$117 Find Cheap Flights from San Juan to Illinois - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from San Juan to Illinois departing on 9/20. 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.
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Cheap Flights from San Juan to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicagononstop$184
St. Louis
St. Louis1 stop$314
Chicago
Chicagononstop$184
St. Louis
St. Louis1 stop$314

Book Cheap San Juan to Illinois Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Juan to Illinois 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 San Juan to Illinois

Thu, Aug 27 - Sat, Aug 29
Frontier Logo
7:14 pm - 11:27 pm
SJU
-
ORD
5h 13mnonstop
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
$184Frontier
Thu, Aug 27 - Sun, Aug 30
Frontier Logo
7:14 pm - 11:27 pm
SJU
-
ORD
5h 13mnonstop
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
$185Frontier
Thu, Aug 27 - Fri, Aug 28
Frontier Logo
7:14 pm - 11:27 pm
SJU
-
ORD
5h 13mnonstop
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
$188Frontier
Fri, Sep 4 - Sun, Sep 6
Frontier Logo
7:14 pm - 11:27 pm
SJU
-
ORD
5h 13mnonstop
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
$196Frontier
Fri, Aug 28 - Sun, Aug 30
Frontier Logo
7:14 pm - 11:27 pm
SJU
-
ORD
5h 13mnonstop
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
$197Frontier
Wed, Aug 26 - Fri, Aug 28
Frontier Logo
7:14 pm - 11:27 pm
SJU
-
ORD
5h 13mnonstop
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
$198Frontier
Wed, Aug 26 - Sun, Aug 30
Frontier Logo
7:14 pm - 11:27 pm
SJU
-
ORD
5h 13mnonstop
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
$199Frontier
Tue, Aug 25 - Tue, Sep 1
Frontier Logo
7:14 pm - 11:27 pm
SJU
-
ORD
5h 13mnonstop
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
$204Frontier
Thu, Aug 27 - Mon, Aug 31
Southwest Logo
6:30 am - 1:45 pm
SJU
-
MDW
8h 15m
2 stops
Southwest Logo
5:00 am - 1:45 pm
MDW
-
SJU
7h 45m
1 stop
$256Southwest
Thu, Aug 27 - Mon, Aug 31
Southwest Logo
8:55 pm - 11:25 am
SJU
-
MDW
15h 30m
2 stops
Southwest Logo
3:10 pm - 11:50 pm
MDW
-
SJU
7h 40m
2 stops
$286Southwest
Booking Insights

KAYAK's insights & trends for San Juan to Illinois flights

Get data-powered insights and trends into flights from San Juan to Illinois to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from San Juan Luis Munoz Marin Intl Airport to Illinois?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from San Juan Luis Munoz Marin Intl Airport to Illinois departing in August.

Flight prices are below average for this route right now.

Flights to Illinois from San Juan Luis Munoz Marin Intl Airport usually cost between $242 and $434 in August.
The lowest price found in the past 5 days was $184 on Frontier (Aug 27-Aug 29).

What is the cheapest San Juan Luis Munoz Marin Intl Airport to Illinois flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Illinois from San Juan Luis Munoz Marin Intl Airport found in the last 5 days was to Chicago, at $160 round-trip. The most popular route is from San Juan Luis Munoz Marin Intl Airport (SJU) to Chicago O'Hare Intl Airport (ORD), and the cheapest round-trip airline ticket found on this route in the last 5 days was $160.

What is the cheapest time of day to fly to Illinois?

The average price for all round-trip flights from San Juan Luis Munoz Marin Intl Airport to Illinois depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Illinois is generally at night, when round-trip flights cost $430 on average. Morning departures are around 8% more expensive than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the morning, which is peak travel time and where the average cost of a ticket is $523.

Can I save money by flying with a layover from San Juan Luis Munoz Marin Intl Airport to Illinois?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $389, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from San Juan Luis Munoz Marin Intl Airport to Illinois?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Juan Luis Munoz Marin Intl Airport to Illinois, 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 from San Juan Luis Munoz Marin Intl Airport to Illinois is February, when tickets cost $227 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $447 and $373 respectively.

What’s the cheapest day of the week to fly from San Juan to Illinois?

The average price of all round-trip flights from San Juan Luis Munoz Marin Intl Airport to Illinois clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from San Juan to Illinois, look for departures on Thursdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Illinois, Monday is the cheapest day to fly and Friday is the most expensive.

How far in advance should I book a flight from San Juan Luis Munoz Marin Intl Airport to Illinois?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from San Juan Luis Munoz Marin Intl Airport to Illinois, 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 on the flight from San Juan Luis Munoz Marin Intl Airport to Illinois, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Good to know

Low season

November

Cheapest flight

$117
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly with an average 16% increase in price.
Flight from San Juan to St. Louis

FAQs - booking Illinois flights

  • How does KAYAK find such low prices on flights from San Juan to Illinois?

    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 from San Juan to Illinois.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San Juan to Illinois?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from San Juan to Illinois is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from San Juan to Illinois?

    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 from San Juan to Illinois 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 from San Juan to Illinois?

    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 from San Juan to Illinois 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 Illinois

  • Looking for a cheap flight? 25% of our users found tickets from San Juan to the following destinations at these prices or less: Chicago $173 one-way - $326 round-trip

Reviews of the top 5 airlines serving from San Juan to Illinois

 
See real verified KAYAK customer reviews for airlines flying from San Juan to Illinois. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from San Juan to Illinois? 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 4236 reviews
8.0Comfort
7.5Entertainment
8.6Crew
7.0Food
8.1Boarding
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
CVG - MDW
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.

Terrible all around. Left prior review detailing massive delay/cancellation to then rebook travel. Topping on the cake was lost luggage even after travel to ultimate destination was secured on a new plane(s).

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.

Never went on board this flight. Kayak uses Underpricer (which is a scam business) as it's "customer service provider". This customer service is a classic bait and switch "service". I Got caught in the UnderPricer Bait and switch scam. 14 hours on the phone with people from India with heavy accents and upselling me to useless products. The original sell was a flight on spirit. Then they contact me later, an say after they have my money that the flight is no good as is is only one seat for a party of two. I am still in dispute to get my money back. Went to Spirit direct and had a beautiful vacation. I should never have used Kayak and their rip off artists UnderPricer.

I like everything about Southwest. From customer service to crew and prices. I travel a lot during the year and Southwest is the best!!

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

I almost missed my connection in Chicago due to having to wait on a gate to be open I am assuming. Having to run from E terminal to C terminal and I barely made it there before they closed the door. This may not be the actual airline's fault it's crazy how there is so little time between flight especially when they are placed so far apart in the airport.

The Wi-Fi did not work, so you weren't able to watch entertainment on your own device. They did not have wired headphones so you couldn't watch it on the in-seat entertainment screen either. There was plenty of time to do a drink and snag service but the flight attendants chose not to.

Great experience, boarding was fast and efficient, so much so that we arrived to Chicago very early

The flight did not have its customary snacks during the flight. Apparently they were never loaded on the plane.

The seats on this flight weren’t as comfortable as we had expected. Even leaned back these seats left us feeling crappy in our backs. Also we had to use our own tablets for movies, but nothing in the seats in front of us to hold the tablets up.

The head rest is too big and cannot be placed differently/removed. Causes one head to tilt forward and increase back pain

Awful. There was a minor problem with a fridge and they had us 2 hours in the runway before take off. The paper work alone took them half hour. There was no attemp to make up time up while in teansit and when we arrived, they had us another half hour in the plane because of traffic. I, and a bunch of people, lost their onnection flights for 5 to 10 minutes. Not even the attemp to wait given thar all delays, but the taxing, were United's fault. Then another 45 mins to get an agent and no flight alternatives for 2 days. Im am very disapointed with this "premium carrier".

IT WAS A LONG TIME SINCE THE LAST TIME I TRAVELED. I THOUGHT I WAS TO BE LOST BUT EVERYONE WAS PRETTY NICE WITH ME AND MADE MY EXPERIENCE NICE. THANKS

There was a delay that was unexpected. The seats were uncomfortable for the length of the flight.

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

Take this flight regularly. Every single week same thing. Departure delayed. Make up some time in the air. Land at ORD and then wait for gate in "L" concourse Terminal 3 for 30-40 min-which yields a very delayed final arrival. Plus I get to taxi around and see every runway and drive over the bridge (IFKYK) over the expressway 2-4 times in most cases. Change the sched of incoming plane/work with FAA to improve traffic flow at ORD/change the timing of these flights. Whatever it takes. But do better.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

AA was a very good experience. The employees are wonderful

We had a very pleasant flight with very comfortable seats and nice staff.

Seats in coach aren't padded enough for a 6 hour flight

My trip was delayed for more than 3 hours without any explanation. Also I have a business meeting that I lost.

the handling of my luggage. It was Lost or stolen At my destination.

If we travel with carry on expected to being able to carry the luggage. Could be good if take in consideration the date of reservation to do that

Uncomfortable seats at row 40 A and 40 C, they didn’t recline. Also, my prior seat selection was not honored.

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)

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.

we were delayed because of some safety check that wasn't done or available

They announced at the last minute that international travelers had to checkin at counter. This created a long line and unnecessary stress.

I cannot say this enough, I NEVER BOARDED OR HAVE HAD ANY TRAVEL IN THE PAST YEAR. However your app says ive been traveling a lot lately. GET REAL HUMANS TO GIVE CUSTOMER SUPPORT.

late lack information taney changed my sit even after i had checked i. a day prior and had been at airport checked in for 5 hrs. i have medical condition that i need to sit in aisle but changes to window. only apparent at boarding and they had no explanation why they changed my boarding pass and had no other seats. very bizarre, uncaring and disrespectful. Made my trip very challenging I should sue you. will NEVEr fly JB again. Ever. Would have blasted in social media but did not want to disclose my medical disability.

Frontier line changes my flight schedule with out my authorization. They never ask me and with out my concern they cut off 4 hours of my vacation they force my to leave 4 hours early from Puerto Rico.

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

I guess you get what you pay for. The seats are very uncomfortable and very little space. The snacks were pricey.

Flight was changed (according to Frontier, by Kayak) without my notification. And all flights were delayed by at least an hour and a half. Uncomfortable plane. Bad service. Will never fly Frontier again.

Was left with many other passengers in SJU by frontier airlines due to delay caused by frontier. Worst experience ever and worst airline ever.

It was horrible. My plane was delayed until the next day resulting in me losing a day of work. It’s absolutely unacceptable and I won’t be flying with you any more and I will strongly caution others to avoid your airline as well.

When we arrived we lasted 48 minutes to be able to get off the plane without air and the plane turned off more than half of the passengers because after they started to leave they realized that the bridge was defective

Pro: The stuff was great. Friendly, patient and caring. Our seat row was clean. The bath room was clean. Our flights were close to on time. Con: The leg room is too small. No blankets or pillows. No entertainment devices at all. I can’t remember to have a food choice. I would fly again with frontier for short distances.

Great option to American Airlines. Affordable prices when compared to AA. Prices in AA to and from Puerto Rico are like Fly Emirates to Kwait.

The flights were right on time. The issue that was the most difficult was the lack of legroom on the planes

Everything you need to know for your flight from San Juan to Illinois

Information on your arrival and departure airports