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

Arajet, Spirit Airlines, and United Airlines 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 25 per week as of September 2025. The most frequent departure day is Mon, with 16% 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 12 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 3 per day as of September 2025. The most frequent departure time is 8:00AM, with 84% 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 11 operators available for flights from Chicago to Caribbean as of September 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.

$93 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

9:06 pm - 2:51 amORD-SJU

4h 45mnonstop

8:43 pm - 11:57 pmSJU-ORD

5h 14mnonstop

$196Spirit Airlines

Find Deal

vie., oct. 31 - lun., nov. 3

7:25 am - 12:54 amORD-SJU

16h 29m2 stops

7:43 pm - 11:57 pmSJU-ORD

5h 14mnonstop

$200Spirit Airlines

Find Deal

sáb., oct. 18 - vie., oct. 24

8:52 am - 2:44 pmORD-SJU

4h 52mnonstop

1:05 am - 7:38 amSJU-ORD

7h 33m1 stop

$217United Airlines

Find Deal

mar., oct. 21 - mar., oct. 21

8:52 am - 2:44 pmORD-SJU

4h 52mnonstop

3:56 pm - 8:03 pmSJU-ORD

5h 07mnonstop

$218United Airlines

Find Deal

mar., oct. 21 - vie., oct. 24

11:50 am - 11:59 pmORD-SJU

11h 09m1 stop

5:30 am - 10:39 pmSJU-ORD

18h 09m1 stop

$222American Airlines

Find Deal

mar., oct. 21 - mié., oct. 22

5:56 pm - 3:24 pmMDW-SJU

20h 28m1 stop

9:00 am - 11:25 pmSJU-MDW

15h 25m1 stop

$226Frontier

Find Deal

mar., oct. 21 - mar., oct. 28

7:00 am - 4:25 pmORD-SJU

8h 25m1 stop

5:43 pm - 11:58 pmSJU-ORD

7h 15m1 stop

$227Delta

Find Deal

mar., oct. 21 - vie., oct. 24

6:21 am - 3:22 pmMDW-SJU

8h 01m1 stop

3:22 pm - 11:41 pmSJU-MDW

9h 19m1 stop

$230Frontier

Find Deal

vie., oct. 3 - sáb., oct. 4

7:48 pm - 11:06 amORD-NAS

14h 18m1 stop

2:00 pm - 4:59 pmNAS-ORD

3h 59mnonstop

$343American Airlines

Find Deal

sáb., dic. 13 - jue., dic. 18

5:32 am - 12:35 pmORD-GCM

6h 03m1 stop

1:50 pm - 10:44 pmGCM-ORD

9h 54m1 stop

$352Delta

Find Deal

lun., dic. 15 - vie., dic. 19

Frontier flights from Chicago to Caribbean

Our best Frontier deals on Chicago to Caribbean flight tickets

Frontier

Oct 21

MDW5:56 pmChicago Midway

20h 28m

1 stop

SJU3:24 pmSan Juan Luis Munoz Marin Intl

Oct 28

SJU9:00 amSan Juan Luis Munoz Marin Intl

15h 25m

1 stop

MDW11:25 pmChicago Midway

$226

Find similar

Frontier

Oct 3

MDW6:21 amChicago Midway

8h 01m

1 stop

SJU3:22 pmSan Juan Luis Munoz Marin Intl

Oct 4

SJU3:22 pmSan Juan Luis Munoz Marin Intl

9h 19m

1 stop

MDW11:41 pmChicago Midway

$230

Find similar

Frontier

Oct 28

MDW5:56 pmChicago Midway

22h 58m

1 stop

SJU5:54 pmSan Juan Luis Munoz Marin Intl

Nov 2

SJU10:39 pmSan Juan Luis Munoz Marin Intl

11h 53m

1 stop

MDW8:32 amChicago Midway

$237

Find similar

Spirit Airlines flights from Chicago to Caribbean

Our best Spirit Airlines deals on Chicago to Caribbean flight tickets

Spirit Airlines

Oct 31

ORD9:06 pmChicago O'Hare Intl

4h 45m

SJU2:51 amSan Juan Luis Munoz Marin Intl

Nov 3

SJU8:43 pmSan Juan Luis Munoz Marin Intl

5h 14m

ORD11:57 pmChicago O'Hare Intl

$196

Find similar

Spirit Airlines

Oct 18

ORD7:25 amChicago O'Hare Intl

16h 29m

2 stops

SJU12:54 amSan Juan Luis Munoz Marin Intl

Oct 24

SJU7:43 pmSan Juan Luis Munoz Marin Intl

5h 14m

ORD11:57 pmChicago O'Hare Intl

$200

Find similar

Spirit Airlines

Oct 25

ORD3:00 pmChicago O'Hare Intl

4h 40m

SJU8:40 pmSan Juan Luis Munoz Marin Intl

Oct 29

SJU3:19 pmSan Juan Luis Munoz Marin Intl

7h 14m

1 stop

ORD9:33 pmChicago O'Hare Intl

$201

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

vie. 10/31

9:06 pm-2:51 am

Nonstop4h 45m

San Juan Luis Munoz Marin Intl

lun. 11/3

8:43 pm-11:57 pm

Nonstop5h 14m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 10/18

7:25 am-12:54 am

2 stops16h 29m

San Juan Luis Munoz Marin Intl

vie. 10/24

7:43 pm-11:57 pm

Nonstop5h 14m

$200

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 10/21

8:52 am-2:44 pm

Nonstop4h 52m

San Juan Luis Munoz Marin Intl

mar. 10/21

1:05 am-7:38 am

1 stop7h 33m

$217

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 10/21

8:52 am-2:44 pm

Nonstop4h 52m

San Juan Luis Munoz Marin Intl

vie. 10/24

3:56 pm-8:03 pm

Nonstop5h 07m

$218

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 10/21

11:50 am-11:59 pm

1 stop11h 09m

San Juan Luis Munoz Marin Intl

mié. 10/22

5:30 am-10:39 pm

1 stop18h 09m

$222

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

mar. 10/21

5:56 pm-3:24 pm

1 stop20h 28m

San Juan Luis Munoz Marin Intl

mar. 10/28

9:00 am-11:25 pm

1 stop15h 25m

$226

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mar. 10/21

7:00 am-4:25 pm

1 stop8h 25m

San Juan Luis Munoz Marin Intl

vie. 10/24

5:43 pm-11:58 pm

1 stop7h 15m

$227

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

vie. 10/3

6:21 am-3:22 pm

1 stop8h 01m

San Juan Luis Munoz Marin Intl

sáb. 10/4

3:22 pm-11:41 pm

1 stop9h 19m

$230

ChicagoNassau

ORD - NAS

ORDNAS

Chicago O'Hare Intl

sáb. 12/13

7:48 pm-11:06 am

1 stop14h 18m

Nassau Intl

jue. 12/18

2:00 pm-4:59 pm

Nonstop3h 59m

$343

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

lun. 12/15

5:32 am-12:35 pm

1 stop6h 03m

George Town Owen Roberts Intl

vie. 12/19

1:50 pm-10:44 pm

1 stop9h 54m

$352

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, October 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 $329. If you don’t want to visit Caribbean in October, then you should wait until April to fly from Chicago, when ticket prices are also cheap, with an average price of $357.

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 $396. 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 $305. 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 $388 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 $316 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 11% 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	$126
Fastest flight time	3h 18m
Direct flights	Every day
Airports in Caribbean	3 airports

The best one-way flight to Caribbean from Chicago in the past 72 hours is $126. The best round-trip flight deal from Chicago to Caribbean found on momondo in the last 72 hours is $355.

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

Direct flights go from Chicago to Caribbean every day.

There are 3 airports near Caribbean: George Town Owen Roberts Intl (GCM), Nassau Intl (NAS), 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 September 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 (26.56% of total bookings). The next most popular plane models are Airbus A321neo (18.88%), Boeing 737-900 (13.45%), and Boeing 737 MAX 8 (11.84%).

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 5.8 3,165 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $139	Free Cancellation	Rating 6.3 8,041 reviews	Search Spirit Airlines flights
Copa Airlines	PriceFrom $188	Free Cancellation	Rating 7.6 1,536 reviews	Search Copa Airlines flights
Delta	PriceFrom $196	Free Cancellation	Rating 7.9 7,974 reviews	Search Delta flights
United Airlines	PriceFrom $226	Free Cancellation	Rating 7.4 8,926 reviews	Search United Airlines flights
Arajet	PriceFrom $232	Free Cancellation	Rating 7.0 35 reviews	Search Arajet flights
JetBlue	PriceFrom $261	Free Cancellation	Rating 7.2 2,912 reviews	Search JetBlue flights
Air Canada	PriceFrom $335	Free Cancellation	Rating 7.1 10,000 reviews	Search Air Canada flights
American Airlines	PriceFrom $350	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines 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.