What airlines fly to Caribbean?

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Caribbean from Chicago according to our data. American Airlines is the first choice among our users, with 36% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 11 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

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

The number of flights available between Chicago and Caribbean is 91 per week as of July 2025. The most frequent departure day is Thu, with 16% of weekly flights leaving on this day.

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

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

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

The number of flights available between Chicago and Caribbean is 13 per day as of July 2025. The most frequent departure time is 8:00AM, with 76% of daily flights leaving at noon.

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?

There are 10 operators available for flights from Chicago to Caribbean as of July 2025.

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.

$91 Cheap Flights from Chicago to Caribbean in 2025

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Find the cheapest flights from Chicago to Caribbean

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

6:23 pm - 12:06 amORD-SJU

4h 43mnonstop

10:16 pm - 9:22 amSJU-ORD

12h 06m1 stop

$189Spirit Airlines

Find Deal

Mon, Aug 11 - Fri, Aug 15

12:55 pm - 6:34 pmORD-SJU

4h 39mnonstop

7:40 pm - 11:56 pmSJU-ORD

5h 16mnonstop

$190Spirit Airlines

Find Deal

Thu, Sep 25 - Mon, Sep 29

10:51 am - 7:18 pmMDW-SJU

7h 27m1 stop

3:39 am - 9:51 amSJU-MDW

7h 12m1 stop

$235Frontier

Find Deal

Sat, Aug 30 - Fri, Sep 5

10:51 am - 11:59 pmMDW-SJU

12h 08m1 stop

3:39 am - 9:51 amSJU-MDW

7h 12m1 stop

$238Frontier

Find Deal

Sat, Sep 6 - Fri, Sep 19

6:03 am - 2:15 pmORD-PUJ

7h 12m1 stop

3:30 pm - 7:30 pmPUJ-ORD

5h 00mnonstop

$307American Airlines

Find Deal

Mon, Aug 18 - Wed, Aug 27

8:35 am - 2:15 pmORD-PUJ

4h 40mnonstop

3:30 pm - 7:30 pmPUJ-ORD

5h 00mnonstop

$327American Airlines

Find Deal

Mon, Aug 18 - Wed, Aug 27

11:40 am - 10:40 pmMDW-SJU

10h 00m1 stop

7:45 am - 3:35 pmSJU-MDW

8h 50m2 stops

$351Southwest

Find Deal

Sat, Sep 6 - Sat, Sep 13

6:35 am - 4:40 pmMDW-SJU

9h 05m1 stop

5:50 am - 1:20 pmSJU-MDW

8h 30m2 stops

$357Southwest

Find Deal

Thu, Oct 9 - Mon, Oct 13

6:00 am - 3:34 pmMDW-MBJ

9h 34m1 stop

4:59 pm - 12:28 pmMBJ-MDW

19h 29m2 stops

$389Delta

Find Deal

Sun, Sep 21 - Fri, Sep 26

6:00 am - 3:36 pmMDW-MBJ

9h 36m1 stop

1:20 pm - 9:12 pmMBJ-MDW

7h 52m1 stop

$410Delta

Find Deal

Mon, Sep 1 - Sat, Sep 6

Spirit Airlines flights from Chicago to Caribbean

Our best Spirit Airlines deals on Chicago to Caribbean flight tickets

Spirit Airlines

Aug 11

ORD6:23 pmChicago O'Hare Intl

4h 43m

SJU12:06 amSan Juan Luis Munoz Marin Intl

Aug 15

SJU10:16 pmSan Juan Luis Munoz Marin Intl

12h 06m

1 stop

ORD9:22 amChicago O'Hare Intl

$189

Find similar

Spirit Airlines

Sep 25

ORD12:55 pmChicago O'Hare Intl

4h 39m

SJU6:34 pmSan Juan Luis Munoz Marin Intl

Sep 29

SJU7:40 pmSan Juan Luis Munoz Marin Intl

5h 16m

ORD11:56 pmChicago O'Hare Intl

$190

Find similar

Spirit Airlines

Nov 6

ORD6:55 amChicago O'Hare Intl

4h 38m

SJU1:33 pmSan Juan Luis Munoz Marin Intl

Nov 13

SJU2:38 pmSan Juan Luis Munoz Marin Intl

5h 22m

ORD6:00 pmChicago O'Hare Intl

$191

Find similar

Frontier flights from Chicago to Caribbean

Our best Frontier deals on Chicago to Caribbean flight tickets

Frontier

Aug 30

MDW10:51 amChicago Midway

7h 27m

1 stop

SJU7:18 pmSan Juan Luis Munoz Marin Intl

Sep 5

SJU3:39 amSan Juan Luis Munoz Marin Intl

7h 12m

1 stop

MDW9:51 amChicago Midway

$235

Find similar

Frontier

Sep 6

MDW10:51 amChicago Midway

12h 08m

1 stop

SJU11:59 pmSan Juan Luis Munoz Marin Intl

Sep 19

SJU3:39 amSan Juan Luis Munoz Marin Intl

7h 12m

1 stop

MDW9:51 amChicago Midway

$238

Find similar

Frontier

Aug 30

MDW10:51 amChicago Midway

21h 08m

1 stop

SJU8:59 amSan Juan Luis Munoz Marin Intl

Sep 6

SJU4:42 pmSan Juan Luis Munoz Marin Intl

17h 36m

1 stop

MDW9:18 amChicago Midway

$239

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 8/11

6:23 pm-12:06 am

Nonstop4h 43m

San Juan Luis Munoz Marin Intl

Fri 8/15

10:16 pm-9:22 am

1 stop12h 06m

$189

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 9/25

12:55 pm-6:34 pm

Nonstop4h 39m

San Juan Luis Munoz Marin Intl

Mon 9/29

7:40 pm-11:56 pm

Nonstop5h 16m

$190

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 8/30

10:51 am-7:18 pm

1 stop7h 27m

San Juan Luis Munoz Marin Intl

Fri 9/5

3:39 am-9:51 am

1 stop7h 12m

$235

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 9/6

10:51 am-11:59 pm

1 stop12h 08m

San Juan Luis Munoz Marin Intl

Fri 9/19

3:39 am-9:51 am

1 stop7h 12m

$238

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 8/18

6:03 am-2:15 pm

1 stop7h 12m

Punta Cana

Wed 8/27

3:30 pm-7:30 pm

Nonstop5h 00m

$307

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 8/18

8:35 am-2:15 pm

Nonstop4h 40m

Punta Cana

Wed 8/27

3:30 pm-7:30 pm

Nonstop5h 00m

$327

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 9/6

11:40 am-10:40 pm

1 stop10h 00m

San Juan Luis Munoz Marin Intl

Sat 9/13

7:45 am-3:35 pm

2 stops8h 50m

$351

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 10/9

6:35 am-4:40 pm

1 stop9h 05m

San Juan Luis Munoz Marin Intl

Mon 10/13

5:50 am-1:20 pm

2 stops8h 30m

$357

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 9/21

6:00 am-3:34 pm

1 stop9h 34m

Montego Bay Sangster Intl

Fri 9/26

4:59 pm-12:28 pm

2 stops19h 29m

$389

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 9/1

6:00 am-3:36 pm

1 stop9h 36m

Montego Bay Sangster Intl

Sat 9/6

1:20 pm-9:12 pm

1 stop7h 52m

$410

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

What is the cheapest month to fly to Caribbean?

In general, September is the cheapest month to fly from Chicago to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $295. If you don’t want to visit Caribbean in September, then you should wait until October to fly from Chicago, when ticket prices are also cheap, with an average price of $313.

What is the cheapest day to depart on your flight to Caribbean?

The cheapest day to depart from Chicago to Caribbean is on a Monday when prices can be found for as low as $395. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $449. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean.

What is the cheapest time of day to depart on your flight to Caribbean?

In the evening is the cheapest time of day to fly from Chicago to Caribbean when you can find flight prices for as low as $303. Flying to Caribbean in the evening is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $444.

What is the cheapest Chicago to Caribbean flight route?

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

How far in advance should I book a flight to Caribbean?

You are more likely to see cheaper flights to Caribbean from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $375 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Chicago for as low as $302 on momondo.

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

There are 4 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?

You could potentially save up to 20% on your flight if you consider stops on a Chicago to Caribbean flight.

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	$91
Fastest flight time	3h 18m
Direct flights	Every day
Airports in Caribbean	6 airports

The best one-way flight to Caribbean from Chicago in the past 72 hours is $91. The best round-trip flight deal from Chicago to Caribbean found on momondo in the last 72 hours is $189.

The fastest flight from Chicago to Caribbean takes 3h 18m

Direct flights go from Chicago to Caribbean every day.

There are 6 airports near Caribbean: Nassau Intl (NAS), Saint Thomas Island Cyril E King (STT), Punta Cana (PUJ), Montego Bay Sangster Intl (MBJ), Providenciales (PLS), San Juan Luis Munoz Marin Intl (SJU)

Search flight deals

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?
There are 10 operators available for flights from Chicago to Caribbean as of July 2025.
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?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Caribbean is Boeing 737-800 (22.39% of total bookings). The next most popular plane models are Airbus A321neo (20.36%), Boeing 737-900 (13.75%), and Boeing 737 MAX 9 (11.79%).

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
Frontier	PriceFrom $106	Free Cancellation	Rating 5.9 3,239 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $139	Free Cancellation	Rating 6.3 8,048 reviews	Search Spirit Airlines flights
Delta	PriceFrom $190	Free Cancellation	Rating 8.0 7,981 reviews	Search Delta flights
Copa Airlines	PriceFrom $193	Free Cancellation	Rating 7.5 1,493 reviews	Search Copa Airlines flights
United Airlines	PriceFrom $226	Free Cancellation	Rating 7.4 8,900 reviews	Search United Airlines flights
Arajet	PriceFrom $235	Free Cancellation	Rating 7.1 32 reviews	Search Arajet flights
JetBlue	PriceFrom $261	Free Cancellation	Rating 7.2 2,914 reviews	Search JetBlue flights
Air Canada	PriceFrom $335	Free Cancellation	Rating 7.1 9,851 reviews	Search Air Canada flights
American Airlines	PriceFrom $346	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Southwest	PriceFrom $352	Free Cancellation	Rating 8.0 4,246 reviews	Search Southwest 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.