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Cheap flights from Chicago to Caribbean Islands from $57

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 Islands departing on 12/9. 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 Islands

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Caribbean Islands 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 Islands.

Cheap last minute flights

Planning a quick getaway from Chicago to Caribbean Islands? 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 Islands, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Caribbean Islands

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

All round-trip flight deals to Caribbean Islands

The cheapest plane tickets to Caribbean Islands 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
4:58 pm - 2:02 amORD-SJU
7h 04m1 stop
10:01 pm - 9:24 amSJU-ORD
13h 23m1 stop
$128Frontier
Find Deal
Mon, Dec 9 - Tue, Dec 17
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
2:05 am - 9:43 amSJU-ORD
9h 38m1 stop
$226United Airlines
Find Deal
Mon, Dec 9 - Fri, Dec 13
12:53 pm - 12:36 amORD-SJU
9h 43m1 stop
2:05 am - 10:53 amSJU-ORD
10h 48m1 stop
$255United Airlines
Find Deal
Mon, Dec 9 - Fri, Dec 13
6:00 am - 2:20 pmMDW-SJU
6h 20m1 stop
2:02 pm - 10:20 pmSJU-MDW
10h 18m1 stop
$334Delta
Find Deal
Tue, Jan 28 - Fri, Feb 7
4:14 pm - 11:55 amORD-PUJ
17h 41m1 stop
3:43 pm - 6:55 pmPUJ-ORD
5h 12mnonstop
$343American Airlines
Find Deal
Mon, Mar 3 - Thu, Mar 6
5:10 am - 2:21 pmORD-PUJ
7h 11m1 stop
5:05 pm - 12:09 amPUJ-ORD
9h 04m1 stop
$353American Airlines
Find Deal
Tue, Jan 7 - Tue, Jan 14
6:00 am - 2:22 pmMDW-PUJ
6h 22m1 stop
3:47 pm - 10:20 pmPUJ-MDW
8h 33m1 stop
$353Delta
Find Deal
Tue, Jan 14 - Tue, Jan 28
4:00 pm - 1:40 pmORD-GCM
20h 40m1 stop
4:00 pm - 1:11 pmGCM-ORD
22h 11m1 stop
$592Air Canada
Find Deal
Wed, Jan 29 - Sun, Feb 2
6:10 pm - 12:35 pmORD-NAS
17h 25m2 stops
1:35 pm - 8:58 amNAS-ORD
20h 23m2 stops
$603Air Canada
Find Deal
Mon, Dec 16 - Thu, Dec 19
4:58 pm - 2:02 amORD-SJU
7h 04m1 stop
$57Frontier
Find Deal
Mon, Dec 9
9:32 am - 4:15 pmORD-SJU
4h 43mnonstop
$58Spirit Airlines
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Wed, Jan 1
1:15 pm - 10:22 pmORD-SJU
7h 07m1 stop
$105United Airlines
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Sat, Jan 25
6:00 am - 2:20 pmMDW-SJU
6h 20m1 stop
$162Delta
Find Deal
Tue, Jan 14
5:45 am - 2:22 pmORD-PUJ
6h 37m1 stop
$165Delta
Find Deal
Tue, Jan 14
2:20 pm - 7:55 pmORD-SJU
4h 35mnonstop
$188United Airlines
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Tue, Mar 11
11:45 am - 3:45 pmORD-PUJ
26h 00m1 stop
$214American Airlines
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Thu, Nov 28
8:20 am - 2:00 pmORD-SJU
4h 40mnonstop
$218American Airlines
Find Deal
Sun, Mar 9
7:25 pm - 11:02 amORD-PLS
14h 37m1 stop
$250JetBlue
Find Deal
Tue, May 20
7:25 pm - 11:02 amORD-PLS
14h 37m1 stop
$336JetBlue
Find Deal
Mon, May 19
1:09 pm - 11:40 pmORD-SJU
8h 31m1 stop
12:57 pm - 12:33 amSJU-ORD
13h 36m1 stop
$237Spirit Airlines
Find Deal
Sun, Nov 24 - Fri, Dec 6
1:09 pm - 11:40 pmORD-SJU
8h 31m1 stop
2:17 pm - 5:47 pmSJU-ORD
5h 30mnonstop
$250Spirit Airlines
Find Deal
Sun, Nov 24 - Thu, Dec 5
2:46 pm - 12:33 amORD-SJU
7h 47m1 stop
9:49 pm - 9:54 amSJU-ORD
14h 05m1 stop
$258Frontier
Find Deal
Tue, Nov 26 - Thu, Dec 5
8:50 am - 8:36 pmMDW-SJU
9h 46m1 stop
6:20 am - 11:42 amSJU-MDW
7h 22m1 stop
$258Frontier
Find Deal
Tue, Nov 26 - Wed, Dec 4
7:05 am - 5:10 pmORD-SJU
8h 05m1 stop
7:10 am - 5:15 pmSJU-ORD
12h 05m1 stop
$369Delta
Find Deal
Mon, Nov 25 - Fri, Dec 6
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
5:50 pm - 11:20 pmSJU-ORD
7h 30m1 stop
$398United Airlines
Find Deal
Tue, Nov 26 - Wed, Dec 4
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
4:52 pm - 8:11 pmSJU-ORD
5h 19mnonstop
$405United Airlines
Find Deal
Sun, Nov 24 - Mon, Nov 25
6:00 am - 2:31 pmORD-SJU
6h 31m1 stop
3:41 pm - 11:59 pmSJU-ORD
10h 18m1 stop
$414Delta
Find Deal
Sun, Nov 24 - Mon, Nov 25
8:12 am - 2:37 pmORD-PUJ
4h 25mnonstop
6:00 pm - 8:48 amPUJ-ORD
16h 48m1 stop
$454American Airlines
Find Deal
Mon, Nov 25 - Sat, Dec 7
6:55 pm - 11:42 amORD-PUJ
14h 47m1 stop
3:27 pm - 12:14 amPUJ-ORD
10h 47m1 stop
$468American Airlines
Find Deal
Sun, Nov 24 - Fri, Dec 6
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
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$158Spirit Airlines
Find Deal
Tue, Jan 7 - Tue, Jan 14
6:00 am - 12:29 pmORD-PUJ
4h 29mnonstop
6:45 pm - 9:59 pmPUJ-ORD
5h 14mnonstop
$190Frontier
Find Deal
Tue, Jan 7 - Tue, Jan 14
6:00 am - 12:29 pmORD-PUJ
4h 29mnonstop
6:45 pm - 9:59 pmPUJ-ORD
5h 14mnonstop
$193Frontier
Find Deal
Tue, Jan 7 - Tue, Jan 14
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
4:52 pm - 8:11 pmSJU-ORD
5h 19mnonstop
$321United Airlines
Find Deal
Fri, Feb 28 - Thu, Mar 6
8:05 am - 2:40 pmORD-SJU
4h 35mnonstop
3:36 pm - 7:06 pmSJU-ORD
5h 30mnonstop
$354American Airlines
Find Deal
Wed, Dec 11 - Tue, Dec 17
8:05 am - 1:45 pmORD-SJU
4h 40mnonstop
3:25 pm - 7:40 pmSJU-ORD
5h 15mnonstop
$375American Airlines
Find Deal
Wed, May 14 - Thu, May 29
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
8:35 am - 11:54 amSJU-ORD
5h 19mnonstop
$389United Airlines
Find Deal
Sat, Dec 7 - Wed, Dec 11
8:30 am - 2:55 pmMDW-PUJ
4h 25mnonstop
3:30 pm - 7:45 pmPUJ-MDW
5h 15mnonstop
$695Southwest
Find Deal
Sat, Mar 8 - Thu, Mar 13
9:05 am - 3:30 pmMDW-PUJ
4h 25mnonstop
3:55 pm - 8:10 pmPUJ-MDW
5h 15mnonstop
$724Southwest
Find Deal
Thu, Mar 6 - Sun, Mar 9

Southwest flights from Chicago to Caribbean Islands

Our best Southwest deals on Chicago to Caribbean Islands flight tickets
Southwest
Feb 2
MDW1:20 pmChicago Midway
9h 30m
2 stops
SJU12:50 amSan Juan Luis Munoz Marin Intl
Feb 5
SJU2:55 pmSan Juan Luis Munoz Marin Intl
6h 50m
1 stop
MDW7:45 pmChicago Midway
Southwest
Jan 15
MDW1:20 pmChicago Midway
9h 20m
1 stop
SJU12:40 amSan Juan Luis Munoz Marin Intl
Jan 23
SJU2:55 pmSan Juan Luis Munoz Marin Intl
6h 50m
1 stop
MDW7:45 pmChicago Midway
Southwest
Jan 28
MDW10:05 amChicago Midway
12h 20m
2 stops
SJU12:25 amSan Juan Luis Munoz Marin Intl
Feb 3
SJU6:00 amSan Juan Luis Munoz Marin Intl
7h 45m
1 stop
MDW11:45 amChicago Midway

Frontier flights from Chicago to Caribbean Islands

Our best Frontier deals on Chicago to Caribbean Islands flight tickets
Frontier
Dec 9
ORD4:58 pmChicago O'Hare Intl
7h 04m
1 stop
SJU2:02 amSan Juan Luis Munoz Marin Intl
Dec 17
SJU10:01 pmSan Juan Luis Munoz Marin Intl
13h 23m
1 stop
ORD9:24 amChicago O'Hare Intl
Frontier
Feb 22
ORD8:44 pmChicago O'Hare Intl
10h 51m
1 stop
SJU9:35 amSan Juan Luis Munoz Marin Intl
Feb 26
SJU6:35 amSan Juan Luis Munoz Marin Intl
9h 50m
1 stop
ORD2:25 pmChicago O'Hare Intl
Frontier
Dec 6
ORD6:07 pmChicago O'Hare Intl
21h 16m
1 stop
SJU5:23 pmSan Juan Luis Munoz Marin Intl
Dec 12
SJU7:16 pmSan Juan Luis Munoz Marin Intl
16h 38m
1 stop
ORD9:54 amChicago O'Hare Intl

See travel insights to Caribbean Islands from

How to get the cheapest flight ticket from Chicago to Caribbean Islands

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 day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Chicago to Caribbean Islands is on a Tuesday. Travelers who choose to depart for Caribbean Islands on a Tuesday will often find tickets for as low as $355. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $415. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest Chicago to Caribbean Islands flight route?

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

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

There are 4 cabin classes available to choose from on Chicago to Caribbean Islands 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 Islands flights?

You could potentially save up to 1% on your flight if you consider stops on a Chicago to Caribbean Islands flight.

Cheap Chicago to Caribbean Islands flight deals and tips

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

Best Price Found

$57

Fastest flight time

3h 21m

Direct flights

Every day

Airports in Caribbean Islands

6 airports
The best one-way flight to Caribbean Islands from Chicago in the past 72 hours is $57. The best round-trip flight deal from Chicago to Caribbean Islands found on momondo in the last 72 hours is $117.
The fastest flight from Chicago to Caribbean Islands takes 3h 21m
Direct flights go from Chicago to Caribbean Islands every day.
There are 6 airports near Caribbean Islands: George Town Owen Roberts Intl (GCM), Nassau Intl (NAS), Punta Cana (PUJ), 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 Islands?

    Prices for flights from Chicago to Caribbean Islands were last updated today.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Caribbean Islands.

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

    The travel and health documents you'll need for your trip to Caribbean Islands may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean Islands. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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


Best airlines flying from Chicago to Caribbean Islands

Compare and see reviews for airlines that fly from Chicago to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $65Free CancellationRating
6.1
3,536 reviews
Search Frontier flights
JetBluePriceFrom $137Free CancellationRating
7.4
3,389 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $166Free CancellationRating
6.3
8,169 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $267Free CancellationRating
7.4
9,172 reviews
Search United Airlines flights
SouthwestPriceFrom $275Free CancellationRating
8.1
5,005 reviews
Search Southwest flights
DeltaPriceFrom $324Free CancellationRating
8.0
8,755 reviews
Search Delta flights
American AirlinesPriceFrom $324Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Copa AirlinesPriceFrom $379Free CancellationRating
7.7
1,779 reviews
Search Copa Airlines flights
Air CanadaPriceFrom $514Free CancellationRating
7.0
8,246 reviews
Search Air Canada flights

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Caribbean Islands. momondo saves you time and could save you money on your trip.

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

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

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

momondo provides multiple filters to help you find the best flight to Caribbean Islands from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

If you are simply researching potential flights to Caribbean Islands, momondo offers a useful price alert feature which will track prices for flights to Caribbean Islands from Chicago and alert you when they change.


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