SJU - CHI

$118 Find Cheap Flights from San Juan 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 from San Juan to Chicago departing on 6/6. 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 in flight searches from San Juan to Chicago.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Juan to Chicago.
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Everything you should know

Cheapest round-trip
$159
Typical prices: $453-$254
Frontier
週四 4/23週一 4/27
SJU - ORD • 1 stop
Cheapest non-stop
$162
Typical prices: $470-$281
Spirit Airlines
週四 4/9週一 4/13
SJU - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United's Economy Plus offers extra legroom for comfort.
Spirit's Big Front Seat provides more space for a fee.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $159 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, Spirit Airlines and others. Average duration is 5h 17m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 36% average savings
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 96% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $157 (round-trip)
Shortest trip • 6h 38m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 20% compared to booking last minute.
Insights
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When to travel
Cheapest • 37% price drop
Most popular
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Flight Deals

Cheap Flights from San Juan to Chicago (SJU-CHI)

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

週四, 4月 23 - 週一, 4月 27
Frontier Logo
6:00 am - 9:17 pm
SJU
-
ORD
16h 17m
1 stop
Frontier Logo
2:07 pm - 11:43 pm
ORD
-
SJU
8h 36m
1 stop
$159Frontier
週四, 4月 9 - 週一, 4月 13
Spirit Airlines Logo
1:29 am - 5:45 am
SJU
-
ORD
5h 16mnonstop
Spirit Airlines Logo
12:29 pm - 6:00 pm
ORD
-
SJU
4h 31mnonstop
$162Spirit Airlines
週一, 4月 13 - 週六, 4月 18
Spirit Airlines Logo
1:29 am - 5:45 am
SJU
-
ORD
5h 16mnonstop
Spirit Airlines Logo
6:40 am - 12:58 am
ORD
-
SJU
17h 18m
1 stop
$163Spirit Airlines
週四, 4月 9 - 週一, 4月 13
Spirit Airlines Logo
1:29 am - 5:45 am
SJU
-
ORD
5h 16mnonstop
Spirit Airlines Logo
12:45 pm - 9:59 pm
ORD
-
SJU
8h 14m
1 stop
$166Spirit Airlines
週四, 5月 7 - 週一, 5月 11
Frontier Logo
6:46 pm - 6:44 pm
SJU
-
ORD
24h 58m
1 stop
Frontier Logo
5:30 pm - 2:08 am
ORD
-
SJU
7h 38m
1 stop
$168Frontier
週六, 4月 25 - 週六, 5月 2
Frontier Logo
8:00 am - 3:23 pm
SJU
-
ORD
8h 23m
1 stop
Frontier Logo
7:34 pm - 11:29 pm
ORD
-
SJU
26h 55m
1 stop
$169Frontier
週四, 4月 16 - 週日, 4月 26
Frontier Logo
11:30 am - 11:59 pm
SJU
-
ORD
13h 29m
1 stop
Frontier Logo
1:22 pm - 12:33 pm
ORD
-
SJU
22h 11m
1 stop
$170Frontier
週五, 4月 24 - 週一, 4月 27
Multiple Airlines Logo
3:23 pm - 10:39 pm
SJU
-
ORD
8h 16m
1 stop
Multiple Airlines Logo
7:50 am - 12:58 am
ORD
-
SJU
16h 08m
1 stop
$173Multiple Airlines
週四, 4月 16 - 週一, 4月 27
Multiple Airlines Logo
11:30 am - 11:59 pm
SJU
-
ORD
13h 29m
1 stop
Multiple Airlines Logo
7:50 am - 12:58 am
ORD
-
SJU
16h 08m
1 stop
$175Multiple Airlines
週五, 4月 24 - 週一, 4月 27
Frontier Logo
3:23 pm - 10:26 pm
SJU
-
MDW
8h 03m
1 stop
Frontier Logo
6:00 am - 2:08 pm
MDW
-
SJU
7h 08m
1 stop
$176Frontier
Booking Insights

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

Get data-powered insights and trends into flights from San Juan to Chicago 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 Chicago?

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 Chicago departing in April.

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

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

The cheapest return flight from San Juan Luis Munoz Marin Intl Airport to Chicago costs $229 on the route between San Juan Luis Munoz Marin Intl Airport (SJU) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 36% cheaper than other San Juan Luis Munoz Marin Intl Airport-Chicago routes. It is also the most popular route.

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

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

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

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

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 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 from San Juan Luis Munoz Marin Intl Airport to Chicago is February, where tickets cost $189 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $386 and $359 respectively.

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

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $287 on average.

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

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 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 on the flight from San Juan Luis Munoz Marin Intl Airport to Chicago, you should book around 2 weeks before departure, which saves you about 20% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Expert advice

Expert advice for your flight from San Juan to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Joe Cortez

Joe Cortez

Expert on Spirit Airlines

Joe Cortez is a seasoned managing editor in aviation with over a decade of industry experience. His work has been featured on prominent platforms such as FlyerTalk and TripSavvy, establishing him as a respected voice in aviation journalism.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Gabriel Leigh

Gabriel Leigh

Expert on SJU

Gabriel is a writer and video creator. As senior content producer for Flightradar24 and Monocle’s transport correspondent, he keeps a close eye on aviation in particular. He has also written travel articles for the likes of The New York Times. Born in New York but raised around the world, he now lives in Sweden. He’s been to 75 countries, flying 2.3 million miles on 113 airlines and through 234 airports in the process.

Good to know

Low seasonMarch
Cheapest flight$118
Best time to beat the crowds but there is an average 19% increase in price.
Most popular time to fly with an average 4% increase in price.
Flight from San Juan Airport to Chicago O'Hare Airport

When to book flights from San Juan to Chicago

Are your dates flexible? Find out the best times to travel from San Juan to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking San Juan to Chicago flights

  • What is the cheapest flight from San Juan Luis Munoz Marin Intl Airport to Chicago?

    In the last 3 days, the lowest price for a flight from San Juan Luis Munoz Marin Intl Airport to Chicago was $118 for a one-way ticket and $159 for a round-trip.

  • Do I need a passport to fly between San Juan and Chicago?

    Yes, you'll most likely have to show a valid passport before boarding the plane in San Juan and on arrival in Chicago.

  • Which airlines offer Wi-Fi service onboard planes from San Juan to Chicago?

    American Airlines, Aer Lingus, Iberia, and Delta offer inflight Wi-Fi service on the San Juan to Chicago flight route.

  • Which aircraft models fly most regularly from San Juan to Chicago?

    The Airbus A321neo is the aircraft model that flies most regularly on the San Juan to Chicago flight route.

  • Which airline alliances offer flights from San Juan to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between San Juan and Chicago, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from San Juan to Chicago?

    There are nonstop flights from San Juan to Chicago on a daily basis.

  • Which is the best airline for flights from San Juan to Chicago, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from San Juan to Chicago are Southwest and Delta. With an average price for the route of $458 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $261 and an overall rating of 7.9.

  • How does KAYAK find such low prices on flights from San Juan 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 from San Juan to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from San Juan 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 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 to San Juan with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from San Juan 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 from San Juan up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from San Juan Luis Munoz Marin Intl Airport to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $324 or less one-way and $348 or less round-trip.

Prefer to fly direct from San Juan to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from San Juan Luis Munoz Marin Intl to Chicago.
Find which airlines fly direct from San Juan Luis Munoz Marin Intl Airport to Chicago, which days they fly and book direct flights.

Direct departures

San Juan Luis Munoz Marin Intl to Chicago

Monday

American Airlines,Spirit Airlines,United Airlines, +1 more

American Airlines,Spirit Airlines, +2 more

Tuesday

American Airlines,Spirit Airlines,United Airlines, +1 more

American Airlines,Spirit Airlines, +2 more

Wednesday

American Airlines,Spirit Airlines,United Airlines, +1 more

American Airlines,Spirit Airlines, +2 more

Thursday

American Airlines,Spirit Airlines,United Airlines, +1 more

American Airlines,Spirit Airlines, +2 more

Friday

American Airlines,Spirit Airlines,United Airlines, +1 more

American Airlines,Spirit Airlines, +2 more

Saturday

American Airlines,Southwest,Spirit Airlines, +2 more

American Airlines,Southwest, +3 more

Sunday

American Airlines,Southwest,Spirit Airlines, +2 more

American Airlines,Southwest, +3 more

See more direct flights

Direct returns

Chicago to San Juan Luis Munoz Marin Intl

Monday

American Airlines,Spirit Airlines,United Airlines, +1 more

American Airlines,Spirit Airlines, +2 more

Tuesday

American Airlines,Spirit Airlines,United Airlines, +1 more

American Airlines,Spirit Airlines, +2 more

Wednesday

American Airlines,Spirit Airlines,United Airlines, +1 more

American Airlines,Spirit Airlines, +2 more

Thursday

American Airlines,Spirit Airlines,United Airlines, +1 more

American Airlines,Spirit Airlines, +2 more

Friday

American Airlines,Spirit Airlines,United Airlines, +1 more

American Airlines,Spirit Airlines, +2 more

Saturday

American Airlines,Southwest,Spirit Airlines, +2 more

American Airlines,Southwest, +3 more

Sunday

American Airlines,Southwest,Spirit Airlines, +2 more

American Airlines,Southwest, +3 more

See more direct flights

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

 
See real verified KAYAK customer reviews for airlines flying from San Juan to Chicago. 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 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.
7.4
United AirlinesOverall score based on 9530 reviews
7.3Comfort
7.7Boarding
7.1Entertainment
8.1Crew
6.6Food
Airline reviews

3 hour delay…. Nearly 2 hours sitting on tarmac. Do better, United. Or at least have the sense to not say “we hope you enjoyed your flight with us” upon disembarking.

2.0 MediocreJill, Mar 2026
LGA - ORD
Read more United Airlines reviews

3 hour delay…. Nearly 2 hours sitting on tarmac. Do better, United. Or at least have the sense to not say “we hope you enjoyed your flight with us” upon disembarking.

Flights were on time. Free Wifi on plane. Everything was well organized.

Economy plus was so cramped I could not use my laptop. It was beyond bad.

Would've been great if Lufthansa union cockpit pilots didn't strike for 2 days and caused a chaos to my returning plans to USA, and then after rebooking a flight 2 days later tge plane departed 35 min later. So I did not have a good experience.

They never clean the toilet, and the food is worse

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

No real complaints. The in flight food was much better than I expected. The in flight entertainment was excellent.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Horrible Flight significantly delayed. Not due to united issue. But trying to rebook connection flight and get information about overnight accommodation was difficult. Agent did not seem to care or have any interest to help.

For the price point it was very good. Definitely leave on the earlier flights as it can become terribly crowded later in the day

Absolutely horrible. Flight was delayed 4 hours and they had no clue what was going on.

Delayed our flight to accommodate another flight but didn’t make the decision to do so until we were supposed to board despite having all the same information hours prior. Arrived so delayed that we didn’t get a gate and had to deplane on the tarmac and get bussed to terminal in the rain after 1am. Arrived to the terminal and due to construction could not get a ride share - had to either take the air train to Howard beach or stand in line with 200 other people waiting for a taxi.

Onboard functioning wide-variety entertainment on a budget and having an open pantry is nice. Seats are not comfortable but go provide plenty of legroom for a 6'2" 260lbs man.

Even though the weather made a lot of flights become cancelled Jet Blue made the flight that was supposed to leave at 9 pm and we left at 12:15 am and I was so grateful- Thanks to the Senior Jet Blue Staff who made those decisions

Worst customer service ever experienced on the planet, dirty plane, no communication, and severe delays

Flight cancelled 2 hours prior to boarding. No explanation. No refunds.

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.

Arrived as recommended at 8:15 a.m. for an 1115 flight, that kept getting delayed delayed and delayed and then finally canceled. Instructed for the split flight to go to Fort Lauderdale, and then find our way from there back to New York. I don't think I will ever trust flying with JetBlue again. This was my second horrific experience and I am really angry.

Delayed by 1.5 hours. Terrible apologies, half hearted at best. It will be a LONG time until i book w Jet Blue again. Very disappointed.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

I understand that there is a catering issue - water should be the minimum stock. During the flight, not once that the attendants came through with water. The conversations in the kitchen were very loud and they were swearing. I do not expect any white glove service, at the minimum, we should be cordial. It was almost an inconveniece that we were on the flight. And it made us feel if you even dare question us, we'll make you deplane.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

Spirit is awful. Do not fly spirit. Nothing but delays, cancellations.

Nothing. We didn’t even have a pilot until one hour after our flight was set to depart and now we are waiting for a gate on a very hot packed aircraft. Spirit has lost its goddamn minds and we will never fly again. On the way down the delay went from 5 minutes to 6 hours to cancelled.

Delayed 11 hours with two being on our destinations tarmac, no compensation or refund and was told I would actually get charged a $200 cancellation fee if I decided to switch airlines for my return flight. For their inconvenience they gave a $10 meal voucher to split between two people in a airport.

Like Spirit but bad that you have to pay for water 🙃

If there are delays, it takes less than a minute for a Spirit employee to make an announcement. It’s very simple.

Flight was cancelled without explanation or option for same day or next day flight

For a change, friendly staff at check-in and in flight.

Delayed both in takeoff and landing, trash plane no amenities, I've said it before but I'll never fly Spirit again.

It’s was a cheap flight and they got us there safely. It’s just their whole business model that make the experience “meh.” They make you paranoid about whether your personal item is too big. They make you paranoid about being crammed into a middle seat at the back of the plane. They purposely cram people together leaving multiple rows completely empty and even after the door closes the FA’s announce that everyone has to sit in their assigned seat. We knew what we were buying and in that regard we got a cheap and safe flight but it felt like they do their best to take any enjoyment out of the experience. That’s all on management, not the crew.

Had to pay for my bag a mini weekender bag 100 dollar fee

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

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

Information on your arrival and departure airports