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$61 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 9/11. 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
Fri 7/12
Fri 7/19

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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 Cana1 stop$222
Montego Bay
Montego Bay1 stop$254
Santo Domingo
Santo Domingo1 stop$255
Oranjestad
Oranjestad1 stop$290
Nassau
Nassau1 stop$303
Kingston
Kingston1 stop$388
Simpson Bay
Simpson Bay1 stop$240
Providenciales
Providenciales1 stop$322
George Town
George Town1 stop$298
Aguadilla
Aguadilla1 stop$262
St. John's
St. John's2 stops$586

Good to know

Low season

September

High season

March

Cheapest flight

$61
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 15% 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 6% 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 10000 reviews
7.9Comfort
8.6Crew
7.4Food
8.2Boarding
8.0Entertainment
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

Standard flight experience, but there is only power at the seat to row 20 on the aircraft, on my initial check in it did not say that was the case

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

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?

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

Original flight delayed several times and finally canceled at 2:30 in the morning. Staff at the gate was not very helpful in resolving problems or communicating why there were delays. I spent 34 hours at the airport before I could leave, they couldn't book me on another early flight even after canceling my original flight. Next flight available after my original flight was canceled was 22 hours later. I will never fly American Airlines again.

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.

My flight was uncomfortable and crammed. There were no pockets to store things, I couldn’t move my seat back slightly. Beverages including soda cost extra. My husband flew on another spirit airline flight, which was delayed a total of 48 hours, only to be canceled.

Two delays in less than 24hrs. They need to improve everything and restructure the whole company.

Terrible leg room, seats don’t recline, delayed flight, and even water isn’t free onboard

Flight was canceled less than 6 hours before takeoff, rebooked on a flight that was twice as long and left earlier so we couldn’t make it, when using text support option took over 2 hours to speak with someone.

Not enough help at airport during boarding process. Flight was delayed. Overall WORST flying experience I’ve ever had. Will NEVER FLT SPIRIT AGAIN

Terrible legroom, seats do not recline, tray table the size of an iPhone, delayed flight, have to pay 5$ to get a cup of water onboard.

Could have TV/Movie and some water ou soda free

Flight was good and clean but delayed over an hour on the return flight.

The non stop flight and able to go into Atlantic City airport. They could lower the prices. It starts out low but then if you want to bring luggage and pick your seat the price goes up quite a bit.

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

Did not realize seats did not recline. Best to travel in an exit row... No question

I strongly dislike Frontier. I find them barebones, the seats not particularly comfortable, the nickel and diming is maddening, the app is TERRIBLE - super confusing to navigate, and the last 4 frontier flights I have flown have been on AVERAGE 2 hours late, one ruining a fancy night out in Vegas with reservations made well in advance, which was nodded to with a measly 5000 miles, which translates to almost nothing. At least credit a free checked bag or something.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

Book cheap flights from Chicago to Caribbean

Recent round-trip flight deals

9/10Tue
1 stopSpirit Airlines
29h 15mORD-SJU
9/11Wed
1 stopSpirit Airlines
22h 07mSJU-ORD
$106
9/10Tue
1 stopSpirit Airlines
29h 15mORD-SJU
9/11Wed
2 stopsSpirit Airlines
25h 20mSJU-ORD
$127
7/9Tue
1 stopFrontier
9h 10mORD-SJU
7/16Tue
1 stopFrontier
15h 43mSJU-ORD
$160
7/9Tue
1 stopFrontier
6h 35mMDW-SJU
7/16Tue
1 stopFrontier
10h 23mSJU-MDW
$160
9/10Tue
2 stopsAmerican Airlines
8h 48mORD-SJU
9/18Wed
2 stopsAmerican Airlines
9h 01mSJU-ORD
$286
8/18Sun
nonstopAmerican Airlines
4h 00mORD-MBJ
8/23Fri
nonstopAmerican Airlines
4h 35mMBJ-ORD
$293
7/9Tue
1 stopDelta
9h 48mORD-NAS
7/17Wed
1 stopDelta
7h 48mNAS-ORD
$351
7/15Mon
2 stopsDelta
15h 35mORD-NAS
7/23Tue
2 stopsDelta
17h 10mNAS-ORD
$356
11/17Sun
nonstopUnited Airlines
4h 07mORD-PLS
11/22Fri
nonstopUnited Airlines
4h 38mPLS-ORD
$443
7/30Tue
1 stopUnited Airlines
15h 34mORD-NAS
8/8Thu
1 stopUnited Airlines
10h 20mNAS-ORD
$487

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Recent one-way flight deals

9/11Wed
1 stopSpirit Airlines
6h 45mORD-SJU
$61
6/18Tue
1 stopFrontier
6h 32mMDW-SJU
$66
9/7Sat
2 stopsAmerican Airlines
8h 25mORD-NAS
$98
6/25Tue
1 stopAmerican Airlines
5h 30mORD-NAS
$122
7/23Tue
2 stopsDelta
8h 38mORD-NAS
$127
8/8Thu
1 stopJetBlue
6h 14mORD-NAS
$132
6/25Tue
2 stopsDelta
15h 25mORD-NAS
$133
8/11Sun
nonstopUnited Airlines
4h 36mORD-PUJ
$143
8/6Tue
nonstopUnited Airlines
4h 36mORD-PUJ
$177
7/23Tue
1 stopJetBlue
14h 15mORD-PLS
$178

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Last minute flights from Chicago to Caribbean

Last minute flight, train and bus deals

6/17Mon
multi-stopSpirit Airlines
16h 01mORD-SJU
7/17Wed
multi-stopSpirit Airlines
7h 05mSJU-ORD
$215
6/17Mon
multi-stopSpirit Airlines
16h 01mORD-SJU
7/17Wed
nonstopSpirit Airlines
5h 09mSJU-ORD
$220
6/17Mon
multi-stopFrontier
7h 45mMDW-SJU
6/19Wed
multi-stopFrontier
14h 26mSJU-MDW
$231
6/17Mon
multi-stopFrontier
7h 45mMDW-SJU
6/19Wed
multi-stopFrontier
12h 16mSJU-MDW
$243
6/15Sat
multi-stopAmerican Airlines
13h 49mORD-SJU
6/17Mon
multi-stopAmerican Airlines
17h 34mSJU-ORD
$345
6/14Fri
multi-stopAmerican Airlines
12h 34mORD-SJU
6/16Sun
multi-stopAmerican Airlines
13h 35mSJU-ORD
$375
6/15Sat
nonstopUnited Airlines
4h 47mORD-SJU
6/24Mon
nonstopUnited Airlines
5h 11mSJU-ORD
$466
6/14Fri
nonstopUnited Airlines
4h 00mORD-MBJ
6/16Sun
nonstopUnited Airlines
4h 24mMBJ-ORD
$616
6/14Fri
multi-stopDelta
8h 52mORD-NAS
6/18Tue
multi-stopDelta
16h 45mNAS-ORD
$662
6/17Mon
multi-stopDelta
17h 07mORD-PLS
6/20Thu
multi-stopDelta
17h 30mPLS-ORD
$877

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