$64 Find Cheap Flights from Puerto Rico to Illinois

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

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Illinois, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Illinois, as well as popular online travel agencies
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KAYAK's insights & trends for flights to Illinois

Get data-powered insights and trends for flights to Illinois to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest flight to Illinois?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

The cheapest ticket to Illinois from Puerto Rico found in the last 72 hours was to Chicago Midway Airport, at $179 round-trip. The most popular route is San Juan Luis Munoz Marin Intl Airport (SJU) to Chicago Midway Airport (MDW) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $179.

What is the cheapest month to fly from Puerto Rico to Illinois?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Puerto Rico to Illinois, 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 Puerto Rico to Illinois is February, when tickets cost $210 (return) on average. On the other hand, the most expensive months are March and June, when the average cost of round-trip tickets is $369 and $351 respectively.

How far in advance should I book a flight from Puerto Rico to Illinois?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Illinois, 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 Puerto Rico to Illinois, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Which is the cheapest airport to fly into in Illinois?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Illinois is Chicago O'Hare Intl Airport (ORD), with an average flight price of $240.


Good to know

Low seasonMarch
High seasonDecember
Cheapest flight$64
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 23% increase in price.
Flight from San Juan Airport to Chicago O'Hare Airport

FAQs for booking flights from Puerto Rico to Illinois

  • How does KAYAK find such low prices on flights from Puerto Rico to Illinois?

    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 Puerto Rico to Illinois.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Puerto Rico to Illinois 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 Puerto Rico to Illinois?

    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 Puerto Rico to Illinois 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 Puerto Rico to Illinois?

    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 Puerto Rico to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest day to fly to Illinois?

    Based on KAYAK data, the cheapest day to fly to Illinois is Friday where round-trip tickets can be as cheap as $321. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $437 on average.

  • What is the cheapest time of day to fly to Illinois?

    The cheapest time of day to fly to Illinois is generally at night, when round-trip flights cost $241 on average. Morning departures are around 11% cheaper than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $476.

Top 5 airlines serving from Puerto Rico to Illinois

 
See real verified KAYAK customer reviews for airlines flying to Illinois. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Puerto Rico to Illinois. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Puerto Rico to Illinois? 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 4294 reviews
8.0Comfort
8.2Boarding
7.1Food
8.6Crew
7.6Entertainment
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

So far so good but food and entertainment are not available for this flight

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

Everything was on time, we arrived early, everything worked well.

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

As my first time on Spirit, I thought that it was good.

It was smooth and easy. The only real negative was it took over an hour to get our luggage after the flight

Terrible-extreme delay with very little communication, plane was overfull, luggage was returned on baggage claim in filthy condition.

Lower cost is the reason to fly Spirit. Should give free baggage with credit card.

Very difficult. Flew out on Dec 24th and it was a mess. They know it is going to be the busiest time of the year and they had no organization. Finally they called for people going on certiam flights so they could get them thru thw line then we had to rush to our gate to get in li e to board.We missed our flight do to being stuck at the border of Mexico. They would not work with us to make an affordable price so we had to wait a day with no where to go and pay 280 more for our flights. I would think that a complimentary drink would be nice. But we had to pay 4.49 for a coke. Not an overall good experience

I very late and supose be in home at 12 pm from yesterday but I stiill in detroi airport

I’ve now flown Spirit a few times and while the general perception of Spirit I feel is poor, I’ve had a great experience each time. They do charge extra for everything but you should know that going in

Horrible. Take off was delayed by an hour. They were letting people board d the plane right before takeoff. I was delayed an hour when I arrived and late for my meeting. Spirit is NEVER on time.

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

I guess you get what you pay for. The seats are very uncomfortable and very little space. The snacks were pricey.

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

Book cheap flights from Puerto Rico to Illinois

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Illinois found on KAYAK in the last 72 hours.
5/29Thu
1 stopSpirit Airlines
13h 38mSJU-ORD
6/5Thu
nonstopSpirit Airlines
4h 46mORD-SJU
$188
5/29Thu
1 stopSpirit Airlines
13h 38mSJU-ORD
6/2Mon
nonstopSpirit Airlines
4h 46mORD-SJU
$192
5/11Sun
1 stopFrontier
12h 30mSJU-MDW
5/16Fri
1 stopFrontier
7h 42mMDW-SJU
$298
5/10Sat
1 stopFrontier
11h 45mSJU-ORD
5/11Sun
1 stopFrontier
6h 50mORD-SJU
$298
8/20Wed
1 stopAmerican Airlines
17h 14mSJU-STL
8/27Wed
1 stopAmerican Airlines
11h 57mSTL-SJU
$300
8/21Thu
2 stopsAmerican Airlines
10h 28mSJU-STL
8/26Tue
1 stopAmerican Airlines
15h 55mSTL-SJU
$357
6/17Tue
1 stopUnited Airlines
9h 34mSJU-STL
7/5Sat
2 stopsUnited Airlines
12h 24mSTL-SJU
$371
9/11Thu
1 stopSouthwest
10h 10mSJU-MDW
9/16Tue
1 stopSouthwest
6h 25mMDW-SJU
$397
8/28Thu
2 stopsSouthwest
9h 10mSJU-MDW
9/1Mon
1 stopSouthwest
8h 05mMDW-SJU
$418
6/14Sat
1 stopUnited Airlines
9h 00mSJU-STL
6/28Sat
2 stopsUnited Airlines
12h 29mSTL-SJU
$432

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Illinois found on KAYAK in the last 72 hours.
5/29Thu
1 stopSpirit Airlines
13h 38mSJU-ORD
$64
5/29Thu
1 stopSpirit Airlines
13h 38mSJU-ORD
$69
5/29Thu
2 stopsAmerican Airlines
10h 01mSJU-STL
$110
6/14Sat
1 stopUnited Airlines
9h 00mSJU-STL
$123
5/29Thu
2 stopsAmerican Airlines
10h 01mSJU-STL
$130
6/6Fri
2 stopsUnited Airlines
12h 15mSJU-STL
$132
5/8Thu
1 stopFrontier
20h 36mSJU-ORD
$140
6/7Sat
1 stopFrontier
10h 01mSJU-ORD
$144
5/31Sat
nonstopSouthwest
5h 20mSJU-MDW
$191
6/10Tue
1 stopSouthwest
7h 45mSJU-MDW
$196

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Last minute flights to Illinois

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights to Illinois that are departing in the next 10 days.
5/5Mon
multi-stop
13h 25mSJU-ORD
5/12Mon
nonstop
4h 46mORD-SJU
$260
5/2Fri
multi-stop
7h 53mSJU-ORD
6/3Tue
nonstop
4h 46mORD-SJU
$274
5/2Fri
nonstopSpirit Airlines
5h 23mSJU-ORD
6/3Tue
nonstopSpirit Airlines
4h 46mORD-SJU
$285
5/1Thu
multi-stopSpirit Airlines
11h 55mSJU-ORD
5/6Tue
nonstopSpirit Airlines
4h 41mORD-SJU
$301
5/4Sun
multi-stopFrontier
20h 36mSJU-ORD
5/12Mon
multi-stopFrontier
6h 50mORD-SJU
$309
5/1Thu
multi-stopFrontier
20h 36mSJU-ORD
5/5Mon
multi-stopFrontier
22h 55mORD-SJU
$324
5/5Mon
multi-stopUnited Airlines
10h 40mSJU-ORD
6/2Mon
nonstopUnited Airlines
4h 51mORD-SJU
$524
5/2Fri
nonstopAmerican Airlines
5h 30mSJU-ORD
6/4Wed
nonstopAmerican Airlines
4h 40mORD-SJU
$525
5/1Thu
multi-stopUnited Airlines
8h 35mSJU-ORD
6/2Mon
nonstopUnited Airlines
4h 51mORD-SJU
$558
5/2Fri
nonstopAmerican Airlines
5h 30mSJU-ORD
5/10Sat
nonstopAmerican Airlines
4h 40mORD-SJU
$564

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Everything you need to know for your flight to Illinois

Cabin class types available on flights to Illinois

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

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