CHI - SJU

$62 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 4/8. 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.
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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

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to San Juan.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
6:25 pm - 10:32 amORD-SJU
15h 07m1 stop
6:35 am - 10:58 amSJU-ORD
5h 23mnonstop
$135Spirit Airlines
Find Deal
Tue, Apr 8 - Sat, Apr 19
6:00 am - 12:12 amORD-SJU
17h 12m1 stop
8:59 pm - 12:58 amSJU-ORD
4h 59mnonstop
$137Spirit Airlines
Find Deal
Sat, May 10 - Thu, May 15
8:04 am - 1:45 pmORD-SJU
4h 41mnonstop
8:59 pm - 12:58 amSJU-ORD
4h 59mnonstop
$139Spirit Airlines
Find Deal
Sat, May 3 - Sat, May 10
9:22 am - 5:21 pmORD-SJU
6h 59m1 stop
2:55 am - 10:40 amSJU-ORD
8h 45m1 stop
$163Frontier
Find Deal
Tue, Apr 1 - Tue, Apr 1
12:02 pm - 11:41 pmORD-SJU
10h 39m1 stop
6:28 pm - 5:23 pmSJU-ORD
23h 55m1 stop
$168Frontier
Find Deal
Tue, Mar 25 - Wed, Apr 2
7:10 am - 4:27 pmORD-SJU
8h 17m1 stop
1:55 pm - 9:00 pmSJU-ORD
8h 05m1 stop
$271Delta
Find Deal
Wed, Apr 30 - Sat, May 10
6:04 am - 2:19 pmMDW-SJU
7h 15m1 stop
3:34 pm - 10:22 pmSJU-MDW
7h 48m1 stop
$271Delta
Find Deal
Sun, Apr 27 - Sat, May 3
6:20 am - 4:00 pmORD-SJU
8h 40m1 stop
6:05 am - 3:04 pmSJU-ORD
9h 59m1 stop
$277JetBlue
Find Deal
Fri, May 2 - Tue, May 6
7:25 am - 6:45 pmMDW-SJU
10h 20m1 stop
3:20 pm - 10:30 pmSJU-MDW
8h 10m1 stop
$336Southwest
Find Deal
Sat, Apr 26 - Sat, May 3
7:25 am - 6:45 pmMDW-SJU
10h 20m1 stop
10:20 am - 7:40 pmSJU-MDW
10h 20m2 stops
$353Southwest
Find Deal
Sat, Apr 26 - Sat, May 3

Expert advice for your flight from Chicago to San Juan

Our travel pros reveal their best tips for your Chicago to San Juan 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

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.

Flights from Chicago to San Juan - Travel Insights & Trends

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 $153 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 this route. The average price for a return flight for this route is $153.

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 Sunday 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 $293 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $579 and $443 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 $661, 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 7 weeks before departure.

Good to know

Low season

September

High season

March

Cheapest flight

$62
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 19% 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 $62 for a one-way ticket and $135 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 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 $462 and an overall rating of 8.1, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $422 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 $153 or less one-way and $383 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

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Tuesday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Wednesday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Thursday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Friday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Saturday

Air Canada, Air New Zealand, Alaska Airlines, +4 more

Air Canada, Air New Zealand, +5 more

Sunday

Air Canada, Air New Zealand, Alaska Airlines, +4 more

Air Canada, Air New Zealand, +5 more

See more direct flights

Direct returns

San Juan Luis Munoz Marin Intl to Chicago

Monday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Tuesday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Wednesday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Thursday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Friday

Air Canada, Air New Zealand, Alaska Airlines, +3 more

Air Canada, Air New Zealand, +4 more

Saturday

Air Canada, Air New Zealand, Alaska Airlines, +4 more

Air Canada, Air New Zealand, +5 more

Sunday

Air Canada, Air New Zealand, Alaska Airlines, +4 more

Air Canada, Air New Zealand, +5 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.
8.1
SouthwestOverall score based on 4333 reviews
8.7Crew
8.1Comfort
8.2Boarding
7.6Entertainment
7.1Food
Airline reviews

WiFi on the flight was not working. Thus, entertainment options were limited.

8.0 ExcellentJames, Feb 2025SRQ - DEN
Read more Southwest reviews

WiFi on the flight was not working. Thus, entertainment options were limited.

Great flight staff. Ease of boarding. Overall, very uneventful and easy trip.

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Wi Fi was horrible kept cutting out the whole time and too expensive

I really like open seating. I hate that I've heard this is going away. This is one of the unique things that makes Southwest my goto choice.

Boarding was a little late, but made up for it. It was quick to taxi to the runway, since it's a smallish airport.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

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.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

We arrived early and finally made it to our gate almost an hour after.

Was a pain having to leave the plane and reboard but glad the plane was fixed

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.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

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!

The flight was delayed over an hour and we had to sit on the plane. Crew does not apologize due to the delay. Spirit will NEVER do anything to give a customer a better experience. A child next to me was kicking me the whole time. I don't ever enjoy flying with Spirit.

Easy! As long as you don’t mind no frills, our flight was enjoyable and on time

Fantastic. Had handicapped traveler and they helped us through security, helped with boarding, helped put wheelchair together, and were all very patient. A pleasant change from previous spirit flights I’ve taken. Highly recommend.

Really nice, flight attendants were so helpful with me and my kids. Extremely grateful, keep up the good work and spirit :)

Early arrival. Great landing. Pilot updates. Too cold in plane.

Better to put road truck seat in plain it so uncomfortable can not adjustable and fill metal don’t have cushions at all it’s very hard to travel for five hours

Since they are a budget airline, I wasn’t expecting too much but they did some things well. They were on time, the plane was clean, boarding was fairly straightforward and the staff was cheerful and friendly. The only downside was comfort. The seats were fairly hard and after a 2 hour flight your rear end is not feeling so great. Maybe a little more cushion in the seats, Frontier!

They cancelled the flight and did nothing. I should be compensated for my uber rides to and from airport. Not a good service by frontier or kayak.

No frills for sure. No gate announcements about flight delay, not even water to drink on the flight.

food not having to pay for it, reclining seat would be nice, more leg room, HEAT!!!!!!!

An absolutely fraudulent experience. Extremely unprofessional. Terrible in all ways possible. Rude staff, flight attendants, and deceptive "policies."

The worst service , the agents from the counter are really bad . Poor customer service . They didnt help me to get in the flight . I was on line when they close the flight without telling and I couldn’t board the plane . I will like to get my money back ey back because it was their fault. Really bad management , bad manners, bad additud

The check in process was a mess for no reason. I spent an hour waiting in line trying to get them to print my boarding pass and as a result I missed my flight.

The airline used deceptive tactics to charge us more for our trip. Search Frontier Class Action Lawsuit to find out more or read the hundreds of reviews that have nearly identical stories.. don't fly this airline.. you've been warned.

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

Information on your arrival and departure airports

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