$151 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 9/25. 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

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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

Fri, Sep 26 - Thu, Oct 2
Delta Logo
12:55 pm - 9:20 pmSJU-COS
10h 25m1 stop
Delta Logo
6:00 am - 4:08 pmCOS-SJU
8h 08m1 stop
$375Delta
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Mon, Oct 6 - Thu, Oct 16
United Airlines Logo
1:05 am - 1:11 pmSJU-COS
14h 06m2 stops
United Airlines Logo
7:00 am - 5:30 pmCOS-SJU
8h 30m1 stop
$391United Airlines
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Thu, Aug 21 - Sun, Aug 31
American Airlines Logo
7:05 pm - 10:01 amSJU-COS
16h 56m2 stops
American Airlines Logo
6:02 am - 11:59 pmCOS-SJU
15h 57m2 stops
$401American Airlines
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Wed, Aug 6 - Tue, Aug 19
American Airlines Logo
7:05 pm - 10:01 amSJU-COS
16h 56m2 stops
American Airlines Logo
10:52 am - 11:59 pmCOS-SJU
11h 07m2 stops
$437American Airlines
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Tue, Oct 7 - Thu, Oct 16
United Airlines Logo
7:00 am - 5:32 pmSJU-COS
12h 32m2 stops
United Airlines Logo
7:00 am - 5:30 pmCOS-SJU
8h 30m1 stop
$451United Airlines
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Tue, Aug 5 - Mon, Aug 18
American Airlines Logo
12:59 am - 10:01 amSJU-COS
11h 02m1 stop
American Airlines Logo
6:02 am - 11:59 pmCOS-SJU
15h 57m2 stops
$469American Airlines
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Thu, Aug 28 - Mon, Sep 1
Southwest Logo
5:00 am - 2:15 pmSJU-COS
11h 15m2 stops
Southwest Logo
5:30 am - 6:45 pmCOS-SJU
11h 15m2 stops
$485Southwest
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Thu, Aug 21 - Sun, Aug 31
American Airlines Logo
3:15 pm - 11:44 pmSJU-COS
10h 29m1 stop
American Airlines Logo
6:02 am - 11:59 pmCOS-SJU
15h 57m2 stops
$492American Airlines
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Tue, Jul 1 - Tue, Jul 8
Southwest Logo
7:00 am - 4:00 pmSJU-COS
11h 00m2 stops
Southwest Logo
12:40 pm - 11:25 pmCOS-SJU
8h 45m1 stop
$507Southwest
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Thu, Aug 21 - Sun, Aug 31
Delta Logo
12:50 pm - 8:41 pmSJU-COS
9h 51m1 stop
Delta Logo
6:00 am - 4:36 pmCOS-SJU
8h 36m1 stop
$525Delta
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Good to know

Low seasonMarch
High seasonJanuary
Cheapest flight$151
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 3% lower on average.
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.

Top 4 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 4287 reviews
7.6Entertainment
8.2Boarding
8.0Comfort
7.1Food
8.6Crew
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Boarding was tough as we had to take a bus out to the plane and walk up a lot of stairs. Difficult with heavy carry-ons that said I got an entire empty row of seats, which was excellent for an international flight. Food was very mediocre but happy with the comfort so not complaining.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

Delta is better for short flights and very low need for customer service. Avoid for longer flights

I was supposed to be on business class at first class from Denver back to Miami due to weather changes. I missed my connection and it’s put on a flight to Fort Lauderdale. Instead of honoring my business class/1st class ticket, they put me in coach, but there were two first class seats open. I think it’s absolutely disgusting that I paid for first class $1300 ticket and they put me in economy and they had to open seats available and I have still not been refunded the difference. I ended up having to eat a snack box instead of the meal I was supposed to get and did not get home till 2 AM so I think that’s a little pathetic that I had to live off crackers for dinner And my poor dog ate some cheese and salami. Oh yes, apparently when they switched me to the new flight they forgot to mention I had a service dog

Excellent service despite turbulence during the flight. Flight attendants were remarkable!

Flight attendant moved my bag without notifying me and was rude to me when I asked him about it. There was no reason to move it.

The gate attendant let me walk right by her with a bag too big for the overhead compartment

Plane temperature was comfortable (not to hot) when boarding and waiting for takeoff.

Food choices were very limited. Taste of the dishes was average.

I liked all the informational texts. I always knew where to go and when .

Not as good as expected Air Can needs to improve totally rated on internet as worst

Received an email the night before showing that there would be seatback entertainment on our flight. We get on and there was no seatback entertainment. And then it was a scramble to try to set up the iPads for the kids before takeoff so they could watch something for the four hour flight.

The reason I don’t fly United. No in seat entertainment for a long flight and inconsistent WiFi and entertainment available from my device.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

Honestly, I haven’t flown American in years, probably due to the pandemic and my being unable to travel for certain periods in the last two years, but it was a good experience to dig out or obtain a new American Airlines account after many years of traveling for business with American in the past.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious.

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious. this return flight not as tasty, but filling.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Weather delay for 2.5 hours followed by half hour crew delay, did not have ginger ale, uncomfortable seats

The pilots are always hauling in the sky. No issues with boarding only problem was layover was shortened too much by weather but luckily the next flight was still boarding and did not missit

So awful Unreliable Unfriendly Bad Mad Mean Smelly Hot Late Overbooked Understaffed Expensive Cramped Narcs If they were a fruit they’d be rotten durian

Everything you need to know for your flight to Colorado Springs

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

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