CHI - SJU

$127 Find Cheap Flights from Chicago to San Juan Airport - 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 Chicago to San Juan departing on 8/4. 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 San Juan Luis Munoz Marin Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Juan.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Juan.
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Everything you should know

Cheapest round-trip
$259
Typical prices: $251-$457
Frontier
Thu 8/27Thu 9/3
ORD - SJU • 1 stop
Cheapest non-stop
$260
Typical prices: $256-$472
Frontier
Wed 8/26Thu 9/3
ORD - SJU • 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 6 inches more legroom on this medium-haul route.
American Main Cabin Extra includes early boarding and complimentary drinks.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $259 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, Frontier and others. Average duration is 4h 53m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 81% average savings
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 81% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $202 (round-trip)
Shortest trip • 6h 35m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 24% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
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Flight Deals
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Flight Deals

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

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

Thu, Aug 27 - Thu, Sep 3
Frontier Logo
8:05 am - 4:11 pm
ORD
-
SJU
31h 06m
1 stop
Frontier Logo
7:14 pm - 11:27 pm
SJU
-
ORD
5h 13mnonstop
$259Frontier
Wed, Aug 26 - Thu, Sep 3
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
Frontier Logo
7:14 pm - 11:27 pm
SJU
-
ORD
5h 13mnonstop
$260Frontier
Sun, Jul 5 - Wed, Jul 15
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
Frontier Logo
7:14 pm - 11:27 pm
SJU
-
ORD
5h 13mnonstop
$261Frontier
Sat, Aug 15 - Fri, Aug 28
American Airlines Logo
6:59 am - 9:55 pm
ORD
-
SJU
13h 56m
1 stop
American Airlines Logo
12:55 am - 5:00 am
SJU
-
ORD
5h 05mnonstop
$262American Airlines
Mon, Jul 6 - Sat, Jul 11
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
Frontier Logo
7:14 pm - 11:27 pm
SJU
-
ORD
5h 13mnonstop
$263Frontier
Sat, Aug 22 - Wed, Aug 26
Southwest Logo
7:50 am - 4:40 pm
MDW
-
SJU
7h 50m
2 stops
Southwest Logo
5:15 am - 12:05 pm
SJU
-
MDW
7h 50m
2 stops
$266Southwest
Sat, Aug 22 - Sat, Aug 29
Delta Logo
5:30 am - 4:38 pm
ORD
-
SJU
10h 08m
1 stop
Delta Logo
5:49 pm - 11:57 pm
SJU
-
ORD
7h 08m
1 stop
$266Delta
Thu, Aug 27 - Thu, Sep 3
American Airlines Logo
5:20 pm - 11:15 pm
ORD
-
SJU
4h 55mnonstop
American Airlines Logo
1:38 pm - 12:35 am
SJU
-
ORD
11h 57m
1 stop
$267American Airlines
Wed, Aug 26 - Tue, Sep 1
Delta Logo
10:54 am - 10:29 pm
MDW
-
SJU
10h 35m
1 stop
Delta Logo
2:59 pm - 10:36 pm
SJU
-
MDW
8h 37m
1 stop
$281Delta
Fri, Aug 21 - Mon, Aug 24
Southwest Logo
9:10 am - 8:05 pm
MDW
-
SJU
9h 55m
1 stop
Southwest Logo
5:00 am - 11:45 am
SJU
-
MDW
7h 45m
1 stop
$286Southwest
Booking Insights

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

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

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

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

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

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

The cheapest return flight from Chicago to San Juan Luis Munoz Marin Intl Airport costs $200 on the route between Chicago O'Hare Intl Airport (ORD) and San Juan Luis Munoz Marin Intl Airport (SJU). Over the past month, this route was, on average, 81% cheaper than other Chicago-San Juan Luis Munoz Marin Intl Airport routes. It is also the most popular route.

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

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

For Chicago to San Juan Airport, Monday is the cheapest day to fly on average and Friday is the most expensive. Flying from San Juan Airport back to Chicago, the best deals are generally found on Friday, with Sunday being the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to San Juan Luis Munoz Marin Intl Airport, 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 Chicago to San Juan Luis Munoz Marin Intl Airport is April, where tickets cost $316 (return) on average. On the other hand, the most expensive months are December and October, where the average cost of round-trip tickets is $631 and $483 respectively.

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

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 $423, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to San Juan Luis Munoz Marin Intl Airport, 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 Chicago to San Juan Luis Munoz Marin Intl Airport, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to San Juan

 
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 seasonOctober
Cheapest flight$127
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Chicago O'Hare Airport to San Juan

When to book flights from Chicago to San Juan

Are your dates flexible? Find out the best times to travel from Chicago to San Juan 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 Chicago to San Juan Airport flights

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

    In the last 5 days, the lowest price for a flight from Chicago to San Juan Luis Munoz Marin Intl Airport was $127 for a one-way ticket and $259 for a round-trip.

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

    Yes, you’ll need a passport to travel to San Juan Airport from Chicago.

  • Which airports will I be using when flying from Chicago to San Juan Airport?

    Chicago is served by 2 major airports and there is only 1 main airport in San Juan Airport. You will leave Chicago from one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be arriving at San Juan Luis Munoz Marin Intl.

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

    American Airlines, JetBlue, and Alaska Airlines offer inflight Wi-Fi service on the Chicago to San Juan Airport flight route.

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

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

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

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Chicago to San Juan are Southwest and Delta. With an average price for the route of $464 and an overall rating of 7.9, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $383 and an overall rating of 7.8.

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

    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 Chicago to San Juan Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San Juan Airport from 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 from Chicago to San Juan Airport?

    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 San Juan Airport with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to San Juan Airport?

    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 San Juan Airport from Chicago 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 Chicago to San Juan Luis Munoz Marin Intl Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $203 or less one-way and $357 or less round-trip.

Prefer to fly direct from Chicago to San Juan Airport?

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

Direct departures

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

Direct returns

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

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

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San Juan. 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 Chicago to San Juan? 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.
7.9
SouthwestOverall score based on 4246 reviews
8.6Crew
8.0Comfort
7.5Entertainment
7.0Food
8.1Boarding
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

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

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

it was great. the crew is exceptional. the flight was on time.

Agents at gate were not immediately available to solve problems and once they did they didn’t fix all the fight connections

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Smooth travel. Immediate update prior flight delay so I can arrange myself properly without too rush.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

My flight was completely full. Making me very stressful with people walking around all the time. I believe airlines can do better for entertain people during the flight.

The United website was easy to use and had all the information I needed. I needed to change my flight and it was accomplished easily on line. I was also easily able to upgrade and for a reasonable price. Boarding went smoothly and the flight was in time. The service was good in board but the crew did not seem happy at all. Limited availability of meals - not much choice for purchase and in business class they ran out of one of the meal choices by row 4. .

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

Delayed delayed. Poor professionalism. Our seats changed and we pay for them

The plane was broken so we had to change planes.

Uncomfortable seats and flight attendant was rude as she insisted on waking up my husband to ask him if he wanted a drink. When he said that he was sleeping, she replied “without an attitude “. He was seated at 8c

Airlines must do something with overweight people... Maybe reserve a business class seat for them, or you could pay the consequences if someone overweight seat side by side to you in economy.

Iberia didn’t let me check in online or select my seats, the experience overall was not very pleasant

When I agreed to give up my two seats because of overbooking by the airline, I should have been offered some sort of reward or credit towards a future flight. I was not. It was not until the next day when I mentioned it to a Jet Blue employee that I was advised to call 1-800-JetBlue. So here I am, having done Jet Blue a favor and I had to do the work to find out if I was going to get a credit. Such service

A nightmare. Scheduled flight delayed 2 hours then cancelled because pilot timed out . Unable to find another pilot. Really?! Weather certainly a factor, but JetBlue seemed totally unprepared for the chaos that ensued when flight routes were cancelled. More cancelled flights, finally many of us who had been bumped from other flights were allowed to board a Boston bound plane around 3:00am, delay after delay, sat on tarmac for another half hour while pilot dealt with weight distribution issues (?), arrived in Boston 4:30. Crew were wonderful- same attendants all day and night and they were exhausted. Fortunately for me and my son that Boston was our final destination, not so lucky for many who missed connecting flights.

JetBlue is always consistent and great, the food is limited in selection, but at least you can grab as much as you want on snacks and drinks at the Blue Locker.

Very well organized both boarding and deplaning. Very satisfied with the service I received.

Flight was on time arrived at the destination 10min early they kept in touch via email

at the time for boarding the lady just call Group A and no other goups and everybody from A to F go inside without the right turn,and when we get in theres no more spsce for carry on , the ones that get in at not correct group from the back occupy our space !!!!! a mess !!!!

The boarding and flight were ok, but there were several painful issues. The flight was 3:20 in the air and almost four hours door to door, but they only had snack packs on the plane. They really need to have food on longer flights or make it clear to everyone that they won’t have food. They also advertise free WiFi, but it did not work for 90% of this flight. Again, almost four hours door to door. If I had known I was flying spirit for JetBlue prices then I would have planned differently.

I think the food / snack service was very poor. tehy could have done better. Evrything else was great

No wifi, not even while close to the continental US or Puerto Rico, no entertainment whatsoever (TVs not working). Totally disappointing.

Wifi screens were great. Both flights were delayed, spending all day flying home and then getting home at 3am ruins the next day also.

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 !!!!!!!

First of all we hade waited 3 hours in the airplane waiting to leave. Second the return schedule was changed and it messed up my entire vaction. I won't buy never again another flight and recommend to nobody traveling with them.

Better than expected. Staff were friendly and nice on both flights.

The worst. They don’t follow procedure for boarding per group. Flight got delayed for no understandably reasons, they changed our destination from PR to Miami, left us inside a plane for more than 8 hours, then cancelled flight in Miami leaving us stranded. Poorly managed re-accommodation for a new flight and overnight stay so I have to spend in a new ticket and my own hotel room to been able to get to my office next day. Lost 2 days of work and as a doctor, patients loosing their appointments. to other flights and besides

I liked the price of the flight and the chance to buy a seat with no person seated in the middle seat.. Also the flight was right on time.

The flight left over two hours late. They charged me $180 to bring a carry on. There was an error with the spelling of my name and Frontair agent lied that I would need to pay $200 for her to fix the spelling, and pressured me that if I don't do it quick I would lose the flight. I called back and another agent said it costs $75 to fix. All in all, this company is a complete scam.

I took my first and last flight with FRONTIER. The seats are not able to be reclined so it’s not a very comfortable experience when you take a flight of 3 hours or longer. You must pay for your luggage either carry on or check in, so taking all this in consideration at the end what you think you’re saving your paying in services that should be included. Not a beverage in sight. . You’re seriously better off getting on a proper airline such as Delta, AA, United, etc.

Horrible and worse flight ever. Was left at the airport in SJU by my flight to JFK after several delay at Santa Domingo. Will never recommend Frontier to any one. After leaving, frontier customer service ask me to rebook and pay for another flight to from SJU to JFK. Worse airline ever. You pay for everything with frontier airline.

Frontier notifying me earlier of flight delay of over 2 hours.

Excellent crew. WE all know Frontier its a low cost airline but the travel time was about 30 minutes and the crew was phenomenal. I was with a group of 10 more and we are enjoy our flight. The only issue was in SJU waiting for the luggage.

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

Information on your arrival and departure airports