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

The number of flights available between Chicago and Caribbean is 26 per day as of December 2025. The most frequent departure time is 8:00AM, with 74% of daily flights leaving at noon.

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

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

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

The number of flights available between Chicago and Caribbean is 183 per week as of December 2025. The most frequent departure day is Mon, with 15% of weekly flights leaving on this day.

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 34% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 12 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

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 11 operators available for flights from Chicago to Caribbean as of December 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.

$72 Cheap Flights from Chicago to Caribbean in 2025/26

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Find the cheapest flights from Chicago to Caribbean

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:18 am - 7:43 pm

ORD

SJU

8h 25m1 stop

5:25 pm - 11:15 pm

SJU

ORD

7h 50m1 stop

$195Multiple Airlines

Sat, Feb 21 - Mon, Mar 2

6:00 am - 3:06 pm

MDW

SJU

7h 06m1 stop

5:25 pm - 1:08 pm

SJU

MDW

21h 43m1 stop

$195Frontier

Tue, Mar 3 - Thu, Mar 5

7:45 am - 6:05 pm

ORD

SJU

8h 20m1 stop

11:06 am - 7:36 pm

SJU

ORD

10h 30m1 stop

$196JetBlue

Tue, Jan 13 - Fri, Jan 23

12:17 pm - 6:49 pm

ORD

SJU

4h 32mnonstop

1:22 pm - 4:37 pm

SJU

ORD

5h 15mnonstop

$197Spirit Airlines

Sat, Jan 24 - Wed, Feb 4

12:41 pm - 11:44 pm

ORD

SJU

9h 03m1 stop

5:10 am - 11:48 am

SJU

ORD

8h 38m1 stop

$202JetBlue

Fri, Feb 27 - Mon, Mar 2

5:15 am - 1:38 pm

ORD

GCM

7h 23m1 stop

2:34 pm - 11:46 pm

GCM

ORD

10h 12m1 stop

$240Spirit Airlines

Sat, Jan 10 - Sat, Jan 17

5:45 am - 12:30 pm

ORD

PUJ

4h 45mnonstop

6:00 pm - 9:10 pm

PUJ

ORD

5h 10mnonstop

$249Arajet

Wed, Feb 25 - Sun, Mar 1

10:27 am - 5:12 pm

ORD

PUJ

4h 45mnonstop

5:47 am - 8:57 am

PUJ

ORD

5h 10mnonstop

$251Arajet

Sat, Feb 21 - Sat, Feb 28

10:22 am - 3:28 pm

ORD

MBJ

4h 06mnonstop

4:38 pm - 8:15 pm

MBJ

ORD

4h 37mnonstop

$377American Airlines

Sun, Mar 1 - Fri, Mar 6

5:00 am - 2:26 pm

ORD

MBJ

8h 26m1 stop

4:38 pm - 8:15 pm

MBJ

ORD

4h 37mnonstop

$381American Airlines

Sun, Mar 1 - Fri, Mar 6

Frontier flights from Chicago to Caribbean

Our best Frontier deals on Chicago to Caribbean flight tickets

Frontier

Mar 3

MDW6:00 amChicago Midway

7h 06m

1 stop

SJU3:06 pmSan Juan Luis Munoz Marin Intl

Mar 5

SJU5:25 pmSan Juan Luis Munoz Marin Intl

21h 43m

1 stop

MDW1:08 pmChicago Midway

$195

Find similar

Frontier

Mar 3

MDW6:00 amChicago Midway

7h 06m

1 stop

SJU3:06 pmSan Juan Luis Munoz Marin Intl

Mar 10

SJU6:30 amSan Juan Luis Munoz Marin Intl

12h 43m

1 stop

MDW6:13 pmChicago Midway

$196

Find similar

Frontier

Feb 14

MDW8:00 amChicago Midway

27h 27m

1 stop

SJU1:27 pmSan Juan Luis Munoz Marin Intl

Feb 18

SJU5:25 pmSan Juan Luis Munoz Marin Intl

23h 01m

1 stop

MDW2:26 pmChicago Midway

$197

Find similar

Southwest flights from Chicago to Caribbean

Our best Southwest deals on Chicago to Caribbean flight tickets

Southwest

Jan 21

MDW1:50 pmChicago Midway

8h 45m

2 stops

SJU12:35 amSan Juan Luis Munoz Marin Intl

Jan 28

SJU5:40 amSan Juan Luis Munoz Marin Intl

7h 35m

1 stop

MDW11:15 amChicago Midway

$245

Find similar

Southwest

Mar 6

MDW9:15 amChicago Midway

4h 15m

PUJ3:30 pmPunta Cana

Mar 11

PUJ2:35 pmPunta Cana

5h 05m

MDW6:40 pmChicago Midway

$383

Find similar

Southwest

Jan 31

MDW8:15 amChicago Midway

4h 20m

PUJ2:35 pmPunta Cana

Feb 5

PUJ3:30 pmPunta Cana

7h 55m

1 stop

MDW9:25 pmChicago Midway

$391

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/21

9:18 am-7:43 pm

1 stop8h 25m

San Juan Luis Munoz Marin Intl

Mon 3/2

5:25 pm-11:15 pm

1 stop7h 50m

$195

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 3/3

6:00 am-3:06 pm

1 stop7h 06m

San Juan Luis Munoz Marin Intl

Thu 3/5

5:25 pm-1:08 pm

1 stop21h 43m

$195

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 1/13

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Fri 1/23

11:06 am-7:36 pm

1 stop10h 30m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/24

12:17 pm-6:49 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

Wed 2/4

1:22 pm-4:37 pm

Nonstop5h 15m

$197

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 2/27

12:41 pm-11:44 pm

1 stop9h 03m

San Juan Luis Munoz Marin Intl

Mon 3/2

5:10 am-11:48 am

1 stop8h 38m

$202

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/10

5:15 am-1:38 pm

1 stop7h 23m

George Town Owen Roberts Intl

Sat 1/17

2:34 pm-11:46 pm

1 stop10h 12m

$240

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 2/25

5:45 am-12:30 pm

Nonstop4h 45m

Punta Cana

Sun 3/1

6:00 pm-9:10 pm

Nonstop5h 10m

$249

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 2/21

10:27 am-5:12 pm

Nonstop4h 45m

Punta Cana

Sat 2/28

5:47 am-8:57 am

Nonstop5h 10m

$251

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 3/1

10:22 am-3:28 pm

Nonstop4h 06m

Montego Bay Sangster Intl

Fri 3/6

4:38 pm-8:15 pm

Nonstop4h 37m

$377

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 3/1

5:00 am-2:26 pm

1 stop8h 26m

Montego Bay Sangster Intl

Fri 3/6

4:38 pm-8:15 pm

Nonstop4h 37m

$381

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, April 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 $349. If you don’t want to visit Caribbean in April, then you should wait until January to fly from Chicago, when ticket prices are also cheap, with an average price of $351.

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 $389. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $446. 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 $321. 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 $447.

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 $395 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 $338 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 38% 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	$153
Fastest flight time	3h 22m
Direct flights	Every day
Airports in Caribbean	195 airports

The best one-way flight to Caribbean from Chicago in the past 72 hours is $153. The best round-trip flight deal from Chicago to Caribbean found on momondo in the last 72 hours is $315.

The fastest flight from Chicago to Caribbean takes 3h 22m

Direct flights go from Chicago to Caribbean every day.

There are 195 airports in Caribbean. From Chicago there are direct flights to George Town Owen Roberts Intl (GCM), Nassau Intl (NAS), Montego Bay Sangster Intl (MBJ), Providenciales (PLS).

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 11 operators available for flights from Chicago to Caribbean as of December 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 (24.94% of total bookings). The next most popular plane models are Airbus A321neo (21.85%), Boeing 737 MAX 8 (16.01%), and Boeing 737-900 (11.44%).

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 $108	Free Cancellation	Rating 5.8 3,082 reviews	Search Frontier flights
JetBlue	PriceFrom $142	Free Cancellation	Rating 7.2 2,896 reviews	Search JetBlue flights
Spirit Airlines	PriceFrom $145	Free Cancellation	Rating 6.3 8,191 reviews	Search Spirit Airlines flights
Delta	PriceFrom $186	Free Cancellation	Rating 7.9 8,007 reviews	Search Delta flights
Copa Airlines	PriceFrom $188	Free Cancellation	Rating 7.6 1,556 reviews	Search Copa Airlines flights
United Airlines	PriceFrom $215	Free Cancellation	Rating 7.4 9,091 reviews	Search United Airlines flights
Arajet	PriceFrom $236	Free Cancellation	Rating 6.8 38 reviews	Search Arajet flights
Southwest	PriceFrom $277	Free Cancellation	Rating 7.9 4,249 reviews	Search Southwest flights
Air Canada	PriceFrom $335	Free Cancellation	Rating 7.1 10,534 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.