Find cheap flights from Illinois to Caribbean Islands

Find cheap flights from Illinois to Caribbean Islands

Search hundreds of travel sites at once for deals on flights to Caribbean Islands

Round-trip
Economy
Zurich (ZRH)
Caribbean Islands
Fri 4/23
Fri 4/30
Any month
Compare vs. KAYAK |

Good to know

Low season

AugustBest time to beat the crowds with an average 5% drop in price.

High season

DecemberMost popular time to fly with an average 13% increase in price.

Average price round-trip

$395(avg. price over the last 2 weeks)

Good deal round-trip

$128or less

Good deal one-way

$72or less

FAQs for booking flights from Illinois to Caribbean Islands

Which airlines have a flexible cancellation policy for flights from Illinois to Caribbean Islands due to COVID-19?

Which airlines apply social distancing measures on flights from Illinois to Caribbean Islands due to COVID-19?

How does KAYAK find such low prices on flights from Illinois to Caribbean Islands?

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Illinois to Caribbean Islands?

What is the Hacker Fare option on flights from Illinois to Caribbean Islands?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Illinois to Caribbean Islands?

Top 5 airlines serving from Illinois to Caribbean Islands

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 29,186 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "The crew was not overly friendly"

Pros: "Movies"
Cons: "Comfort. Jetblue offers betwee seats ne apacing betqeen rows"

Pros: "Great crew"

Pros: "Crew friendly, attentive."
Cons: "Baggage connection between Delta and partner KLM not made and luggage left in Atlanta."

Cons: "More leg room and seat width. I don’t like having other passengers pressed against me."

Pros: "Nice service"

Pros: "Love it"

Cons: "In the last months I have travel 3 times , this is the first with Delta. I can say it has been the best experience I had. Good entertainment, the access to texting and the variety of snacks make superior this airline."

Pros: "Crew was awesome. Very friendly."
Cons: "I’m 6 foot tall and I found my seat space feeling crowded. I found myself wishing for just 2 more inches of legroom. It feels that airplanes are being built for quantity of passengers, not quality of flight."

Pros: "Crew was very fast but not enough during boarding and people had brought oversized carry on luggage to the gate requiring stowing. We had checked a carry-on at check in and paid $30 while several people got theirs stowed for free which seemed unfair."
Cons: "The charging for checked luggage has created a situation that was unfair for all travellers and ultimately made the plane’s departure late. This policy drives people to bring too much luggage into the cabin, putting at risk the safety of others and delays."

Pros: "The friendliness of the passengers and most of the crew."
Cons: "One of the younger female flight attendants was rude . She was collecting trash and took my neighbor’s (aisle seat) trash but wouldn’t take mine. I tapped her elbow to show that I had trash, she looked at me but didn’t take it. She returned and still refused until I exclaimed. She rolled her eyes."

Cons: "Cabin was cold enough to store meat. Entertainment system was poor at best. And, of course, the seats were too small and uncomfortable. Time to start looking at other airlines."

Cons: "At least one hour late"

Pros: "I liked the cookies and juice. The interactive screen to watch something. The cleanliness. The price. On time. The service. Thank you. The excitement of flying."

Cons: "I was flying standby. I checked the list on line and my name was number 5. I get to the gate and there’s just a handful of customers. The agent said there was enough seats for the standbys I wait and wait for my name to be called but no luck. My name wasn’t cleared yet. Finally I was the next to last one to get a seat. The gate agent who didn’t ask for my name tells me I was all the down at the bottom of the list. While I am glad that I got on I wish I knew what method is use to get your name on the stand by list?"

Cons: "Cabin was too hot since the very beginning. Even in first class."

Pros: "The counter assistant change my seats and my wife and me seat together"
Cons: "Hot cabin"

Pros: "Although our flight was fully booked. The crewmembers on this flight was professional, friendly and efficient. We boarded quickly and took off on time. We even arrived ahead of schedule. Each passenger was given free headphones and complimentary beverages and snacks. I love Delta they are a cut above the rest. They are constantly striving to put the customers needs and wants top priority"
Cons: "Tight seats need more legroom"

Pros: "On time. Pleasant crew although one was a little green. Short flight. Good communication."
Cons: "Squished into a seat that I paid extra for more room. Yes I had more leg room, but my legs were pressed Up against the person next to me. And for the extra money I paid, the snacks could be a little more substantial. And only a small glass of soda. Really, if this was Delta comfort What were the cheap seats like?"

Pros: "Attentive, respectful and nice crew, swift take off and landing and awesome views"
Cons: "Nothing. Everything went well"

Pros: "The crew at the airport was very courteous and helpful."
Cons: "No food; not even offered water; I asked a Delta employee about our seats and she was very unprofessional (mind you I'm traveling with kids and my boarding pass said that seats were to be assigned at the gate)."

Pros: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos, please reimburse on the credit card"
Cons: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos of the studio and musicians"

Cons: "Entertainment app from Go Go didn’t Work."

Pros: "Arrived early. Got a beverage & snack which is becoming rarer with American carriers. Video selection was very good. Staff was nice and attentive. Overall a good flight at a reasonable price."
Cons: "Narrow corridor to seats"

Pros: "Everything escept the seat that was too small. I also had problems with the entertainment when trying to see movies."
Cons: "Seats too small ant could not watch Movies beacause the screen was defective."

Cons: "Flight was delayed over 1hr."

Pros: "Buen entretenimiento."

Cons: "La incomodidad de los asientos además que la escala fue de más de 6 horas y fuimos los últimos en abordar. Para colmo los asientos fueron los últimos de la fila y ni siquiera eran reclinables. Creo que deben tomar en consideración a las personas que estamos tantas horas en la escala y permitirles abordar primero además de darles asientos más cómodos más aún si hemos comprado los boletos con tanto tiempo de anticipación."

Pros: "Giid free sandwixh. Very good entertainment system. Good seats."

Pros: "Well, the seats and the lavatories are smaller than ever. And I am quite petite."

Pros: "Excelente"

Pros: "Entertainment is very good"
Cons: "Send my carry on bag, outside."

Pros: "Left on time, no hassles at boarding. We were in premium economy and seating was comfortable for both of us, not-too-tall people. FA were quite friendly."
Cons: "One bathroom wouldn't flush, which was a problem with limited facilities and a full flight."

Pros: "Friendly crew"
Cons: "Long layover in Atlanta. Terrible terminal setup in LAX . Although we were on two connecting Delta flights, we had to leave the arriving terminal and take a bus to another. The second terminal (Terminal 2) was small, crowded, and had few food options."

Pros: "Late delay notification"
Cons: "Called the airline directly to verify the status of flight within 24hrs and everything was on schedule according to them. Even tho the airport at San Juan have not night arrivals due to the effects of Hurricane Maria, and on previous days the same flight had been moved to a morning schedule for that reason. I was notified of the delay within hours of departure of the connecting flight."

Cons: "Small plane"

Pros: "The flight left on time and we got in 15 minutes before the scheduled time. Awesome service from gate to gate."
Cons: "I didn't like that I had to pay for my bags and still purchase food on plane. The price for ticket is already overpriced to begin with. Fuel is cheaper, the planes burn less fuel due to updated design and still the tickets are three times the cost of five years ago. No one should have to pay for bags period. Show that you really care."

Pros: "Getting on board was smooth and efficient. Service was friendly on flight. Arrived on time."
Cons: "Not applicable."

Pros: "I didn't like anything because the fly leat 3 hours"

Pros: "Really liked the plan"

Pros: "Left reasonably on time, arrived a bit early, able to find overhead storage for my roll-on, even boarding in Zone 3"
Cons: "Very tightly packed; minimal comfort for the flight."

Pros: "Movie selection"

Pros: "The crew was nice"
Cons: "I didn't like the fact that I didn't get my luggage with me when I arrived to casablanca as I lived 4 hours away from the casablanca. I have to come back the next day to get my luggage. I was very mad about it.plus I noticed one of my luggage has been damaged so now I have to buy another one because I can t use it. It was disgusting."

Pros: "Food was OK. Crew was very friendly"
Cons: "No Entertainment for a 4 hour flight. Plane was very old."

Pros: "The flight crew was nice and polite. They served drinks and snacks in a timely manner while on the flight."
Cons: "Flight was scheduled to leave early, the plane arrived, but they couldn't turn the plane around fast enough. We left the gat late, then pilot said we would still be arriving half an hour early. We arrived about 45 minutes late, and that was a problem because our connecting flight was due to depart now in 15 minutes. Lightning forced the airport to shutdown, which was great, we had a chance to catch our flight, but we were stuck in the airplane, and we couldn't get to our gate until the all-clear. I know this is not Delta's fault, but they did arrive quite late on a flight that, according to them, would be early. They also never communicated to the other flight that there were several passengers catching that connection. So by the time we had ran to catch our connection they had closed the ramp. Lightning hit again, and they shutdown the airport once again, so the airplane was still at the gate for about an hour, and they did not allow the 20+ passengers to board that plane, which was right there. So frustrating. The only thing that saved it was that our new flight was the new airbus, and although it left an hour and a half later, the comfort level was phenomenal."

Pros: "Although I am a vegetarian, It was nice Delta was serving sandwiches."

Pros: "newer aircraft; good entertainment options; large overhead storage compartments"
Cons: "cramped passenger space"

Pros: "Crew was VERY friendly and helpful."
Cons: "No changing table in restroom made it hard to change infant."

Pros: "Excellent choices for entertainment in the 737-900ER. 110V AC and USB ports at each seat, lots of choices for movies and games on seatback screen. Free sandwiches handed out on board."
Cons: "Intercom didn't work super well. JFK is a terrible airport for connections."

Pros: "You were on time, that is the most important thing in a fly"
Cons: "You could improve your entertainment, you are not a cheap company"

Cons: "The seats are very uncomfortable but other than that it was wonderful!"

Pros: "Service and comfort"
Cons: "Food"

Cons: "Had an issue with my passport and the manager at the check in counter was rude and not helpful."

Pros: "Great crew; efficient, kind and accessible."
Cons: "Entertainment system. Tiny screens and no options."

Pros: "Good"
Cons: "Good service"

Pros: "The food"
Cons: "Everything ok"

Cons: "Copa check-in in Chicago was awful, and it wasn’t just for my family and me. The manger and several employees were rude and seemed clueless about what they were doing. I shouldn’t be surprised that none of our luggage arrived because of the unorganized check-in but it just added to the frustration."

Pros: "Good food (especially the Fruit platter we get when departing from Panama and the Guayaba juice that's available in all flights), very short layover, short flying time, allowed 2 checked bags plus a carry-on and a personal item."
Cons: "Web-checking still a little buggy (I'm not allowed to web checking when going to the USA, when departing from the USA and my destination address is in a different country I'm still forced to choose a US State to continue). Also Panama Tucumen Airport is awful, crowded, expensive and usually dirty."

Pros: "On the flight from Chicago to Panamá crew was exceptional, friendly and attentive, I was very impressed with the service,PLEASE DON’T CHANGE ANYTHING , from Panamá to Costa Rica the crew was completely different, the service was efficient but not friendly, a smiling face makes a difference."
Cons: "The process of boarding was a little confusing but it went quickly, keep up the good work"

Cons: "Food on COPA is terrible."

Pros: "Online check in was great! Time saver! Left right on time! The food was good. Female captain! woot woot! :)"
Cons: "Night flights are hard. I couldn't sleep comfortably on the seat.. I've flown other airlines and seats are more comfortable. They didn't provide a blanket or pillow. Kept constantly waking up and felt tired when they served breakfast. No screens with entertainment for each seat available. Had a bit of a hard time with decompression, I don't know if it has to do with the aircraft, but I had never experienced discomfort while landing. My luggage was damaged."

Pros: "so I can't really speak on experiences of flying but this was as great and easy experience. The staff was very accommodating and understanding. I am more than willing to fly with them again!"
Cons: "Nothing, everything was great!"

Pros: "Change flight without notifying me"
Cons: "Change flight without notification"

Pros: "Everything"

Pros: "The seats were comfortable, they served a free snack and also a adult beverage"

Pros: "Very friendly service and very helpful even though there is a language difference, they were great in making me feel comfortable."

Pros: "Roomy seats."
Cons: "One bathroom had a faulty toilet. The other had a door that would not lock. Some seat back pockets were in bad shape."

Pros: "Service was good"

Pros: "Nothing"
Cons: "Very old, uncomfortable airplane. Business class is a joke. Cabin temperature Was either too cold or too hot"

Pros: "Everything was great!"

Cons: "-lost my luggage -no entertainment on flight from Panama to Punta Cana"

Pros: "Every time I fly or my son-in-law connect through there it is the wonderful. We've never had such painless connections ever!"
Cons: "Was surprised warm beverages weren't served. A coffee would have been nice."

Pros: "Good servoe"
Cons: "No WIFI connection movie selections"

Cons: "Uncomfortable seats. I ordered Kosher meals, but they did not have any available, so I pretty much watched everyone else eat while I couldn't."

Pros: "copa is punctual with the flights and offer a good service in the air."

Pros: "Service was excellent"

Pros: "Es la Primera vez qué vuelo con Uds. Me gusto La amabilidad del personal. Sigan así no cambien."
Cons: "Uds deberían llamar primero a Los grupos finales, ejemplo 5 ó 6 para evitar incomodidades por el pasillo."

Pros: "The crew was great the food and service"
Cons: "For a 5 hour plus flight would have liked a more updated cabin with a charging station for electronic devices and possibly an entertainment center"

Pros: "Evrything fine!!!"
Cons: "No whell chair wait for me only this!!"

Pros: "Drinks"
Cons: "No entertainment OR WIFI?!"

Pros: "All. A lot better. Of. Any. USA are line"
Cons: "All"

Pros: "The crew was really nice"
Cons: "There weren’t good options on food, and even it’s a 5 hours flight there was not internet or screen on the chairs."

Pros: "They provide any of your requests is they have it"
Cons: "Everything was fine"

Pros: "Crew was courteous, and very polite."

Pros: "Food was ok"
Cons: "No WiFi, no outlets, no entertainment for international flights seems very outdated."

Pros: "Short flight and thankfully I slept a bit."
Cons: "The stewardesses just say in their area. Never offered extra coffee or drinks. No snacks. Food was pathetic."

Pros: "Friendly service, food and drink included, and free luggage. Seats had limited leg room, but otherwise comfortable. Would select this airline again!"

Cons: "Older plane with less room from Chicago to Panama, but other than that everything was great."

Pros: "The crew and staff were wonderful and professional"

Pros: "Nothing. Even when it's the cheapest flight, th insignificant price difference vs. other airlines doesn't compensate the awful experience"
Cons: "The treatment of the crew was unrespectul. The food is extremely bad. The airplane and seats were uncomfortable."

Pros: "Duration of flight."
Cons: "Food"

Cons: "Hice el webcheck in y aun asi me pusieron de ultimo en toda línea, entiendo que habian los que se quedaron del dia anterior, pero puso estrés en mi, también salimos tarde, y mas valijas se quedaron en Chicago y en lugar de mandarlas a mi casa, tuve que viajar 3 hours al aeropuerto y recogerlas yo misma despues que me habían dicho que las mandarían."

Pros: "Service."
Cons: "nothing"

Pros: "Great service."

Pros: "nothing"
Cons: "custumer service"

Pros: "Planes are clean and crew is nice"
Cons: "Overall they are a poorly organized airline and there is almost no entertainment."

Pros: "Comfortable leg room Friendly cabin crew"
Cons: "Very limited food options, International flights have poor entertainment options, Very old seats and covers gave a very dull impression"

Pros: "I love flying Copa! My friend and I had only a 40 minute layover on Tuesday morning from San Jose, CR to Panama City to Chicago. We were pretty worried about missing the flight in Panama City because that meant we missed our fight home. The crew was wonderful and changed our seats to the front of the plane so we wouldn't miss the flight. If he hadn't had done that, we 100% would have missed the flight .I will recommend Copa to everyone."

Pros: "Food and drinks."
Cons: "Bad entertainment selection and screen."

Pros: "Everything"
Cons: "No comments"

Pros: "Free novies"
Cons: "Food service and better social distancing"

Pros: "The flight was great. Smooth ride with little turbulence. Great FREE entertainment options on screen. Boarding was quick and orderly for a full flight. Ability to charge my phone."
Cons: "Cramped seats. Limited snack option."

Pros: "Dear American, stop lying to your passengers stating that the flights are full, when in fact, they are not. Customers are willing to pay for upgrades but you give them no way to do so."

Cons: "Feeling of being cramped"

Pros: "Nice personnel"
Cons: "Crowded"

Pros: "Good food. Friendly crew. On time, etc."
Cons: "Recycling/reduce waste. Gluten-free choices."

Pros: "Service from crew was fine"
Cons: "No delay! Got notification that our flight was one half hour earlier. Then boarded aircraft, and it had electrical problems. Delayed. We had to get off. Then board another aircraft."

Cons: "Lateness, seat comfort and gate checking a duffel bag"

Cons: "I didn't like having someone put a red tag on my carry on for valet when it didn't have to be taken. I would have rather kept it near me!"

Pros: "The have the lotus cookies which is my favorite ."

Cons: "Poor service"

Cons: "did not get my requested wheel chair service."

Pros: "On time"
Cons: "Cold cabin"

Cons: "Flight was delayed almost two hours due to crew staffing issues."

Pros: "Crew was really good"
Cons: "Other than the crew rest really bad"

Pros: "Got an option to upgrade to first class and it wasnt expensive either, my first time flying first class"

Pros: "Great crew. Nice passengers."
Cons: "Food not so good"

Pros: "Unfavourable crew. Pilot was very good and detailed though."
Cons: "The smell on airplane, was not offered any water to drink."

Pros: "Crew was nice"
Cons: "Sounds like an ok airline if you fly 1st or business class. Don't be fooled by great reviews"

Cons: "i ask the crew for help to locate my luggage because we didnt pick it up after we landed in chicago for custom check! we were told in thailand that our bag will be going to wichita and we did not need to pick it up in chicago, when i try to do the self check in their machine didnt work! so i had to wait in line, and then wheni ask the crew member for help to locate my luggage she said she is too busy!!!!!"

Pros: "All connections-smooth"

Cons: "Only airline we flew that didn’t have pre boarding for families with small children."

Cons: "The handle for the window shade was torn off"

Pros: "Same as above."

Pros: "Exit row seating."

Pros: "On time departures. Friendly crew."
Cons: "Nothing"

Pros: "very friendly staff"

Pros: "Nothing to expect from Domestic fight."

Cons: "Should be allowed one checked bag per person at no charge."

Cons: "We ordered fruits meal but the crew didn't get the request. I have a confirmation email of the meal"

Cons: "No entertainment. There wasn't even a drop down screen for a movie."

Pros: "The space , the TVs , the free drinks and the service"
Cons: "Nothing"

Pros: "The crew was able to seat my husband and I together at the last minute as my husband has mobility issures"
Cons: "The crew seemed like they could care less about the passengers. Choice of either one snack bag of pretzels or a biscotti ~ very minimal. No headphones were offered for the movies."

Pros: "Snacks"
Cons: "Not good movie available"

Pros: "tv!"
Cons: "babies crying"

Pros: "All flights were on time Greatly enjoyed the trip"

Pros: "Much better than the trip to chicago"

Cons: "Boarding seemed extremely unorganized. Crew skipped group 2 when calling groups to board, resulting in a mad rush."

Pros: "On time"
Cons: "Crew was unhelpful, not prepared, only cookies for food, no personal entertainment, and charged check-in bag fee."

Pros: "Everyone was polite, helpful, and courteous."

Pros: "There were too many gate changes ."

Pros: "I like that they have complimentary snacks"

Pros: "I entered the airport from the beginning everything is fine.On board service is also very thoughtful"
Cons: "I feel I have been treated unfairly. Boarding time. Crew many times took the Americans boarding pass 。when my hands was in half the time。Just because I'm not American?"

Pros: "Nothing I like"
Cons: "Family trip ruined because of the delay departure. And the airline is not able to do anything to make this situation better. The wait line is over an hour. Most ppl miss their flights. The crew member at the desk is very rude and doesn't have patience to explain my questions. Unsatisfied experience ever!"

Pros: "The planes people and service."

Pros: "The ride was smooth the airplane was the food was OK the stewardess were kind"
Cons: "The ride was smooth the airplane was the food was OK the stewardess were kind"

Cons: "I didn't like the American airline people who checked my bag. She threw it because I told her nothing was breakable in it."

Pros: "Nothing"
Cons: "Constant delays and cancellenations"

Pros: "That I got a soda"
Cons: "Delayed at Ohare by an hour. Sitting on the Tarmac for a half hour in Reagan, waiting for a gate. This was our leg back to DC, after our leg to Chicago four days previously. On that trip I did a review and gave the whole trip a 1 out of 5 stars. That trip was the trip from hell, with delays, waiting on the Tarmac, deplaning, almost cancelled, more waiting on the Tarmac, wheels up in Reagan, wheels down in ORD, and then more Tarmac waiting for a gate. So I was already more than perturbed when this trip had similar outcomes."

Cons: "Economy seats on United are always incredibly uncomfortable, but the timing of the flight, and our on-time departure and Earley landing could not have been better. We will certainly fly United again on this route!"

Pros: "The food options and that we were offered drinks multiple times."
Cons: "Nothing! It was excellent"

Cons: "Lack of information about getting Visa Schengen to pass a transit hours cost me $300 and loosing my trip"

Pros: "Good movies"
Cons: "They delayed the flight like 5 different times and then the luggage took over a half hour"

Pros: "Fast wi fi and decent selection of in flight stuff on devices. Landed early!"

Pros: "Excellent crew excellent a young small brunette was not very friendly or accommodating. Otherwise the whole crew would have gotten 5 starts. Everything else was wonderful!"

Pros: "The effort of the crew to do as much as they could. Even at basic econ fare. Profits dictate. People are crammed as much as possible. We felt like folding chairs. But what can be done?"
Cons: "See above"

Pros: "The air line didn’t let me aboard my fly cause my baby Of 6 months!! Was needed a ticket to fly!!!! So I was on time to aboard, but the airline say was too late Really sad."

Pros: "Getting a meal and drink"

Pros: "Everything was fine"
Cons: "Baggage check-in fees should be lower than $30"

Pros: "Fast & efficient"
Cons: "Not much"

Cons: "Flight never happened because of hurricane yet I never got my money back. Natural disasters should qualify for a refund not a voucher."

Pros: "It was a jet"
Cons: "But the captain was missing for over an hour"

Cons: "No Inflight Wifi Service/Movie Access"

Pros: "Friendly captain!"
Cons: "Legs cramped"

Pros: "Thank you"

Pros: "We landed safely"
Cons: "20-30 minutes on the tarmac to take off. 30 minute wait after we arrived at the gate to have United staff attempt to line up the jetway with the cabin door. United is really firing on all cylinders lately"

Cons: "Broken luggage"

Pros: "Staff and easy boarding"

Pros: "It was a good flight. The attendants were courteous and accomodating. There was nothing to complain about."

Cons: "Delays"

Cons: "The United mobile app as well as my emails stated that the gate was B3. Upon arriving at gate B3 and attempting to board, I was alerted that I was at the incorrect gate. The gate was switched to C11. However, my app did not alert me nore did it reflect the gate change. I didn't receive a text or email update. I had to run to the different concourse nearly missing the fling."

Pros: "I was wirried about making the connection. Enddd up with an hour which was ample."

Pros: "I very much enjoyed the male flight attendant in coach. He was fun, attentive and very interacting."
Cons: "I liked all but the seating. Even for coach is too small in my opinion. Pilot flew awesome."

Pros: "Getting home."

Pros: "Forced me to check my bag and now it's broken"

Pros: "Smooth ride and on time staff was great"
Cons: "I didn't like that I had to pay for my luggage that was really horrible they find anywhere to nickel and dime you but glad they let mine be a carry on"

Cons: "missing USB charger had to "burn fuel" prior to take-off not enougb space for carry-on"

Pros: "Very polite and helpful staff"
Cons: "Food could be better"

Pros: "No wifi on plane, unable to use the United app."

Pros: "Service"
Cons: "Total disaster due to some snow, excessive delays"

Pros: "On time , smooth flying, great service"

Pros: "Still stuck here"

Cons: "Cost too much."

Cons: "There are 2 maintenance problems on 2 different planes that caused major delays in Chicago. This is the last time I'm taking United."

Pros: "The staff was efficient, friendly, funny and honest. Smooth landing, great service. Thank you!"

Pros: "The price"
Cons: "The size of the plane"

Cons: "My luggage was lost"

Cons: "My seat doesn't recline, on top of being as comfortable as a rock. Passenger in front of my threw their garbage everywhere"

Pros: "That I got home safe"
Cons: "It was a very uncomfortable ride"

Pros: "Stuardis"

Pros: "Airline personnel were friendly and smiling"

Pros: "Service"
Cons: "Old plane..."

Cons: "and smiling faces. I actually have no complaints. All went"

Pros: "Consistenty"

Cons: "With maintenance delays, I wouldn't make any connections."

Pros: "Same as for first leg"

Pros: "The service since I am handicap"

Cons: "Last row seats. Nothing of space, man seating next to me in the isle seat couldn't accomodate his legs inside the available space."

Pros: "Very good"

Pros: "Hassle free"
Cons: "The seats are terribly uncomfortable."

Cons: "seats"

Pros: "That I made it there in one piece."
Cons: "Not worth saving a couple dollars. Front tier airlines does not allow you to pick your seats before hand nor does it allow you to select baggage and the app, it is recessed for whatever reason. The seats are extremely tiny the tree table is so small you can barely fit an English muffin on it. There is no entertainment whatsoever, there is no Internet on the plane, and if you want anything to eat or drink besides water you will be paying for it. I’m sorry to say but flying on frontier was more like a punishment for me. I always fly American and wanted to save a few dollars what a mistake! With American most the planes that I have flown in have free movie entertainment and everybody seat the seats are comfortable And recline. And the snacks are free along with the soda. Please think twice before flying frontier."

Cons: "We sat on the run way for almost an hour and a half and the seats were very rough."

Pros: "Friendly staff, good seats."
Cons: "Baggage prices"

Pros: "Everyone was very nice, the seats were roomie!"
Cons: "Everything was good!"

Cons: "Honestly I wouldn't fly through this airline again. Although the price was low, once you add cost for luggage and seating, it is not actually a low price. Could not get comfortable, even when we paid for the better seats on the return."

Pros: "Likely the most uncomfortable plane I've ever been on. Seats feature zero padding, the inability to recline, and a tray table the size of a DVD case. I'm 5' 9" 148 pounds, young and very healthy. I left the plane with a twisted up neck like I've never had before. I landed safely so I MUST be thankful for that, but if I was booking I would want to know this information. Since I'm the wiser now I will not book with Frontier again. Also it was an extra $90 for my CARRY ON round trip. It notified me it would be extra when I booked online but didn't specify how much. What a surprise. I spent more on the fees for the bag than I spent on the bag itself (and most of the contents for that matter)."

Pros: "Frontier is ALWAYS LATE."

Pros: "Nothing, I will never use Frontier again. They are just RUDE to the customers."
Cons: "Charged $60 at last minute to bring a small personal bag."

Cons: "I find the Frontîer website difficult to use for check -in & getting boarding passes"

Pros: "Staff is enthusiastic"
Cons: "Seats don't recline. Minimal padding"

Pros: "Friendly staff"
Cons: "Non reclining seats. No internet or entertainment. Bad communication with food service and overall instructions."

Pros: "Friendly staff"

Pros: "When we landed and exited the plane"
Cons: "Charging for carryines just ain't worth it. I'm not ever flying frontier or spirit. The extra cost for no hassle will be worth it."

Cons: "Look like frontier is always late"

Pros: "Attendants were friendly, plane was clean, and the experience was overall great."
Cons: "It would have been nice if the plane carried wifi or some kind of tv/music option for entertainment."

Pros: "well managed boarding process."
Cons: "personal pain difficulty with cabin air pressure during descent. Unusual in my experience in planes this large. Occurs more often in smaller regional airplanes."

Cons: "Trip had over 8 hours of delays."

Cons: "They lost my baggage..."

Cons: "Very very poor service"

Cons: "no free snack? not even a bag of peanuts?! disappointing"

Pros: "The price"
Cons: "The seats don't recline, the boarding passes didn't scan anywhere we tried to scan into."

Cons: "Forgot about luggage charges, seat selection charge and the seats don't recline - pretty horrible for a red eye."

Pros: "Nothing."
Cons: "Charged me for a carry on. Charged for drinks. Plane was extremely uncomfortable. Staff was rude. Never fly Frontier."

Cons: "Waiting for luggage for at least 2 hrs. Receive different answer every tin you callreagarding charges. Will never use them again"

Pros: "Newer aircraft."
Cons: "Had to pay for sift drinks, sparking water, etc. No entertainment. Seats do not recline."

Cons: "See above."

Cons: "All the extra expenses for seats, baggage, ect."

Pros: "Good bare-bones airline - low price if you don't need carry-on or check luggage, don't need reclining seats, don't mind middle seats, don't want any snacks, etc."
Cons: "No participation in TSA Pre-Check"

Pros: "In spite of the apparently hard-and-fast rule about exit row seats costing extra, a friendly and intelligent young man at the desk at the boarding gate made an exception for me. I am 6'4' tall and a retired firefighter, first responder, ambulance driver, and former EMT. Having a person well-trained for emergencies located in an exit row seat is a potential benefit for the airline as well as for a tall passenger. Your man made a good decision and I appreciated it greatly."
Cons: "I don't favor the large surcharge for exit row seats, especially after the plane is loaded and there are such seats remaining empty. I would suggest dropping the price at that point to $10 or $20 to fill the seats.At least you would make some extra $ instead of zero if no one feels they can afford the seat upgrade. You will gain many more loyal flyers."

Pros: "Quick boarding"
Cons: "Terrible seats"

Pros: "Budget before adding bags"
Cons: "Bag costs Delay Airport I was stuck at - Chicago Very basic plane Poor info in airport - unnerving"

Cons: "Poor gate change (multiple) communication, not enough room for all travelers in gate section. Bad experience all around"

Cons: "Horrible fight."

Pros: "Politeness"
Cons: "Overall everything"

Pros: "Middle seat was empty"
Cons: "The delay. No food. No apologies"

Cons: "Delayed for 4 hours"

Pros: "Nice and helpful employees, good experience"
Cons: "Nothing"

Cons: "Delay after delay without much updating"

Cons: "Delayed 3.5 hours for no reason."

Pros: "Everything went as planned"

Pros: "Same as above."
Cons: "NA"

Pros: "Nice, new plane."
Cons: "Small trays."

Cons: "Horrible!!! Late doy and I Need to pay for my hand luggage. Never travel with Frontier!"

Pros: "Carry on charge not happy."
Cons: "Carry on charge is ridiculous."

Cons: "Food"

Pros: "The over all experience"

Cons: "3 HR unknown delay"

Pros: "Easy boarding easy check in"
Cons: "Nothing that bad, chairs are maybe a bit thin but not terribly uncomfortable"

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Illinois to Caribbean Islands

Airlines flying from Illinois to Caribbean Islands have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Illinois to Caribbean Islands

Mandatory masks

Masks required on board, masks provided on flights from Illinois to Caribbean Islands

Social distancing seating

Middle seats unavailable to book on flights from Illinois to Caribbean Islands

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Illinois to Caribbean Islands

Book cheap flights from Illinois to Caribbean Islands

Recent round-trip flight deals

5/16
Sun
nonstop
Multiple Airlines
4h 49m
ORD - SJU
5/20
Thu
nonstop
Multiple Airlines
5h 10m
SJU - ORD
5/9
Sun
1 stop
Multiple Airlines
17h 12m
ORD - SJU
5/13
Thu
nonstop
Multiple Airlines
5h 22m
SJU - ORD
5/9
Sun
nonstop
Multiple Airlines
4h 46m
ORD - SJU
5/13
Thu
nonstop
Multiple Airlines
5h 22m
SJU - ORD
5/5
Wed
1 stop
Spirit Airlines
15h 07m
ORD - STT
5/7
Fri
1 stop
Spirit Airlines
13h 21m
STT - ORD
5/2
Sun
nonstop
Multiple Airlines
4h 47m
ORD - SJU
5/7
Fri
1 stop
Multiple Airlines
10h 44m
SJU - ORD
5/2
Sun
1 stop
Spirit Airlines
9h 02m
ORD - SJU
5/7
Fri
1 stop
Spirit Airlines
7h 45m
SJU - ORD
5/9
Sun
nonstop
Multiple Airlines
4h 46m
ORD - SJU
5/13
Thu
nonstop
Multiple Airlines
5h 22m
SJU - ORD
5/18
Tue
1 stop
Spirit Airlines
7h 33m
ORD - STT
5/21
Fri
1 stop
Spirit Airlines
13h 21m
STT - ORD
5/2
Sun
1 stop
Multiple Airlines
11h 11m
ORD - SJU
5/5
Wed
nonstop
Multiple Airlines
5h 24m
SJU - ORD
5/2
Sun
nonstop
Multiple Airlines
4h 46m
ORD - SJU
5/14
Fri
nonstop
Multiple Airlines
5h 22m
SJU - ORD
5/9
Sun
1 stop
Spirit Airlines
8h 51m
ORD - SJU
5/12
Wed
1 stop
Spirit Airlines
7h 45m
SJU - ORD
5/9
Sun
1 stop
Spirit Airlines
17h 12m
ORD - SJU
5/20
Thu
1 stop
Spirit Airlines
10h 44m
SJU - ORD
5/5
Wed
1 stop
Spirit Airlines
7h 52m
ORD - SJU
5/12
Wed
1 stop
Spirit Airlines
7h 45m
SJU - ORD
5/17
Mon
1 stop
Spirit Airlines
15h 07m
ORD - STT
5/20
Thu
1 stop
Spirit Airlines
7h 36m
STT - ORD
5/3
Mon
nonstop
United Airlines
4h 46m
ORD - SJU
5/4
Tue
1 stop
United Airlines
12h 50m
SJU - ORD
5/2
Sun
1 stop
United Airlines
10h 32m
ORD - SJU
5/6
Thu
1 stop
United Airlines
8h 40m
SJU - ORD
7/24
Sat
1 stop
Frontier
9h 10m
ORD - NAS
7/29
Thu
1 stop
Frontier
8h 09m
NAS - ORD
5/24
Mon
1 stop
Delta
11h 08m
MDW - SJU
5/28
Fri
1 stop
Delta
8h 23m
SJU - MDW
9/2
Thu
1 stop
Copa Airlines
19h 39m
ORD - PUJ
9/7
Tue
1 stop
Copa Airlines
12h 41m
PUJ - ORD
5/3
Mon
1 stop
JetBlue
9h 59m
ORD - NAS
5/8
Sat
1 stop
JetBlue
10h 42m
NAS - ORD
Show more results

Recent one-way flight deals

5/17
Mon
nonstop
Frontier
4h 49m
ORD - SJU
5/24
Mon
nonstop
Frontier
4h 49m
ORD - SJU
5/9
Sun
1 stop
Spirit Airlines
11h 37m
ORD - SJU
5/4
Tue
nonstop
American Airlines
4h 41m
ORD - SJU
5/9
Sun
1 stop
Spirit Airlines
8h 51m
ORD - SJU
5/5
Wed
1 stop
Spirit Airlines
7h 05m
ORD - STT
5/4
Tue
1 stop
United Airlines
11h 24m
ORD - SJU
5/4
Tue
1 stop
Spirit Airlines
7h 48m
ORD - STT
5/23
Sun
nonstop
Frontier
4h 52m
ORD - SJU
5/19
Wed
1 stop
Spirit Airlines
8h 51m
ORD - SJU
4/27
Tue
1 stop
Spirit Airlines
9h 02m
ORD - SJU
5/22
Sat
nonstop
Frontier
4h 52m
ORD - SJU
5/22
Sat
1 stop
Delta
8h 58m
MDW - SJU
5/21
Fri
1 stop
Multiple Airlines
18h 36m
ORD - SJU
5/10
Mon
nonstop
United Airlines
4h 46m
ORD - SJU
5/11
Tue
1 stop
Delta
6h 20m
MDW - SJU
5/2
Sun
1 stop
Multiple Airlines
6h 55m
ORD - NAS
8/11
Wed
1 stop
Copa Airlines
30h 54m
ORD - PUJ
5/3
Mon
1 stop
JetBlue
10h 51m
ORD - MBJ
6/12
Sat
2 stops
Major Airline
17h 01m
ORD - MBJ
Show more results
-
1
  • Round-trip
  • One-way
  • Multi-city
  • Trip Builder
  • Economy
  • Premium Economy
  • Business
  • First
  • Multiple
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First