Find cheap flights from Illinois to Caribbean

Find cheap flights from Illinois to Caribbean

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Round-trip
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Boston (BOS)
Caribbean
Fri 6/25
Fri 7/2
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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

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Top 5 airlines serving from Illinois to Caribbean

Scores according to KAYAK customer reviews

8.1
JetBlue
Overall score based on 19,582 reviews
8.3
Boarding
8.2
Comfort
8.6
Crew
7.9
Entertainment
7.8
Food
Airline reviews

Cons: "Tv dont work in a fly of 4hr 30 min"

Cons: "Was 2hrs behind schedule"

Pros: "Free wireless"
Cons: "I'm not in Charlotte"

Pros: "Service was awesome, 100% recommended"

Cons: "The food can be better."

Pros: "Loved the roomy seats"
Cons: "Sound system was low quality. Hard to here the movie."

Pros: "Unbelievable for the price."
Cons: "Nothing bad to say."

Cons: "My first flight was delayed an hour due to pilot error (we left the gate on time, but sat on the tarmac for an hour). This caused me to miss my connecting flight, which stranded me at JFK because they only had one flight per day to my destination. JetBlue's customer service told me I could not reach my destination until the next day, which was unacceptable (I had a morning interview). In fact, the only thing they said they could do was *PARTIALLY* refund my ticket, even though they stranded me in a completely different city. They also said I would "be able to" book a new flight with a different carrier, which cost roughly $400, using my own money. In the end, I spent about an hour talking with customer service until they were "nice enough" to do a partial refund with an additional credit equaling the remainder of my $400 ticket to fly with them in the future. It was still a very poor interaction with customer service."

Pros: "Clean plane"
Cons: "Took 3+ hours to get in the plane"

Cons: "The cabin crew was a little lacking and the captain did not mentioned that we had landed almost a full hour later than scheduled."

Pros: "Pilot’s smooth take off and landing."
Cons: "The weather haha."

Pros: "It was a great trip for the cost."
Cons: "Nothing."

Pros: "Free WiFi. Cute vids for Holloween"
Cons: "Nothing!"

Pros: "Seat space for each passenger"

Pros: "Nothing!"
Cons: "IT WAS TWO BOURS LATE!"

Pros: "The crew talked a big game. They were ready for anything, including loss of cabin pressure, paid snacks, and even a water landing."
Cons: "No water landing! I was excited to float around on a hot day, go down an awesome slide, and catch some sick waves, but come on people, we never even got a chance!"

Pros: "Everything,the crew etc"
Cons: "No complaints"

Pros: "The seats were comfortable."
Cons: "Flight was very late leaving Chicago. We sat on the plane for quite a while (over 30 min) shut up tight with little air circulation AND no information about why we were not leaving the gate. Flight crew were not very friendly - almost "marched" up and down the aisle and barked at people."

Pros: "comfortable seats TV great beverages--actually get can or bottle"
Cons: "when we checked it, did not put us together"

Cons: "I missed my second flight because my first flight had a 5 hour delay. UNACCEPTABLE. They should always have a back up plan if they come across mechanical issues. TIME IS MONEY!"

Cons: "We arrived later for almost 2 hours"

Pros: "I dont usually fly, staff was friendly and helpful, made my experience less stressful."

Pros: "On time!"

Pros: "Our flight attendant Jeramy was FABULOUS!!"

Cons: "No movies just Direct TV."

Pros: "Bring her own earphones as then u can listen to their varied entertainment channels. Gave free snacks & there was quite an assortment so I wasn’t stuck w pretzels again. Free soft drinks; nice flight attendants & smooth ride from Chicago to NY"

Pros: "No gate, waited 2 hours in plane"

Pros: "Everything is ok"
Cons: "Not a thing"

Cons: "When I scanned my boarding pass the Jetblue staff member told me my carry on was too big and had to be checked. This was puzzling to me because I travel often and do not have a problem with that bag. As I was sitting on the plane I saw everyone's bag's were bigger especially the man next to me. His was significantly larger and he had a large duffle bag between his legs causing him to manspread into my area. and yet i was told "make sure your purse is under the seat" seriously?! What about his giant duffle bag and huge carry on roller?!"

Cons: "Turbulence was terrible, understand that is not JetBlue issue - wanted to note."

Pros: "I love how JetBlue has reasonable prices and offers great snacks in board. The planes are comfortable."
Cons: "This is not the first JetBlue flight I have been on that was delayed. In fact, most JetBlue flights I’ve been on have been delayed! Luckily I didn’t have connections and wasn’t in a rush but it’s disappointing."

Pros: "Flying Friday before the holiday could alway be a challenge but we arrived only a couple minutes late. It was a perfect flight even with a full house."

Pros: "Captain and crew"
Cons: "Luggage handling"

Pros: "Everything"
Cons: "N/A"

Pros: "Service was prompt, reps were courteous, flight was on time and they provide snacks... been flying them for over 10 years and have NOT had one bad experience."
Cons: "N/A"

Pros: "The ride was smooth"
Cons: "No complaints"

Pros: "You took great care of my wife who needed a wheelchair. the flight itself was delayed due to weather. I totally understand. I love the extra legroom"

Cons: "Movies didn't work and we were one hour delayed on the runway."

Pros: "The only good things about this flight were: - The crew at the gate were very friendly and attentive - We arrived safely without incident"
Cons: "We were delayed 2 times before boarding. We were delayed 1 more time while on the plane. The pilot told us there was equipment trouble that had been fixed, but there was paperwork to fill out and it would only be a few minutes...and then radio silence for 30 minutes before pulling back. The flight attendants rushed through the pre-flight announcents and I could only understand about 60% of it due to speed, volume and accent. Despite asking me for my drink order, it never came...and I only heard a few soda cans pop open at all. Did they just decide not to serve us? She even gave me a napkin for it. Luckily when they put the snack basket in front of me, there was a tiny bottle of water, which I grabbed...little did I know, that was all I would get. The flight attendants were just tapping in the back of the plane the rest of the flight. They didn’t even bother collecting garbage until we were on final approach. They also never did the normal checks before landing."

Pros: "Information about length of flight and what to expect. Smooth flight"
Cons: "My tv screen didn't work"

Pros: "They refund me the money"
Cons: "I almost lost my international connection, had to pay double to get my destination on time"

Pros: "Ez check in with kiosk"
Cons: "I would like to see an organic food option, even with a fee if necessary. Recommendation, fruit like banana or apple. Certified organic."

Pros: "Boarding system efficient. Lots of leg room. Choice of snacks. Good service."

Pros: "Gave me my refund!"
Cons: "Flight was delayed 5 times without sufficient reason. Weather was clear. Had to ask for a refund after the 6th delay. Missed an important event."

Pros: "Smooth flight"
Cons: "Tvs were off for the entire flight, and no explanation."

Pros: "This was my first time with JetBlue and I was pleasantly surprised with the size of the plane. It was pretty comfortable"

Pros: "Friendly staff and the on board entertainment and snacks"
Cons: "The last time I took JetBlue the flight was delayed by almost 3 hours"

Pros: "I appreciated the fact that we didn't take off until the weather was clear and it was safe to fly. I am glad that they were concerned about our safety."

Pros: "the plane was good!"
Cons: "the plane boarded late"

Pros: "I had heard about limited food options during covid flights but everything was tasty and generous. I always appreciate it when my initial flight books my check-in to my final stop and gives me all my boarding passes at once and Delta did just that. They were also really good at communicating updates like changes to the gate."
Cons: "People should just be prepared to be asked more questions than usual. It can definitely make you feel nervous but just remember that the new covid restrictions are stressful for flight staff just as much as they are stressful for you. Be cooperative and honest and you shouldn't have any problems."

Pros: "Kosher snacks! Thank you. Screens and outlets at every seat. Safe, controlled Covid protocols including de-boarding. Excellent!"

Cons: "We arrived around 39 minutes early and the whole process was very smooth"

Pros: "The crew was not overly friendly"

Pros: "Calm and safe, just like I like it."

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

Pros: "Great crew"

Pros: "All good."
Cons: "Price"

Pros: "Son got wings, so was happy."
Cons: "No entertainment."

Pros: "Nice service"

Cons: "It was late"

Pros: "Love it"

Pros: "Good snack selection. Crew was personable."

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: "Crew was nice and welcoming"
Cons: "Well, if our plane had been leaving on time it would've been superb."

Pros: "Helpful"
Cons: "More print media to read on"

Pros: "Crew was great."
Cons: "Couldn’t hear/understand the pilot"

Pros: "The boarding was fast and very well handled."

Cons: "It was delayed"

Pros: "N/A"
Cons: "Chinese Eastern did not try to help and solve my problem."

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: "It was a smooth boarding, flight and exit out of the plane."

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"

Cons: "From the begging they changed the flights for something totally different. It was a 14 hour trip. Awful"

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: "I was with my friend"
Cons: "Delayed 12+ hours"

Pros: "Buen entretenimiento."

Pros: "I was given a complimentary upgrade."

Cons: "It takes time and worries to find the air train and Aeroflot registration."

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

Pros: "The service was amazing , the staff was honestly friendly and nice"

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

Pros: "Great service, nice agent friendly"

Pros: "Excelente"

Cons: "I was unable to fly at all due to a spelling error on my ticket. The airline refused to alter the ticket. Worst experience of my life, ruined my Christmas"

Cons: "Layover"

Pros: "Short flight"
Cons: "Too cold Not friendly boarding agent"

Cons: "Small plane"

Cons: "Had a death in the family and no one would help me get back home"

Cons: "I am a 5'3" 125# woman who, unfortunately, had a middle seat assignment. The passenger to my right, on the aisle, weighed approximately 375# and took up 1/3 of my seat. The arm was not able to go down comfortably, and when it did it was not usable . The passenger on my left, window seat, was probably 6'7" and had to sit with a man spread in order to fit. I could not move and was extremely uncomfortable. The plane was overbooked so I was unable to move. Therefore, worst flight ever. Plus, I paid for a full seat and was only able to occupy half of it."

Pros: "Movie selection"

Pros: "The in-flight service was good."

Pros: "Nothing"
Cons: "Poor hospitality by alaska airline staff, especially by MrPavel at gate H4, 01nov2016, prior boarding around 0730am"

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

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

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"

Pros: "the flights were on time"
Cons: "the plane was packed. the audio on the entertainment system did not work. the flight attendant gave me water and a juice, but handed them both at the same time and I spilled some juice to avoide the person next to me on this packed flight."

Pros: "On time"
Cons: "Meals and more options to drink during flight. No entertainment system"

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"

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: "excellent service"

Pros: "Everything"

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

Pros: "Service was good"

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: "Great crew from Chicago to Panama City. Accommodating and attentive."
Cons: "Ah, the usual airline stuff that we just have to live with."

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!"

Pros: "Free food and Cocktails!! On time and quick boarding. My first flight with Copa Airlines, won't be my last!!"

Pros: "The food and service"
Cons: "Maybe more entertainment for a 5 hour flight"

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: "Flight was overbooked and I got bumped. Needs to be ther for work very inconvienant"

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: "Liked the dairy free options for the meal."
Cons: "Didn't have an individual tv to watch movies on, or cell phone charger. Given the price however, this was acceptable."

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: "plane was comfortable"
Cons: "Flight attendants weren't very polite."

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."

Cons: "Not enough smiling from the crew"

Pros: "Once again everyone was so wonderful and helpful"
Cons: "Lower luggage cost. I spent $110 additional on this trip since since I wasn't well informed (my fault)"

Pros: "Nothing"
Cons: "Everything"

Pros: "Nothing"
Cons: "Staff crabage"

Cons: "Check in"

Cons: "People should be restrained from jamming entrance to aircraft BEFORE their zone is called."

Cons: "Boarding"

Cons: "Good"

Pros: "Nothing"
Cons: "Delays, gate changes, lack of notification, last minute changes."

Pros: "Arrived 30 min early"

Pros: "SEAT was comfortable"
Cons: "Service"

Pros: "Estaba todo bien."
Cons: "Pero no me gusto q havia mucha turbulencia. Y mis photos queria esplotar."

Pros: "Good"

Cons: "We waiting 2hours... delay Something to fixing on plane! I miss good business in Tampa because of that"

Pros: "Nice service. Exceptionally new plane about a year old to the month."
Cons: "Need to ask people to prepare to deplane. Perhaps use rear door to expedite process"

Cons: "not clean"

Pros: "a smooth ride. we left a half an hour late."
Cons: "paying the carry on fee"

Pros: "Very comfortable ride and spacious"

Pros: "Bag charged"

Cons: "Terrible information and no service."

Cons: "Short-staffed, so short tempered workers.kiosks did not work. Nickled and dimed on everything. Like flying in prison. No light and a cold hard bench seat. Awful."

Cons: "Look like frontier is always late"

Pros: "Nothing."
Cons: "Everything."

Pros: "uh the "big front seat" was decent? fairly roomy and still cheap"
Cons: "fuckin screaming children everywhere, it was horrendous"

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

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

Cons: "I did not like the long delay"

Cons: "Late late late arrival."

Cons: "delays with NO feedback"

Cons: "there were too many delays and the situation was handled poorly. I do not plan to fly Frontier again in the future."

Cons: "They nickle and dime you to death. They even charge you for soda!"

Pros: "Getting where I was going"
Cons: "Everything else."

Cons: "See above."

Pros: "Nothing"
Cons: "Everything"

Pros: "Very efficient."
Cons: "No free beverage."

Pros: "Politeness"
Cons: "Overall everything"

Cons: "to expensive to cary on a bag."

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

Pros: "The tate"
Cons: "Paying for bags"

Pros: "I was upgraded for free!"
Cons: "The payment necessary for baggage."

Cons: "Everything!!"

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

Pros: "Aircraft"
Cons: "Nothing"

Cons: "Food"

Cons: "Lots of screaming children, but I had to fly to Orlando."

Pros: "It was very punctual"

Pros: "Very informative on where to go!"
Cons: "Not very informational on security policy"

Pros: "Everything was good, no complaints"

Pros: "Staff"

Cons: "The Chicago airport was terrible both times. Things not clearly marked. Staff not friendly or available. Long term parking very hard to find and pricing very unclear. Didn't realize we would have to pay additional for just a seat and carry on luggage"

Pros: "Cheap..."
Cons: "Delaaaays"

Pros: "The staff not pointing things out in the beginning!"

Pros: "HORRIBLE lending.."
Cons: "....."

Pros: "nothing..."
Cons: "everything... I will never travel on spirit again if I can help it."

Pros: "Perfect"
Cons: "Keep up the good work"

Pros: "Nothing"
Cons: "I dint like anything"

Pros: "No fanfare, no hassle."

Cons: "Trip to Chicago snack and drink cart only came by at beginning"

Pros: "All"
Cons: "Nothing"

Cons: "I was not given anything to drink"

Pros: "Landed early and gate open. Great trip all over he way even though in a middle seat"

Cons: "Same as above."

Pros: "אני אוצה לקבל זיכוי על כל החודשים שחייבים אותי ב 19.90 ש״ח למרות שכלל לא השתמשתי בכרטיס. מה גם שנאמר לי בשעתו בחנות שאין כלל עלות עבור הכרטיס הנ״ל. כשהתברר לי שיש עלות חודשית( לדעתי זוהי הונאה לשמה)חזרתי לחנות כדי לבטל את הכרטיס ואמרו לי שזה בלתי אפשרי. ניסיתי ליצור קשר עם cal ולא הצלחתי בשעתו. אתמול סוף סוף הצלחתי לבטל את הכרטיס ואודה לכם באם יוחזר לי התשלום החודשי אותו אתם כביתם ממני בחודשים האחרונים. לדעתי מדובר ב 4 חודשים. תודה מראש טובה ברנר ת. ז 042388421"

Pros: "seat more comfortable than most airlines"

Cons: "... and they charge a penalty if you go to their counter first without going first to the check-in kiosk? Cheaper, sure, but totally lacks class"

Pros: "Cheap fare"
Cons: "Expensive bag check fees of $52 across the board, even though signs listed a variable scale based on weight that would have been cheaper. Apparently that's only available if you check in early and weigh your bags yourself or something, IDK..."

Pros: "Inexpensive ticket prices due to getting rid of many services that I don't use or care for."
Cons: "No reading material related to Spirit airlines. There should be something like a small magazine in the seat back promoting your business for customers to read."

Pros: "Reshedule"
Cons: "Poor services"

Pros: "Inexpensive"
Cons: "Very cramped. No reclining. This is the city bus of airlines."

Pros: "Nothing"
Cons: "Everything"

Pros: "Price"
Cons: "Managed to catch a virus so couldn't travel (doctor's orders). Partial credit was given when I'd much rather just have a refund."

Pros: "If you're traveling light, the airfare is great. Only pay for what you need - no food, no luggage, etc."
Cons: ""Read the fine print" is what I was essentially told when I learned I had to pay $50 to check my suitcase. I booked via Kayak - who gives no indication of the several fee options to check luggage, beginning from $30 online at spirit.com and so on. Disliked the service and structure, won't fly Spirit or book through Kayak again."

Pros: "I didn't like anything"

Cons: "I was charged an extra $50 to check-in my bag at the counter! Quite mean! I wasn't preinformed!"

Pros: "Nothing"
Cons: "I didn't like anything"

Pros: "Nothing"

Pros: "They were able to switch us to emergency row seating."
Cons: "Too expensive for everything. No room at all for anything. Super uncomfortable"

Pros: "Nothing."
Cons: "i had to pay my on board luggage, the chair doesn't reclinate, no food, no intertainment and the price was not that cheap to justify all of these down sides"

Cons: "It was delayed so long that they canceled it"

Cons: "Very unsophisticated passengers"

Pros: "Nothing"
Cons: "Everything"

Cons: "delayed"

Pros: "Price was good and everyone was friendly"
Cons: "No room to move"

Pros: "Everything, the extra roomy seat, the fact that I did not have to buy what I did not need!"
Cons: "My first trip was cancelled due to mechanical problems but I was put up in a very nice hotel which compensated for the inconvenience. I will definitely fly Spirit again."

Pros: "boarding was smooth"
Cons: "super tight space"

Pros: "Everything, nice service and no delays."

Pros: "I was disgrace by ur checking casher . i dont feel good about it"

Pros: "Nothing"
Cons: "Everything"

Pros: "Cheap price"
Cons: "Extremely small seat space"

Pros: "What a great concept!"

Cons: "A lot of hidden charges."

Pros: "Flights left as scheduled. Smooth travel."
Cons: "We got to the airport really early. No flights to Minneapolis available. Just two per day between O'hare and Minneapolis."

Cons: "Don't like being nickeled and dimed for basic services."

Cons: "there is no free luggage. the luggage fee even more than the ticket."

Pros: "nothing."
Cons: "EVERYTHING!!!!!!"

Pros: "They was taking care of me at all"
Cons: "Nothing at all"

Cons: "Paying for a seat No music"

Pros: "It got me where I needed to go without too much fuss."
Cons: "The decent and landing back into LAX was really scary - and without any warning or reassurance from the captain. Everyone thought we were crashing."

Pros: "Everything went smoothly"

Pros: "The tickets were cheep"
Cons: "There was no Wi-Fi on any of my flights."

Cons: "knees pressed into seat ahead"

Read more about JetBlue
COVID-19 information

Safety measures for airlines flying from Illinois to Caribbean

Airlines flying from Illinois to Caribbean 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

Mandatory masks

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

Social distancing seating

Middle seats unavailable to book on flights from Illinois to Caribbean

Pre-flight testing

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

Book cheap flights from Illinois to Caribbean

Recent round-trip flight deals

8/17
Tue
1 stop
Spirit Airlines
7h 48m
ORD - STT
8/25
Wed
1 stop
Spirit Airlines
10h 14m
STT - ORD
8/25
Wed
1 stop
Spirit Airlines
6h 33m
ORD - STT
8/31
Tue
1 stop
Spirit Airlines
9h 17m
STT - ORD
8/17
Tue
1 stop
Spirit Airlines
12h 37m
ORD - SJU
8/25
Wed
1 stop
Spirit Airlines
11h 09m
SJU - ORD
8/24
Tue
1 stop
Spirit Airlines
11h 45m
ORD - SJU
9/1
Wed
1 stop
Spirit Airlines
11h 09m
SJU - ORD
8/17
Tue
1 stop
Spirit Airlines
8h 47m
ORD - STT
8/25
Wed
1 stop
Spirit Airlines
10h 14m
STT - ORD
8/18
Wed
1 stop
Spirit Airlines
9h 25m
ORD - SJU
8/25
Wed
1 stop
Spirit Airlines
11h 09m
SJU - ORD
8/24
Tue
1 stop
Spirit Airlines
12h 32m
ORD - SJU
9/1
Wed
1 stop
Spirit Airlines
7h 17m
SJU - ORD
8/10
Tue
1 stop
Spirit Airlines
13h 08m
ORD - SJU
8/25
Wed
1 stop
Spirit Airlines
7h 17m
SJU - ORD
8/9
Mon
nonstop
Multiple Airlines
4h 55m
ORD - SJU
8/18
Wed
1 stop
Multiple Airlines
11h 09m
SJU - ORD
9/22
Wed
nonstop
Multiple Airlines
4h 55m
ORD - SJU
9/28
Tue
1 stop
Multiple Airlines
11h 07m
SJU - ORD
9/8
Wed
1 stop
Multiple Airlines
6h 34m
ORD - SJU
9/15
Wed
nonstop
Multiple Airlines
5h 21m
SJU - ORD
11/3
Wed
nonstop
Frontier
4h 55m
ORD - SJU
12/2
Thu
nonstop
Frontier
5h 21m
SJU - ORD
9/10
Fri
1 stop
Delta
10h 04m
ORD - SJU
9/14
Tue
1 stop
Delta
11h 45m
SJU - ORD
9/21
Tue
1 stop
Delta
6h 25m
MDW - SJU
9/25
Sat
1 stop
Delta
11h 01m
SJU - MDW
6/29
Tue
1 stop
Multiple Airlines
7h 50m
ORD - STT
7/4
Sun
1 stop
Multiple Airlines
9h 29m
STT - ORD
9/26
Sun
nonstop
Multiple Airlines
4h 55m
ORD - SJU
9/29
Wed
1 stop
Multiple Airlines
11h 07m
SJU - ORD
11/6
Sat
nonstop
Frontier
4h 55m
ORD - SJU
12/1
Wed
nonstop
Frontier
5h 21m
SJU - ORD
9/5
Sun
1 stop
Delta
6h 25m
MDW - SJU
9/14
Tue
1 stop
Delta
11h 01m
SJU - MDW
10/28
Thu
1 stop
Copa Airlines
25h 44m
ORD - PUJ
10/31
Sun
1 stop
Copa Airlines
20h 02m
PUJ - ORD
8/12
Thu
1 stop
JetBlue
7h 30m
ORD - PLS
8/18
Wed
1 stop
JetBlue
8h 54m
PLS - ORD
Show more results

Recent one-way flight deals

8/25
Wed
1 stop
Spirit Airlines
6h 33m
ORD - STT
8/31
Tue
1 stop
Spirit Airlines
9h 25m
ORD - SJU
8/31
Tue
1 stop
Spirit Airlines
12h 32m
ORD - SJU
7/10
Sat
1 stop
Spirit Airlines
13h 08m
ORD - SJU
8/10
Tue
1 stop
Spirit Airlines
13h 08m
ORD - SJU
8/15
Sun
1 stop
Frontier
8h 15m
ORD - NAS
7/29
Thu
1 stop
Spirit Airlines
13h 08m
ORD - SJU
8/10
Tue
1 stop
Frontier
8h 15m
ORD - NAS
7/10
Sat
1 stop
Spirit Airlines
13h 08m
ORD - SJU
7/10
Sat
1 stop
Frontier
9h 15m
ORD - NAS
7/20
Tue
1 stop
Frontier
8h 15m
ORD - NAS
9/20
Mon
nonstop
Frontier
4h 55m
ORD - SJU
10/2
Sat
1 stop
Delta
10h 04m
ORD - SJU
8/21
Sat
1 stop
Delta
9h 07m
ORD - SJU
8/31
Tue
1 stop
Delta
9h 07m
MDW - SJU
7/29
Thu
1 stop
Multiple Airlines
15h 15m
ORD - NAS
10/13
Wed
1 stop
JetBlue
9h 55m
ORD - NAS
10/28
Thu
1 stop
Copa Airlines
25h 44m
ORD - PUJ
8/11
Wed
2 stops
United Airlines
16h 29m
ORD - STT
7/17
Sat
2 stops
American Airlines
13h 44m
ORD - STT
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