CHI - SJU

$92 Find Cheap Flights from Chicago to San Juan Airport

1 adult
1 adult, Economy

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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Expert advice
Booking Insights
Expert advice

Expert advice for your flight from Chicago to San Juan

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
Spirit Airlines

Spirit's Big Front Seat offers 20-inch width and 11-inch extra legroom for a nominal fee.


Spirit's Wi-Fi offers gate-to-gate connectivity, ensuring online access throughout your flight.

United Airlines

United's Economy Plus offers up to 6 inches more legroom, enhancing comfort on medium-haul flights.


Purchase Priority Boarding to secure overhead bin space, especially useful on crowded flights.

American Airlines

Main Cabin Extra offers early boarding and complimentary drinks, ideal for a comfortable medium-haul journey.


Download the American Airlines app for access to inflight entertainment on your personal device.

Airports
ORD

For a quick commute to downtown Chicago, take the CTA Blue Line from ORD, which runs 24/7 and avoids traffic delays.

Read more about ORDby Stefanie Waldek
SJU

From SJU, a taxi or Uber to Old San Juan takes about 25 minutes, offering a convenient option for city access.

Read more about SJUby Gabriel Leigh
Our travel experts
Joe Cortez

Joe Cortez

Expert on Spirit Airlines

Joe Cortez

Joe Cortez

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.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

Stefanie Waldek

Stefanie Waldek

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.

Read more
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

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.

Read more
Gabriel Leigh

Gabriel Leigh

Expert on SJU

Gabriel Leigh

Gabriel Leigh

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.

Read more
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.

Find cheap flights to San Juan Airport
Find cheap flights to San Juan Airport

Planning a trip from Chicago to San Juan? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.

What is the most popular layover airport when flying from Chicago to San Juan Airport?

Percentage of 1-stop round-trip flights from Chicago to San Juan Airport chosen by KAYAK users via each layover airport in the last 12 months (only includes trips with the same layover airport on both legs).

Orlando (MCO) is the top choice – 29% of KAYAK users who clicked on 1-stop flights from Chicago to San Juan Airport picked an itinerary connecting there.

What is the cheapest layover airport when flying from Chicago to San Juan Airport?

Average round-trip price for 1-stop flights from Chicago to San Juan Airport clicked by KAYAK users in the last 12 months (only includes trips with the same layover airport on both legs).

Flights via Philadelphia (PHL) offer the most affordable fares, with an average round-trip price of $133.

Which layover airport offers the shortest total travel time from Chicago to San Juan Airport?

Shortest average total travel time for 1-stop one-way flights from Chicago to San Juan Airport via different layover airports, based on KAYAK user data from the last 12 months.

Consider flying via Detroit (DTW) for the shortest journey. The average one-way travel time for flights connecting there is 6h 45m.

Which layover airport has the quickest connection when flying from Chicago to San Juan Airport?

Average layover duration at different layover airports for 1-stop one-way flights from Chicago to San Juan Airport, based on KAYAK user data from the last 12 months.

If you prefer a quick connection, Detroit (DTW) often has the shortest layovers from Chicago to San Juan Airport, with an average of 0h 46m.

Good to know

Low seasonSeptember
Cheapest flight$92
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 9% 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.

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 $150 or less one-way and $274 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

Spirit Airlines, United Airlines, American Airlines

Spirit Airlines, United Airlines, +1 more

Tuesday

American Airlines, Spirit Airlines, United Airlines

American Airlines, Spirit Airlines, +1 more

Wednesday

Spirit Airlines, United Airlines, American Airlines

Spirit Airlines, United Airlines, +1 more

Thursday

Spirit Airlines, United Airlines, American Airlines

Spirit Airlines, United Airlines, +1 more

Friday

Spirit Airlines, United Airlines, American Airlines

Spirit Airlines, United Airlines, +1 more

Saturday

United Airlines, American Airlines, Spirit Airlines

United Airlines, American Airlines, +1 more

Sunday

Spirit Airlines, United Airlines, American Airlines

Spirit Airlines, United Airlines, +1 more

See more direct flights

Direct returns

San Juan Luis Munoz Marin Intl to Chicago

Monday

Spirit Airlines, United Airlines, American Airlines

Spirit Airlines, United Airlines, +1 more

Tuesday

American Airlines, Spirit Airlines, United Airlines

American Airlines, Spirit Airlines, +1 more

Wednesday

Spirit Airlines, United Airlines, American Airlines

Spirit Airlines, United Airlines, +1 more

Thursday

Spirit Airlines, United Airlines, American Airlines

Spirit Airlines, United Airlines, +1 more

Friday

Spirit Airlines, United Airlines, American Airlines

Spirit Airlines, United Airlines, +1 more

Saturday

United Airlines, American Airlines, Spirit Airlines

United Airlines, American Airlines, +1 more

Sunday

Spirit Airlines, United Airlines, American Airlines

Spirit Airlines, United Airlines, +1 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.
8.0
SouthwestOverall score based on 4244 reviews
8.6Crew
7.0Food
7.5Entertainment
8.1Boarding
8.0Comfort
Airline reviews

Southwest's seats are the least comfortable I have ever sat in.

4.0 OkayDavid, Aug 2025DTW - STL
Read more Southwest reviews

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

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

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

The plane was broken so we had to change planes.

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

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

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

It was a good an early bird pleasant and quiet

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

The spirit flight was on time. The airplane itself was surprisingly very nice. We had great seats. Seems like there's more room. Only complaint is that I didn't get a full refund for my mistakenly buying the baggage twice.

The flight times got delayed multiple times due to weather which is understandable, but later the time got prepared 30min. Made to the flight barely but got stressed too much.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

Good crew and safe. However, comfort and being nickeled-and-dimed are my issues. $75 each way for luggage is exhortation. The space to the next seat is so close you cannot open a laptop. The magazine rack doesn’t hold your items. Not a fan.

WiFi could have been a little more consistent - otherwise a phenomenal and positive experience. The 1000 mile giveaway was awesome!!!

Amazing flying experience, even in not the best of weather. The staff made us comfortable and the flight was actually pretty smooth.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

My first flight was delayed 5 hours. The 2nd flight was canceled til the next day and the never even tried to compensate for it. Worse I was delayed again on the flight the rebooked me on.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

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

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

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

Information on your arrival and departure airports

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