$93 Find Cheap Flights from Chicago to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Caribbean departing on 8/23. 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.
1 adult
1 adult, Economy

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Flights Deals

Best Caribbean Flight Deals from Chicago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cananonstop$238
Santo Domingo
Santo Domingo1 stop$333
Montego Bay
Montego Bay1 stop$308
Oranjestad
Oranjestad1 stop$328
Nassau
Nassau1 stop$417
Kingston
Kingston1 stop$329
Simpson Bay
Simpson Bay1 stop$313
Providenciales
Providenciales1 stop$457
George Town
George Town1 stop$467
St. John's
St. John's1 stop$594
Aguadilla
Aguadilla1 stop$230
Punta Cana
Punta Cananonstop$238
Santo Domingo
Santo Domingo1 stop$333
Montego Bay
Montego Bay1 stop$308
Oranjestad
Oranjestad1 stop$328
Nassau
Nassau1 stop$417
Kingston
Kingston1 stop$329
Simpson Bay
Simpson Bay1 stop$313
Providenciales
Providenciales1 stop$457
George Town
George Town1 stop$467
St. John's
St. John's1 stop$594
Aguadilla
Aguadilla1 stop$230

Cheap Flights from Chicago to Caribbean

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Caribbean

Sat, Aug 30 - Fri, Sep 5
Frontier Logo
7:46 pm - 8:59 amORD-SJU
12h 13m1 stop
Frontier Logo
3:40 am - 2:53 pmSJU-ORD
12h 13m1 stop
$185Frontier
Find Deal
Sat, Aug 30 - Fri, Sep 5
Frontier Logo
10:51 am - 8:59 amMDW-SJU
21h 08m1 stop
Frontier Logo
3:40 am - 11:56 amSJU-MDW
9h 16m1 stop
$185Frontier
Find Deal
Tue, Jul 8 - Tue, Jul 15
Spirit Airlines Logo
10:43 am - 12:05 amORD-SJU
12h 22m1 stop
Spirit Airlines Logo
4:43 pm - 7:04 amSJU-ORD
15h 21m1 stop
$207Spirit Airlines
Find Deal
Tue, Jul 8 - Tue, Jul 15
Spirit Airlines Logo
10:43 am - 12:05 amORD-SJU
12h 22m1 stop
Spirit Airlines Logo
4:43 pm - 7:04 amSJU-ORD
15h 21m1 stop
$214Spirit Airlines
Find Deal
Sat, Aug 9 - Sat, Aug 16
American Airlines Logo
4:56 pm - 11:05 amORD-PUJ
17h 09m1 stop
American Airlines Logo
3:25 pm - 7:25 amPUJ-ORD
17h 00m1 stop
$275American Airlines
Find Deal
Mon, Jul 14 - Tue, Jul 22
American Airlines Logo
8:45 pm - 3:50 pmORD-PUJ
18h 05m1 stop
American Airlines Logo
12:05 pm - 11:57 pmPUJ-ORD
12h 52m1 stop
$276American Airlines
Find Deal
Tue, Jul 1 - Mon, Jul 7
United Airlines Logo
6:03 pm - 11:54 pmORD-SJU
4h 51mnonstop
United Airlines Logo
1:10 am - 10:53 amSJU-ORD
10h 43m1 stop
$308United Airlines
Find Deal
Tue, Nov 4 - Fri, Nov 14
Delta Logo
10:35 am - 11:21 pmMDW-SJU
10h 46m1 stop
Delta Logo
3:30 pm - 9:44 pmSJU-MDW
8h 14m1 stop
$331Delta
Find Deal
Tue, Jul 8 - Wed, Jul 16
United Airlines Logo
9:23 am - 3:05 pmORD-PUJ
4h 42mnonstop
United Airlines Logo
4:35 pm - 11:30 pmPUJ-ORD
7h 55m1 stop
$333United Airlines
Find Deal
Sun, Nov 9 - Fri, Nov 14
Delta Logo
6:00 am - 2:23 pmORD-PUJ
6h 23m1 stop
Delta Logo
2:03 pm - 9:12 pmPUJ-ORD
9h 09m1 stop
$335Delta
Find Deal
Useful Info

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 price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Caribbean.

The cheapest ticket to Caribbean from Chicago found in the last 72 hours was to San Juan, at $194 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 72 hours was $194.

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

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $1,052 on average.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Caribbean is September, when tickets cost $303 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $566 and $424 respectively.

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

The average price of all round-trip flights from Chicago to Caribbean clicked on KAYAK for each day over the last 12 months.

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

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

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 7 weeks before departure.


Good to know

Low seasonSeptember
High seasonMarch
Cheapest flight$93
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 21% increase in price.
Flight from Chicago O'Hare 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.

  • 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 $300 on average. Morning departures are around 3% 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 $434.

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.

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.
8.0
DeltaOverall score based on 7946 reviews
7.3Food
7.9Entertainment
8.2Boarding
7.9Comfort
8.5Crew
Airline reviews

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

10.0 ExcellentHartaj, Jun 2025EWR - RDU
Read more Delta reviews

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Great flight! Only complaint I had was that I didn’t get breakfast that morning because I don’t eat eggs for breakfast.. I ate an energy bar I bought in the airport which I had never done before. Otherwise, another great Delta flight!

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

Boarding was a breeze, however, two of the flights that I boarded with Spirit did not have Wi-Fi available.

Seats uncomfortable, hard to check luggage, etc. It was like the last flight out of Hanoi

Need screens for tv/movies. Seats are more cramped than any other airlines. Seats are hard. They don’t recline. And in flight time should not be used for sales pitches.

Good experience except for the drunk woman who was with a child. Sad

The ease of booking the flight was very good. Speaking with customer service was also good. However, the crew people are unfriendly and unwelcoming which I found this as unprofessional. As far as comfort it was mediocre. This was my first time flying Spirit and I chose them because of the flight times met my needs and my budget. However, I would be reluctant to fly on Spirit again. In addition, if the crew were more friendly and at least appeared somewhat happy and welcoming personally it would probably make the experience of flying with Spirit better.

Tell them to chose a better, less bumpy route :( my seat had no window all the way at the end 😔

Seats too hard, too much lumbar. Space between rows was extremely tight, so tight hard to place item under seat in front of me. No tv screens. Zero plugs for charging phones. Too many sales pitches

Prepaid for 1 bag but my prior airline did not provide it to me in time to check it with Spirit and I could not get my $75 refunded.

Plane delayed which seems to be the norm with spirt. Everything is an up charge. I had to pay an additional fee because I was late getting back to my car. Will never fly spirit again

It was horrible. We were not allowed on the flight by spirit staff at the gate during boarding because I had a guitar. The same guitar I had at check in which I paid for and they said I can take it on the plane. We missed our flight, lost our luggage, and had to pay another $900 to rebook flights. Worst travel experience ever and spirit staff are the worst staff ever.

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

I never got to experience the flight because they delayed my first flight and I missed this one. Then Frontier didn't want to help me rebook a flight to get me to my final destination.

The Boarding process in Denver was chaotic, and since the line was so long, we were lined up very far from the gate. If there were any announcements from the gate staff, we didn't hear them. The flight attendants were spectacular. The only negative part of the flight was sitting by a 2 1/2 year old who was unruly and unfortunately had parents that matched his behaviors. Also, the restaurants in Denver on the E concourse, they didn't have food (passengers could only order 1 item on the entire menu) or the restaurants had 12-14 people waiting for orders to be prepared and another 6 people waiting to order. If you have a layover in Denver and need to grab food, be prepared to visit the shops with pre-packaged sandwiches, or you can visit another concourse but it may take a while to transit throughout the airport.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

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

I liked the price of the flight and the chance to buy a seat with no person seated in the middle seat.. Also the flight was right on time.

Plane was down graded and I lost my uncharged exit row with more leg room. No mention or offer of refund from podium. Flight attendant was nice to explain this happens often and that I could request a refund via online form submission. I did this and have heard nothing back.

Worst airline experience. They were rude and kept changing our seats and/or giving our seats away so our family didn’t get to sit with each other. Almost everyone we dealt with at both airports with this airline was rude. The app kept giving us wrong information making things take longer. Dealing with them before TSA can take close to an hour…longer than I’ve ever had to deal with before. Never using this airline again.

Everything you need to know for your flight to Caribbean

Cabin class types available on flights to Chicago

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

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