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$61 Find cheap flights from Chicago to Caribbean Islands

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 Islands 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
Sat 7/13
Sat 7/20

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Best Caribbean Islands Flight Deals

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

Punta Cana
Punta Cananonstop$206
Montego Bay
Montego Bay1 stop$259
Santo Domingo
Santo Domingo1 stop$235
Oranjestad
Oranjestad1 stop$291
Nassau
Nassau1 stop$303
Kingston
Kingston1 stop$351
Simpson Bay
Simpson Bay1 stop$240
Providenciales
Providenciales1 stop$317
George Town
George Town1 stop$298
Aguadilla
Aguadilla1 stop$258
St. John's
St. John's1 stop$614

Good to know

Low season

September

High season

March

Cheapest flight

$61
Best time to beat the crowds with an average 10% 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 Islands flights

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

    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 Islands.

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

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

    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 Islands 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 Islands?

    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 Islands 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 5 airlines serving from Chicago to Caribbean Islands

Need help choosing which airline to fly with from Chicago to Caribbean Islands? 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
8.0Entertainment
8.2Boarding
8.6Crew
7.4Food
Airline reviews

It was very cold because the air conditioner was on high power, and my son got sick.

4.0 OkayAnonymous, Jun 2024ORD - SEA
Read more about Delta reviews

It was very cold because the air conditioner was on high power, and my son got sick.

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.

The baggage handlers broke the handle on my bag that they put under the plane that I checked on the jetway. They traded it out for a less quality bag in Tulsa. But, they said they would try to fix it. Bologna! There was no fixing that bag handle. Someone didn’t care how they treated the bag.

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.

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.

The bag drop process took longer than other airlines. The boarding and crew were good. The seats do not recline and have minimal padding. The snacks/drinks are for purchase only. The flight was on time with no issues. I would fly them again if the cost was significantly less.

Crew was excellent. Flight was overbooked No seat assignment until the last moment.

My flight was delayed then cancelled My elder parents were upstairs waiting for a spirit rep to bring them downstairs to where my sister waited for 2 hours. My elder parents are not able to walk . My dad was wet of urine from where he could not hold it .waiting for some spirit personnel to wheel chair them back down stairs to where my sister was waiting for them for two hours . That is not ok

Poor response to delay, getting on plane, off plane and back on again

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.

Online check-in was not user-friendly. Too many fees, not cost effective.

They wouldn’t let us on the flight even tho we were an hour early. No refund not even our bags that were prepaid

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.

I did not enjoy the trip home on Frontier for several reasons: there is too much cost besides the flight, which was more than I would normally pay, then having to pay for luggage, and carry-on, seat (if you want to reserve when booking) then you must pay over $3 for a can of soda, and $4 for a snack. A cup of water is free.

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.

Book cheap flights from Chicago to Caribbean Islands

Recent round-trip flight deals

9/10Tue
1 stopSpirit Airlines
6h 45mORD-SJU
9/11Wed
1 stopSpirit Airlines
15h 16mSJU-ORD
$131
9/10Tue
1 stopSpirit Airlines
6h 45mORD-SJU
9/11Wed
nonstopSpirit Airlines
4h 59mSJU-ORD
$136
7/16Tue
1 stopFrontier
11h 36mMDW-SJU
7/23Tue
1 stopFrontier
8h 18mSJU-MDW
$160
7/9Tue
1 stopFrontier
9h 10mORD-SJU
7/16Tue
1 stopFrontier
15h 43mSJU-ORD
$165
12/7Sat
1 stopAmerican Airlines
17h 22mORD-MBJ
12/12Thu
nonstopAmerican Airlines
4h 35mMBJ-ORD
$298
8/16Fri
1 stopAmerican Airlines
7h 24mORD-PUJ
8/23Fri
1 stopAmerican Airlines
8h 09mPUJ-ORD
$300
8/15Thu
1 stopUnited Airlines
8h 06mORD-PLS
8/18Sun
1 stopUnited Airlines
10h 03mPLS-ORD
$317
10/1Tue
1 stopUnited Airlines
6h 31mORD-NAS
10/5Sat
1 stopUnited Airlines
7h 32mNAS-ORD
$327
10/22Tue
1 stopDelta
10h 52mMDW-SJU
10/31Thu
1 stopDelta
8h 19mSJU-MDW
$344
7/16Tue
1 stopDelta
6h 26mORD-NAS
7/24Wed
2 stopsDelta
17h 10mNAS-ORD
$366

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Recent one-way flight deals

9/11Wed
1 stopSpirit Airlines
6h 45mORD-SJU
$61
7/16Tue
1 stopSpirit Airlines
10h 36mORD-SJU
$68
7/10Wed
1 stopFrontier
16h 41mMDW-SJU
$80
7/10Wed
1 stopFrontier
16h 41mMDW-SJU
$82
7/1Mon
1 stopAmerican Airlines
15h 45mORD-NAS
$122
10/21Mon
nonstopAmerican Airlines
3h 56mORD-MBJ
$127
8/12Mon
nonstopUnited Airlines
4h 36mORD-PUJ
$137
10/25Fri
1 stopDelta
10h 52mMDW-SJU
$195
7/13Sat
nonstopUnited Airlines
4h 47mORD-SJU
$203
8/31Sat
2 stopsDelta
18h 04mMDW-PUJ
$211

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Last minute flights from Chicago to Caribbean Islands

Last minute flight, train and bus deals

6/18Tue
multi-stopFrontier
6h 32mMDW-SJU
6/21Fri
multi-stopFrontier
12h 53mSJU-MDW
$201
6/18Tue
multi-stopFrontier
11h 33mMDW-SJU
6/22Sat
multi-stopFrontier
7h 23mSJU-MDW
$207
6/17Mon
multi-stopSpirit Airlines
16h 01mORD-SJU
6/26Wed
multi-stopSpirit Airlines
13h 55mSJU-ORD
$235
6/17Mon
multi-stopSpirit Airlines
16h 01mORD-SJU
6/20Thu
multi-stopSpirit Airlines
12h 49mSJU-ORD
$240
6/15Sat
multi-stopAmerican Airlines
15h 33mORD-SJU
6/17Mon
multi-stopAmerican Airlines
7h 15mSJU-ORD
$345
6/14Fri
multi-stopAmerican Airlines
14h 33mORD-SJU
6/16Sun
multi-stopAmerican Airlines
11h 24mSJU-ORD
$375
6/15Sat
nonstopUnited Airlines
4h 00mORD-MBJ
6/19Wed
multi-stopUnited Airlines
10h 23mMBJ-ORD
$576
6/16Sun
nonstopUnited Airlines
4h 00mORD-MBJ
6/26Wed
multi-stopUnited Airlines
8h 58mMBJ-ORD
$623
6/14Fri
multi-stopDelta
7h 40mORD-NAS
6/18Tue
multi-stopDelta
7h 51mNAS-ORD
$667
6/14Fri
multi-stopDelta
15h 25mORD-NAS
6/18Tue
multi-stopDelta
7h 51mNAS-ORD
$672

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