecting in Denver. My new flight is more than 24 hours later and I have no room, vouchers, or compensation, and might also be bumped from the one tomorrow.

Frontier is terrible. Paid for exit row, not given exit row, refused to refund fee.

2 hour delay due to late plane, wrong size plane causing overbooking, and people getting off and on the plane after boarding was completed.

We had to wait in line over an hour just to check our bags. It's a good thing we were so early to the airport. Only one clerk was working and the line was around the corner and down the hall. No good. I felt bad for her. Not sure how she kept her sanity with all the upset people. Then we get to our gate and there is no seating. Everyone was standing. Then I realize it is not a gate at all, we still have to be shuttled to our airplane. Ugh. Then we were late taking off and missed a window of opportunity before the airport runways were shut down for some reason. (not frontier's fault the runway shut down.) The seats on the airline are crammed and there is no cushion. Never had a tighter seating arrangement while flying. My 6' 4" husband was absolutely miserable the whole time with knees digging in to the seat in front of him. You think you are getting a good deal on a ticket, and then wham! I had to pay 75 dollars for our checked bags and 75 dollars for a carry on. No other airline does that!!! And also, there is a 40 pound weight limit on checked bags... Would have been cheaper flying with another airline, and I would have at least gotten a snack and drink. Was thankful for the tiny cup of water at least.

This was one of the first frontier airline flights this spring that wasn't delayed. It actually left on time. Some of the flight crew did not look happy, they didn't smile when the passengers were boarding or getting off the plane, and the passengers initiated greetings, not the staff. To me this was an odd experience to have with any flight/airline. I had a bad experience booking this flight. The price didn't solidify until late hours into the night. Ever time I purchased the ticket, I either received a denial email or an error because the price has changed, but it was never reflected on the flyfrontier or kayak websites until way after midnight on the date of travel. This caused me anxiety and irritation with the websites. Then I noticed a mishap with my name on my voucher as I went to check in, it was incorrect. When I proceeded to correct it, Frontier had no easy, let alone free, way to remedy it. I couldn't correct my name without a $75 charge, I couldn't cancel my voucher to repurchase it with the correct name without a $100 charge, because it was too close to departure. Then calling frontier was nearly impossible to remedy the situation with a human. It's already difficult to want to choose frontier because of all the upcharges, but you feel kinda trapped into doing so because it's the more affordable airline.

They canceled flight. Hard to believe there was even a plane incoming for us to get on

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.

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