Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Illinois 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 Illinois to Caribbean Islands departing on 1/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

Find the cheapest flights from Illinois to Caribbean Islands

Cheap round-trip flights

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

Cheap last minute flights

Planning a quick getaway from Illinois 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 Illinois to Caribbean Islands

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

All round-trip flight deals to Caribbean Islands

The cheapest plane tickets to Caribbean Islands found on KAYAK recently.
9:58 am - 8:22 pmORD-SJU
8h 24m1 stop
2:17 pm - 5:47 pmSJU-ORD
5h 30mnonstop
$174Spirit Airlines
Find Deal
Sun, Dec 8 - Fri, Dec 13
7:25 am - 1:57 amMDW-SJU
16h 32m1 stop
3:59 am - 9:31 amSJU-MDW
7h 32m1 stop
$174Frontier
Find Deal
Sun, Dec 15 - Thu, Dec 19
8:00 am - 11:25 pmORD-SJU
13h 25m1 stop
9:59 pm - 12:58 amSJU-ORD
4h 59mnonstop
Sat, Feb 15 - Sat, Feb 22
9:32 pm - 12:01 pmORD-SJU
12h 29m1 stop
9:49 pm - 9:54 amSJU-ORD
14h 05m1 stop
Sun, Dec 8 - Thu, Dec 12
1:20 pm - 12:40 amMDW-SJU
9h 20m1 stop
2:55 pm - 7:45 pmSJU-MDW
6h 50m1 stop
$200Southwest
Find Deal
Wed, Jan 15 - Thu, Jan 23
1:20 pm - 12:40 amMDW-SJU
9h 20m1 stop
6:00 am - 4:50 pmSJU-MDW
12h 50m2 stops
$220Southwest
Find Deal
Wed, Jan 15 - Wed, Jan 22
9:00 am - 3:38 pmORD-SJU
4h 38mnonstop
8:35 am - 11:54 amSJU-ORD
5h 19mnonstop
$240United Airlines
Find Deal
Wed, Dec 11 - Wed, Dec 18
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
2:05 am - 8:59 amSJU-ORD
8h 54m1 stop
$245United Airlines
Find Deal
Wed, Dec 11 - Tue, Dec 17
4:23 pm - 3:50 amORD-SJU
9h 27m1 stop
4:05 am - 10:12 amSJU-ORD
8h 07m1 stop
$321JetBlue
Find Deal
Thu, Jan 30 - Sun, Feb 2
10:11 am - 10:22 amORD-NAS
23h 11m1 stop
10:44 am - 5:18 pmNAS-ORD
7h 34m1 stop
$386JetBlue
Find Deal
Sun, Jan 5 - Mon, Jan 13
10:59 am - 2:21 amORD-SJU
13h 22m1 stop
$57Frontier
Find Deal
Fri, Jan 10
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
$58Spirit Airlines
Find Deal
Tue, Dec 31
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
$59Spirit Airlines
Find Deal
Sun, Dec 8
11:25 am - 12:35 amORD-SJU
11h 10m2 stops
$100Southwest
Find Deal
Mon, Feb 24
5:45 am - 5:35 pmMDW-SJU
9h 50m1 stop
$100Southwest
Find Deal
Wed, Jan 22
1:13 pm - 8:40 pmORD-SJU
29h 27m2 stops
Tue, Dec 10
7:15 am - 1:22 pmMDW-SJU
28h 07m2 stops
Sat, Dec 14
6:55 pm - 11:20 amORD-GCM
15h 25m1 stop
$195JetBlue
Find Deal
Fri, Jan 3
1:54 pm - 10:34 amORD-NAS
19h 40m1 stop
$242Copa Airlines
Find Deal
Sun, Dec 29
6:00 am - 2:20 pmORD-GCM
7h 20m1 stop
$266JetBlue
Find Deal
Sat, Nov 23
1:09 pm - 11:40 pmORD-SJU
8h 31m1 stop
9:20 pm - 12:49 amSJU-ORD
5h 29mnonstop
$275Spirit Airlines
Find Deal
Sat, Nov 16 - Wed, Nov 20
1:10 pm - 7:40 pmORD-SJU
4h 30mnonstop
2:48 pm - 10:56 amSJU-ORD
22h 08m2 stops
$278Spirit Airlines
Find Deal
Mon, Nov 18 - Wed, Nov 20
7:46 pm - 7:49 pmORD-SJU
22h 03m1 stop
2:48 pm - 10:56 amSJU-ORD
22h 08m2 stops
$281Spirit Airlines
Find Deal
Mon, Nov 18 - Wed, Nov 20
1:09 pm - 11:40 pmORD-SJU
8h 31m1 stop
3:59 am - 12:05 pmSJU-ORD
10h 06m1 stop
Sat, Nov 16 - Tue, Nov 19
5:00 am - 3:46 pmORD-PUJ
8h 46m1 stop
4:37 pm - 8:05 pmPUJ-ORD
5h 28mnonstop
Sun, Nov 17 - Wed, Nov 20
6:48 pm - 9:25 amORD-SJU
12h 37m1 stop
3:59 am - 12:05 pmSJU-ORD
10h 06m1 stop
$318Frontier
Find Deal
Sat, Nov 16 - Tue, Nov 19
7:42 am - 7:17 pmMDW-SJU
9h 35m1 stop
8:22 pm - 1:31 pmSJU-MDW
19h 09m1 stop
$325Frontier
Find Deal
Mon, Nov 18 - Mon, Nov 25
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
4:52 pm - 8:11 pmSJU-ORD
5h 19mnonstop
$354United Airlines
Find Deal
Tue, Nov 19 - Mon, Nov 25
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
2:05 am - 9:10 amSJU-ORD
9h 05m1 stop
$400United Airlines
Find Deal
Tue, Nov 19 - Mon, Nov 25
6:54 am - 2:15 amORD-PUJ
17h 21m1 stop
6:34 pm - 12:16 pmPUJ-ORD
19h 42m1 stop
$421Copa Airlines
Find Deal
Sat, Nov 16 - Sat, Nov 23
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
2:17 pm - 5:47 pmSJU-ORD
5h 30mnonstop
$138Spirit Airlines
Find Deal
Sun, Dec 8 - Tue, Dec 17
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$159Spirit Airlines
Find Deal
Fri, Jan 24 - Wed, Jan 29
6:10 am - 1:00 pmORD-PUJ
4h 50mnonstop
6:54 pm - 10:11 pmPUJ-ORD
5h 17mnonstop
$186Frontier
Find Deal
Mon, Jan 27 - Thu, Jan 30
6:10 am - 1:00 pmORD-PUJ
4h 50mnonstop
6:10 pm - 9:27 pmPUJ-ORD
5h 17mnonstop
$189Frontier
Find Deal
Mon, Jan 20 - Fri, Jan 24
8:05 am - 1:45 pmORD-SJU
4h 40mnonstop
3:25 pm - 7:40 pmSJU-ORD
5h 15mnonstop
$191American Airlines
Find Deal
Tue, May 6 - Thu, May 8
9:00 am - 3:38 pmORD-SJU
4h 38mnonstop
8:35 am - 11:54 amSJU-ORD
5h 19mnonstop
$240United Airlines
Find Deal
Wed, Dec 11 - Wed, Dec 18
8:05 am - 2:40 pmORD-SJU
4h 35mnonstop
3:36 pm - 7:06 pmSJU-ORD
5h 30mnonstop
$313American Airlines
Find Deal
Mon, Dec 9 - Thu, Dec 12
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
4:52 pm - 8:11 pmSJU-ORD
5h 19mnonstop
$326United Airlines
Find Deal
Fri, Nov 29 - Wed, Dec 4
8:35 am - 2:15 pmMDW-SJU
4h 40mnonstop
1:00 pm - 5:20 pmSJU-MDW
5h 20mnonstop
$430Southwest
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
$499Southwest
Find Deal
Sat, Jan 25 - Sat, Feb 1

Frontier flights from Illinois to Caribbean Islands

Our best Frontier deals on Illinois to Caribbean Islands flight tickets
Frontier
Dec 15
MDW7:25 amChicago Midway
16h 32m
1 stop
SJU1:57 amSan Juan Luis Munoz Marin Intl
Dec 19
SJU3:59 amSan Juan Luis Munoz Marin Intl
7h 32m
1 stop
MDW9:31 amChicago Midway
Frontier
Nov 28
ORD8:51 amChicago O'Hare Intl
17h 54m
1 stop
SJU4:45 amSan Juan Luis Munoz Marin Intl
Dec 5
SJU7:16 pmSan Juan Luis Munoz Marin Intl
16h 38m
1 stop
ORD9:54 amChicago O'Hare Intl
Frontier
Dec 16
MDW7:25 amChicago Midway
16h 32m
1 stop
SJU1:57 amSan Juan Luis Munoz Marin Intl
Dec 20
SJU6:00 amSan Juan Luis Munoz Marin Intl
9h 06m
1 stop
MDW1:06 pmChicago Midway

Southwest flights from Illinois to Caribbean Islands

Our best Southwest deals on Illinois to Caribbean Islands flight tickets
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 15
MDW1:20 pmChicago Midway
9h 20m
1 stop
SJU12:40 amSan Juan Luis Munoz Marin Intl
Jan 22
SJU6:00 amSan Juan Luis Munoz Marin Intl
12h 50m
2 stops
MDW4:50 pmChicago Midway
Southwest
Feb 2
MDW1:20 pmChicago Midway
9h 30m
2 stops
SJU12:50 amSan Juan Luis Munoz Marin Intl
Feb 5
SJU6:00 amSan Juan Luis Munoz Marin Intl
12h 50m
2 stops
MDW4:50 pmChicago Midway

How to get the cheapest flight ticket from Illinois 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 airline that flies to Caribbean Islands from Illinois?

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

What is the cheapest Illinois to Caribbean Islands 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 Illinois - Caribbean Islands flight prices

Can stopping save me money on Illinois to Caribbean Islands flights?

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

Cheap Illinois to Caribbean Islands flight deals and tips

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

Best Price Found

$57

Fastest flight time

3h 21m

Direct flights

Every day

Airports in Caribbean Islands

5 airports
The best one-way flight to Caribbean Islands from Illinois in the past 72 hours is $57. The best round-trip flight deal from Illinois to Caribbean Islands found on momondo in the last 72 hours is $174.
The fastest flight from Illinois to Caribbean Islands takes 3h 21m
Direct flights go from Illinois to Caribbean Islands every day.
There are 5 airports near Caribbean Islands: 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 Islands?

    Prices for flights from Illinois to Caribbean Islands are updated daily.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Illinois to Caribbean Islands.

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

    The necessary travel and health documents for your Caribbean Islands 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 Islands?


Best airlines flying from Illinois to Caribbean Islands

Compare and see reviews for airlines that fly from Illinois to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $65Free CancellationRating
6.1
3,551 reviews
Search Frontier flights
JetBluePriceFrom $137Free CancellationRating
7.5
3,447 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $166Free CancellationRating
6.3
8,167 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $194Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $267Free CancellationRating
7.4
9,194 reviews
Search United Airlines flights
SouthwestPriceFrom $275Free CancellationRating
8.1
5,045 reviews
Search Southwest flights
DeltaPriceFrom $275Free CancellationRating
8.0
8,788 reviews
Search Delta flights
Copa AirlinesPriceFrom $379Free CancellationRating
7.7
1,809 reviews
Search Copa Airlines flights
Air CanadaPriceFrom $514Free CancellationRating
7.0
8,198 reviews
Search Air Canada flights

Why use momondo?

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

Finding the right flight to Caribbean Islands from Illinois 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 Islands quick and easy, saving you time and money.

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

Yes. momondo allows you to filter the results for Illinois to Caribbean Islands flights to just show those with flexible booking policies.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Caribbean Islands from Illinois.

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

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


An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Tue 11/19
Tue 11/26
Email me momondo's favorite deals

Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

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