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$62 Find cheap flights from Puerto Rico to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 6/4. 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
Sat 6/22
Sat 6/29

Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, 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 Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 43,800,826 times on KAYAK, and here is why:

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Flights to Chicago - Travel Insights & Trends

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

What is the cheapest day to fly to Chicago?

The average price of all flights to Chicago clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Friday where tickets can be as cheap as $285. On the other hand, the most expensive day to fly is Monday, where prices are $352 on average.

What is the cheapest month to fly to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago, 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 to Chicago is January, where tickets cost $196 on average for one-way flights. On the other hand, the most expensive months are March and April, where the average cost of tickets from Puerto Rico is $363 and $314 respectively. For return trips, the best month to travel is January with an average price of $196.

What is the cheapest time of day to fly to Chicago?

The average price for all flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to Chicago is generally in the morning, when flights cost $275 on average. The most expensive time of day to fly to Chicago is generally in the evening, which is peak travel time and where the average cost of a ticket is $317.

What is a good deal for flights to Chicago?

If you’re looking for cheap airfare to Chicago, 25% of our users found tickets to Chicago for the following prices or less: From San Juan Luis Munoz Marin Intl Airport $117 one-way - $255 round-trip.

How far in advance should I book a flight to Chicago?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 15 days before departure.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Midway Airport, with an average flight price of $104.

Which airlines fly to Chicago?

Many airlines fly to Chicago, the most common ones being Spirit Airlines, United Airlines, and American Airlines. See the amount of flights per week for popular airlines flying to Chicago.

Which airline offers the most flights to Chicago?

Of the 14 airlines that fly to Chicago, American Airlines offers the most flights, with around 4,234 per week, followed by United Airlines with 3,372 flights per week.

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago O'Hare Airport (ORD), Chicago Midway Airport (MDW) and Chicago Greater Rockford Airport (RFD). The busiest airport is Chicago O'Hare Airport (ORD), with 77% of all flights arriving there.

How long is the flight to Chicago?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously any flights that include a layover will also be longer. The most popular routes to Chicago on KAYAK are from San Juan, which takes 5h 08m, Aguadilla, which takes 7h 26m, and Culebra, which takes 11h 09m.

How many direct flights to Chicago are there each day?

There are around 1,703 direct flights from within Puerto Rico to Chicago every day. Most flights depart in the morning, with 6:00 am the most common departure time and 49% of flights departing in the morning.

How many direct flights to Chicago are there each week?

Each week there are around 11,921 direct flights from within Puerto Rico to Chicago. The most common day for departures is Friday, with 16% of flights taking off on this day.

How many long-haul flights are there to Chicago each week?

There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Chicago. Instead, there are 33 medium-haul flights (3-6 hour flight duration), with the most arriving from San Juan Luis Munoz Marin Intl Airport.

How many cities have direct flights to Chicago?

From Puerto Rico, there are direct flights to Chicago from 1 city. This city is San Juan Luis Munoz Marin Intl Airport and there are 33 direct flights each week.

Good to know

Low season

February

High season

December

Cheapest flight

$62
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from San Juan Airport to Chicago O'Hare Airport

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    The distance between Chicago Midway Airport and downtown Chicago is 9 miles, which makes it the closest of the 3 Chicago airports. Chicago O'Hare Airport is 16 miles away from the center and Chicago Greater Rockford is 79 miles away.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $193. The cheapest price found on KAYAK in the last 2 weeks cost $75 and departed from San Juan Luis Munoz Marin Intl Airport.

  • How does KAYAK find such low prices on flights to Chicago?

    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 to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to 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 to Chicago?

    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 Chicago 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 to Chicago?

    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 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 Chicago

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Prefer to fly non-stop to Chicago?

Find which airlines fly direct to Chicago, which days they fly and book direct flights.

Nonstop departures

Puerto Rico to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Nonstop returns

Chicago to Puerto Rico

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights
See more direct flights

Top 5 airlines serving from Puerto Rico to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Puerto Rico to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Chicago? 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 10561 reviews
8.0Entertainment
8.2Boarding
7.9Comfort
8.6Crew
7.4Food
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.

The comfort is typical of what I would expect from main cabin. I've been on flights with other airlines where the seats needed to be changed, the cushions were non-existent. So happy this was not the case. I enjoyed the movie selection. Happy pillow and blanket was provided since I forgot my own. The food was also ok. Great that we arrived early and my luggage arrived undamaged. Again in the past (not with Delta), luggage was lost or broken.

Crew went over and above to be helpful. Plane had mechanical problems that caused us to depart late.

The 676 plane is much more comfortable in business class than the A330 and he food was a little better. I didn’t use the entertainment.

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.

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.

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Left on time. Arrived early. Turbulence coming in and gate not open due to early arrival but expected.

The CX617 from HK to BKK was delayed more than 1.5 hours.

The plane was old and in new of a cleaning up and renovating on the interior. Seats and carpets were very worn and dirty looking. Cushioning on the seats was broken down and not as comfortable as newer jet seats. Food was a little below average but okay. Staff were friendly and hard working but did not pick up debris or food they spilled when collecting from the customers. But they were very helpful and professional.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The flight was fine. The itinerary change from original booking was not good. We were originally leaving at 12:50 pm. The change to 8:29pm put us getting home in the early morning hours the next day. Then having to wait over an hour on the ground for a parking place to get off the plane was exhausting.

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

Flight was delayed...not horribly late. Just before push back engine shut down for a quick replacement item that took about five minutes. After that, everything was smooth and the pilot was able to make up time in the air so that our arrival time was not too far off the original anticipated arrival time.

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 Puerto Rico to Chicago

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Chicago found on KAYAK in the last 72 hours.
9/10Tue
1 stopSpirit Airlines
14h 36mSJU-ORD
9/17Tue
1 stopSpirit Airlines
10h 30mORD-SJU
$137
8/20Tue
1 stopSpirit Airlines
14h 31mSJU-ORD
8/26Mon
1 stopSpirit Airlines
16h 53mORD-SJU
$149
8/20Tue
nonstopSpirit Airlines
5h 13mSJU-ORD
8/26Mon
1 stopSpirit Airlines
15h 56mORD-SJU
$151
9/10Tue
nonstopSpirit Airlines
5h 14mSJU-ORD
9/17Tue
1 stopSpirit Airlines
16h 53mORD-SJU
$152
6/6Thu
1 stop
11h 16mSJU-MDW
6/10Mon
1 stop
9h 38mMDW-SJU
$197
6/9Sun
1 stop
25h 56mSJU-ORD
6/12Wed
1 stop
10h 19mORD-SJU
$224
8/8Thu
1 stopFrontier
12h 55mSJU-MDW
8/13Tue
1 stopFrontier
12h 21mMDW-SJU
$270
6/5Wed
1 stopFrontier
7h 23mSJU-MDW
6/10Mon
1 stopFrontier
17h 41mMDW-SJU
$271
9/25Wed
1 stopUnited Airlines
7h 29mSJU-ORD
9/28Sat
nonstopUnited Airlines
4h 47mORD-SJU
$284
6/13Thu
1 stopUnited Airlines
8h 20mBQN-ORD
6/16Sun
2 stopsUnited Airlines
24h 37mORD-BQN
$794

Search by stops

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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 Chicago found on KAYAK in the last 72 hours.
6/4Tue
1 stopSpirit Airlines
15h 04mSJU-ORD
$62
6/3Mon
1 stopSpirit Airlines
13h 48mSJU-ORD
$63
6/11Tue
1 stopSpirit Airlines
10h 17mSJU-ORD
$67
5/31Fri
1 stopFrontier
11h 58mSJU-MDW
$114
5/30Thu
1 stopFrontier
13h 28mSJU-MDW
$122
5/31Fri
1 stopUnited Airlines
7h 55mSJU-ORD
$133
6/1Sat
1 stopAmerican Airlines
14h 09mSJU-ORD
$152
5/28Tue
1 stopAmerican Airlines
7h 04mSJU-ORD
$156
5/29Wed
nonstopUnited Airlines
5h 11mSJU-ORD
$198
5/26Sun
1 stopDelta
8h 30mSJU-MDW
$286

Search by stops

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Last minute flights to Chicago

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 Chicago that are departing in the next 10 days.
5/26Sun
nonstopSpirit Airlines
5h 10mSJU-ORD
5/29Wed
multi-stopSpirit Airlines
20h 42mORD-SJU
$231
5/26Sun
nonstop
5h 10mSJU-ORD
6/2Sun
multi-stop
10h 46mORD-SJU
$234
5/26Sun
nonstop
5h 10mSJU-ORD
5/31Fri
multi-stop
13h 13mORD-SJU
$236
5/26Sun
nonstopSpirit Airlines
5h 10mSJU-ORD
5/31Fri
nonstopSpirit Airlines
4h 53mORD-SJU
$248
5/28Tue
multi-stopFrontier
28h 54mSJU-MDW
6/3Mon
multi-stopFrontier
12h 21mMDW-SJU
$275
5/28Tue
multi-stopFrontier
28h 54mSJU-MDW
6/3Mon
multi-stopFrontier
12h 21mMDW-SJU
$284
5/25Sat
nonstopAmerican Airlines
5h 15mSJU-ORD
5/28Tue
multi-stopAmerican Airlines
9h 35mORD-SJU
$308
5/25Sat
multi-stopAmerican Airlines
8h 54mSJU-ORD
5/28Tue
multi-stopAmerican Airlines
12h 45mORD-SJU
$311
5/26Sun
multi-stopUnited Airlines
12h 30mSJU-ORD
6/2Sun
multi-stopUnited Airlines
13h 29mORD-SJU
$434
5/28Tue
nonstopUnited Airlines
5h 11mSJU-ORD
5/30Thu
nonstopUnited Airlines
4h 50mORD-SJU
$484

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Flights to Chicago

Return flight deals:

Chicago - Puerto Rico

Cabin classes:

$1,177
$949
$1,432
$141