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Find cheap flights from Chicago to Caribbean from $63

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 6/11. 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.
1 adult
0 bags
Mon 6/10
Mon 6/17

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Best Caribbean Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cananonstop$221
Montego Bay
Montego Bay1 stop$259
Santo Domingo
Santo Domingo1 stop$218
Oranjestad
Oranjestad1 stop$264
Nassau
Nassau1 stop$346
Kingston
Kingston1 stop$354
Simpson Bay
Simpson Bay1 stop$242
Providenciales
Providenciales1 stop$453
George Town
George Town1 stop$464
Aguadilla
Aguadilla1 stop$236
St. John's
St. John's1 stop$534

Good to know

Low season

September

High season

March

Cheapest flight

$63
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 16% 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 to Caribbean from Chicago 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 to Caribbean with an airline and back to Chicago 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 to Caribbean from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Caribbean

  • Morning departure is around 15% more expensive than an evening flight, on average*.
  • 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.
See more tips
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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 10751 reviews
7.4Food
8.6Crew
8.2Boarding
8.0Entertainment
7.9Comfort
Airline reviews

Boarding was chaotic. I didn’t finish dinner because I went to bed early. Breakfast omelet was overcooked and tasteless but croissant was better than usual. Plane was dirty—crumbs in every seam and lavatory was poorly maintained (paint peeling, etc.) and toilet paper had not been refreshed before takeoff. No cubby for storage in first and seat was narrow.

4.0 OkayPatricia, May 2024DTW - CDG
Read more about Delta reviews

Boarding was chaotic. I didn’t finish dinner because I went to bed early. Breakfast omelet was overcooked and tasteless but croissant was better than usual. Plane was dirty—crumbs in every seam and lavatory was poorly maintained (paint peeling, etc.) and toilet paper had not been refreshed before takeoff. No cubby for storage in first and seat was narrow.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight delayed then canceled! I will NEVER fly Spirit Airlines again and will tell all my friends!

Absolutely terrible. The boarding process had zero organization. Mobs of people trying to board. People were climbing over my child's stroller with her in it. No families were boarded first. Boarding was delayed with no reasoning or notification that it would be late. We were then stuck on the plane for 45 minutes after landing. Then waited over two hours for our luggage. There was zero communication with the travelers. Never have I experienced such I professionalism and disgrace of others. Extremely disappointed.

For it to have left on time! Instead of two hours early with zero notice

Flight kept delayed from morning to late afternoon so I had to make other arrangements

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.

Terrible… missed our flight due to ridiculously long time to go thru baggage check-in!

The crew was not great or professional. It seemed like they didn't really want to be there. A true lack of effort for accommodating customers.

Everything was really good but the seats are not very comfortable.

I paid for WiFi, but it (WiFi) was very very slow, will never take again! Impossible open Utube 😤😤😤

I had no legroom, although I paid for extra legroom. I could barely put my bag in front of my feet and under the seat. The Wi-Fi was horrible. In fact the flight attendant said that they had to reboot it and see if it was going to work and never did.

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Book cheap flights from Chicago to Caribbean

Recent round-trip flight deals

5/21Tue
1 stopSpirit Airlines
8h 00mORD-SJU
5/28Tue
1 stopSpirit Airlines
21h 33mSJU-ORD
$104
5/21Tue
1 stopSpirit Airlines
8h 00mORD-SJU
5/28Tue
2 stopsSpirit Airlines
22h 16mSJU-ORD
$118
6/6Thu
1 stopFrontier
11h 32mMDW-SJU
6/14Fri
1 stopFrontier
12h 53mSJU-MDW
$218
6/6Thu
1 stopFrontier
11h 32mMDW-SJU
6/12Wed
1 stopFrontier
12h 16mSJU-MDW
$219
5/13Mon
nonstopAmerican Airlines
4h 35mORD-PUJ
5/16Thu
nonstopAmerican Airlines
5h 05mPUJ-ORD
$371
5/13Mon
1 stopAmerican Airlines
9h 05mORD-PUJ
5/16Thu
nonstopAmerican Airlines
5h 05mPUJ-ORD
$374
9/1Sun
1 stopDelta
8h 03mMDW-PUJ
9/5Thu
1 stopDelta
9h 37mPUJ-MDW
$435
7/6Sat
nonstopUnited Airlines
4h 00mORD-MBJ
7/13Sat
nonstopUnited Airlines
4h 24mMBJ-ORD
$437
8/23Fri
1 stopDelta
15h 54mMDW-PUJ
8/28Wed
2 stopsDelta
19h 01mPUJ-MDW
$440
7/24Wed
1 stopUnited Airlines
6h 13mORD-PLS
7/28Sun
1 stopUnited Airlines
15h 25mPLS-ORD
$482

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Recent one-way flight deals

6/11Tue
1 stopSpirit Airlines
10h 29mORD-SJU
$63
9/18Wed
1 stopSpirit Airlines
13h 11mORD-SJU
$64
7/1Mon
nonstopFrontier
4h 39mORD-PUJ
$82
7/29Mon
nonstopFrontier
4h 41mORD-PUJ
$86
6/20Thu
1 stopAmerican Airlines
8h 15mORD-SJU
$112
7/20Sat
1 stopAmerican Airlines
17h 38mORD-SJU
$137
5/25Sat
nonstopUnited Airlines
4h 47mORD-SJU
$189
8/31Sat
1 stopDelta
16h 29mMDW-PUJ
$206
10/5Sat
2 stopsDelta
17h 32mMDW-MBJ
$211
8/8Thu
nonstopUnited Airlines
4h 36mORD-PUJ
$270

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Last minute flights from Chicago to Caribbean

Last minute flight, train and bus deals

5/12Sun
nonstopFrontier
4h 41mORD-PUJ
5/15Wed
nonstopFrontier
5h 29mPUJ-ORD
$179
5/13Mon
nonstopFrontier
4h 41mORD-PUJ
5/16Thu
nonstopFrontier
5h 14mPUJ-ORD
$190
5/13Mon
nonstopSpirit Airlines
4h 53mORD-SJU
5/20Mon
multi-stopSpirit Airlines
13h 48mSJU-ORD
$192
5/14Tue
nonstopSpirit Airlines
4h 53mORD-SJU
5/16Thu
nonstopSpirit Airlines
5h 10mSJU-ORD
$217
5/12Sun
nonstopAmerican Airlines
4h 40mORD-SJU
5/14Tue
multi-stopAmerican Airlines
7h 04mSJU-ORD
$260
5/14Tue
nonstopAmerican Airlines
4h 40mORD-SJU
5/15Wed
multi-stopAmerican Airlines
10h 40mSJU-ORD
$262
5/12Sun
multi-stopUnited Airlines
8h 42mORD-SJU
5/15Wed
multi-stopUnited Airlines
7h 35mSJU-ORD
$286
5/12Sun
multi-stopUnited Airlines
8h 25mORD-PUJ
5/15Wed
multi-stopUnited Airlines
10h 52mPUJ-ORD
$318
5/11Sat
multi-stopDelta
17h 15mORD-PUJ
5/14Tue
multi-stopDelta
17h 50mPUJ-ORD
$440
5/12Sun
multi-stopDelta
13h 56mORD-PUJ
5/15Wed
multi-stopDelta
16h 15mPUJ-ORD
$460

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