$102 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 12/22. 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
1 adult, Economy, 0 bags

KAYAK searches 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
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
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Everything you should know

Cheapest round-trip
$164
Overall average: $349
Multiple Airlines
Thu 1/15Sun 1/18
SJU - ORD • Non-stop
Cheapest non-stop
$187
Typical prices: $246-$457
Spirit Airlines
Fri 1/23Mon 1/26
SJU - ORD • Non-stop
Top airlines
American Airlines
Most flights • 21 per week
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
BQN-CHI
Cheapest
SJU-CHI
Most popular
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 19% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Puerto Rico to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Puerto Rico to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Puerto Rico to Chicago

Thu, Jan 15 - Sun, Jan 18
Multiple Airlines Logo
1:22 pm - 4:37 pm
SJU
-
ORD
5h 15mnonstop
Multiple Airlines Logo
7:45 am - 11:40 pm
ORD
-
SJU
13h 55m1 stop
$164Multiple Airlines
Wed, Feb 4 - Sat, Feb 7
Multiple Airlines Logo
11:06 am - 7:36 pm
SJU
-
ORD
10h 30m1 stop
Multiple Airlines Logo
6:03 am - 5:00 pm
ORD
-
SJU
8h 57m1 stop
$165Multiple Airlines
Sat, Jan 17 - Mon, Jan 19
Frontier Logo
4:35 pm - 10:13 pm
SJU
-
MDW
7h 38m1 stop
Frontier Logo
6:10 am - 3:27 pm
MDW
-
SJU
7h 17m1 stop
$167Frontier
Fri, Jan 9 - Thu, Jan 15
Frontier Logo
7:10 am - 5:07 pm
SJU
-
ORD
11h 57m1 stop
Frontier Logo
7:45 am - 11:40 pm
ORD
-
SJU
13h 55m1 stop
$168Frontier
Fri, Jan 9 - Mon, Jan 12
Multiple Airlines Logo
5:18 pm - 10:36 pm
SJU
-
ORD
31h 18m2 stops
Multiple Airlines Logo
3:32 pm - 12:59 am
ORD
-
SJU
7h 27m1 stop
$169Multiple Airlines
Thu, Feb 12 - Fri, Feb 27
JetBlue Logo
1:44 pm - 11:10 pm
SJU
-
ORD
11h 26m1 stop
JetBlue Logo
12:41 pm - 11:44 pm
ORD
-
SJU
9h 03m1 stop
$180JetBlue
Fri, Jan 23 - Sun, Jan 25
Southwest Logo
6:10 am - 1:55 pm
SJU
-
MDW
9h 45m2 stops
Southwest Logo
3:15 pm - 12:40 am
MDW
-
SJU
7h 25m1 stop
$225Southwest
Wed, Jan 21 - Sun, Jan 25
United Airlines Logo
1:09 am - 6:16 pm
BQN
-
ORD
19h 07m2 stops
United Airlines Logo
1:00 pm - 11:57 pm
ORD
-
BQN
8h 57m1 stop
$476United Airlines
Wed, Jan 21 - Sun, Jan 25
United Airlines Logo
1:09 am - 9:40 am
BQN
-
ORD
10h 31m1 stop
United Airlines Logo
2:27 pm - 11:57 pm
ORD
-
BQN
7h 30m1 stop
$485United Airlines
Fri, Jan 9 - Mon, Jan 12
JetBlue Logo
5:01 am - 5:43 pm
BQN
-
ORD
14h 42m2 stops
JetBlue Logo
6:45 am - 8:53 pm
ORD
-
BQN
12h 08m2 stops
$657JetBlue
Booking Insights

KAYAK's insights & trends for flights to Chicago

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 flight to Chicago?

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

In the last 3 days, the lowest price for a flight to Chicago was $102 for a one-way ticket from Aguadilla and $164 for a round-trip. The most popular route searched for by our users was for flights from San Juan to Chicago and the best round-trip deal found in the last 3 days was $164.

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 February, where tickets cost $263 on average for one-way flights. On the other hand, the most expensive months are December and August, where the average cost of tickets from Puerto Rico is $431 and $362 respectively. For return trips, the best month to travel is February with an average price of $263.

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 $198 one-way - $289 round-trip.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Chicago, 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, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 67 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 Greater Rockford Airport, with an average flight price of $172.

Good to know

Low seasonMarch
Cheapest flight$102
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Aguadilla to Chicago O'Hare Airport

FAQs - booking Chicago flights

  • What is the cheapest flight to Chicago?

    In the last 3 days, the lowest price for a flight to Chicago was $102 for a one-way ticket from Aguadilla and $164 for a round-trip. The most popular route searched for by our users was for flights from San Juan to Chicago and the best round-trip deal found in the last 3 days was $164.

  • 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 $341. The cheapest price found on KAYAK in the last 2 weeks cost $109 and departed from San Juan Luis Munoz Marin Intl Airport.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Friday where tickets can be as cheap as $383. On the other hand, the most expensive day to fly is Sunday, where prices are $507 on average.

  • 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.

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

    The cheapest time of day to fly to Chicago is generally at night, when flights cost $256 on average. The most expensive time of day to fly to Chicago is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $477.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $198 or less one-way and $289 or less round-trip.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the 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.
7.9
DeltaOverall score based on 8009 reviews
7.9Entertainment
8.5Crew
7.3Food
8.1Boarding
7.9Comfort
Airline reviews

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

10.0 ExcellentVenkata Krishna, Dec 2025
ATL - SDF
Read more Delta reviews

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

For some reason, I couldn't choose my seat. The airline gave me a seat when I got there. Not happy about that. Otherwise, everything else was great!

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

United has come a long way, it’s been a fantastic experience traveling with them.

This flight leg was fantastic - super comfortable and a great selection of things to watch on the TV. Staff were excellent, really above and beyond.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Excellent all round, first time flying United. App is very helpful.

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Flight, food and crew were all good, friendly and very satisfactory.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Premium economy seat was decent. As always poor headphones, poor food and beverage, crew is not overly friendly

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

My baby was crying uncontrollably for the longest time and the entire crew was SO supportive, I’m so appreciative of them. Thank you so much for the support during an exhausting moment. We got very lucky.

Flight was on time. Friendly crew. Gate agents in the other hand were very unfriendly.

Bought round trip tickets. Ended up upgrading to first class. Both flights were new planes but hadn’t been equipped with WiFi and there were no charging ports at my seat despite it being new and first class accommodations.

Like: seats that don't move; fast boarding; engaging crew; low-prices; individual gate at LGA; access to restrooms at the gate Dislike: no water on the flight

To be Honest they canceled my flight and didn't have other options. Until 4 says later and I have a 2yr old very disappointed.

The whole thing everything was poorly managed poorly handled spirit doent deserve to be in business period.

Nothing. It was delayed three times and then canceled and we had to drive 15 hours to get home and rent a car.

Excellent experience when I am looking for a budget airline where the main expectation is getting me from point A to point B with no frills.

Had to deplane for undisclosed mechanical issue. Landed in Chicago 3 hours late. Food voucher at FLL came just as we were recording. Crew and agents were troopers--better than Spirit last night.

We spent 5 1/2 hours at Ohare cause our flight was diverted cause of rain in the area. We missed appts that we had set on Tuesday and cause we were flying back the next day on the 7am flight we had no time to reschedule anything. Other airlines were landing and taking off fine having no issues. It was only Spirit. Very frustrating flight and I understand why the flights are only around 25-30% full.

Not clean and was told I would get a great seat and it was not great at all

Good- no snacks on a 4+ hour flight is painful but more painful was the lack of WiFi.

Flight got delayed for 5 hours no good explanation was offered ;(

Horrible. I would never fly Frontier again. The booking process is tricky at best, but fraudulent in my opinion. Frontier customer service did nothing to rectify my purchase -- I ended up paying more than double what I could have gotten from other airlines and nearly triple what I thought I was buying from Frontier. Their booking practices are unfair to the consumer.

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

Better than expected. Staff were friendly and nice on both flights.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

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