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Cheap flights from Chicago to Caribbean from $55

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Caribbean departing on 11/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago to Caribbean

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Caribbean that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Caribbean.

Cheap last minute flights

Planning a quick getaway from Chicago to Caribbean? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Caribbean, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Caribbean

Find recent round-trip train or bus tickets from Chicago to Caribbean.

All round-trip flight deals to Caribbean

The cheapest plane tickets to Caribbean found on KAYAK recently.
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$117Spirit Airlines
Find Deal
Tue, Jan 21 - Wed, Jan 29
9:32 am - 4:15 pmORD-SJU
4h 43mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$128Spirit Airlines
Find Deal
Wed, Jan 8 - Wed, Jan 15
9:59 pm - 10:50 amMDW-SJU
10h 51m1 stop
6:00 am - 3:43 pmSJU-MDW
11h 43m1 stop
$128Frontier
Find Deal
Mon, Jan 6 - Mon, Jan 27
8:44 pm - 12:48 amORD-SJU
26h 04m1 stop
6:35 am - 2:25 pmSJU-ORD
9h 50m1 stop
$133Frontier
Find Deal
Sat, Feb 22 - Wed, Feb 26
10:40 am - 10:35 pmORD-SJU
9h 55m1 stop
4:15 pm - 7:40 pmSJU-ORD
5h 25mnonstop
$206American Airlines
Find Deal
Mon, Mar 3 - Thu, Mar 6
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
8:35 am - 11:54 amSJU-ORD
5h 19mnonstop
$211United Airlines
Find Deal
Tue, Dec 10 - Fri, Dec 13
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
2:05 am - 8:59 amSJU-ORD
8h 54m1 stop
$256United Airlines
Find Deal
Sat, Dec 7 - Mon, Dec 9
6:00 am - 5:15 pmMDW-SJU
9h 15m1 stop
1:49 pm - 10:06 pmSJU-MDW
10h 17m1 stop
$324Delta
Find Deal
Tue, Dec 10 - Fri, Dec 13
6:00 am - 5:15 pmMDW-SJU
9h 15m1 stop
3:25 pm - 10:06 pmSJU-MDW
8h 41m1 stop
$334Delta
Find Deal
Tue, Dec 10 - Fri, Dec 13
7:09 pm - 2:14 pmORD-PUJ
17h 05m1 stop
3:40 pm - 7:05 pmPUJ-ORD
5h 25mnonstop
$343American Airlines
Find Deal
Sat, Feb 22 - Wed, Feb 26
6:10 pm - 12:42 amORD-SJU
4h 32mnonstop
$55Spirit Airlines
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Mon, Nov 25
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
$58Spirit Airlines
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Tue, Dec 31
5:28 pm - 2:19 amORD-SJU
6h 51m1 stop
$63Frontier
Find Deal
Mon, Jan 20
4:20 pm - 1:44 amMDW-SJU
7h 24m1 stop
$63Frontier
Find Deal
Mon, Feb 24
3:40 pm - 6:12 amORD-SJU
12h 32m1 stop
$100United Airlines
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Sat, Jan 11
1:15 pm - 10:22 pmORD-SJU
7h 07m1 stop
$113United Airlines
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Fri, Jan 31
6:00 am - 4:34 pmMDW-PUJ
8h 34m1 stop
$160Delta
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Sun, Jan 5
3:41 pm - 11:45 pmMDW-SJU
6h 04m1 stop
$162Delta
Find Deal
Sun, Jan 19
8:05 am - 2:35 pmORD-PUJ
4h 30mnonstop
$171American Airlines
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Fri, Jan 10
7:29 pm - 12:14 pmORD-PUJ
14h 45m2 stops
$177American Airlines
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Fri, Jan 3
8:04 pm - 10:07 amORD-SJU
12h 03m1 stop
5:40 am - 9:04 amSJU-ORD
5h 24mnonstop
$194Spirit Airlines
Find Deal
Wed, Nov 20 - Tue, Nov 26
8:04 pm - 10:07 amORD-SJU
12h 03m1 stop
2:45 am - 10:56 amSJU-ORD
10h 11m1 stop
$213Spirit Airlines
Find Deal
Wed, Nov 20 - Mon, Nov 25
2:41 pm - 2:52 amMDW-SJU
10h 11m1 stop
6:20 am - 11:42 amSJU-MDW
7h 22m1 stop
$244Frontier
Find Deal
Sun, Nov 24 - Wed, Dec 4
8:49 pm - 10:48 amORD-SJU
11h 59m1 stop
5:03 pm - 11:47 pmSJU-ORD
8h 44m1 stop
$264Frontier
Find Deal
Sun, Nov 24 - Fri, Dec 6
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
2:05 am - 10:44 amSJU-ORD
10h 39m1 stop
$326United Airlines
Find Deal
Thu, Nov 21 - Mon, Nov 25
1:50 pm - 11:59 pmORD-SJU
8h 09m1 stop
7:10 am - 5:03 pmSJU-ORD
11h 53m1 stop
$364Delta
Find Deal
Sat, Nov 23 - Mon, Nov 25
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
2:05 am - 9:10 amSJU-ORD
9h 05m1 stop
$388United Airlines
Find Deal
Thu, Nov 21 - Sun, Nov 24
8:19 am - 4:55 pmORD-PUJ
6h 36m1 stop
6:05 pm - 8:42 amPUJ-ORD
16h 37m1 stop
$408American Airlines
Find Deal
Thu, Nov 21 - Wed, Nov 27
1:54 pm - 12:42 amORD-SJU
8h 48m2 stops
4:38 pm - 10:14 pmSJU-ORD
7h 36m1 stop
$414American Airlines
Find Deal
Sun, Nov 24 - Tue, Nov 26
6:00 am - 4:40 pmORD-PUJ
8h 40m1 stop
3:44 pm - 11:59 pmPUJ-ORD
10h 15m1 stop
$423Delta
Find Deal
Thu, Nov 21 - Mon, Nov 25
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$143Spirit Airlines
Find Deal
Wed, Jan 29 - Sat, Feb 8
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$159Spirit Airlines
Find Deal
Fri, Jan 10 - Tue, Jan 14
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
4:52 pm - 8:11 pmSJU-ORD
5h 19mnonstop
$211United Airlines
Find Deal
Tue, Dec 10 - Fri, Dec 13
6:00 am - 12:29 pmORD-PUJ
4h 29mnonstop
6:45 pm - 9:59 pmPUJ-ORD
5h 14mnonstop
$246Frontier
Find Deal
Mon, Dec 9 - Thu, Dec 12
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
8:35 am - 11:54 amSJU-ORD
5h 19mnonstop
$251United Airlines
Find Deal
Sat, Dec 7 - Tue, Dec 10
8:05 am - 2:35 pmORD-PUJ
4h 30mnonstop
3:35 pm - 6:50 pmPUJ-ORD
5h 15mnonstop
$339American Airlines
Find Deal
Mon, Jan 13 - Thu, Jan 16
8:05 am - 1:45 pmORD-SJU
4h 40mnonstop
3:20 pm - 7:40 pmSJU-ORD
5h 20mnonstop
$346American Airlines
Find Deal
Tue, Apr 8 - Tue, Apr 15
6:00 am - 12:50 pmORD-PUJ
4h 50mnonstop
2:00 pm - 5:27 pmPUJ-ORD
5h 27mnonstop
$376Frontier
Find Deal
Mon, Feb 24 - Sat, Mar 8
8:35 am - 2:15 pmMDW-SJU
4h 40mnonstop
1:00 pm - 5:20 pmSJU-MDW
5h 20mnonstop
$405Southwest
Find Deal
Sat, May 3 - Sat, May 10
9:35 am - 4:00 pmMDW-PUJ
4h 25mnonstop
5:00 pm - 8:00 pmPUJ-MDW
5h 00mnonstop
$588Southwest
Find Deal
Sat, Jan 18 - Sat, Jan 25

United Airlines flights from Chicago to Caribbean

Our best United Airlines deals on Chicago to Caribbean flight tickets
United Airlines
Dec 10
ORD2:20 pmChicago O'Hare Intl
4h 35m
SJU8:55 pmSan Juan Luis Munoz Marin Intl
Dec 13
SJU8:35 amSan Juan Luis Munoz Marin Intl
5h 19m
ORD11:54 amChicago O'Hare Intl
United Airlines
Dec 7
ORD2:20 pmChicago O'Hare Intl
4h 35m
SJU8:55 pmSan Juan Luis Munoz Marin Intl
Dec 9
SJU2:05 amSan Juan Luis Munoz Marin Intl
8h 54m
1 stop
ORD8:59 amChicago O'Hare Intl
United Airlines
Nov 21
ORD2:20 pmChicago O'Hare Intl
4h 35m
SJU8:55 pmSan Juan Luis Munoz Marin Intl
Nov 25
SJU2:05 amSan Juan Luis Munoz Marin Intl
10h 39m
1 stop
ORD10:44 amChicago O'Hare Intl

Spirit Airlines flights from Chicago to Caribbean

Our best Spirit Airlines deals on Chicago to Caribbean flight tickets
Spirit Airlines
Jan 21
ORD1:44 pmChicago O'Hare Intl
4h 37m
SJU8:21 pmSan Juan Luis Munoz Marin Intl
Jan 29
SJU9:26 pmSan Juan Luis Munoz Marin Intl
5h 25m
ORD12:51 amChicago O'Hare Intl
Spirit Airlines
Jan 8
ORD9:32 amChicago O'Hare Intl
4h 43m
SJU4:15 pmSan Juan Luis Munoz Marin Intl
Jan 15
SJU9:26 pmSan Juan Luis Munoz Marin Intl
5h 25m
ORD12:51 amChicago O'Hare Intl
Spirit Airlines
Jan 6
ORD1:00 pmChicago O'Hare Intl
4h 36m
SJU7:36 pmSan Juan Luis Munoz Marin Intl
Jan 15
SJU9:26 pmSan Juan Luis Munoz Marin Intl
5h 25m
ORD12:51 amChicago O'Hare Intl

How to get the cheapest flight ticket from Chicago to Caribbean

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies to Caribbean from Chicago?

Frontier. Frontier, Spirit Airlines, and Copa Airlines are the most popular carriers operating from Chicago to Caribbean

What is the cheapest Chicago to Caribbean flight route?

Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl. Fly from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl for the best Chicago - Caribbean flight prices

How many flights depart from Chicago to Caribbean on average per day?

The number of flights available between Chicago and Caribbean is 9 per day as of November 2024. The most frequent departure time is 9:00AM, with 68% of daily flights leaving at noon.

What cabin class options are available on Chicago to Caribbean flights?

There are 2 cabin classes available to choose from on Chicago to Caribbean flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Caribbean flights?

No. A direct flight is the cheapest option for a flight between Chicago to Caribbean.

Cheap Chicago to Caribbean flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Caribbean

Best Price Found

$55

Fastest flight time

3h 21m

Direct flights

Every day

Airports in Caribbean

5 airports
The best one-way flight to Caribbean from Chicago in the past 72 hours is $55. The best round-trip flight deal from Chicago to Caribbean found on momondo in the last 72 hours is $117.
The fastest flight from Chicago to Caribbean takes 3h 21m
Direct flights go from Chicago to Caribbean every day.
There are 5 airports near Caribbean: George Town Owen Roberts Intl (GCM), Nassau Intl (NAS), Montego Bay Sangster Intl (MBJ), Providenciales (PLS), San Juan Luis Munoz Marin Intl (SJU)

  • When did momondo last update prices for flights from Chicago to Caribbean?

    Prices for flights from Chicago to Caribbean refresh daily.

  • How many operators does momondo search for flights from Chicago to Caribbean?

  • How old do you have to be to fly from Chicago to Caribbean?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Caribbean.

  • What documentation or ID do you need to fly to Caribbean?

    The required travel and health documents for your Caribbean trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Chicago to Caribbean?


Best airlines flying from Chicago to Caribbean

Compare and see reviews for airlines that fly from Chicago to Caribbean with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $65Free CancellationRating
6.1
3,542 reviews
Search Frontier flights
JetBluePriceFrom $137Free CancellationRating
7.4
3,402 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $166Free CancellationRating
6.3
8,175 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $267Free CancellationRating
7.4
9,173 reviews
Search United Airlines flights
SouthwestPriceFrom $275Free CancellationRating
8.1
5,015 reviews
Search Southwest flights
DeltaPriceFrom $324Free CancellationRating
8.0
8,765 reviews
Search Delta flights
American AirlinesPriceFrom $324Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Copa AirlinesPriceFrom $379Free CancellationRating
7.7
1,786 reviews
Search Copa Airlines flights
Air CanadaPriceFrom $514Free CancellationRating
7.0
8,235 reviews
Search Air Canada flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Caribbean?

Finding the right flight to Caribbean from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Caribbean quick and easy, saving you time and money.

Can I find flights from Chicago to Caribbean with flexible booking policies on momondo?

All flight searches from Chicago to Caribbean on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Caribbean?

momondo helps you find the best flight between Chicago and Caribbean by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Caribbean right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Caribbean from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


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Popular flights according to clicks in the last 7 days on momondo