$88 Find Cheap Flights from Caribbean to Chicago

Delta flight was great from the check in all the way to arrival. However, I had a very bad experience. I requested a wheelchair and the wheelchair employee that went to pick me up from the plane in Boston to bring me to the baggage claims told me I have to pay him. I was under the impression that it was a free service and I usually give tips but the person forced me to pay and since I said no because I was upset with his demand when my daughter walked in to pick me up he demanded payment from my daughter who paid him thinking maybe now it is a charged service.

6 hour delay including one after we were boarded. Horrible experience.

Horrible. Grateful to be alive but spent 13 hours at airport only to return back to my familys house and flight changed to next day. They tried to fix a part on plane, had no back up plane and after 10 hours , reattempted the flight and it STILL wasn't fixed. We got a meal voucher and rescheduled flight but there should be some other compensation for the 15 hours spent in airport

Overall it was not that bad! The delay on the second leg to Indianapolis , was really unexpected!!

Nothing unusual. It was fine. I hate having to pay extra for my seat.

Everything was Okay. I was disappointed our luggage didn’t arrive with us and came in a flight 7 hours later. Representative said the will be delivered to the hotel. They have not arrived 24 hours later

We splurged and decided to fly first class. Seats were roomy. But flight crew arrived late to the airport. That delayed our flight. Most of the passengers had to try to make connections flights. I felt bad for them. We checked 4 bags. We got three from the baggage claim carousel. 4th one was lost. Delta online help wasn’t good. Baggage claim staff were sympathetic and nice but we waited around for almost 2 hours and it had t been found. They did find it several hours later and we had to drive back to airport to retrieve it. I won’t be splurging on 1st. Lass again anytime soon. I think we got worse service. I am also not a huge fan of delta but we have family in ATL so we don’t have a ton of choice. What should have been an easy flight turned into a stressful event due to flight crew tardiness and baggage mishandling.

In thirty years of traveling, mostly with Delta, this was the worst day ever.

The flight was so late that I had to change connecting flights, turning a five-hour trip into a fourteen-hour nightmare.

I am so shocked at the service in first class. We were not greeted or offered a beverage for 45 minutes into the flight. She did however have time to write a long note. I just wanted a snack and something to drink. We were never offered coffee and the snacks came after dinner? It was the oddest flight I have ever been on. The gentleman next to me got up and gave our dinner box’s to the flight attendant and asked for a second glass of wine for each of us. Our dinner boxes sat on our tray for 20 minutes. She was rather distracted. He then asked another flight attendant for wine… finally we had a second glass. I was trying to give her some grace, she also told the man next me we couldn’t have any more wine because we drank it all… after landing the seasoned traveler next me ask for her employee number. Then it was a mutiny! She was refusing and it got tense. The captain came and asked what was happening, the flight attendants totally gave a biased account of the fact. The captain told the police the man I was seated next to was intoxicated! That was completely inaccurate and it really escalated things. I policeman found me at the luggage carousel to verify the facts. The flight attendants made false accusations that he touched them! That never happened. It was a very poorly trained crew. I am so anngry and shock by the entire experience! It was terrible service! I would like a refund for what I paid to be in first class and the most uncomfortable flight ever. I always fly Delta, it has been wonderful. I was so flustered by the entire experience! Please give me an update on this matter! Thank you, Kelle Myers

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

The plane used to go to Chicago was a bit outdated and needed a refresh

My connecting gate in .Chicago was across the aisle from my arriving gate. Otherwise I would not have made my connection. So that was very fortunate.

when you can say you don't remember being at any point upset during a flight, the airline is winning .

The staff was very friendly. The seats seemed quite small. Overall the flight was pleasant.

It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!

Charging and entertainment didn't work. The meal was horrible. They only came by with the drink cart one time for the 8 hour flight. They did come by with water a couple times.

Exceptional, I’d like to specifically recognize Robert for his outstanding customer service. He is professional, pleasant, and personable.

Bad, but r that was because Chicago to stl flight 14 hours late.

Some sort of compensation for missing work because of a cancelled flight that was United’s fault

Flights were on time both ways, such a big plus! Staff was very accommodating and friendly. Question the choice of snacks that, which on both flights was dairy based. Appreciated using bottled water.

This flight was fine but had no time to breathe as the connection was late from Sea to ORD.. Super stressful. If we checked bags, the trip would have been very distressed.

Seats were very uncomfortable. I paid extra for a seat with more leg room, the seat was no different than a seat at the back of the plane. Flight attendant was rude.

Seating accommodations in Premium Economy are excellent. Some of the food was very good but leaving room for improvement. All the AA Associates were courteous and professional.

the food choice of packaged chips and popcorn was utterly ridiculous for first class

Check in agent was helpful and nice. Flight was OK. Our flight in Chicago was delayed 8 hours without an explination. This was our journey home. After a horrible flight experience on on the way to our vacation where our plane was diverted for an emergency medical issue, was grounded for hours, we missed our connecting flight by 25 minutes, and it took a day yo get re-booked, this was yet another bad experience that American seemed unwilling to help out with, much less compensate us for the

Late and next flight even later. Who leaves at 245 am and arrives at 330 am ? No wifi, 4 hr flight and one bag of pretzels? AA should be ashamed

No problems on this flight. Entertainment system worked well. On time take off and arrival. Smooth most of the way.

Fantastic! If it had not been for a check-in agent in Knoxville I may have not gotten my passes on British Airways. I couldn’t check-in online because British Airways had messed us the info on my tickets to London & Inverness. AA’s was great! British Airways was a continuous series of delays and frustrations.

Extreme weather delays. Missed my flight to France and I ended up leaving the plane.

Got on quickly and easily. When it turned out the other two seats in my row would be occupied, a nearby flight attendant immediately let me know that I could move one row behind me since it was an empty row, I moved into the window seat where I could relax enough to take a little nap. Can’t ask for much more.

We had a 40 mins delay, but the pilot was good about keeping up informed. No food/snacks or drinks when u in the air-they have to be purchased. They charge for every single thing .

I’m not a fan of Spirit Airlines from a not-so-good experience the last time & I swore I would not fly this airline again- bc they charge for EVERYTHING. I only flew Spirit this time bc it wasn’t my choice. I decided to use a “Mystery Ticket” bc of the great price, not knowing it would choose this airline! I found out on this trip how they pick a random seat with a “sticker” for a prize-are we in first grade? just doesn’t seem right & now the first 3 or 4 rows get special treatment-we all paid for our tickets, not just them.

particularly nothing to like plane just turned to be a hmm flying bus, yet in buses from another country at least drink and snack are free ... and seat could be just a bit more ..adjustable? ok ok i know i am asking for too much but ..dreaming is not forbidden yet

Fantastic !!! Seamless boarding. Meticulously clean. We left and arrived early.

The flight was delayed, and we waited for more than an hour on the plane.

You get what you pay for, but those tickets weren't cheap, so I expected better, but Spirit is just one of those airlines.

Cancelled the return flight moments before boarding, horrible customer service in assisting with any rebooking. Never again will I fly Spirit.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

The seats were dirty with crumbs and trash , looked it had not been cleaned up from a previous flight

Nothing about the flight was good. The crew was rude and unwilling to assist would never recommend this airline to anyone and for sure will not fly it again

The plane was very clean, the flight attendants were chipper and accommodating. It was roomy

There was extremely long wait times to check in my bags and pass through TSA. I almost missed my flights on several occasions.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

There were a lot of issues at the gate in Atlanta — which caused delays in boarding and getting to our destination. The aircraft and crew were excellent.

It was fine. The flight was delayed for 3 hours. I had things scheduled in Detroit, and I let a lot of people down by not being there on time.

First time experience and though you'll pay for *everything* meaning bags, water/snacks, even a question with a service agent - - all in all, not a bad experience whatsoever.

Long lines, rude staff, everything that's offered you have to pay for.

Among the worst flights I’ve taken. Never again. Staff was horrible across the entire Frontier workforce. Flight attendants were legitimately yelling at and arguing with each other while on board - toxic environment (really guys? at work and in front of customers no less?). Frontier intentionally assigned my partner and I (who booked together) to opposite ends of the plane despite plenty of seats together - straight up predatory practices to take people’s money. Seats are legit the absolute worst. Not even free coffee. Absolute garbage airline with wild hidden fees and the worst staff in the business. They will for sure have a deadly accident soon. Never again, not for any where not for any price.