Find cheap flights from Toledo to Caribbean Islands

Find cheap flights from Toledo to Caribbean Islands

Round-trip
Economy
Toledo (TOL)
Caribbean Islands
Mon 10/26
Mon 11/2
Any month
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Good to know

Low season

February Best time to beat the crowds with an average 6% drop in price.

High season

March Most popular time to fly with an average 12% increase in price.

Average price of a round-trip

$699 (avg. price over the last 2 weeks)

Good deal for a round-trip

$431 or less

Top tips for finding cheap flights to Caribbean Islands

  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be November and December. The cheapest month to fly to Caribbean Islands is January.
  • Morning departure is around 514% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs - booking Caribbean Islands flights

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

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

What is the Hacker Fare option on flights to Caribbean Islands?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Caribbean Islands?

Top airline flying Toledo Express to Caribbean Islands

Scores according to KAYAK customer reviews

7.2
American Airlines
Overall score based on 44,781 reviews
7.5
Boarding
7.1
Comfort
7.8
Crew
6.8
Entertainment
6.7
Food
Airline reviews

Cons: "Almost 4 hour delay."

Pros: "Crew was snappy in getting people in plane and checking in carry ons since occupancy had been reached."
Cons: "Lack of adjustable headrest on seat."

Pros: "Crew helped us find new seats on board."
Cons: "American Airlines changed our seats after ticket purchase so that we were not sitting together. We chose seats at check-in in San Francisco so that we could sit together. When we landed in Miami we discovered our seats had been changed yet again and we were seated in different rows, middle seat!"

Pros: "Smooth ride"

Cons: "Feeling of being cramped"

Cons: "Crampt space, cold cabin"

Pros: "Service"
Cons: "Seats and space"

Pros: "Turkey sandwich snd boarding went smoothly"
Cons: "There was no entertainment and since there is no WiFi for most of the flight due to being over water the flight seemed longer than what it actually was."

Cons: "Poor service"

Pros: "I loved everything. No complaints. American airlines is one of the best airlines I have flown with."

Pros: "I liked that we got to San Juan safely. The crew on board was very accommodating."
Cons: "Due to the delays, we missed our jumper flight and American refused to compensate. Also, only had two cookies all day from 8:05am until 3:45 pm! No sandwiches as promised. We were delayed approximately 4 hours total. Had to take a taxi ($85) to Fajardo to HOPEFULLY catch last ferry to Culebra. Guess AmericansAirlines doesn’t care if you have to sleep at the dock!"

Cons: "Dallas to San Juan San Juan Dallas American Airlines has the worst seat of any airline flown by us fare almost 2000 dollars for round trip and the seat is small hard uncomfortable even for a short flight this is no business class!!"

Pros: "On time"
Cons: "Cold cabin"

Cons: "The seats are very tight."

Cons: "Last minute cancellation and reschedule if original flight with 20 people hounding the gate for standby status. Craziness. These last minute revisions mist stop"

Pros: "Direct flight"
Cons: "Horrible customer service, excessive baggage fees, rude counter staff, no leg room, narrow seats"

Pros: "USB Outlets are nice to have"
Cons: "Nothing was bad on this flight"

Pros: "Boarding process"
Cons: "Delay, no food,"

Pros: "Schedule was punctual. The entertainment was superb. Good crew. The overhead bins were, for some reason, larger which aided the boarding process."
Cons: "I guess the lack of snack options but that is just the way it is nowadays."

Pros: "Really glad this segment exists!"

Pros: "Can't think of anything good"
Cons: "SEE: Customer Relations request #1-249830721"

Pros: "Nice crew clean airplane"
Cons: "Initial flight was cancelled after 2 hours delay. My next flight was scheduled the earliest possible by AA which was 24 hours later. No transportation,hotel or miles compensation for this. I had work and responsabilities the next day. TThe scheduled trip was supposed to take off at 7:45. Boarding started late and was very slow. My bag fit the meassurements and still was forced to check it (which I did not want to do as I did not want to be waiting an hour for my bag at my arrival as I had work early the next day. In addition there was airplaine traffic as it was "rush hour" instead of flying at 7:45 we departed almost at 9pm!!!! Have to pay for food Quality of tv monitors very poor And in an uncomfortable position No movie options No wifi although stated the aircraft has Non functioning electrical plug"

Pros: "Nothing"
Cons: "Never made it to San Juan to catch my cruise. To top things off I was a ship for two days without my luggage and underwears. Never again!!! Thank you JetBlue!!!"

Cons: "That all the passengers were rechecked at the Gate by TSA without offering any explanation as to why, if it was a domestic flight, why were they requiring ID again. And checking bags."

Pros: "On time smooth"

Pros: "The pilot was a riot, the flight was on time. Again, nothing wrong, nothing special. As it should be (if only we had more leg and seat room, and I am pretty streamline)."

Pros: "Friendly staff. Landed early. Offered a free bag."
Cons: "They moved the flight earlier, which was not fun. And, there were no entertainment centers."

Pros: "Nothing"
Cons: "Super old planes, no had a tv."

Pros: "Puntuality"

Pros: "Crew was good."
Cons: "The television was in the aisle and couldn't be properly seen. Also there was no outlet charger. During boarding, even thou they called by group number, the crew allowed a queue in the front, making it confusing who was in line and who wasn't. Better wait till the end to board that get in that mess"

Cons: "There seets are two small. And they dont sell alcohol. That sucks."

Cons: "The airline had trouble with the plane. After we waited 3 hrs in the plane they cancel the flight. They offer a hotel but it was very dirty"

Pros: "Nothing. My fight from San Juan to Miami on Friday Oct. 7 was cancelled because of hurricane Matthews, since I didnot buy a roundtrip with AA they did not reimburse or offer me a credit for my returning flight. I contacted AA in two ocassions and both times their personnel were impersonal and even rude to me with the whole situation. I ended up losing $250 because of choosing American Airlines. I will do my best to avoid traveling with American ever again, and I will spread the word, as well. I felt robbed, so unfair."
Cons: "Everything"

Pros: "Friendly polite staff. Plane left and arrived on time."

Cons: "No have owned screen TV"

Pros: "Even when the plane was full they managed to help passengers to get seated."
Cons: "If you still flying economy class, why would you have to pay extra for exit row where the seats are the same. Only received pretzel and a cup of drink on a 3 hour flight once."

Pros: "Everything"
Cons: "Nothing"

Pros: "Comfortable seat"
Cons: "Lack of entertainment"

Cons: "One hour delay sitting inside the plane with no pilot!! And to top it off, the air conditioner was off!! Will never fly American ever again."

Pros: "Overall good flight"
Cons: "I did not like the time needed for boarding/ settling in. But that is a factor of people not following instructions. Not the crew."

Cons: "Terrible airport assistance, many unnecessary customs checks, uncomfortable seats, on flight bad service and late flight times."

Pros: "I was going home"
Cons: "Late flight no pilots andt broke my luggage."

Cons: "I didn't like the American airline people who checked my bag. She threw it because I told her nothing was breakable in it."

Cons: "Gg"

Pros: "Everything was on time, no delays."

Pros: "Should have individual tv's like jet blue does. There shoul be a family travel area for people travelin with todlers. better service and better food. Faster luggage pick up."
Cons: "Nothing. Expesive flights, an unprofessional flight attendant name Sarah, fighting with the customers. No entertainment. It was a nightmare"

Pros: "I live the service which make me feel good. Also the flight was very quiet and the crew help me in everything I asked."

Pros: "The great atendance and on time bording"
Cons: "There is no More options of free food included with the ticket fly and it was a longer flight and there wasn't no tv, no entertament"

Pros: "My window seat was all."
Cons: "I didn't get a call about the delay like other passengers, only an email at 7am as I was in line to check in for the 8:25am flight 395. The female crew members, a dark haired woman and a short blond haired woman both would have ignored me if the other two people seated by me did not also try to get their attention. The dark haired woman gave the guy next to me headphones and when I held out my hand she just looked at me and walked away as if she'd been called away. Which she hadn't she came back and started with the row immediately behind us and the guy next to me was nice enough to give me his. Also after nearly waiting 4 hours, 9 minutes before boarding we were given food vouchers and told to "run and hurry" and get food "to go" so most people didn't even bother using the vouchers because of that. I've had better flights with American Airlines, I just didn't know this one would be so poor. Definitely way below average expectations."

Read more about American Airlines
COVID-19 information

Safety measures for airlines flying from Toledo to Caribbean Islands

Airlines flying from Toledo to Caribbean Islands have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters

Mandatory masks

Masks required on board, masks provided

Social distancing seating

Middle seats unavailable to book

Pre-flight testing

Testing for antibodies, testing for symptoms

Book cheap flights from Toledo to Caribbean Islands

Recent round-trip flight deals

2/1
Mon
2 stops
American Airlines
23h 29m
TOL - SJU
2/3
Wed
2 stops
American Airlines
20h 22m
SJU - TOL
11/14
Sat
3 stops
Multiple Airlines
35h 49m
TOL - SJU
11/22
Sun
3 stops
Multiple Airlines
27h 46m
SJU - TOL
11/5
Thu
2 stops
American Airlines
13h 02m
TOL - SJU
11/6
Fri
2 stops
American Airlines
32h 04m
SJU - TOL
11/5
Thu
2 stops
American Airlines
11h 46m
TOL - SJU
11/6
Fri
2 stops
American Airlines
26h 10m
SJU - TOL
11/14
Sat
2 stops
American Airlines
17h 24m
TOL - SJU
11/22
Sun
2 stops
American Airlines
15h 09m
SJU - TOL
11/14
Sat
2 stops
American Airlines
15h 00m
TOL - SJU
11/22
Sun
1 stop
American Airlines
31h 29m
SJU - TOL
11/14
Sat
3 stops
Multiple Airlines
30h 59m
TOL - SJU
11/22
Sun
3 stops
Multiple Airlines
27h 46m
SJU - TOL
11/14
Sat
2 stops
American Airlines
15h 00m
TOL - SJU
11/22
Sun
2 stops
American Airlines
17h 27m
SJU - TOL
11/14
Sat
1 stop
American Airlines
19h 44m
TOL - SJU
11/22
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American Airlines
30h 01m
SJU - TOL
10/30
Fri
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American Airlines
9h 40m
TOL - SJU
11/1
Sun
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American Airlines
8h 13m
SJU - TOL
1/28
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American Airlines
14h 24m
TOL - POS
1/30
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American Airlines
29h 20m
POS - TOL
2/13
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American Airlines
23h 19m
TOL - PUJ
2/20
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American Airlines
7h 59m
PUJ - TOL
2/13
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American Airlines
23h 19m
TOL - PUJ
2/20
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American Airlines
10h 38m
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American Airlines
19h 09m
TOL - PUJ
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American Airlines
10h 38m
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American Airlines
23h 19m
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3/1
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American Airlines
21h 58m
PUJ - TOL
2/25
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American Airlines
23h 18m
TOL - PUJ
3/1
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American Airlines
26h 11m
PUJ - TOL
2/25
Thu
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American Airlines
26h 30m
TOL - PAP
3/1
Mon
2 stops
American Airlines
14h 05m
PAP - TOL
11/5
Thu
1 stop
American Airlines
6h 59m
TOL - SJU
11/6
Fri
1 stop
American Airlines
7h 29m
SJU - TOL
12/3
Thu
2 stops
American Airlines
21h 50m
TOL - FPO
12/6
Sun
2 stops
American Airlines
34h 39m
FPO - TOL
2/2
Tue
2 stops
American Airlines
13h 41m
TOL - CUR
2/16
Tue
2 stops
American Airlines
15h 07m
CUR - TOL
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Recent one-way flight deals

12/1
Tue
2 stops
American Airlines
21h 34m
TOL - SJU
12/1
Tue
1 stop
American Airlines
6h 23m
TOL - SJU

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