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 8/20. 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.
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, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Juan to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$225
Typical prices: $247-$423
Frontier
Fri 8/7Sun 8/16
SJU - ORD • 1 stop
Cheapest non-stop
$227
Typical prices: $249-$472
Frontier
Thu 9/3Sun 9/6
SJU - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United Economy Plus adds up to six extra inches of legroom over standard economy.
American Main Cabin Extra includes early boarding and complimentary drinks.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $225 (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, Frontier and others. Average duration is 5h 03m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 49% 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 58m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 68% price drop
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
Expert advice
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

Fri, Aug 7 - Sun, Aug 16
Frontier Logo
6:00 am - 12:15 pm
SJU
-
ORD
31h 15m
1 stop
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
$225Frontier
Fri, Sep 4 - Tue, Sep 8
United Airlines Logo
3:56 pm - 8:05 pm
SJU
-
ORD
5h 09mnonstop
United Airlines Logo
8:55 am - 2:44 pm
ORD
-
SJU
4h 49mnonstop
$227United Airlines
Wed, Aug 26 - Tue, Sep 1
Frontier Logo
6:11 pm - 10:26 pm
SJU
-
ORD
5h 15mnonstop
Frontier Logo
12:29 am - 6:26 am
ORD
-
SJU
4h 57mnonstop
$228Frontier
Thu, Aug 20 - Tue, Aug 25
American Airlines Logo
1:38 pm - 11:30 pm
SJU
-
ORD
10h 52m
1 stop
American Airlines Logo
5:20 pm - 11:15 pm
ORD
-
SJU
4h 55mnonstop
$232American Airlines
Thu, Aug 27 - Sat, Aug 29
American Airlines Logo
5:10 pm - 12:35 am
SJU
-
ORD
8h 25m
1 stop
American Airlines Logo
6:59 pm - 9:43 am
ORD
-
SJU
13h 44m
1 stop
$236American Airlines
Tue, Aug 25 - Mon, Aug 31
Southwest Logo
8:20 am - 2:45 pm
SJU
-
MDW
7h 25m
1 stop
Southwest Logo
5:00 am - 1:45 pm
MDW
-
SJU
7h 45m
1 stop
$236Southwest
Wed, Aug 19 - Tue, Aug 25
Delta Logo
12:56 pm - 10:36 pm
SJU
-
MDW
10h 40m
1 stop
Delta Logo
10:54 am - 10:29 pm
MDW
-
SJU
10h 35m
1 stop
$246Delta
Fri, Aug 21 - Thu, Aug 27
Delta Logo
2:59 pm - 10:36 pm
SJU
-
MDW
8h 37m
1 stop
Delta Logo
6:05 am - 1:42 pm
MDW
-
SJU
6h 37m
1 stop
$256Delta
Wed, Aug 19 - Mon, Aug 24
Delta Logo
2:59 pm - 10:36 pm
SJU
-
MDW
8h 37m
1 stop
Delta Logo
6:05 am - 4:38 pm
MDW
-
SJU
9h 33m
1 stop
$266Delta
Fri, Sep 4 - Mon, Sep 7
Southwest Logo
6:30 am - 1:45 pm
SJU
-
MDW
8h 15m
2 stops
Southwest Logo
3:15 pm - 11:05 pm
MDW
-
SJU
6h 50m
1 stop
$286Southwest
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 August.

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 $227 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, 49% 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 Thursdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago, Monday 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 May, where tickets cost $64 (return) on average. On the other hand, the most expensive months are June and July, where the average cost of round-trip tickets is $887 and $558 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 $431 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 12 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
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 seasonNovember
Cheapest flight$118
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from San Juan to Chicago Midway 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 5 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 $225 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, 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?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between San Juan and Chicago, with SkyTeam 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, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from San Juan to Chicago are United Airlines and American Airlines. With an average price for the route of $476 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $463 and an overall rating of 7.1.

  • 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 $194 or less one-way and $435 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,Frontier,United Airlines

American Airlines,Frontier, +1 more

Tuesday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Wednesday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Thursday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Friday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Saturday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Sunday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

See more direct flights

Direct returns

Chicago to San Juan Luis Munoz Marin Intl

Monday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Tuesday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Wednesday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Thursday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Friday

American Airlines,Frontier,United Airlines

American Airlines,Frontier, +1 more

Saturday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

Sunday

American Airlines,Frontier,Southwest, +1 more

American Airlines,Frontier, +2 more

See more direct flights

Reviews of the top 4 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 9866 reviews
7.7Boarding
8.1Crew
7.3Comfort
6.6Food
7.1Entertainment
Airline reviews

Very easy ! Use the kiosk and bag drop and right to security within 10 min

10.0 ExcellentJoanne, Jun 2026
DEN - ORD
Read more United Airlines reviews

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

I flew from Barcelona to Chicago on UA yesterday. The flight was on time, the pilots did a great job and the flight attendants were super nice. All of them. Also food was good, and the drinks, including wine were served a few times during our flight. I highly recommend this airline.

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

The clerk at check in for my bags was very rude. My credit card was hacked during my vacation and she told me it was not possible to pay in cash for my bag. “You bought the cheapest ticket, you should have bought a ticket that included a bag. If you cannot pay with a credit card, we will not let you on this flight”. She spoke to her supervisor and then told me , I could ask other passengers, if they would use their credit card to check my bag. I had to beg 5 different people, till one agreed to use their credit card. I payed them cash of course. This was a very stressful and humiliating experience for me. I strongly suggest you build in some kind of provision for travelers who got robbed.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

The aircraft was fine, it’s was just the service. The flight got canceled several times and that was very inconvenient for my 69 years old mom.

My checked in luggage cost was $59, almost ticket price. The first 13 rows were empty, but fly attendant did not alow women with little boy change her middle sit, sweet boy was crying, I am so sorry for mother and passengers. At the end of the flight the cabin became impossible cold. Only good was timing of departure and early landing, but it suppose to be normal.

I tried to book a flight with Jet Blue. Your third party company hijacked my attempt with a website that looked like I was booking with Jet Blue. I realized it when I paid. I tried to cancel and was told by a man in India that there were no refunds. $735 stolen, Thanks Kayak!

It was inexplicably canceled and we are stuck in LA, haven't gotten home and it has been an inconvenience having lost work (on unpaid leave for my husband).

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

They lost my luggage and refuse to help. Terrible airline. I've never experienced worse customer service in my life. Pretty much just told me too bad that I lost all my luggage, not caring that I am stuck in Europe for 2 weeks with absolutely nothing.

You should have had Wifi to make it much enjoyable.

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

The flight was delayed after already taxiing from the gate due to a malfunction. After 3 hours we were told the flight was canceled. The next flight available was Sunday. My daughter and I stayed overnight in the airport due to this issue. I was given a $12 meal voucher. Unacceptable

Whole experience was poor. Delayed 2 hours. Lied about the delays. Was all jet blues fault and tried to blame on air traffic control. Sent out other let trips and wouldn't allow people to switch aircraft.

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

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

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

Zero issues with this flight. Crew was outstanding and flight was super. Plane was clean and fine. The seats need more padding and water should be provided without cost. I recognize it's Frontier but there are some things that should still be part of the flight. But still very satisfied with the experience and quality.

They switched our terminal 3 times and we were delayed for four plus hours!!!

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

Information on your arrival and departure airports