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Cheap flights from Illinois to Caribbean from $51

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Caribbean departing on 2/2. 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 Illinois to Caribbean

Cheap round-trip flights

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

Cheap last minute flights

Planning a quick getaway from Illinois 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 Illinois to Caribbean

Find recent round-trip train or bus tickets from Illinois 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
$106Spirit Airlines
Find Deal
Fri, Jan 10 - Fri, Jan 17
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$116Spirit Airlines
Find Deal
Fri, Jan 31 - Tue, Feb 4
7:15 am - 12:35 amMDW-SJU
15h 20m1 stop
11:45 am - 12:09 pmSJU-MDW
26h 24m1 stop
$134Frontier
Find Deal
Mon, Jan 13 - Thu, Jan 23
11:33 am - 2:21 amMDW-SJU
12h 48m1 stop
1:28 pm - 2:19 pmSJU-MDW
26h 51m1 stop
$139Frontier
Find Deal
Mon, Jan 13 - Thu, Jan 16
4:58 pm - 2:02 amORD-SJU
7h 04m1 stop
2:17 pm - 5:47 pmSJU-ORD
5h 30mnonstop
Mon, Dec 9 - Fri, Dec 13
6:07 pm - 2:49 amORD-SJU
6h 42m1 stop
8:31 pm - 11:58 pmSJU-ORD
5h 27mnonstop
Mon, Dec 16 - Fri, Dec 20
5:10 am - 8:55 pmORD-SJU
13h 45m1 stop
6:21 pm - 11:56 pmSJU-ORD
7h 35m1 stop
$210American Airlines
Find Deal
Sun, Dec 8 - Thu, Dec 12
12:53 pm - 12:36 amORD-SJU
9h 43m1 stop
2:05 am - 10:53 amSJU-ORD
10h 48m1 stop
$222United Airlines
Find Deal
Mon, Dec 9 - Fri, Dec 13
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
2:05 am - 10:53 amSJU-ORD
10h 48m1 stop
$226United Airlines
Find Deal
Mon, Dec 9 - Fri, Dec 13
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
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
$51Spirit Airlines
Find Deal
Sun, Feb 2
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
$58Spirit Airlines
Find Deal
Sat, Jan 4
4:20 pm - 1:44 amMDW-SJU
7h 24m1 stop
$63Frontier
Find Deal
Mon, Feb 24
8:07 am - 5:49 pmMDW-SJU
7h 42m1 stop
$64Frontier
Find Deal
Tue, Feb 25
5:50 pm - 6:12 amORD-SJU
10h 22m1 stop
$105United Airlines
Find Deal
Sat, Jan 18
7:00 am - 2:53 pmORD-NAS
6h 53m1 stop
$121JetBlue
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Sat, Jan 25
9:00 am - 3:38 pmORD-SJU
4h 38mnonstop
$121United Airlines
Find Deal
Sun, Mar 2
1:57 pm - 2:09 amORD-PUJ
10h 12m1 stop
$163Copa Airlines
Find Deal
Fri, Jan 17
11:44 am - 10:50 pmORD-SJU
10h 06m1 stop
$175JetBlue
Find Deal
Tue, Mar 18
3:04 pm - 11:34 amORD-PUJ
19h 30m1 stop
$291Copa Airlines
Find Deal
Sun, Mar 9
1:09 pm - 11:40 pmORD-SJU
8h 31m1 stop
8:31 pm - 11:58 pmSJU-ORD
5h 27mnonstop
$228Spirit Airlines
Find Deal
Fri, Nov 29 - Tue, Dec 24
6:30 pm - 1:29 amORD-SJU
28h 59m1 stop
2:17 pm - 5:47 pmSJU-ORD
5h 30mnonstop
Thu, Nov 28 - Wed, Dec 4
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
2:05 am - 9:43 amSJU-ORD
9h 38m1 stop
$308United Airlines
Find Deal
Fri, Nov 29 - Mon, Dec 9
6:30 pm - 1:29 amORD-SJU
28h 59m1 stop
3:03 pm - 8:24 amSJU-ORD
19h 21m1 stop
$330Frontier
Find Deal
Thu, Nov 28 - Wed, Dec 4
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
4:52 pm - 8:11 pmSJU-ORD
5h 19mnonstop
$331United Airlines
Find Deal
Fri, Nov 29 - Wed, Dec 4
2:31 pm - 11:14 pmMDW-SJU
6h 43m1 stop
6:00 am - 11:41 amSJU-MDW
7h 41m1 stop
$344Frontier
Find Deal
Thu, Nov 28 - Fri, Dec 6
1:30 pm - 12:30 amMDW-SJU
9h 00m2 stops
6:10 am - 2:15 pmSJU-MDW
10h 05m1 stop
$398Southwest
Find Deal
Fri, Nov 29 - Tue, Dec 10
6:01 am - 5:15 pmORD-SJU
9h 14m2 stops
12:51 pm - 10:05 pmSJU-ORD
11h 14m2 stops
$399American Airlines
Find Deal
Fri, Nov 29 - Tue, Dec 24
6:49 pm - 12:05 pmORD-PUJ
15h 16m1 stop
3:30 pm - 6:45 pmPUJ-ORD
5h 15mnonstop
$407American Airlines
Find Deal
Sun, Dec 1 - Fri, Dec 6
11:25 am - 12:30 amORD-SJU
11h 05m2 stops
11:45 am - 9:30 pmSJU-ORD
11h 45m2 stops
$444Southwest
Find Deal
Fri, Nov 29 - Fri, Dec 6
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:55 amSJU-ORD
5h 29mnonstop
$157Spirit Airlines
Find Deal
Thu, Feb 6 - Wed, Feb 12
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$158Spirit Airlines
Find Deal
Thu, Jan 9 - Thu, Jan 16
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$159Spirit Airlines
Find Deal
Thu, Jan 9 - Thu, Jan 16
6:10 am - 12:39 pmORD-PUJ
4h 29mnonstop
6:54 pm - 10:11 pmPUJ-ORD
5h 17mnonstop
$190Frontier
Find Deal
Tue, Jan 14 - Tue, Jan 28
6:10 am - 12:39 pmORD-PUJ
4h 29mnonstop
6:10 pm - 9:27 pmPUJ-ORD
5h 17mnonstop
$196Frontier
Find Deal
Mon, Jan 13 - Fri, Jan 17
8:05 am - 1:45 pmORD-SJU
4h 40mnonstop
3:10 pm - 7:25 pmSJU-ORD
5h 15mnonstop
$201American Airlines
Find Deal
Tue, May 6 - Thu, May 8
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
8:35 am - 11:54 amSJU-ORD
5h 19mnonstop
$315United Airlines
Find Deal
Fri, Feb 28 - Sat, Mar 8
9:00 am - 3:38 pmORD-SJU
4h 38mnonstop
8:35 am - 11:54 amSJU-ORD
5h 19mnonstop
$328United Airlines
Find Deal
Sun, Dec 8 - Fri, Dec 13
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
9:05 am - 2:20 pmORD-MBJ
4h 15mnonstop
2:48 pm - 6:10 pmMBJ-ORD
4h 22mnonstop
Mon, Jan 6 - Mon, Jan 13

Spirit Airlines flights from Illinois to Caribbean

Our best Spirit Airlines deals on Illinois to Caribbean flight tickets
Spirit Airlines
Jan 10
ORD1:44 pmChicago O'Hare Intl
4h 37m
SJU8:21 pmSan Juan Luis Munoz Marin Intl
Jan 17
SJU9:26 pmSan Juan Luis Munoz Marin Intl
5h 25m
ORD12:51 amChicago O'Hare Intl
Spirit Airlines
Jan 31
ORD1:44 pmChicago O'Hare Intl
4h 37m
SJU8:21 pmSan Juan Luis Munoz Marin Intl
Feb 4
SJU9:26 pmSan Juan Luis Munoz Marin Intl
5h 25m
ORD12:51 amChicago O'Hare Intl
Spirit Airlines
Jan 25
ORD1:44 pmChicago O'Hare Intl
4h 37m
SJU8:21 pmSan Juan Luis Munoz Marin Intl
Jan 28
SJU9:26 pmSan Juan Luis Munoz Marin Intl
5h 25m
ORD12:51 amChicago O'Hare Intl

Frontier flights from Illinois to Caribbean

Our best Frontier deals on Illinois to Caribbean flight tickets
Frontier
Jan 13
MDW7:15 amChicago Midway
15h 20m
1 stop
SJU12:35 amSan Juan Luis Munoz Marin Intl
Jan 23
SJU11:45 amSan Juan Luis Munoz Marin Intl
26h 24m
1 stop
MDW12:09 pmChicago Midway
Frontier
Jan 13
MDW11:33 amChicago Midway
12h 48m
1 stop
SJU2:21 amSan Juan Luis Munoz Marin Intl
Jan 16
SJU1:28 pmSan Juan Luis Munoz Marin Intl
26h 51m
1 stop
MDW2:19 pmChicago Midway
Frontier
Jan 27
MDW11:33 amChicago Midway
12h 46m
1 stop
SJU2:19 amSan Juan Luis Munoz Marin Intl
Jan 30
SJU11:45 amSan Juan Luis Munoz Marin Intl
26h 24m
1 stop
MDW12:09 pmChicago Midway

See travel insights to Caribbean from

How to get the cheapest flight ticket from Illinois 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 day to depart on your flight to Caribbean?

The cheapest day to depart from Illinois to Caribbean is on a Tuesday when prices can be found for as low as $354. 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.

What is the cheapest Illinois to Caribbean flight route?

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

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

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

You could potentially save up to 23% on your flight if you consider stops on a Illinois to Caribbean flight.

Cheap Illinois to Caribbean flight deals and tips

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

Best Price Found

$51

Fastest flight time

3h 23m

Direct flights

Every day

Airports in Caribbean

5 airports
The best one-way flight to Caribbean from Illinois in the past 72 hours is $51. The best round-trip flight deal from Illinois to Caribbean found on momondo in the last 72 hours is $106.
The fastest flight from Illinois to Caribbean takes 3h 23m
Direct flights go from Illinois to Caribbean every day.
There are 5 airports near Caribbean: George Town Owen Roberts Intl (GCM), Nassau Intl (NAS), Punta Cana (PUJ), Montego Bay Sangster Intl (MBJ), San Juan Luis Munoz Marin Intl (SJU)

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

    Prices for flights from Illinois to Caribbean were last updated today.

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

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

    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 Illinois to Caribbean.

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

    The necessary travel and health documents for your Caribbean trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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


Best airlines flying from Illinois to Caribbean

Compare and see reviews for airlines that fly from Illinois to Caribbean with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $65Free CancellationRating
6.1
3,524 reviews
Search Frontier flights
JetBluePriceFrom $137Free CancellationRating
7.4
3,364 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $166Free CancellationRating
6.3
8,173 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $194Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $262Free CancellationRating
7.4
9,153 reviews
Search United Airlines flights
SouthwestPriceFrom $275Free CancellationRating
8.1
4,982 reviews
Search Southwest flights
DeltaPriceFrom $319Free CancellationRating
8.0
8,736 reviews
Search Delta flights
Copa AirlinesPriceFrom $379Free CancellationRating
7.7
1,776 reviews
Search Copa Airlines flights
Air CanadaPriceFrom $514Free CancellationRating
7.0
8,273 reviews
Search Air Canada flights

Why use momondo?

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

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

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

momondo does allow users to show only those flights to Caribbean from Illinois which offer a flexible booking policy as well as other useful filters and features.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Illinois to Caribbean.

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

Of course. momondo tracks the price of Illinois to Caribbean flights. All you need is a valid email address and we will do the rest; it is that quick and easy.


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