$114 Find Cheap Flights from Puerto Rico to Chicago O'Hare Airport - Compare and Save

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Cheap Flights from Puerto Rico to O'Hare Intl

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Puerto Rico to O'Hare Intl

Fri, Jan 15 - Mon, Jan 18
Frontier Logo
5:02 pm - 9:13 amSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
18h 11m1 stop Tampa
Frontier Logo
8:25 am - 12:37 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
26h 12m1 stop Fort Lauderdale
$227Frontier
Thu, Dec 3 - Sat, Dec 5
Frontier Logo
6:25 am - 1:56 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
9h 31m1 stop Fort Lauderdale
Frontier Logo
5:24 pm - 2:13 amORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
6h 49m1 stop Orlando
$227Frontier
Thu, Mar 4 - Tue, Mar 9
American Airlines Logo
6:10 am - 9:50 amSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 40mnonstop
American Airlines Logo
6:48 pm - 1:25 amORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 37mnonstop
$257American Airlines
Thu, Jan 14 - Mon, Jan 25
American Airlines Logo
7:03 am - 10:35 amSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 32mnonstop
American Airlines Logo
5:01 pm - 11:39 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 38mnonstop
$257American Airlines
Thu, Dec 3 - Tue, Dec 8
United Airlines Logo
8:25 am - 11:49 amSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 24mnonstop
United Airlines Logo
1:30 pm - 10:22 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
6h 52m1 stop Washington, D.C. Dulles Intl
$262United Airlines
Fri, Dec 4 - Mon, Dec 14
United Airlines Logo
4:55 pm - 8:26 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 31mnonstop
United Airlines Logo
10:35 am - 10:22 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
9h 47m1 stop Washington, D.C. Dulles Intl
$262United Airlines
Fri, Dec 4 - Mon, Dec 14
JetBlue Logo
6:38 am - 1:30 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
8h 52m1 stop Fort Lauderdale
JetBlue Logo
2:59 pm - 1:59 amORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
9h 00m1 stop Fort Lauderdale
$262JetBlue
Mon, Dec 7 - Sat, Dec 12
Multiple Airlines Logo
10:30 am - 11:33 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
15h 03m1 stop Fort Lauderdale
Multiple Airlines Logo
4:00 pm - 1:07 amORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
7h 07m1 stop Atlanta Hartsfield-Jackson
$266Multiple Airlines
Fri, Nov 20 - Tue, Jan 5
Multiple Airlines Logo
6:00 am - 3:57 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
11h 57m1 stop Baltimore/Washington
Multiple Airlines Logo
7:00 am - 11:47 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
14h 47m1 stop Fort Lauderdale
$271Multiple Airlines
Tue, Nov 24 - Tue, Dec 1
JetBlue Logo
6:00 am - 1:32 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
9h 32m1 stop Fort Lauderdale
JetBlue Logo
2:59 pm - 1:59 amORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
9h 00m1 stop Fort Lauderdale
$283JetBlue
Booking Insights

KAYAK's insights & trends for flights to O'Hare Intl

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 flight to Chicago O'Hare Airport?

In the last 5 days, the cheapest flight deal to Chicago O'Hare Airport was found on the route from Aguadilla, at $227 return. The most popular connection is from San Juan to Chicago O'Hare Airport and KAYAK users have found round-trip deals for as low as $227 in the last 5 days.

What is the cheapest day to fly to Chicago?

Based on KAYAK data, the cheapest day to fly to Chicago is Thursday where round-trip tickets can be as cheap as $416. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $612 on average.

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

The cheapest month for flights to Chicago O'Hare Intl Airport is February, where tickets cost $223 on average for return flights. On the other hand, the most expensive months are June and November, where the average cost of tickets from Puerto Rico is $437 and $385 respectively. For one-way flights, the best month to travel is December with an average price of $162.

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

The cheapest time of day to fly to Chicago O'Hare Intl Airport is generally at night, when round-trip flights cost $419 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 $507.

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 $318 round-trip.

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

To get a below average price, you should book around 2 weeks before departure, which saves you about 5% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low season

September

Cheapest flight

$114
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Aguadilla to Chicago O'Hare Airport

FAQs - booking Chicago O'Hare Airport flights

  • What is the cheapest flight to Chicago O'Hare Airport?

    In the last 5 days, the cheapest flight deal to Chicago O'Hare Airport was found on the route from Aguadilla, at $227 return. The most popular connection is from San Juan to Chicago O'Hare Airport and KAYAK users have found round-trip deals for as low as $227 in the last 5 days.

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

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

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $345. The cheapest price found on KAYAK in the last 2 weeks cost $118 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.

Top tips for finding cheap flights to Chicago O'Hare Airport

  • Looking for cheap airfare to Chicago O'Hare Airport? 25% of our users found round-trip tickets to Chicago O'Hare Airport for the following prices or less: From San Juan Luis Munoz Marin Intl $933

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

Reviews of the top 4 airlines serving from Puerto Rico to O'Hare Intl

 
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.
7.3
United AirlinesOverall score based on 10461 reviews
7.7Boarding
6.7Food
7.1Entertainment
7.3Comfort
8.1Crew
Airline reviews

I had bad experience with United airline. No live rep, they only have AI that respond to customers concern

2.0 MediocreJOHN, Oct 2026
Read more United Airlines reviews

I had bad experience with United airline. No live rep, they only have AI that respond to customers concern

Flight and crew were great. Need more legroom and do not allow seats to recline.

We arrived to Chicago nearly 30 minutes early, which was great, but then was on the ground for over an hour because the gate was not available. The issue I had was the pilot estimation was frustrating. First he said he was informed it would be 20 minutes but he said "it will probably be more like 10 minutes". After 30 minutes he came back on the comm and said it would be another 10 minutes, maybe 20. I understand he was only giving estimates but he also layered in his own gut feel. We were never told why we didn't have a gate even after our scheduled entry.

Just sat on the run way after we arrived early

The Code Share with Air Canada was not very streamlined. I had to check in at airport (not online) on the outbound and return flights

Stored my cloth purse under seat in front off me as instructed. When I retrieved it, half of it was soaked, along with everything inside it. I don’t really know how that could have been prevented because the area did not look wet, but I was not happy about it.

Phx - ORD was nice 737 with starlink and the ORD - grr was ancient bare bones airbus with not even a power port lol

It was easy to board, and the staff was friendly and helpful. What could have been better is that I shouldn't have to pay extra for a seat that doesn't recline.

Was on the plane sitting longer than the actual flight in air was, boarded at 5:45p and didn't take off until 6:50p flight was only about 30 minutes long. Just was poor experience will booking more with American Airlines.

The couple in front of me were constantly talking over the announcement from the captain and this was annoying me.

It was so nice! I wish that we can have direct flights to El Salvador 😊😊

Jet Blue cancelled my flight after I had boarded. They attempted to rebook me for a new flight two days later. I was able to rebook with a different airline, but not until the next morning. As such, I was forced to get an expensive hotel and missed important work meetings Monday morning. I am very disappointed with the customer service and will be pursuing full reimbursement for my hotel cost.

I will NEVER fly with this clown show airline again. Idiots. All of them. Unprepared. Unfriendly. Miserable employees. NEVER. EVER. AGAIN

Easy experience even with the outbound flight being delayed. The seating and space was comfortable and the crew seemed very nice and helpful.

Flight was smooth, amenities (entertainment options and power outlets) were good, sears decent)

Flight team was very courteous only complaint wS the boarding process and mandatory bag check

Disaster This is why I stick to delta You get what you pay for

Well, its a hit or miss when boarding most of the time your employees just let everyone enter immediately In one bum rush. Then out of know where tell the passengers only let A can enter then b then c etc. So make a decision and stick to it. Do it by alphabet and have famn strick compliance. Let the public know. That makes easier on passengers.

It was a pretty smooth flight, I tend to get mini anxiety attacks during flights, however, this time was pretty smooth and I was able to relax. The only thing, I was having issues to connect to the Flyfi internet. I was not able to connect at all, I turned off my phone a couple times and didnt work.

I volunteered to let them put my carry on suitcase in the baggage storage area. But when we landed I was told it was being unloaded IN A DIFFERENT TERMINAL! I had to walk (painful for me) a long way to retrieve my bag and my ride had to move from the waiting area they were in to a totally different one. Not happy.

It was close to its perfect the flake could be took off early, landed early, didn’t have to wait for my daughter stroller luggage came out quick, very efficient, very good flight

The amount of gate changes and delays is completely unacceptable. This has happened on 3 of 4 trips between Chicago and Dallas in 2026.

The delay update was very late. I had a stressful short connection and RAN through Chicago to get to the next flight, only to find the plane wasn't at the gate yet an nobody was boarding. I would not have had to run if the delay was updated earlier.

No flight delays. No need to rebook to make connections. Enjoyed second leg of flight on Iberia.

Same the delay was not ideal and the credits to move flights was not sufficient

No food on 4.5 hour flight, wi-fi did not work. Terrible experience for a long haul flight.

The crew were diligent about ensuring that our pet dog remained in his carrier for the entire flight, as is their mandate. I wish that mandate was changed so that our poor, scared pets can be comforted during a flight, whereas service animals get to stay out and about for the whole flight. Thank you.

first leg from san diego to chicago, only had cookies for snack. 1 flavor of sparkling water chicago to washington dc had option of cookies, pretzels, or gold fish. had 2 flavors of sparkling water. 2nd flight better however the best part was there was no delays!!! Got to chicago and washington dc early. That was wonderful!!!!

Business class flight attendant was very good. But our flight was delayed two hours for a “mechanical” bathroom issue that literally took 5 minutes to fix. Our plane landed early from its previous flight but still waited for a mechanic to show up to fix an obvious minor issue for almost three hours. This caused us to miss our connecting flight. They put us up in a Days Inn that was 17 miles away from the airport that took a half hour of driving just to get to and this was at 11pm at night. Then when we finally got back on a plane after a full day delay they left our luggage back in the airport. This was an international flight, so no luggage or belongings after flying 8 hours to a different country. We will NEVER fly American Airlines again.

12 hour wait in pdx to my initial flight to Dallas to hunstville

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

We were delayed three times ,and that destroyed my plans, and reservations

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

Flying Frontier was a nightmare. From the booking through Kayak, checking in, departing and arriving, I will never recommend Kayak or Frontier.

Traveling to a place near O'Hare Intl?

Book flights to O'Hare Intl if you plan to visit one of these locations
Gurnee
Merrillville
South Haven
Oak Brook
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Hammond
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Des Plaines
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Oakbrook Terrace
Portage
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Willowbrook
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Alsip
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Delavan

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