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Find cheap flights from Chicago to Puerto Rico from $74

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 6/5. 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
Fri 6/21
Fri 6/28

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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$309

Good to know

Low season

September

High season

March

Cheapest flight

$74
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 Midway 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 27% more expensive 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 10585 reviews
8.6Crew
7.9Comfort
8.2Boarding
7.4Food
8.0Entertainment
Airline reviews

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

6.0 GoodPeter, May 2024SLC - HNL
Read more about Delta reviews

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Half the bathrooms assigned to economy were out of action

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

Standard flight experience, but there is only power at the seat to row 20 on the aircraft, on my initial check in it did not say that was the case

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

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

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.

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

My flight was cancelled!!! I had to spend 200.00 on another flight!!

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.

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Plane could have been more on time. More leg room .

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

Check in online was easy. Seats aren’t very comfortable

Fecal matter in seat back pocket. Presumably from a kids diaper.

Worst airline to travel with. They treat you like a prisoner in a jailhouse barking out orders and threats. Nickle and dime you to the same price or higher than a respectable airline like one of the big 3 . Might as well fly with standard airlines

Well I mean u get what u pay for so 🤷‍♂️

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.

Book cheap flights from Chicago to Puerto Rico

Recent round-trip flight deals

8/20Tue
1 stopSpirit Airlines
13h 11mORD-SJU
8/24Sat
1 stopSpirit Airlines
9h 04mSJU-ORD
$126
8/20Tue
1 stopSpirit Airlines
10h 30mORD-SJU
8/24Sat
1 stopSpirit Airlines
9h 04mSJU-ORD
$127
6/15Sat
1 stopFrontier
23h 51mMDW-SJU
6/22Sat
1 stopFrontier
12h 16mSJU-MDW
$252
9/23Mon
1 stopFrontier
10h 47mMDW-SJU
9/23Mon
1 stopFrontier
9h 44mSJU-MDW
$253
8/13Tue
1 stopDelta
6h 29mMDW-SJU
8/20Tue
1 stopDelta
10h 44mSJU-MDW
$369
6/11Tue
1 stopJetBlue
8h 08mORD-PSE
6/15Sat
1 stopJetBlue
7h 20mPSE-ORD
$380
6/12Wed
1 stopJetBlue
8h 08mORD-PSE
6/15Sat
1 stopJetBlue
7h 20mPSE-ORD
$382
6/25Tue
1 stopDelta
8h 54mMDW-SJU
7/6Sat
1 stopDelta
9h 45mSJU-MDW
$429
10/2Wed
1 stopUnited Airlines
7h 24mORD-BQN
11/17Sun
2 stopsUnited Airlines
17h 31mBQN-ORD
$535
10/2Wed
2 stopsUnited Airlines
15h 54mORD-BQN
11/17Sun
2 stopsUnited Airlines
17h 31mBQN-ORD
$607

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Recent one-way flight deals

6/5Wed
1 stop
9h 38mMDW-SJU
$74
6/11Tue
1 stopFrontier
11h 33mMDW-SJU
$86
6/18Tue
1 stopSpirit Airlines
10h 29mORD-SJU
$87
7/4Thu
1 stopSpirit Airlines
15h 50mORD-SJU
$88
5/27Mon
1 stopAmerican Airlines
10h 45mORD-SJU
$156
5/25Sat
1 stopAmerican Airlines
16h 55mORD-SJU
$157
5/27Mon
nonstopUnited Airlines
4h 50mORD-SJU
$189
5/27Mon
nonstopUnited Airlines
4h 50mORD-SJU
$242
6/22Sat
1 stopDelta
9h 32mORD-SJU
$482
6/22Sat
1 stopDelta
9h 32mMDW-SJU
$562

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Last minute flights from Chicago to Puerto Rico

Last minute flight, train and bus deals

5/25Sat
nonstopSpirit Airlines
4h 53mORD-SJU
6/5Wed
nonstopSpirit Airlines
5h 09mSJU-ORD
$228
5/25Sat
nonstopSpirit Airlines
4h 53mORD-SJU
6/5Wed
multi-stopSpirit Airlines
21h 23mSJU-ORD
$239
5/26Sun
nonstopUnited Airlines
4h 50mORD-SJU
6/4Tue
multi-stopUnited Airlines
7h 30mSJU-ORD
$333
5/26Sun
multi-stopUnited Airlines
12h 25mORD-SJU
6/4Tue
multi-stopUnited Airlines
7h 30mSJU-ORD
$337
5/26Sun
multi-stopFrontier
8h 26mMDW-SJU
6/1Sat
multi-stopFrontier
9h 31mSJU-MDW
$349
5/26Sun
multi-stopFrontier
12h 07mMDW-SJU
5/31Fri
multi-stopFrontier
14h 04mSJU-MDW
$355
5/26Sun
multi-stopAmerican Airlines
11h 30mORD-SJU
6/1Sat
multi-stopAmerican Airlines
17h 10mSJU-ORD
$363
5/25Sat
multi-stopAmerican Airlines
16h 55mORD-SJU
5/26Sun
multi-stopAmerican Airlines
11h 25mSJU-ORD
$403
5/23Thu
multi-stopDelta
9h 23mMDW-SJU
5/28Tue
multi-stopDelta
7h 06mSJU-MDW
$1,861
5/23Thu
multi-stopDelta
6h 20mMDW-SJU
5/27Mon
multi-stopDelta
7h 06mSJU-MDW
$2,574

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Flights to Puerto Rico

Return flight deals:

Puerto Rico - Chicago

Cabin classes:

$777
$1,063
$906
$59