$261 Find Cheap Flights from Medford 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 Medford to Caribbean departing on 5/5. 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, 0 bags

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Flight Deals

Book Cheap Medford to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Medford 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 Medford to Caribbean

Mon, Apr 13 - Fri, Apr 17
American Airlines Logo
2:08 pm - 9:13 am
MFR
-
SJU
16h 05m
2 stops
American Airlines Logo
11:43 am - 11:59 pm
SJU
-
MFR
15h 16m
2 stops
$466American Airlines
Tue, Jun 2 - Tue, Jun 9
American Airlines Logo
6:35 am - 9:59 pm
MFR
-
SJU
12h 24m
2 stops
American Airlines Logo
6:00 am - 9:54 pm
SJU
-
MFR
18h 54m
2 stops
$522American Airlines
Sat, Jun 13 - Wed, Jun 17
Delta Logo
5:34 pm - 12:54 pm
MFR
-
SJU
16h 20m
2 stops
Delta Logo
7:05 am - 11:22 pm
SJU
-
MFR
19h 17m
2 stops
$639Delta
Mon, May 4 - Wed, May 6
United Airlines Logo
2:07 pm - 12:30 pm
MFR
-
GCM
20h 23m
2 stops
United Airlines Logo
1:35 pm - 11:47 am
GCM
-
MFR
24h 12m
2 stops
$654United Airlines
Mon, Apr 13 - Thu, Apr 16
United Airlines Logo
5:00 am - 5:38 pm
MFR
-
SJU
9h 38m
1 stop
United Airlines Logo
1:00 am - 1:16 pm
SJU
-
MFR
15h 16m
2 stops
$656United Airlines
Tue, Jun 2 - Tue, Jun 9
American Airlines Logo
6:35 am - 11:59 pm
MFR
-
SJU
14h 24m
2 stops
American Airlines Logo
7:00 am - 9:54 pm
SJU
-
MFR
17h 54m
2 stops
$659American Airlines
Sat, Jun 13 - Wed, Jun 17
Delta Logo
5:34 pm - 12:00 pm
MFR
-
SJU
15h 26m
2 stops
Delta Logo
7:05 am - 11:22 pm
SJU
-
MFR
19h 17m
2 stops
$671Delta
Tue, Jun 2 - Mon, Jun 8
United Airlines Logo
2:11 pm - 12:04 pm
MFR
-
SJU
18h 53m
3 stops
United Airlines Logo
2:05 am - 12:04 pm
SJU
-
MFR
12h 59m
2 stops
$749United Airlines
Sat, Jun 13 - Wed, Jun 17
Delta Logo
5:34 pm - 4:29 pm
MFR
-
SJU
19h 55m
2 stops
Delta Logo
2:04 pm - 11:57 pm
SJU
-
MFR
12h 53m
2 stops
$751Delta
Tue, Jun 2 - Tue, Jun 9
United Airlines Logo
2:11 pm - 12:04 pm
MFR
-
SJU
18h 53m
3 stops
United Airlines Logo
4:55 pm - 12:04 pm
SJU
-
MFR
22h 09m
2 stops
$762United Airlines
Booking Insights

KAYAK's insights & trends for Medford to Caribbean flights

Get data-powered insights and trends into flights from Medford to Caribbean to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Medford to Caribbean?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Medford to Caribbean were found on American Airlines ($466) and Delta ($639).

Good to know

Low seasonJune
Cheapest flight$261
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 72% lower on average.
Flight from Medford to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Medford 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 Medford to Caribbean.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Medford 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 Medford 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 Medford 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 Medford 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 Medford to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Medford to Caribbean

 
Need help choosing which airline to fly with from Medford 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.
7.4
United AirlinesOverall score based on 9533 reviews
7.3Comfort
7.7Boarding
8.1Crew
6.6Food
7.1Entertainment
Airline reviews

I had a cancelled flight because of technical issues going to my destination, and a delayed flight coming home. All told it wasn’t a total bust.

8.0 ExcellentAnonymous, Apr 2026
SMF - DEN
Read more United Airlines reviews

I had a cancelled flight because of technical issues going to my destination, and a delayed flight coming home. All told it wasn’t a total bust.

Just a bad day to fly. Flight was delayed from scheduled 6:50 pm departure to 8:50 pm. Combination of factors mostly related to weather at the destination airport (which is where the incoming flight originated) which delayed the inbound flight over an hour. Once on board, we taxied but had to hold again on the taxiway for 10 minutes or so. We did not get wheels up until after 9 pm. The flight was smooth but about 18 minutes from our destination, we had to hold for several minutes more due to weather at ORD. We finally landed at ORD about 11:08 pm (accounting for the time difference, that was about a 3 hour delay from our scheduled departure time). It felt like we were never going to get to our destination. But the flight crew and attendants were very good. The movie selection onboard was also very nice. Got to watch half of a movie just during our taxi from the gate at ATL due to the delay!

Fine. The issues I had were associated with luggage being delayed from Turkey to Tanzania

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

We purchase first class seats for the first time for multiples of standard economy ticket. There was no access to the club lounge and no priority boarding. The meal and the service once on the plane were superior and the seat was nicer, but not worth the price difference. I will be happy to seat in economy and spend the difference on more travel.

The business class seat is exceptional. I wish the food is more palatable.

Wonderful in-seat entertainment with seatback screens and huge selection of quality movies. The ability to bluetooth connect headphones was amazing.

the entire flight felt off. The crew seemed uninterested and disengaged. The food service was really bad - overcooked, bland, weird food service. They actually woke us up to serve chicken wraps in the middle of the night, after dinner and before breakfast. Made no sense. Ultimately, I was glad they did though, because the breakfast had been held for so long it was inedible. Eggs, potatoes, sausage - all disgusting. We were asked to "honor" the lavatories for premium customers and stay in our own cabin: this was also strange. So people in economy didn't pay enough to use the closest toilet to them??? It's a toilet. All in all, not the experience I have come to expect from United Airlines. The return flight from Paris to SFO was better, btw.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports