$106 Find Cheap Flights from Chicago to Caribbean - Compare and Save

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Cheap Flights from Chicago to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cananonstop$348
Santo Domingo
Santo Domingo1 stop$343
Montego Bay
Montego Baynonstop$360
Oranjestad
Oranjestad1 stop$310
Nassau
Nassau2 stops$415
Kingston
Kingston1 stop$475
Simpson Bay
Simpson Bay2 stops$339
Providenciales
Providenciales1 stop$339
George Town
George Town1 stop$347
Aguadilla
Aguadilla1 stop$313
St. John's
St. John's1 stop$534
Punta Cana
Punta Cananonstop$348
Santo Domingo
Santo Domingo1 stop$343
Montego Bay
Montego Baynonstop$360
Oranjestad
Oranjestad1 stop$310
Nassau
Nassau2 stops$415
Kingston
Kingston1 stop$475
Simpson Bay
Simpson Bay2 stops$339
Providenciales
Providenciales1 stop$339
George Town
George Town1 stop$347
Aguadilla
Aguadilla1 stop$313
St. John's
St. John's1 stop$534
Booking Insights

KAYAK's insights & trends for Chicago to Caribbean flights

Get data-powered insights and trends into flights from Chicago to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to Caribbean flight route?

The cheapest ticket to Caribbean from Chicago found in the last 5 days was to San Juan, at $166 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 5 days was $166.

What is the cheapest time of day to fly to Caribbean?

The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $358 on average. Morning departures are around 21% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $523.

Can I save money by flying with a layover from Chicago to Caribbean?

No, with an average price for the route of $672, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago to Caribbean?

The cheapest month for flights from Chicago to Caribbean is August, when tickets cost $429 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $612 and $598 respectively.

What’s the cheapest day of the week to fly from Chicago to Caribbean?

Your flight ticket price will generally be cheaper if you fly to Caribbean on a Tuesday and more expensive on a Thursday. On your return trip to Chicago, you should consider flying back on a Thursday, and avoid Sundays for better deals.

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

To get a below average price on the flight from Chicago to Caribbean, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low season

September

Cheapest flight

$106
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from Chicago Midway Airport to San Juan

FAQs - booking Caribbean flights

  • Are there special amenities for travelers with infants in Chicago O'Hare International Airport ?

    There are mother’s rooms located in each terminal. They have seats, changing tables, and sinks where you can nurse or let your child nap before departure. Designated lactation pods are available in all terminals. There are vending machines that dispense formula, bottles, diapers, and wipes 24 hours a day. Their locations include Main Hall K1 and Gate G2, Concourse G in Terminal 3.

  • What are the public transport options from downtown Chicago to Chicago O'Hare International Airport (ORD)?

    Buses from Peoria Charter Coach Company operate twice a day from Union Station and Jackson & Canal to Terminal 2 with a travel time of approximately 30 minutes. Taxi services are offered by agencies such as Yellow Cab Chicago and Flash Cab, with a commute time of approximately 23 minutes. Shuttles by Jayride company provide transport services on demand, with a commute time of around 22 minutes.

  • Which airline flying from Chicago to the Caribbean provides unaccompanied minor services?

    American Airlines allow children from five to 14 years to travel alone without an adult present. However, an adult must accompany the child to the departure gate and wait until the flight has taken off. Contact information of the adult meeting the child upon arrival must be provided. An airport escort accompanies your child during flight connections and brings them to the authorized adult at the destination.

  • Which airline offering flights from Chicago to the Caribbean has favorable pet policies?

    Delta Air Line allows cats, dogs, and small household birds on board. Your pet is required to stay inside a carrier with the door securely closed for the entirety of the flight. A soft-sided carrier is recommended, with dimensions no larger than approximately 18x11x11 inches. Two pets of the same species can travel in one carrier. There are no maximum weight restrictions for pets flying in the cabin.

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

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Caribbean.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Caribbean is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Caribbean?

    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 Chicago to Caribbean 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 Chicago to Caribbean?

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

Top tips for finding cheap flights to Caribbean

  • Most airlines offering flights from Chicago to the Caribbean depart from Chicago O'Hare International Airport (ORD). American Airlines and Spirit Airlines operate from Terminal 3, while Southwest Airlines and Delta operate from Terminal 5.
  • Chicago O'Hare International Airport (ORD) is the hub for American Airlines. The airline provides multiple daily flights to several destinations in the Caribbean, such as Punta Cana and Santo Domingo.
  • Another airport choice available when departing from Chicago is Chicago Midway International Airport (MDW). This airport is recommended if you are traveling from the city, as it is a short distance from downtown with less traffic congestion. The airport also offers shorter waiting times as it is less busy compared to ORD.
  • Wheelchair assistance is offered while transiting through the airport by all airlines operating in ORD. All washrooms located in the terminals are wheelchair accessible. Braille lettering and raised numbers are installed on the elevator buttons to allow accessibility by the visually impaired.
  • Several airlines offer connecting flights from ORD to the Caribbean with layovers in different cities. Delta flies to Punta Cana International Airport (PUJ) with a layover in Atlanta, while Spirit Airlines has a layover in Fort Lauderdale for the same route. American Airlines offers two-stop flights to the Bahamas' Lynden Pindling International Airport (NAS), with layovers at New York and Miami.

Reviews of the top 5 airlines serving from Chicago to Caribbean

 
Need help choosing which airline to fly with from Chicago to Caribbean? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 10215 reviews
8.1Crew
7.3Comfort
7.7Boarding
7.1Entertainment
6.7Food
Airline reviews

On time, easy boarding. Anytime you sit in an economy seat, it’s uncomfortable. New plane and the bathrooms were in the galley at the back of the plane which seemed odd.

10.0 ExcellentSharon, Sep 2026
Read more United Airlines reviews

On time, easy boarding. Anytime you sit in an economy seat, it’s uncomfortable. New plane and the bathrooms were in the galley at the back of the plane which seemed odd.

Terrible service - they don’t want to be there and bad food. Entertainment system in economy from the 2000s

No drink service but there was no N/A as an option to choose. Seats were extremely tight. I am under 5.5 and I bumped my knees have no idea how taller people could manage.

Flight delayed, last seat on the plane, no arrival Gate available due to the plane departing late

Kayak booked this flight with only 1h 20min layover in Chicago. This made it impossible for me and several other passengers to reach this flight. Moreover, the gate closed boarding in spite of several passengers still on their way without waiting even one more minute. However, the plane departed with 20min (!) delay, i.e., there would have been at least 15 min time to let the delayed passengers board without causing any delays. I complained and as a "thank you" the attendent booked us on the last (!) flight to Indianapolis ~7h later! Thankfully, I caught the spitefulness and the United customer line rebooked the flight to an earlier flight. Although I can't grade this particular flight since I never had a chance to take it, Kayak made the mistake of a too short layover and the crew at the gate was awful.

Flight did not have wifi service. It was experiencing technical difficulties. Definitely and old plane that needs updating.

This flight has a history of leaving late, however, I was pleasantly surprised that it was not delayed this day. The flight went smooth, except I was in a window seat and the wall and my feet were freezing. I found it difficult to sleep due to being so cold, I also was using 2 provided UAL blankets and could not get my feet warm. This was annoying, but I still made it there on time and safe.

Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.

It was a good experience, unfortunately my checked baggages were come late and not arrived on time.

Very stressful to locate United Airline boarding area, delayed flight, changing boarding area again to another location with all tiredness 😩. But flying was fine.

After boarding, the AC was shut off on the flight. At business class, I really could not breathe. I was absolutely dripping sweat. I was told by the FA that there was nothing they could do but I could stand by the door until departure. So, that's what I did. I was clearly in the way while the FAs were trying to do their work, but I had to be able to breathe. After that, of course, I had sweated up a lot so was very uncomfortable for the six hour flight.

DELAYED AGAIN and AGAIN and AGAIN - not only that, you delay in 20 minute increments for hours and hours instead of having an accurate delay understanding.

AA was fine....the overall experience was subpar, but not due to the airline due to broader issues

No ground air conditioner for the plane. Very hot and humid prior to take off which was an uncomfortable period of time.

Check-in process was poor, very poor, only one person to check-in all passengers, so if one passenger had a check-in issue, all other passengers were delayed. All check-ins should have two airline staff to check-in passengers.

The flight up was great no issues. The flight back home was a cluster. I was told the plane I was waiting on was giving to another flight which caused me to miss my connection flight. Granted the airline did great with getting hotel and vouchr for food.

Flight was delayed and so much of inconvenience related to the gate change.

Nothing was good about this flight. Although the flight actually departed more than 3 hours late, due to “air traffic control management” we pushed back from gate 2 hours and 20 minutes late and proceeded to sit 100 yards from gate for and then n tarmac for another 1/2 hour additional 20 minutes

One thing you can always count on is your AA flight getting delayed. This is not surprising when they operate these planes like a greyhound bus with wings.

The seats cushion on my seat (exit row) needs to be replaced. It felt like I was sitting on a bar rather than a seat cushion. Also, I was in the middle seat and I sat next to an oversized guy (window seat) and he took up about 25% of my space. Otherwise, the experience was good. :)

KUDOS TO ALL THE CREW PROVIDING ASSISTANCE WITH PASSENGERS ON A WHEELCHAIR. ON BOTH FLIGHTS THEY HUSTLED TO TAKE MY RELATIVE TO CONNECTION ON TIME. THEY DESERVE A LOT OF CREDIT!

Good experience with this flight. Boarding was smooth with no issues. The short flight was good with quick drink & snack service. Nice easy way to get back from DC.

Very good flight that left on time and arrived earlier than anticipated, which was a plus! The crew members were very welcoming and helpful. However, the temperature on the flight was very cold - almost to the point of extreme discomfort. Additionally, requiring passengers to pay $8 for headphones to access the JetBlue entertainment was disappointing. Those earbud jacks are not used with most technology and would not be able to be used. There was no option to use Bluetooth for my own earbuds. Beyond those inconveniences, the flight was good.

My original flight was cancelled. My replacement flight was delayed over 2 hours. I lost my whole day in NY

Delays were crazy long (over an hour) both for boarding and baggage claim

awful expereince. boarding was a mess and not communicated, then we sat on a hot plane and were at risk of getting kicked off

2 hour delay and a lack of air conditioning on the plane. Not a good combination

Fabulous! This was the first time we've flown with JetBlue and the entire experience was flawless!

First time flying JetBlue and my perception changed. Love it.

Poor, had a 5+ hours delay. Kept sitting in the aircraft with three kids. It was terrible

I got to the airport and the airline told me i did not have a flight. I never got a confirmation email yet I did get charged. Please refund my money asap

Was charged for ticket, unable to check in online, made the line to speak to someone at the counter but was told I did not show up in the system as having a ticket to fly - even though I have the email with confirmation and credit card was charged. I could not purchase another ticket at the counter, only online which was not working. Ended up buying a flight on another airline at the airport. Called customer service to claim the cost of the original ticket, was told I showed up in their system as having a ticket but did not check-in or show up to board the flight. Currently pending review for refund via their customer service team, they were very nice and helpful over the phone despite the many glitches.

Awful. Not water, or chargers or space under the seats, the plane was very old and poor maintenance, seats really dirty, sticky, seats pockets with wires pinching your knees. Connection with no announcements, plane departed 1.30 hour earlier for an extra stop to refueling in Trinidad & Tobago. Even that we had a 3 hrs delay, seated in the plane in the runway.

Really bad. Uncommunicated stop in Trinidad & Tobago for refueling. Extra stop added 3 hours of discomfort without allowing off the seat. Not even water, or chargers or boarding groups.

Staff were unfriendly and rude. Was stuck on runway for 2 hours after arrival in Boston.

Horrible service. No communication from the crew as to why a 6 hour delay then cancellation

We waited in an overcrowded bus for over a half hour. It was uncomfortable. It would have been better to have waited in the terminal in a line

I paid extra for a comfortable seat in the second flight, but the plane didn't have those seats, the first one did

The Arajet person who greeted us initially was unhelpful & rude about the mandatory migration form which has to be completed digitally but the systems don’t work properly. The boarding gate was changed twice and initial boarding was delayed. Once on board we we had to wait an hour and a half before take off. It was hot and there was very little room for tall-ish people to fit their knees in. The crew were pleasant but working in a poor situation. The plane was delayed because we were waiting for people from a delayed interconnecting flight. Arajet must have known that before we were asked to board. Better information, decisions & communication were needed.

My seat was broken and the crew had to find me somewhere else to sit. The crew was extremely courteous about this

During the flight I suddenly felt very sick, and no one from the crew even tried to help me or check on my condition. They seemed completely indifferent and showed no concern for my well-being. I was very disappointed by the lack of care and compassion. I hope the airline improves its customer service and trains its crew to respond better when passengers need assistance.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

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

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

More options for your flight to Caribbean

Complete your trip to Caribbean with a hotel stay or car rental