$168 Find Cheap Flights from Caribbean to Colorado Springs

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Colorado Springs departing on 9/29. 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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Cheap Flights from Caribbean to Colorado Springs

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

Thu, Oct 15 - Tue, Nov 3
United Airlines Logo
2:00 pm - 10:03 pm
SJU
-
COS
10h 03m
1 stop
United Airlines Logo
7:00 am - 6:25 pm
COS
-
SJU
8h 25m
1 stop
$322United Airlines
Thu, Oct 15 - Tue, Nov 3
American Airlines Logo
5:50 pm - 9:25 am
SJU
-
COS
17h 35m
2 stops
American Airlines Logo
12:45 pm - 12:05 pm
COS
-
SJU
20h 20m
2 stops
$342American Airlines
Sat, Sep 19 - Sat, Sep 26
American Airlines Logo
2:05 pm - 9:25 am
SJU
-
COS
21h 20m
2 stops
American Airlines Logo
3:51 pm - 2:45 pm
COS
-
SJU
20h 54m
2 stops
$350American Airlines
Tue, Oct 20 - Tue, Oct 27
United Airlines Logo
2:00 pm - 10:03 pm
SJU
-
COS
10h 03m
1 stop
United Airlines Logo
7:00 am - 9:22 pm
COS
-
SJU
12h 22m
2 stops
$356United Airlines
Sat, Sep 19 - Sat, Sep 26
Delta Logo
12:58 pm - 9:15 pm
SJU
-
COS
10h 17m
1 stop
Delta Logo
6:00 am - 4:31 pm
COS
-
SJU
8h 31m
1 stop
$376Delta
Thu, Oct 15 - Tue, Nov 3
American Airlines Logo
5:50 pm - 9:25 am
SJU
-
COS
17h 35m
2 stops
American Airlines Logo
12:45 pm - 5:30 am
COS
-
SJU
13h 45m
1 stop
$379American Airlines
Tue, Oct 20 - Tue, Oct 27
American Airlines Logo
7:00 pm - 9:25 am
SJU
-
COS
16h 25m
2 stops
American Airlines Logo
3:51 pm - 12:40 pm
COS
-
SJU
18h 49m
2 stops
$416American Airlines
Tue, Oct 20 - Tue, Oct 27
American Airlines Logo
8:30 am - 10:57 pm
SJU
-
COS
16h 27m
2 stops
American Airlines Logo
3:51 pm - 12:40 pm
COS
-
SJU
18h 49m
2 stops
$422American Airlines
Fri, Aug 14 - Sat, Aug 22
Delta Logo
1:06 pm - 9:15 pm
SJU
-
COS
10h 09m
1 stop
Delta Logo
6:00 am - 4:35 pm
COS
-
SJU
8h 35m
1 stop
$435Delta
Tue, Jul 28 - Thu, Aug 13
American Airlines Logo
12:59 am - 11:52 am
SJU
-
COS
12h 53m
1 stop
American Airlines Logo
3:51 pm - 9:43 am
COS
-
SJU
15h 52m
2 stops
$459American Airlines
Useful Info

Good to know

Low seasonJune
Cheapest flight$168
Best time to beat the crowds but there is an average 14% increase in price.
Most popular time to fly with an average 34% increase in price.
Flight from San Juan to Colorado Springs

FAQs for booking flights from Caribbean to Colorado Springs

  • How does KAYAK find such low prices on flights from Caribbean to Colorado Springs?

    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 Caribbean to Colorado Springs.

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

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

    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 Colorado Springs with an airline and back to Caribbean with another airline.

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

    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 Colorado Springs from Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Caribbean to Colorado Springs

 
Need help choosing which airline to fly with from Caribbean to Colorado Springs? 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
SouthwestOverall score based on 4312 reviews
7.5Entertainment
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
Airline reviews

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

2.0 MediocreAnonymous, May 2026
SEA - SMF
Read more Southwest reviews

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

Very friendly and helpful staff on board and United was excellent when I missed my onward flight due to the delay in London. Very well organised meant much less stress

Booked through Kayak Business, had a seat in middle and towards back due to booking rate, not comfortable.

They told us yesterday APR21st that they were cleaning the plane and we got delayed. After that they said they didn't had any crew for the flight so they cancelled the flight till next day.

The flight crew on this leg of my trip was very friendly and pleasant. Every one of them was humorous, as well as helpful and accommodating. This group was BY FAR the best crew I’ve flown with. They deserve kudos.

The rear seat on the second leg should be illegal. There’s no way you should make somebody sit that close to the washroom. Very awkward.

The entertainment options on the seat back video boards were nice.

The international / itallian speakers did not seem as friendly and professional as the others. Drink selections were denied ( a beer) until questioned about lack of ANY beer on the plane and then four options were given.

The boarding process was straightforward. One pertinent observation regarding all boarding procedures is that if an individual requires assistance or possesses a special status and is part of preboarding, it is advisable to limit the number of passengers who can preboard with them, rather than the entire, sometimes large, companion groups. The seats are uncomfortable, and the entertainment options are significantly inferior compared to other airlines. During the snack service, I requested an additional bag of snacks, but my request was denied. Initially, the flight attendant agreed to my request.becoming a strange accurate moment. The flight duration was four hours.

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.

They were fast and I like how they used to entertainment system to play video about the safety.

They lost my bag. ... And I asked them 3 times to 3 different people if my checked bag will maKe it all the way - they all confirmed and at the end it was left at the connection... Bravo

Cancelled BOYH legs of our flight home 30 min before initial boarding

Cancelled the flight half hour before boarding. Then cancelled the connecting flight too.

Delayed due to weather in Dallas (arriving flight arrived late), then boarded the plane only to deboard immediately afterwards, tire needed to be replaced. Flight supposed to depart at 6:15pm but departed at 9:35pm.

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

I would like a refund for the extra cost the seat I paid for. An oversized person sat next to me and I couldn’t fit on my seat and had to move to another seat.

Boarding gate at LAX was too crowded—two gates next to one another

The flight was delayed about an hour for a maintenance specialist to approve the maintenance repair

This flight was delayed but it worked in my favor because my Atlanta to Dallas flight was delayed.

This was a hard flight. 3 delays out of OKC (1 on the Tarmac). Delay in Atlanta coming to Dallas. total travel time was the equivalent of driving from OKC to Atlanta.

Everything you need to know for your flight to Colorado Springs

Information on the airport you'll fly into in Colorado Springs