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

The number of flights available between Chicago and Caribbean is 135 per week as of February 2026. The most frequent departure day is Sat, with 21% 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 35% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 13 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 day?

The number of flights available between Chicago and Caribbean is 19 per day as of February 2026. The most frequent departure time is 8:00AM, with 66% of daily flights leaving at noon.

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

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

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 12 operators available for flights from Chicago to Caribbean as of February 2026.

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.

$59 Cheap Flights from Chicago to Caribbean in 2026

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Find the cheapest flights from Chicago to Caribbean

Round-trip

One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

7:23 pm - 6:58 pm

ORD

SJU

21h 35m

1 stop

11:52 am - 6:18 pm

SJU

ORD

8h 26m

1 stop

$184Spirit Airlines

Sun, Mar 1 - Fri, Mar 6

10:55 am - 11:58 pm

ORD

SJU

12h 03m

1 stop

12:55 pm - 7:51 pm

SJU

ORD

7h 56m

1 stop

$185Spirit Airlines

Mon, Mar 16 - Wed, Mar 18

12:17 pm - 6:49 pm

ORD

SJU

4h 32mnonstop

5:25 pm - 10:46 am

SJU

ORD

19h 21m

1 stop

$186Multiple Airlines

Sat, Feb 14 - Wed, Feb 18

6:00 am - 4:21 pm

MDW

SJU

8h 21m

1 stop

3:53 am - 2:55 pm

SJU

MDW

13h 02m

1 stop

$187Frontier

Sat, Feb 21 - Fri, Feb 27

8:30 am - 12:43 am

ORD

SJU

14h 13m

1 stop

3:36 pm - 11:47 pm

SJU

ORD

9h 11m

1 stop

$187Multiple Airlines

Wed, Mar 4 - Tue, Mar 10

8:15 am - 2:53 am

ORD

SJU

16h 38m

1 stop

5:25 pm - 10:46 am

SJU

ORD

19h 21m

1 stop

$188Frontier

Sat, Feb 21 - Wed, Feb 25

9:22 pm - 12:43 am

MDW

SJU

25h 21m

1 stop

5:25 pm - 2:26 pm

SJU

MDW

23h 01m

1 stop

$188Frontier

Mon, Feb 23 - Wed, Mar 4

5:45 am - 12:30 pm

ORD

PUJ

4h 45mnonstop

7:30 pm - 10:40 pm

PUJ

ORD

5h 10mnonstop

$283Arajet

Mon, Feb 16 - Tue, Feb 17

6:20 pm - 11:10 am

ORD

AUA

15h 50m

1 stop

5:15 pm - 9:10 am

AUA

ORD

16h 55m

1 stop

$331JetBlue

Mon, Mar 30 - Mon, Apr 6

8:20 am - 1:26 pm

ORD

MBJ

4h 06mnonstop

10:07 am - 6:28 pm

MBJ

ORD

8h 21m

1 stop

$367American Airlines

Tue, Mar 3 - Tue, Mar 10

Spirit Airlines flights from Chicago to Caribbean

Our best Spirit Airlines deals on Chicago to Caribbean flight tickets

Spirit Airlines

Mar 1

ORD7:23 pmChicago O'Hare Intl

21h 35m

1 stop

SJU6:58 pmSan Juan Luis Munoz Marin Intl

Mar 6

SJU11:52 amSan Juan Luis Munoz Marin Intl

8h 26m

1 stop

ORD6:18 pmChicago O'Hare Intl

$184

Spirit Airlines

Mar 16

ORD10:55 amChicago O'Hare Intl

12h 03m

1 stop

SJU11:58 pmSan Juan Luis Munoz Marin Intl

Mar 18

SJU12:55 pmSan Juan Luis Munoz Marin Intl

7h 56m

1 stop

ORD7:51 pmChicago O'Hare Intl

$185

Spirit Airlines

Feb 9

ORD12:17 pmChicago O'Hare Intl

4h 32m

SJU6:49 pmSan Juan Luis Munoz Marin Intl

Feb 14

SJU12:32 pmSan Juan Luis Munoz Marin Intl

5h 16m

ORD3:48 pmChicago O'Hare Intl

$188

Frontier flights from Chicago to Caribbean

Our best Frontier deals on Chicago to Caribbean flight tickets

Frontier

Feb 21

MDW6:00 amChicago Midway

8h 21m

1 stop

SJU4:21 pmSan Juan Luis Munoz Marin Intl

Feb 27

SJU3:53 amSan Juan Luis Munoz Marin Intl

13h 02m

1 stop

MDW2:55 pmChicago Midway

$187

Frontier

Feb 21

ORD8:15 amChicago O'Hare Intl

16h 38m

1 stop

SJU2:53 amSan Juan Luis Munoz Marin Intl

Feb 25

SJU5:25 pmSan Juan Luis Munoz Marin Intl

19h 21m

1 stop

ORD10:46 amChicago O'Hare Intl

$188

Frontier

Feb 23

MDW6:00 amChicago Midway

7h 02m

1 stop

SJU3:02 pmSan Juan Luis Munoz Marin Intl

Mar 4

SJU5:25 pmSan Juan Luis Munoz Marin Intl

23h 01m

1 stop

MDW2:26 pmChicago Midway

$192

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 3/1

7:23 pm-6:58 pm

1 stop21h 35m

San Juan Luis Munoz Marin Intl

Fri 3/6

11:52 am-6:18 pm

1 stop8h 26m

$184

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 3/16

10:55 am-11:58 pm

1 stop12h 03m

San Juan Luis Munoz Marin Intl

Wed 3/18

12:55 pm-7:51 pm

1 stop7h 56m

$185

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/14

12:17 pm-6:49 pm

Nonstop4h 32m

San Juan Luis Munoz Marin Intl

Wed 2/18

5:25 pm-10:46 am

1 stop19h 21m

$186

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 2/21

6:00 am-4:21 pm

1 stop8h 21m

San Juan Luis Munoz Marin Intl

Fri 2/27

3:53 am-2:55 pm

1 stop13h 02m

$187

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 3/4

8:30 am-12:43 am

1 stop14h 13m

San Juan Luis Munoz Marin Intl

Tue 3/10

3:36 pm-11:47 pm

1 stop9h 11m

$187

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/21

8:15 am-2:53 am

1 stop16h 38m

San Juan Luis Munoz Marin Intl

Wed 2/25

5:25 pm-10:46 am

1 stop19h 21m

$188

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 2/23

9:22 pm-12:43 am

1 stop25h 21m

San Juan Luis Munoz Marin Intl

Wed 3/4

5:25 pm-2:26 pm

1 stop23h 01m

$188

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 2/16

5:45 am-12:30 pm

Nonstop4h 45m

Punta Cana

Tue 2/17

7:30 pm-10:40 pm

Nonstop5h 10m

$283

ChicagoOranjestad

ORD - AUA

ORDAUA

Chicago O'Hare Intl

Mon 3/30

6:20 pm-11:10 am

1 stop15h 50m

Oranjestad Reina Beatrix

Mon 4/6

5:15 pm-9:10 am

1 stop16h 55m

$331

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 3/3

8:20 am-1:26 pm

Nonstop4h 06m

Montego Bay Sangster Intl

Tue 3/10

10:07 am-6:28 pm

1 stop8h 21m

$367

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 $335. If you don’t want to visit Caribbean in April, then you should wait until October to fly from Chicago, when ticket prices are also cheap, with an average price of $350.

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 $382. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $448. 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 $332. Flying to Caribbean in the evening is an ideal time because this is during off-peak travel hours. Flights at noon are often more expensive with an average ticket price of $478.

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 $391 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 $329 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?

No. A direct flight is the cheapest option for a flight between Chicago to Caribbean.

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	$128
Fastest flight time	3h 25m
Direct flights	Every day
Airports in Caribbean	195 airports

The best one-way flight to Caribbean from Chicago in the past 72 hours is $128. The best round-trip flight deal from Chicago to Caribbean found on momondo in the last 72 hours is $296.

The fastest flight from Chicago to Caribbean takes 3h 25m

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).

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 12 operators available for flights from Chicago to Caribbean as of February 2026.
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 (23.59% of total bookings). The next most popular plane models are Airbus A321neo (21.25%), Boeing 737 MAX 8 (15.23%), and Airbus A318/A319/A320/A321 (9.71%).

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 5.7 3,051 reviews	Search Frontier flights
JetBlue	PriceFrom $119	Free Cancellation	Rating 7.2 2,893 reviews	Search JetBlue flights
Spirit Airlines	PriceFrom $130	Free Cancellation	Rating 6.3 8,408 reviews	Search Spirit Airlines flights
Delta	PriceFrom $136	Free Cancellation	Rating 7.9 8,139 reviews	Search Delta flights
Air Canada	PriceFrom $175	Free Cancellation	Rating 7.1 10,685 reviews	Search Air Canada flights
Arajet	PriceFrom $181	Free Cancellation	Rating 6.6 43 reviews	Search Arajet flights
Copa Airlines	PriceFrom $188	Free Cancellation	Rating 7.6 1,558 reviews	Search Copa Airlines flights
Hahn Air	PriceFrom $213	Free Cancellation	Rating 0.0	Search Hahn Air flights
Avianca	PriceFrom $250	Free Cancellation	Rating 6.5 2,498 reviews	Search Avianca 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.