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Find cheap flights from Puerto Rico to Chicago O'Hare Airport from $104

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to O'Hare Intl departing on 5/14. 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
Tue 6/4
Tue 6/11

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These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
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Flights to O'Hare Intl - Travel Insights & Trends

Get data-powered insights and trends for flights to O'Hare Intl 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 O'Hare Intl Airport 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 $295. On the other hand, the most expensive day to fly is Monday, where prices are $374 on average.

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago O'Hare Intl Airport, 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 O'Hare Intl Airport is October, where tickets cost $224 on average for one-way flights. On the other hand, the most expensive months are June and March, where the average cost of tickets from Puerto Rico is $376 and $346 respectively. For return trips, the best month to travel is October with an average price of $224.

What is the cheapest time of day to fly to Chicago O'Hare Intl Airport?

The average price for all flights to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport is generally at night, when flights cost $274 on average. The most expensive time of day to fly to Chicago O'Hare Intl Airport is generally in the morning, which is peak travel time and where the average cost of a ticket is $362.

What is a good deal for flights to Chicago O'Hare Intl Airport?

If you’re looking for cheap airfare to Chicago O'Hare Intl Airport, 25% of our users found tickets to Chicago O'Hare Intl Airport for the following prices or less: From San Juan Luis Munoz Marin Intl Airport $155 one-way - $259 round-trip.

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights to Chicago O'Hare Intl Airport, 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 65 days before departure.

Which airlines fly to Chicago O'Hare Airport?

In general from Puerto Rico, Spirit Airlines, United Airlines and American Airlines fly the most to Chicago O'Hare Airport. See the amount of flights per week for popular airlines flying to Chicago O'Hare Airport.

Which airline offers the most flights to Chicago O'Hare Intl Airport?

Of the 12 airlines that fly to Chicago O'Hare Intl Airport, United Airlines offers the most flights, with around 5,230 per week, followed by American Airlines with 3,641 flights per week.

How long is the flight to Chicago O'Hare Intl Airport?

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 8h 05m, and Culebra, which takes 11h 09m.

How many direct flights to Chicago O'Hare Intl Airport are there each day?

There are around 1,420 direct flights from within Puerto Rico to Chicago O'Hare Intl Airport every day. Most flights depart in the morning, with 6:00 am the most common departure time and 51% of flights departing in the morning.

How many direct flights to Chicago O'Hare Intl Airport are there each week?

Each week there are around 9,939 direct flights from within Puerto Rico to Chicago O'Hare Intl Airport. The most common day for departures is Wednesday, with 15% of flights taking off on this day.

How many long-haul flights are there to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport. Instead, there are 24 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 O'Hare Intl Airport?

From Puerto Rico, there are direct flights to Chicago O'Hare Intl Airport from 1 city. This city is San Juan Luis Munoz Marin Intl Airport and there are 24 direct flights each week.

Good to know

Low season

January

High season

November

Cheapest flight

$104
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from San Juan Airport to Chicago O'Hare Airport

FAQs - booking Chicago O'Hare Airport flights

  • How far is Chicago O'Hare Airport from central Chicago?

    There are 16 miles between Chicago city center and Chicago O'Hare Airport.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $290. The cheapest price found on KAYAK in the last 2 weeks cost $122 and departed from San Juan Luis Munoz Marin Intl Airport.

  • How does KAYAK find such low prices on flights to Chicago O'Hare Airport?

    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 O'Hare Airport.

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

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

    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 O'Hare Airport 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 O'Hare Airport?

    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 O'Hare Airport 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 O'Hare Airport

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

Prefer to fly non-stop to Chicago O'Hare Intl?

Find which airlines fly direct to O'Hare Intl, which days they fly and book direct flights.

Nonstop departures

Puerto Rico to Chicago O'Hare Intl

Monday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

See more direct flights

Nonstop returns

Chicago O'Hare Intl to Puerto Rico

Monday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

See more direct flights
See more direct flights

Top 5 airlines serving from Puerto Rico to O'Hare Intl

 
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 O'Hare Intl? 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 10826 reviews
8.6Crew
8.2Boarding
7.4Food
8.0Entertainment
7.9Comfort
Airline reviews

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!

8.0 ExcellentCynthia, May 2024ATL - TYS
Read more about Delta reviews

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!

Everything was great. The big planes could still stand to have a bit more leg room. Crew was amazing!!

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.

The flight was excellent, I recommend people to fly with Delta

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

The crew were very welcoming and helpful. I just wish economy had a bit more leg room. My knees were constantly hitting the chair in front of me.

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 would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

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!

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 only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

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!

Our flight was delayed two hours. We nearly missed our connecting flight and had to rush across the airport with little kids and all their luggage. They didn’t give us enough time to walk from one gate to the other, then when we got on, we waited another half hour while the crew loaded cargo. It seems like they could have given passengers more time if they had cargo to load anyway.

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.

Only inflight purchases for food and water. Nothing comes with ticket price. Have to purchase bags, food...

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.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

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.
5/17Fri
1 stopFrontier
27h 43mSJU-ORD
5/20Mon
1 stopFrontier
7h 02mORD-SJU
$179
5/9Thu
nonstopSpirit Airlines
5h 10mSJU-ORD
5/14Tue
3 stopsSpirit Airlines
27h 24mORD-SJU
$180
6/6Thu
1 stopSpirit Airlines
12h 49mSJU-ORD
6/10Mon
nonstopSpirit Airlines
4h 48mORD-SJU
$181
6/5Wed
nonstopSpirit Airlines
5h 09mSJU-ORD
6/8Sat
nonstopSpirit Airlines
4h 47mORD-SJU
$182
5/17Fri
1 stop
17h 10mSJU-ORD
5/20Mon
1 stop
7h 02mORD-SJU
$195
5/8Wed
1 stop
22h 51mSJU-ORD
5/14Tue
1 stop
15h 52mORD-SJU
$237
5/8Wed
1 stopAmerican Airlines
8h 46mSJU-ORD
5/15Wed
1 stopAmerican Airlines
9h 20mORD-SJU
$263
5/9Thu
1 stopAmerican Airlines
9h 40mSJU-ORD
5/13Mon
1 stopAmerican Airlines
14h 00mORD-SJU
$265
7/3Wed
2 stopsUnited Airlines
32h 27mBQN-ORD
7/11Thu
1 stopUnited Airlines
8h 54mORD-BQN
$703
5/26Sun
1 stopUnited Airlines
9h 20mBQN-ORD
5/31Fri
1 stopUnited Airlines
8h 57mORD-BQN
$824

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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.
5/14Tue
1 stopFrontier
21h 35mSJU-ORD
$104
5/30Thu
2 stopsSpirit Airlines
17h 27mSJU-ORD
$105
6/25Tue
1 stopSpirit Airlines
14h 55mSJU-ORD
$106
5/29Wed
2 stopsSpirit Airlines
14h 13mSJU-ORD
$110
5/9Thu
1 stopAmerican Airlines
8h 54mSJU-ORD
$132
5/8Wed
1 stopAmerican Airlines
8h 50mSJU-ORD
$133
5/19Sun
2 stops
33h 27mSJU-ORD
$172
6/3Mon
2 stops
16h 45mMAZ-ORD
$234
5/17Fri
1 stopUnited Airlines
8h 34mSJU-ORD
$252
6/10Mon
2 stopsUnited Airlines
18h 20mSJU-ORD
$298

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Last minute flights to O'Hare Intl

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.
5/10Fri
nonstopSpirit Airlines
5h 10mSJU-ORD
5/14Tue
multi-stopSpirit Airlines
15h 52mORD-SJU
$135
5/9Thu
nonstopSpirit Airlines
5h 10mSJU-ORD
5/14Tue
multi-stopSpirit Airlines
20h 42mORD-SJU
$162
5/10Fri
nonstop
5h 10mSJU-ORD
5/16Thu
multi-stop
10h 46mORD-SJU
$203
5/8Wed
multi-stop
13h 48mSJU-ORD
5/12Sun
multi-stop
12h 52mORD-SJU
$241
5/8Wed
multi-stopAmerican Airlines
8h 50mSJU-ORD
6/7Fri
multi-stopAmerican Airlines
15h 28mORD-SJU
$247
5/9Thu
multi-stopFrontier
21h 35mSJU-ORD
5/11Sat
multi-stopFrontier
16h 25mORD-SJU
$259
5/10Fri
multi-stopFrontier
21h 34mSJU-ORD
5/18Sat
multi-stopFrontier
7h 13mORD-SJU
$262
5/10Fri
multi-stopAmerican Airlines
7h 04mSJU-ORD
5/13Mon
multi-stopAmerican Airlines
11h 45mORD-SJU
$263
5/7Tue
multi-stopUnited Airlines
9h 30mSJU-ORD
5/12Sun
nonstopUnited Airlines
4h 50mORD-SJU
$272
5/10Fri
multi-stopUnited Airlines
10h 35mSJU-ORD
5/18Sat
multi-stopUnited Airlines
12h 25mORD-SJU
$348

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Flights to Chicago O'Hare Airport