CHI - SJU

$82 Find Cheap Flights from Chicago to San Juan Airport

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 5/10. 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

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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Cheap Flight Deals from Chicago to Luis Munoz Marin Intl (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 Luis Munoz Marin Intl 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.

Recent round-trip flight deals from Chicago to San Juan

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to San Juan.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Spirit Airlines Logo
4:35 pm - 12:54 amORD-SJU
7h 19m1 stop
Spirit Airlines Logo
6:09 am - 10:25 amSJU-ORD
5h 16mnonstop
$202Spirit Airlines
Find Deal
Sat, May 10 - Thu, May 15
Spirit Airlines Logo
11:30 am - 5:16 pmORD-SJU
4h 46mnonstop
Spirit Airlines Logo
6:09 am - 10:25 amSJU-ORD
5h 16mnonstop
$203Spirit Airlines
Find Deal
Sun, May 11 - Thu, May 15
Spirit Airlines Logo
8:45 am - 11:46 pmORD-SJU
14h 01m1 stop
Spirit Airlines Logo
12:40 pm - 8:03 pmSJU-ORD
8h 23m1 stop
$204Spirit Airlines
Find Deal
Mon, May 5 - Sat, May 10
Frontier Logo
6:15 am - 2:47 pmMDW-SJU
7h 32m1 stop
Frontier Logo
6:00 am - 12:24 pmSJU-MDW
7h 24m1 stop
$294Frontier
Find Deal
Mon, May 5 - Thu, May 8
Frontier Logo
8:30 am - 7:44 pmMDW-SJU
10h 14m1 stop
Frontier Logo
6:00 am - 5:30 pmSJU-MDW
12h 30m1 stop
$298Frontier
Find Deal
Thu, May 8 - Sun, May 11
Delta Logo
6:00 am - 4:08 pmORD-SJU
9h 08m1 stop
Delta Logo
7:00 am - 5:36 pmSJU-ORD
11h 36m1 stop
$307Delta
Find Deal
Sun, Sep 14 - Thu, Sep 18
American Airlines Logo
8:25 am - 8:10 pmORD-SJU
10h 45m1 stop
American Airlines Logo
11:55 am - 10:34 pmSJU-ORD
11h 39m1 stop
$365American Airlines
Find Deal
Tue, Sep 16 - Fri, Sep 19
Southwest Logo
9:55 am - 10:10 pmMDW-SJU
11h 15m2 stops
Southwest Logo
5:00 pm - 11:45 pmSJU-MDW
7h 45m1 stop
$381Southwest
Find Deal
Tue, Jun 24 - Wed, Jul 2
Southwest Logo
8:50 am - 2:35 pmMDW-SJU
4h 45mnonstop
Southwest Logo
6:00 am - 1:00 pmSJU-MDW
8h 00m1 stop
$397Southwest
Find Deal
Sat, Jun 28 - Thu, Jul 3
Delta Logo
6:00 am - 4:33 pmMDW-SJU
9h 33m1 stop
Delta Logo
6:15 am - 11:53 amSJU-MDW
6h 38m1 stop
$458Delta
Find Deal
Wed, May 21 - Wed, May 28

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. It runs 24/7 and avoids traffic delays.

Read more about ORDby Stefanie Waldek
SJU

For a quick ride to San Juan, taxis and Ubers are available at SJU with reasonable rates and short travel times.

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

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

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to San Juan Luis Munoz Marin Intl Airport.
Our data shows that the cheapest route for a return flight from Chicago to San Juan Luis Munoz Marin Intl Airport cost $201 and was between Chicago O'Hare Intl Airport (ORD) and San Juan Luis Munoz Marin Intl Airport (SJU). On average, the best prices are found if you fly from Chicago Midway Airport (MDW) to San Juan Luis Munoz Marin Intl Airport (SJU). The average price for a return flight for this route is $201.

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, Tuesday is the cheapest day to fly on average and Thursday is the most expensive. Flying from San Juan Airport back to Chicago, the best deals are generally found on Friday, with Monday 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 August, where tickets cost $295 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $574 and $425 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.
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 $417 on average.

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 5 weeks before departure.

Good to know

Low season

September

High season

March

Cheapest flight

$82
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 14% 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 3 days, the lowest price for a flight from Chicago to San Juan Luis Munoz Marin Intl Airport was $82 for a one-way ticket and $202 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, and Delta 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 Boeing 737 MAX 9 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?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago and San Juan Airport, with Star Alliance 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 $469 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 $403 and an overall rating of 8.0.

  • 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.

See more FAQs

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 $288 or less one-way and $397 or less round-trip.

Prefer to fly direct from Chicago to San Juan Airport?

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, Spirit Airlines, United Airlines

American Airlines, Spirit Airlines, +1 more

Tuesday

American Airlines, Spirit Airlines, United Airlines

American Airlines, Spirit Airlines, +1 more

Wednesday

American Airlines, Spirit Airlines, United Airlines

American Airlines, Spirit Airlines, +1 more

Thursday

American Airlines, Spirit Airlines, United Airlines

American Airlines, Spirit Airlines, +1 more

Friday

American Airlines, Spirit Airlines, United Airlines

American Airlines, Spirit Airlines, +1 more

Saturday

American Airlines, Southwest, Spirit Airlines, +1 more

American Airlines, Southwest, +2 more

Sunday

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

American Airlines, Spirit Airlines, +2 more

See more direct flights

Direct returns

San Juan Luis Munoz Marin Intl to Chicago

Monday

American Airlines, Spirit Airlines, United Airlines

American Airlines, Spirit Airlines, +1 more

Tuesday

American Airlines, Spirit Airlines, United Airlines

American Airlines, Spirit Airlines, +1 more

Wednesday

American Airlines, Spirit Airlines, United Airlines

American Airlines, Spirit Airlines, +1 more

Thursday

American Airlines, Spirit Airlines, United Airlines

American Airlines, Spirit Airlines, +1 more

Friday

American Airlines, Spirit Airlines, United Airlines

American Airlines, Spirit Airlines, +1 more

Saturday

American Airlines, Southwest, Spirit Airlines, +1 more

American Airlines, Southwest, +2 more

Sunday

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

American Airlines, Spirit Airlines, +2 more

See more direct flights
See more direct flights

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 4287 reviews
8.6Crew
7.1Food
8.2Boarding
8.0Comfort
7.6Entertainment
Airline reviews

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

8.0 ExcellentJonathan, Apr 2025AUS - MSY
Read more Southwest reviews

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

1.5 hour delay, poor service, no compassion from the crew. Terrible experience

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

Fight was delayed an hour due to operational issues ,then further delayed due to ground control for a total of about 1.30 hours. Salad was completely frozen and flatware was so cold you could barely handle it. Crew was friendly and professional and the flight was smooth. The aircraft was clean and well-serviced.

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.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

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.

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.

Loved staff help @ kiosk, staff on airplane. Commitment to punctuality. I sat in a "blocked" row, where the middle seat had no passenger & loved it! I appreciate not having to pay for water, which I've experienced even on international flights. Only negative was how dirty the bathroom was for a 4.5 hrs flight. But I don't think flight attendants monitor this.

It wasn’t a bad flight just very uncomfortable seating wise.

Your employees need to learn how to talk to people as creations of Yah. We are not their children nor are we lower than them.

Helpful attendants at check-in is very good. The $70 charge for a checked bags I didn't care for.and the constant charges for picking a seat and faster check-in are too much. Please cut the prices by at least 50% would be fantastic!

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The worst flight of my life. Never will I fly frontier again

Landing in terminal 2, but my luggage is terminal 3. We (and others) were looking for it in terminal 1. We probably missed the crew broadcast, but the communication could have been clearer for non native (or elderly) passengers.

I chose the seats when booked the flight and paid for them. However after checking in I found we were assigned different seats!

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

Information on your arrival and departure airports

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