$84 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 11/15. 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
$193
Overall average: $291
Multiple Airlines
Thu 12/4Sun 12/7
SJU - ORD • 1 stop
Cheapest non-stop
$217
Typical prices: $198-$442
Spirit Airlines
Thu 12/4Mon 12/8
SJU - ORD • Non-stop
Top airlines
United Airlines
Most flights • 14 per week
Southwest
Best reviews • 8.0 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
January
Cheapest • 20% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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, Dec 4 - Sun, Dec 7
Multiple Airlines Logo
10:42 am - 6:36 pmSJU-ORD
9h 54m1 stop
Multiple Airlines Logo
7:41 pm - 9:37 amORD-SJU
11h 56m1 stop
$193Multiple Airlines
Find Deal
Thu, Dec 4 - Mon, Dec 8
Frontier Logo
10:42 am - 9:53 pmSJU-MDW
13h 11m1 stop
Frontier Logo
6:15 am - 3:11 pmMDW-SJU
6h 56m1 stop
$196Frontier
Find Deal
Thu, Nov 13 - Sun, Nov 16
Spirit Airlines Logo
3:37 pm - 12:27 amSJU-ORD
10h 50m1 stop
Spirit Airlines Logo
5:10 am - 5:19 pmORD-SJU
10h 09m1 stop
$203Spirit Airlines
Find Deal
Thu, Jan 22 - Mon, Jan 26
Frontier Logo
10:58 am - 7:04 pmSJU-ORD
10h 06m1 stop
Frontier Logo
6:40 am - 5:54 pmORD-SJU
9h 14m1 stop
$209Frontier
Find Deal
Thu, Dec 4 - Mon, Dec 8
Frontier Logo
10:42 am - 9:53 pmSJU-MDW
13h 11m1 stop
Frontier Logo
8:42 pm - 6:23 pmMDW-SJU
19h 41m2 stops
$210Frontier
Find Deal
Thu, Dec 4 - Mon, Dec 8
Spirit Airlines Logo
9:00 am - 12:23 pmSJU-ORD
5h 23mnonstop
Spirit Airlines Logo
5:45 am - 12:26 pmORD-SJU
4h 41mnonstop
$217Spirit Airlines
Find Deal
Wed, Feb 18 - Sun, Feb 22
United Airlines Logo
4:52 pm - 8:20 pmSJU-ORD
5h 28mnonstop
United Airlines Logo
5:45 am - 4:36 pmORD-SJU
8h 51m1 stop
$223United Airlines
Find Deal
Fri, Jan 23 - Tue, Feb 3
Delta Logo
7:30 am - 12:01 pmSJU-MDW
6h 31m1 stop
Delta Logo
12:48 pm - 8:57 pmMDW-SJU
6h 09m1 stop
$227Delta
Find Deal
Thu, Dec 4 - Tue, Dec 9
United Airlines Logo
2:05 am - 8:47 amSJU-ORD
8h 42m1 stop
United Airlines Logo
2:20 pm - 9:00 pmORD-SJU
4h 40mnonstop
$241United Airlines
Find Deal
Fri, Dec 5 - Tue, Dec 9
Southwest Logo
9:40 am - 7:30 pmSJU-MDW
11h 50m1 stop
Southwest Logo
9:20 am - 11:20 pmMDW-SJU
12h 00m1 stop
$317Southwest
Find Deal
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 $84 for a one-way ticket from Aguadilla and $193 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 $193.

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 $254 on average for one-way flights. On the other hand, the most expensive months are August and June, where the average cost of tickets from Puerto Rico is $362 and $357 respectively. For return trips, the best month to travel is January with an average price of $254.

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 $171 one-way - $351 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 $153.

Good to know

Low seasonMarch
Cheapest flight$84
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly with an average 9% increase in price.
Flight from Aguadilla to Chicago Midway 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 $84 for a one-way ticket from Aguadilla and $193 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 $193.

  • 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 $340. 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 $380. On the other hand, the most expensive day to fly is Monday, where prices are $506 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 $253 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 $478.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $171 or less one-way and $351 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.
8.0
SouthwestOverall score based on 4241 reviews
8.6Crew
8.0Comfort
7.0Food
7.5Entertainment
8.1Boarding
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

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

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

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

The flight was on time and crew were nice, seats were tight and there was entertainment available

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.

Just total easy flight experience!! What could you do better..? Hmmm..? There was nothing I can remember. Spirit was a far more comfortable and easy process than American, United & Delta. I'll always look for Spirit and I've told a few people about, since flying this past trip!! I'm a SPIRIT FAN!! Thank You, SPIRIT AIRLINES!! Very, VERY well done, 100%!! See you...SOON!! -Best, Linda R.

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

As expected. Nothing jumps out at me as bad or wrong, but the flight was fine. No complaints with pilot or crew. The flight left on time and arrived earlier than stated. Overall, I will continue to plan on flying with Spirit.

Horrible considering I didn’t go and I bought travel insurance and I didn’t receive a refund.

Departure was right on time. The Orlando base crew from Atlanta to Puerto Rico was the BEST. The return flight crew was OK.

While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

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.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

Traveling to a place near Chicago?

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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.

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