CHI - SJU

$109 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 7/30. 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
$222
Typical prices: $476-$254
American Airlines
Sun 8/23Wed 8/26
ORD - SJU • Non-stop
Cheapest non-stop
$237
Typical prices: $492-$261
Frontier
Fri 8/14Mon 8/24
ORD - SJU • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United's Economy Plus offers extra legroom comfort.
Spirit's Wi-Fi ensures connectivity throughout the flight.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $222 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, United Airlines and others. Average duration is 4h 48m
Direct flights
Direct flights
+1
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Direct flights
Direct flights
+1
Top routes
Cheapest • 43% average savings
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 81% on-time
Best time • Fewest delays
Insights
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Insights
Insights
Top layover airports
Cheapest • Avg $202 (round-trip)
Shortest trip • 6h 32m (one-way)
Insights
Insights
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Insights
When to travel
Cheapest • 24% price drop
Most popular
Good to know
Good to know
+1
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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

Sun, Aug 23 - Wed, Aug 26
American Airlines Logo
5:14 pm - 11:07 pm
ORD
-
SJU
4h 53mnonstop
American Airlines Logo
7:14 pm - 9:00 am
SJU
-
ORD
14h 46m
1 stop
$222American Airlines
Wed, Aug 19 - Wed, Sep 2
Delta Logo
6:40 am - 4:37 pm
ORD
-
SJU
8h 57m
1 stop
Delta Logo
5:45 pm - 11:57 pm
SJU
-
ORD
7h 12m
1 stop
$226Delta
Wed, Aug 19 - Wed, Sep 2
Delta Logo
10:54 am - 10:29 pm
MDW
-
SJU
10h 35m
1 stop
Delta Logo
2:40 pm - 9:46 pm
SJU
-
MDW
8h 06m
1 stop
$226Delta
Wed, Aug 19 - Wed, Sep 2
American Airlines Logo
5:14 pm - 11:07 pm
ORD
-
SJU
4h 53mnonstop
American Airlines Logo
6:51 am - 2:15 pm
SJU
-
ORD
8h 24m
1 stop
$227American Airlines
Fri, Aug 14 - Sat, Aug 22
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
Frontier Logo
6:00 am - 12:25 pm
SJU
-
ORD
7h 25m
1 stop
$228Frontier
Sat, Aug 15 - Sat, Aug 22
Frontier Logo
12:44 am - 6:44 am
ORD
-
SJU
5h 00mnonstop
Frontier Logo
6:00 am - 12:25 pm
SJU
-
ORD
7h 25m
1 stop
$230Frontier
Wed, Aug 19 - Wed, Sep 2
American Airlines Logo
5:01 am - 2:38 pm
ORD
-
SJU
8h 37m
1 stop
American Airlines Logo
6:51 am - 2:15 pm
SJU
-
ORD
8h 24m
1 stop
$231American Airlines
Sun, Aug 23 - Sat, Aug 29
American Airlines Logo
5:14 pm - 11:07 pm
ORD
-
SJU
4h 53mnonstop
American Airlines Logo
10:33 am - 11:00 pm
SJU
-
ORD
13h 27m
1 stop
$232American Airlines
Fri, Aug 28 - Mon, Aug 31
Southwest Logo
2:55 pm - 11:50 pm
MDW
-
SJU
7h 55m
1 stop
Southwest Logo
10:00 am - 6:00 pm
SJU
-
MDW
9h 00m
1 stop
$246Southwest
Tue, Sep 1 - Mon, Sep 7
Southwest Logo
12:45 pm - 10:00 pm
MDW
-
SJU
8h 15m
2 stops
Southwest Logo
6:00 am - 2:30 pm
SJU
-
MDW
9h 30m
2 stops
$276Southwest
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 $199 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, 43% 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, Tuesday 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 May, where tickets cost $319 (return) on average. On the other hand, the most expensive months are December and September, where the average cost of round-trip tickets is $635 and $554 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 $381 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 2 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
Joe Cortez

Joe Cortez

Expert on Spirit Airlines

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.

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$109
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 7% 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 $109 for a one-way ticket and $222 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, Alaska Airlines, Alaska 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 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 $468 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 $430 and an overall rating of 7.9.

  • 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 $135 or less one-way and $306 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,United Airlines,Frontier

American Airlines,United Airlines, +1 more

Tuesday

American Airlines,United Airlines,Frontier

American Airlines,United Airlines, +1 more

Wednesday

American Airlines,United Airlines,Frontier

American Airlines,United Airlines, +1 more

Thursday

American Airlines,United Airlines,Frontier

American Airlines,United Airlines, +1 more

Friday

American Airlines,United Airlines,Frontier

American Airlines,United Airlines, +1 more

Saturday

American Airlines,Southwest,United Airlines, +1 more

American Airlines,Southwest, +2 more

Sunday

American Airlines,Southwest,United Airlines, +1 more

American Airlines,Southwest, +2 more

See more direct flights

Direct returns

San Juan Luis Munoz Marin Intl to Chicago

Monday

American Airlines,United Airlines,Frontier

American Airlines,United Airlines, +1 more

Tuesday

American Airlines,United Airlines,Frontier

American Airlines,United Airlines, +1 more

Wednesday

American Airlines,United Airlines,Frontier

American Airlines,United Airlines, +1 more

Thursday

American Airlines,United Airlines,Frontier

American Airlines,United Airlines, +1 more

Friday

American Airlines,United Airlines,Frontier

American Airlines,United Airlines, +1 more

Saturday

American Airlines,Southwest,United Airlines, +1 more

American Airlines,Southwest, +2 more

Sunday

American Airlines,Southwest,United Airlines, +1 more

American Airlines,Southwest, +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.
7.4
United AirlinesOverall score based on 9700 reviews
8.1Crew
7.1Entertainment
6.6Food
7.3Comfort
7.7Boarding
Airline reviews

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

8.0 ExcellentTimothy, Apr 2026
ORD - CID
Read more United Airlines reviews

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.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

The boarding timing needs to be improved. The flight was delayed again because it took way too long to board. I was already exhausted from sleeping at the airport and spending all day there due to delay from my previous flight that connected in Chicago.

Great until we got to FRA. The next trip leg we were put in Business Class where seats had minimal padding!!!! They were awful and United Airlines needs to have their Lufthansa partner up their game or I won’t fly with them again!!

The space between seat rows seemed to be larger than other airlines. I didn’t check their food or entertainment since I slept most of the way. They do seem to have a lot of options for purchase though.

Kayak sucked. You gave me a confirmation number that was not useable by the jet blue system. Nor did you send any check in emails. I’ll not be using your site again. Nice work.

Direct tv did not work on flight Short flight so no good service offered Arrived early to destination and had to wait for gate to open. Deplaned LATER than if we arrived on time!! Poor planning Jet blue has had something go wrong on every flight I’ve taken with them in last five years. Terribly run airline

Given us a free miles or free flight for waiting for 9 hours I didn’t get home till 5am in the morning and I was supposed to be home at 9:30 touch down.

Excellent price. Everything on time. two bad parts. Kayak said I couldn't sign in for the flight online, but I got an email at the same time from Jet Blue and they let me sign in online. Second bad part was that, although I had provided my known traveler number, neither of my boarding passes, for this flight and the previous one, had TSA pre-check showing.

Jet blue was great But the Jayak system Wasa pure nightmare and wasted so much of my time and energy by not giving me a way to access jet blue to check in the flight back I didn’t even get the number confirmation code 24 hours before. Because I didn’t receive the email with the confirmation code I could NoT CHECk IN. I spoke to a kayak third party and they informed me I could not carry a carry on, on the flight which caused me so much extra stress it was just too much. You can be sure I will not be using it recommending your site. Again.

There was a screen but no earphones that could use the older input so I could listen to anything.

My experience with JetBlue was fine BUT I am very upset with Kayak! JetBlue had delayed our scheduled departure by an hour and you NEVER notified me of the change. I did not hear directly from JetBlue because the trip was booked through Kayak, a mistake I will not repeat. Your reminder of the our trip last week still had the WRONG departure time. Our return trip has also changed, and again no notice from you.

Jet blue just had great service overall! Only a little turbulence heading out of Austin, otherwise the jet stream helped the speed of the trip!

Boarding was quick and efficient. The flight crew were friendly. There were limited food options available on the flight. The pocket guide said there would be salad and sandwich sections available on flights over 3.5 hours. The only food available were snack boxes. And those were limited as well. My flight was over 5 hours. The entertainment system worked well. I had both extra legroom seats and regular coach seats. The seats were not very comfortable. The entertainment controls in the armrest made it difficult to rest my arm without changing the channel on my neighbors TV. Overall, my experience was mediocre.

Our flight was cancelled while we are on our way to the airport. So, no notice. We were rescheduled to another airline with a 2 hour later takeoff and so arrived at our destination on time. We pre-paid American Airlines $190 to upgrade our seats. No refund. So no use for AA or Kayak.

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

The airline cancel mi flight, lost a lot of money!!!

The flight was delayed four times and finally cancelled. The hotel night we paid for and the connecting flight did not happen. There were also additional costs due to the extra night in Miami. I do not recommend this airline.

They cancelled our flight. 2 hours before we were supposed to take off and offered us nothing! We got our money back and that was it. No other flight to get to our cruise no working with another airline or with us to get there. Terrible customer service, no apology.

Not enough crew members so we had to wait for more to arrive and they could never give us updates timing. Not even water for free on board. Bare bones airplane- there wasn’t even a seat back pocket to put things into. Spirit is cheap for a reason but this was dismal

We get stuck in the plane when landed during 45min and no communication from the crew People were listening to their phone and music out loud and nobody told them anything I definitely want stop booking spirit flight it is a disaster

The staff were very helpful. Definitely the stars of my experience. The seats were very uncomfortable.

Good: It was cheap and they got us to our destination safely. Not so Good: Gates experience with many, many nauseatingly (almost) threatening announcements about bags size and how much they were going to charge us if our bag was too big, even to the point of having a gate agent roaming around through the passengers eyeballing bags size and making people go check their bags in the sizers.

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

Checking in at desk in Chicago was horrible. Person was not friendly never smiled and said my flight was not paid for so I had to give another credit card. Then it ended up that I was charged twice. Then after arriving at my destination had to wait on the phone a long time to speak to a person to fix the double charge! Thank goodness the flight was perfect.

Flight was delayed for 12 h. They should stop overlooking flights.

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

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

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

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

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

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

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

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

Information on your arrival and departure airports