$115 Find Cheap Flights from Puerto Rico to Chicago - Compare and Save

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Cheap Flights from Puerto Rico to Chicago

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

Recent round-trip flight deals from Puerto Rico to Chicago

Fri, Oct 9 - Tue, Oct 13
Frontier Logo
7:00 am - 3:30 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
9h 30m1 stop Fort Lauderdale
Frontier Logo
6:00 am - 4:06 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
9h 06m1 stop Atlanta Hartsfield-Jackson
$212Frontier
Fri, Oct 23 - Mon, Oct 26
Frontier Logo
5:11 pm - 11:43 pmSJU  San Juan Luis Munoz Marin Intl-MDW Chicago Midway
7h 32m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:15 am - 4:06 pmMDW  Chicago Midway-SJU San Juan Luis Munoz Marin Intl
8h 51m1 stop Atlanta Hartsfield-Jackson
$212Frontier
Fri, Dec 4 - Tue, Dec 8
JetBlue Logo
6:01 am - 1:26 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
9h 25m1 stop Fort Lauderdale
JetBlue Logo
2:50 pm - 11:28 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
6h 38m1 stop Fort Lauderdale
$213JetBlue
Fri, Nov 6 - Mon, Nov 9
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
2:16 pm - 9:00 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 44mnonstop
$217United Airlines
Fri, Nov 6 - Mon, Nov 9
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
2:16 pm - 9:00 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 44mnonstop
$217United Airlines
Wed, Nov 11 - Mon, Nov 16
JetBlue Logo
5:30 pm - 11:55 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
8h 25m1 stop Fort Lauderdale
JetBlue Logo
1:00 pm - 1:13 amORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
10h 13m1 stop Boston Logan Intl
$217JetBlue
Fri, Jan 22 - Mon, Jan 25
American Airlines Logo
6:17 am - 10:00 amSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 43mnonstop
American Airlines Logo
4:50 pm - 11:37 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 47mnonstop
$221American Airlines
Fri, Jan 29 - Mon, Feb 1
American Airlines Logo
6:17 am - 10:00 amSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
5h 43mnonstop
American Airlines Logo
4:50 pm - 11:37 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
4h 47mnonstop
$221American Airlines
Fri, Oct 23 - Wed, Oct 28
Delta Logo
2:59 pm - 11:57 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
9h 58m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:50 pm - 11:44 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
8h 54m1 stop New York John F Kennedy Intl
$230Delta
Thu, Nov 19 - Mon, Nov 23
Delta Logo
3:15 pm - 8:17 pmSJU  San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl
7h 02m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 4:56 pmORD  Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl
8h 56m1 stop New York John F Kennedy Intl
$230Delta
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 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 $430. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $618 on average.

What is the cheapest month to fly to Chicago?

The cheapest month for flights to Chicago is February, where tickets cost $218 on average for return flights. On the other hand, the most expensive months are June and October, where the average cost of tickets from Puerto Rico is $446 and $383 respectively. For one-way flights, the best month to travel is December with an average price of $168.

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 round-trip flights cost $424 on average. The most expensive time of day to fly to Chicago is generally in the morning, which is peak travel time and where the average cost of a ticket is $514.

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 $322 round-trip.

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

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 26 weeks 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 (RFD), with an average flight price of $133.

Good to know

Low season

November

Cheapest flight

$115
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 28% increase in price.
Flight from San Juan to Chicago Midway 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 $360. The cheapest price found on KAYAK in the last 2 weeks cost $108 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.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $217 or less one-way and $322 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

 
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 4189 reviews
7.5Entertainment
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

WiFi was not working and didn’t have a beverage service

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

The seats were comfortable, and the boarding process was pretty smooth.

Very disappointing that on an international business class flight they would not give me access to the lounge in Boston. They said it was because it was a codeshare flight. International business class should include lounge access regardless of codeshare.

The counter person at the gate was rude and demeaning, to the point that I wouldn't fly this airline again.

Crew was great. Seats are cramped and uncomfortable and I’m a small person.

Awful. Delay after delay. And then again on the tarmac.

Kept changing the takeoff time and the moved it up so arrived when boarding had already started. Then sat waiting to taxi in for a long time

Food was not Good Nuts came very wet & not tasting Good Main course I asked for Steak they got me Chicken because they don’t have more !!!!

It cancelled and we were unable to catch our connecting international flights.

Leaving at 7 when scheduled to leave at 4:20 - you tell me. Understood there was a ground stop. Then having to "reboot" the plane because of a lighting strike, also understood. But basically the flight was a "clusterf#$%".

On boarding crew at the airport called in the boarding numbers too early meaning before the previous line was completed resulting in later numbers getting to board ahead. Also she asked those who boarded from number 3 to have the tags in their carry-on bags and leave it in the jet bridge. Most of the overhead bins were empty though. This is more work for the ground staff in addition to more inconvenience for passengers waiting to get their carry-ons from the jet bridge.

ok, butt flght was delyed for 2,5h from Frankfurt, and next Flight to Columbuse same

I've never seen such poor lack of information at a gate station in 69 years. The flight from COS was to depart at 12:37pm. At boarding time, the gate agent in the microphone mumbled something completely unintelligible. I understood one word. "mechanical". Nothing else. Absolutely nothing else was reported for the next 1-1/2 hours. Past the time for departure, at 12:37pm, the gate agent simply walked away and the station was left unattended, as all of the passengers waited expectantly. The board still said that the flight was ON TIME. That was hard to believe since it was then well past 12:37pm and we all were sitting at the gate and there was absolutely no gate agent anywhere in site. I stopped an employee who was standing somewhere else and said that we can use some information. Much later, the same gate agent said that he will have information for us about 5 minutes but he "doesn't know any more than you do." Of course, five minutes came and went and he did absolutely nothing. One and a half hours after 12:37pm, he opened the door and began boarding. No explanation, no apology. Once we were boarded, the same happened on the plane. We sat. No explanation, no apology, from any flight attendants. Finally, finally, a pilot apologized and explained that there would be a delay. WELL NO KIDDING !

Our flight from Chicago to Des Moines was the problem flight due to a dismissive flight attendant. His conduct was unnecessary and unprofessional.. I will avoid using Americam Airlines again because of the situation. Very disappointing.

Mostly excellent. However, many too many gate changes. Connecting flight at ORD changed gate 6 times.

Mechanical issues and delays. I get it but bad experience. Turned my 3 hour airport experience into a 9 hours

The baggage process at the gate was terrible. Stay was not friendly at all

Flight was delayed because of mechanical. Could not get landing space which caused me to miss my connection. Messy and not organized.

We landed slightly early but then sat in holding area waiting for our gate to clear out for about an hour, so technically we arrived one hour late at the gate at ORD. The airport may be partially responsible here, but regardless of who is responsible, it was a bad experience to be so close yet unable to get off the plane.

Delays and cancellations. Mechanics weren’t on site. Replacement plane took hours to arrive although it should have arrived within 90 minutes. Flight back was cancelled. Ended up driving over 12 hours and wasting 3 days between everything.

Little bit of trouble getting my KTN and pre-check status onto the ticket, but otherwise the counter staff were friendly and truly concerned to get it right.

The flight could have actually taken place. Canceled flight and no option to rebook that day.

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.

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

The flight itself was ok and the pilot was very communicative. However, our flight was delayed for almost 3 hours, the gate was changed 3 times and there was no communication as we were waiting. The flight staff was overall a little crabby...I understand as they probably had a long day but we all did.

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