$452 Find Cheap Flights from Medford to Caribbean

This is the cheapest round-trip 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

Tue, May 5 - Wed, May 13
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
$452United Airlines
Sun, May 3 - Wed, May 6
United Airlines Logo
5:00 am - 5:38 pm
MFR
-
SJU
9h 38m
1 stop
United Airlines Logo
7:20 am - 9:31 pm
SJU
-
MFR
17h 11m
2 stops
$534United Airlines
Tue, Jun 2 - Tue, Jun 9
Delta Logo
5:25 pm - 4:29 pm
MFR
-
SJU
20h 04m
2 stops
Delta Logo
7:00 am - 11:13 pm
SJU
-
MFR
19h 13m
2 stops
$549Delta
Tue, Apr 28 - Mon, May 4
United Airlines Logo
5:00 am - 9:24 pm
MFR
-
SJU
13h 24m
2 stops
United Airlines Logo
7:20 am - 9:31 pm
SJU
-
MFR
17h 11m
2 stops
$559United Airlines
Tue, Jun 2 - Fri, Jun 5
United Airlines Logo
6:35 pm - 12:34 pm
MFR
-
SJU
14h 59m
2 stops
United Airlines Logo
1:00 am - 12:04 pm
SJU
-
MFR
14h 04m
2 stops
$606United Airlines
Sun, May 3 - Wed, May 6
United Airlines Logo
6:36 pm - 5:38 pm
MFR
-
SJU
20h 02m
3 stops
United Airlines Logo
7:40 am - 11:31 pm
SJU
-
MFR
18h 51m
2 stops
$620United Airlines
Tue, Jun 2 - Tue, Jun 9
Delta Logo
5:25 pm - 1:11 pm
MFR
-
SJU
16h 46m
2 stops
Delta Logo
7:00 am - 11:13 pm
SJU
-
MFR
19h 13m
2 stops
$636Delta
Sun, May 3 - Wed, May 6
United Airlines Logo
5:00 am - 5:38 pm
MFR
-
SJU
9h 38m
1 stop
United Airlines Logo
1:40 pm - 9:31 pm
SJU
-
MFR
10h 51m
1 stop
$645United Airlines
Tue, Apr 28 - Mon, May 4
United Airlines Logo
5:00 am - 5:38 pm
MFR
-
SJU
9h 38m
1 stop
United Airlines Logo
7:20 am - 9:31 pm
SJU
-
MFR
17h 11m
2 stops
$649United Airlines
Tue, Jun 2 - Fri, Jun 5
United Airlines Logo
5:00 am - 5:38 pm
MFR
-
SJU
9h 38m
1 stop
United Airlines Logo
1:00 am - 12:04 pm
SJU
-
MFR
14h 04m
2 stops
$655United 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.

What is the cheapest month to fly from Medford to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Medford to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Medford to Caribbean is June, when tickets cost $203 (return) on average. On the other hand, the most expensive months are February and December, when the average cost of round-trip tickets is $1,286 and $1,264 respectively.

Good to know

Low seasonMarch
Cheapest flight$452
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly and prices are also 72% lower on average.
Flight from Medford to George Town

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 9389 reviews
7.3Comfort
7.1Entertainment
8.1Crew
7.7Boarding
6.6Food
Airline reviews

The flight was delayed so we were dead tired, and after that the turbulence was horrible. I was very scared.

4.0 OkayOlga, Mar 2026
IAD - TYS
Read more United Airlines reviews

The flight was delayed so we were dead tired, and after that the turbulence was horrible. I was very scared.

It’s always a great time flying with united airlines.

Good flight. Efficient boarding and competent flight crew. No problems until we arrived at our destination gate. We were early so there was an aircraft at the gate that had to move before we could pull in. Then, due to the type of aircraft we flew, the cabin door could not be opened until some luggage from the cargo bay was offloaded to preserve center of gravity characteristics. So, that further delayed deplaning. Despite being 20 minutes early on landing, we ended up being 5 to 10 minutes late after all the delays.

Everything went well except the turbulence what no one have a control of but pilot and crew handled very good!

There was no WiFi available, there were mechanical problems with the plane and we landed at C 124, then the gate was switched to A 26, then all the way back to C126! For a 75 yo woman traveling alone, this was a difficult journey, indeed!

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

Staff were good. My seat was in need of repair, but for a short flight was not problematic. Usual basic snack and drink setup that you'll find on any US carrier. Over, a decent, basic flight.

Complimentary light meal would be appreciated. But great flight crew service on all legs

Terrible because it was cancelled due to volcanic ash clouds in Guatemala while all other airlines kept flying. Had to pay for a hotel to stay overnight in Houston and try to fly next day.

Flight delayed for more than 16 hrs and no effort was spent to provide an alternate

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports