$121 Find Cheap Flights from Caribbean to Illinois - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Caribbean to Illinois departing on 11/11. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Low season

March

Cheapest flight

$121
Best time to beat the crowds but there is an average 33% increase in price.
Flight from San Juan to St. Louis

FAQs for booking flights from Caribbean to Illinois

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

    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 Caribbean to Illinois.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Caribbean to Illinois 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 Caribbean to Illinois?

    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 from Caribbean to Illinois with an airline and back with another airline.

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

    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 from Caribbean to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines fly most frequently to Illinois?

    Caribbean and Illinois are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (31 flights per week), American Airlines (21 flights per week), and Air Canada (16 flights per week).

  • How many airports are there in Illinois?

    There are 12 airports in Illinois. The busiest airport is Chicago O'Hare Airport (ORD), with 93% of all flights arriving there.

  • Which is the cheapest airport to fly into in Illinois?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Illinois is Chicago O'Hare Intl Airport (ORD), with an average flight price of $304.

  • What is the cheapest day to fly to Illinois?

    Based on KAYAK data, the cheapest day to fly to Illinois is Thursday where round-trip tickets can be as cheap as $447. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $649 on average.

  • What is the cheapest time of day to fly to Illinois?

    The cheapest time of day to fly to Illinois is generally at night, when round-trip flights cost $440 on average. Morning departures are around 7% more expensive than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the morning, which is peak travel time and where the average cost of a ticket is $523.

  • What is the cheapest flight to Illinois?

    The cheapest ticket to Illinois from Caribbean found in the last 5 days was to Chicago O'Hare Intl Airport, at $208 round-trip. The most popular route is Oranjestad (AUA) to Chicago O'Hare Intl Airport (ORD) and the cheapest round-trip airline ticket found on this route in the last 5 days was $208.

  • What is the cheapest month to fly from Caribbean to Illinois?

    The cheapest month for flights from Caribbean to Illinois is December, when tickets cost $216 (return) on average. On the other hand, the most expensive months are January and March, when the average cost of round-trip tickets is $384 and $315 respectively.

  • How far in advance should I book a flight from Caribbean to Illinois?

    To get a below average price on the flight from Caribbean to Illinois, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

  • How many cities have direct flights to Illinois?

    From Caribbean, there are direct flights to Illinois from 5 cities. The city with the most direct flights is San Juan, with 74 direct flights each week.

  • How many direct flights to Illinois are there each day?

    There are around 16 direct flights from within Caribbean to Illinois every day. Most flights (58%) depart in the afternoon.

  • How many direct flights to Illinois are there each week?

    Each week there are around 106 direct flights from within Caribbean to Illinois. The most common day for departures is Saturday, with 20% of flights taking off on this day.

  • How long is the flight to Illinois?

    An average nonstop flight from Caribbean to Illinois takes 11h 30m, covering a distance of 2019 miles. The shortest route is Montego Bay (MBJ) to Chicago O'Hare Intl Airport (ORD) with an average flight time of 4h 26m.

  • How many long-haul flights are there to Illinois each week?

    Each week, there are 102 medium-haul flights (3-6 hour flight duration) and 4 short-haul flights (up to 3 hour flight duration) to Illinois. There aren't any long-haul flights (6-12 hour flight duration).

  • What are the most popular destinations in Illinois?

    Based on KAYAK flight searches, the most popular destination is Chicago (95% of total searches to Illinois). The next most popular destination is St. Louis (5%).

Reviews of the top 5 airlines serving from Caribbean to Illinois

 
Need help choosing which airline to fly with from Caribbean to Illinois? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4217 reviews
8.6Crew
8.1Boarding
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

WiFi was not working and didn’t have a beverage service

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

The seats were comfortable, and the boarding process was pretty smooth.

Flight was great. Almost miss my connecting flight due to late departure from Haneda. Had to run all through airport in Chicago to make the flight. Experience was great for 1st time flyers using ANA Airlines.

Like the fact that the boarding was expedited. But the delay and chaos around the onboarding was not appreciated.

Seats are complete BS for 10 hrs. The guy at counter canceled our return flight from europe. Lufthansa on the way back made United look like a trailer park gathering. If given the opportunity, I will never fly united again. Lufthansa seats werent much better to be fair but the service was a 10 out of 10. Incant express how difficult umited made my trip.

It was a great experience to fly with ANA, the sit is very comfortable.

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

Gluten free snack options and meals that offer both gluten free and dairy free.

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

I almost missed my connection in Chicago due to having to wait on a gate to be open I am assuming. Having to run from E terminal to C terminal and I barely made it there before they closed the door. This may not be the actual airline's fault it's crazy how there is so little time between flight especially when they are placed so far apart in the airport.

Delays and cancellations. Mechanics weren’t on site. Replacement plane took hours to arrive although it should have arrived within 90 minutes. Flight back was cancelled. Ended up driving over 12 hours and wasting 3 days between everything.

Little bit of trouble getting my KTN and pre-check status onto the ticket, but otherwise the counter staff were friendly and truly concerned to get it right.

The flight could have actually taken place. Canceled flight and no option to rebook that day.

Missed connection from delays and times changing multiple times and then involuntarily booked on another airline next day

The flight was delayed in 30 minute increments for a total of 4 hours and 30 minute delay. All other flights to Chicago left on time except for this one flight. If there is an issue with the inbound flight, just let customers know so they can find another flight right away, Once we got on the plane there was another 30 minute delay taking off at 10:30 at night which is very unusual that a flight wouldn't be ready to take off

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

Take this flight regularly. Every single week same thing. Departure delayed. Make up some time in the air. Land at ORD and then wait for gate in "L" concourse Terminal 3 for 30-40 min-which yields a very delayed final arrival. Plus I get to taxi around and see every runway and drive over the bridge (IFKYK) over the expressway 2-4 times in most cases. Change the sched of incoming plane/work with FAA to improve traffic flow at ORD/change the timing of these flights. Whatever it takes. But do better.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Boarding and Delays The boarding process for my American Airlines flight from Copenhagen to Philadelphia was a bit tricky. We experienced a gate change that required a long walk to a new area of the airport. Additionally, boarding was not via a jet bridge; we had to take a shuttle bus to the plane and then carry our luggage up the stairs ourselves. Furthermore, the bag drop didn't open until about 12:20 PM, which was only three hours before our scheduled departure. This meant I couldn't drop my bag off early and had to wait outside of security in order to drop off my bag and use the kiosk. The bag drop self-service kiosks also didn't open until about 12:00 PM when an American Airlines employee unlocked them so that we could print out our boarding passes and bag tags, which further created a backlog. The flight was delayed by over an hour because we had to wait for one of the tires on the plane to be changed. Flight Attendant Professionalism On a positive note, the flight attendant was very professional when handling a passenger who was sitting in the wrong seat. Even though the passenger was persistent and reluctant to move, the flight attendant calmly ensured the assigned passenger could take their seat. Kudos to the flight attendant for keeping his calm and composure, not allowing the issue to escalate, and handling it well under pressure while a line of passengers waited in the aisle to board. In-Flight Service The in-flight service was also fast, prompt, and efficient, although service had to be suspended for the last two hours of the flight due to weather and turbulence, which was outside of the crew's control. Limited Flight Options Please note that American Airlines only operates one flight per day in and out of Copenhagen. This means there are limited options available if your flight is delayed or canceled, which is something to take into consideration when booking.

This may have been the hottest cabin temperatures I have experienced on any flight prior to take off lasting for approximately 30 minutes. I am not typically one to complain but I was genuinely worried about the health of several passengers on the flight due to the extreme temperatures including a small toddler.

The wifi didn't work and I needed to do some work. This was a business trip.

It was my first time in Jetblue flight in 10+ years(?) and the experience was horrible. You were better before. There were ATC delays sitting/waiting in the tarmac for 2 hours, I understand that this isn't Jetblue's problem but how the matter was handled poorly is. Cabin was so warm and hot couldn't get it to cool down for the entire waiting period worse, even during cruise flight. Start, the passengers were spoken to and treated like a little children with no respect. Constant/multiple annoying tone/voice PA announcements of mentioning "... only big/large suitcases are for the bin and small ones need to be placed under the seat, etc,..." I see that flight was delayed and crew were trying to get the plane ready to board as soon as they can but the way they presented was lack of better word, condesending and scolding tone to cattle. It was definite unpleasant, unwelcoming flight experience I have ever had with Jetblue. Whatever happen to smiles and fun employees , pleasant/helpful gate agents, flight attendants, crews, where have they gone? It was dissapointing flight experience overall from everyone. Sorry for the direct transparency.

Flight was cancelled as JetBlue could not find a pilot. Communication was poor and they did nothing for stranded passengers. Flight they rebooked us on was 4 days out.

JetBlue cancelled the flight. We had to rebook on another airline.

JetBlue cancelled the flight along with hundreds of others, for no apparent reason. no recourse, no rebooking options. never booking with them again

Jet Blue cancelled my flight after I had boarded. They attempted to rebook me for a new flight two days later. I was able to rebook with a different airline, but not until the next morning. As such, I was forced to get an expensive hotel and missed important work meetings Monday morning. I am very disappointed with the customer service and will be pursuing full reimbursement for my hotel cost.

You did a great job rescheduling my cancelled flight. However, you made me pay for two seats for $118 even though the seats on the original flight were free. I think that was a very unfair thing to do.

They cancelled the flight after 5 hours at the airport and the only flight they offered was for the next day with a 7.5 layover in fll. This was not going to work for me as this was only a weekend trip and getting into providence at 10 pm a day later caused me to lose Mo ey on hotels money on airport parking a dog sitter etc. they wouldn’t offer any type of a voucher or anything else. All they did was refund the flight which didn’t help me with all the money in time I lost. I was going to see my very sick father

The plane took off very late upon arrival and departure

I volunteered to let them put my carry on suitcase in the baggage storage area. But when we landed I was told it was being unloaded IN A DIFFERENT TERMINAL! I had to walk (painful for me) a long way to retrieve my bag and my ride had to move from the waiting area they were in to a totally different one. Not happy.

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

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

We were delayed three times ,and that destroyed my plans, and reservations

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

The flight itself was ok and the pilot was very communicative. However, our flight was delayed for almost 3 hours, the gate was changed 3 times and there was no communication as we were waiting. The flight staff was overall a little crabby...I understand as they probably had a long day but we all did.

Everything you need to know for your flight to Illinois

Cabin class types available on flights to Caribbean

Cabin classes available on flights to Caribbean. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.