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Find cheap flights from Chicago to Puerto Rico from $63

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 6/11. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Mon 6/10
Mon 6/17

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Best Puerto Rico Flight Deals

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

Aguadilla
Aguadilla1 stop$236

Good to know

Low season

September

High season

March

Cheapest flight

$63
Best time to beat the crowds with an average 20% 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 to Puerto Rico from Chicago 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 to Puerto Rico with an airline and back to Chicago 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 to Puerto Rico from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Puerto Rico

  • Morning departure is around 34% cheaper than an evening flight, on average*.
  • 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.
See more tips
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 5 airlines serving from 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
DeltaOverall score based on 10768 reviews
8.6Crew
7.9Comfort
8.0Entertainment
7.4Food
8.2Boarding
Airline reviews

Boarding was chaotic. I didn’t finish dinner because I went to bed early. Breakfast omelet was overcooked and tasteless but croissant was better than usual. Plane was dirty—crumbs in every seam and lavatory was poorly maintained (paint peeling, etc.) and toilet paper had not been refreshed before takeoff. No cubby for storage in first and seat was narrow.

4.0 OkayPatricia, May 2024DTW - CDG
Read more about Delta reviews

Boarding was chaotic. I didn’t finish dinner because I went to bed early. Breakfast omelet was overcooked and tasteless but croissant was better than usual. Plane was dirty—crumbs in every seam and lavatory was poorly maintained (paint peeling, etc.) and toilet paper had not been refreshed before takeoff. No cubby for storage in first and seat was narrow.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

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

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

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

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

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

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

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

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Do I need to call them or will you handle my complaint ? I paid for one carry-on bag. my email said up to 50 pounds when I got to the counter they charged me $79 more for my 48 pound bag!!! they said nope only 40 pounds. My email says 50 pounds. !!! I’m out another $79!!!

Flight attendant very friendly. Seats not adjustable like before. I was in the middle seat and two big guys next to me isn’t to pleasant. No used to have delays in the past and now is too often.

Seats could use more padding. Kind of hard on the tush.

Amazed that Spirit can even get planes in the air, would never use again.

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Book cheap flights from Chicago to Puerto Rico

Recent round-trip flight deals

5/21Tue
1 stopSpirit Airlines
8h 00mORD-SJU
5/28Tue
1 stopSpirit Airlines
21h 33mSJU-ORD
$104
5/21Tue
1 stopSpirit Airlines
8h 00mORD-SJU
5/28Tue
2 stopsSpirit Airlines
22h 16mSJU-ORD
$118
5/29Wed
2 stops
20h 31mORD-SJU
6/4Tue
1 stop
23h 42mSJU-ORD
$144
5/29Wed
1 stop
19h 25mORD-SJU
6/4Tue
1 stop
14h 18mSJU-ORD
$145
6/6Thu
1 stopFrontier
11h 32mMDW-SJU
6/14Fri
1 stopFrontier
12h 53mSJU-MDW
$218
6/6Thu
1 stopFrontier
11h 32mMDW-SJU
6/12Wed
1 stopFrontier
12h 16mSJU-MDW
$219
6/18Tue
1 stopUnited Airlines
7h 44mORD-BQN
6/24Mon
1 stopUnited Airlines
10h 20mBQN-ORD
$502
5/28Tue
1 stopUnited Airlines
7h 44mORD-BQN
6/3Mon
1 stopUnited Airlines
8h 20mBQN-ORD
$509
6/8Sat
1 stopJetBlue
8h 08mORD-PSE
6/14Fri
1 stopJetBlue
7h 20mPSE-ORD
$525
6/8Sat
1 stopJetBlue
8h 08mORD-PSE
6/14Fri
1 stopJetBlue
7h 20mPSE-ORD
$554

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Recent one-way flight deals

6/11Tue
1 stopSpirit Airlines
10h 29mORD-SJU
$63
9/18Wed
1 stopSpirit Airlines
13h 11mORD-SJU
$64
6/14Fri
1 stopFrontier
7h 01mORD-SJU
$99
6/13Thu
1 stopFrontier
29h 46mORD-SJU
$104
6/20Thu
1 stopAmerican Airlines
8h 15mORD-SJU
$112
7/20Sat
1 stopAmerican Airlines
17h 38mORD-SJU
$137
5/25Sat
nonstopUnited Airlines
4h 47mORD-SJU
$189
5/23Thu
1 stopJetBlue
8h 10mORD-PSE
$373
6/10Mon
1 stopJetBlue
8h 08mORD-PSE
$375
6/10Mon
2 stopsUnited Airlines
24h 37mORD-BQN
$434

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Last minute flights from Chicago to Puerto Rico

Last minute flight, train and bus deals

5/13Mon
nonstopSpirit Airlines
4h 53mORD-SJU
5/20Mon
multi-stopSpirit Airlines
13h 48mSJU-ORD
$192
5/15Wed
nonstop
4h 53mORD-SJU
5/18Sat
multi-stop
23h 09mSJU-ORD
$205
5/14Tue
multi-stop
14h 16mORD-SJU
5/21Tue
multi-stop
23h 08mSJU-ORD
$216
5/14Tue
nonstopSpirit Airlines
4h 53mORD-SJU
5/16Thu
nonstopSpirit Airlines
5h 10mSJU-ORD
$217
5/14Tue
multi-stopFrontier
12h 21mMDW-SJU
5/21Tue
multi-stopFrontier
13h 55mSJU-MDW
$238
5/14Tue
multi-stopFrontier
12h 21mMDW-SJU
5/20Mon
multi-stopFrontier
29h 06mSJU-MDW
$256
5/12Sun
nonstopAmerican Airlines
4h 40mORD-SJU
5/14Tue
multi-stopAmerican Airlines
7h 04mSJU-ORD
$260
5/14Tue
nonstopAmerican Airlines
4h 40mORD-SJU
5/15Wed
multi-stopAmerican Airlines
10h 40mSJU-ORD
$262
5/12Sun
multi-stopUnited Airlines
8h 42mORD-SJU
5/15Wed
multi-stopUnited Airlines
7h 35mSJU-ORD
$286
5/14Tue
multi-stopUnited Airlines
7h 14mORD-BQN
5/17Fri
multi-stopUnited Airlines
10h 21mBQN-ORD
$739

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Flights to Puerto Rico

Return flight deals:

Puerto Rico - Chicago

Cabin classes:

$886
$1,021
$1,230
$59