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$104+ Cheap flights from Chicago (CHI) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Aug 28 — Sep 41
Fri 8/28
Fri 9/4
1 adult, Economy
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Cheap flight deals from Chicago to Caribbean

Cheapest flights from Chicago to Caribbean
Explore the most affordable flight options available from Chicago to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/258:05 am
ORD
-
SJU
1 stop31h 06m
Frontier
Tue 9/16:35 am
SJU
-
ORD
1 stop31h 15m
Frontier
Deal found 7/28$227
This FlightHub deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1812:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Sun 8/307:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 7/28$228
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Mon 8/316:35 am
SJU
-
ORD
1 stop31h 15m
Frontier
Deal found 7/28$229
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Wed 9/98:45 am
SJU
-
ORD
1 stop31h 00m
Frontier
Deal found 7/26$230
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/242:25 pm
ORD
-
SJU
1 stop7h 55m
Frontier
Wed 9/27:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 7/24$232
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1712:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Mon 8/246:35 am
SJU
-
ORD
1 stop31h 15m
Frontier
Deal found 7/27$233
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/268:05 am
ORD
-
SJU
1 stop31h 06m
Frontier
Sun 8/307:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 7/26$235
This Super.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1412:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Thu 8/207:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 7/26$236
This Frontier deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Sat 8/297:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 7/26$237
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:05 am
ORD
-
SJU
1 stop31h 06m
Frontier
Wed 9/98:45 am
SJU
-
ORD
1 stop31h 00m
Frontier
Deal found 7/28$238
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:11 am
ORD
-
SJU
1 stop29h 23m
Frontier
Wed 9/168:45 am
SJU
-
ORD
1 stop31h 00m
Frontier
Deal found 7/26$239
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/258:05 am
ORD
-
SJU
1 stop31h 06m
Frontier
Mon 8/316:35 am
SJU
-
ORD
1 stop31h 15m
Frontier
Deal found 7/28$240

Find flight deals from Chicago to Caribbean

Keep the following information in mind while searching for Chicago to Caribbean flight deals. Data was last updated July 29, 2026.

Round-trip from

$227
(Kiwi.com)

One-way from

$104
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$386

Good round-trip deal

$322 or less

Good one-way deal

$133 or less
From Chicago (CHI) to Caribbean
Search Deals
One-way flight from Chicago (CHI) to Caribbean
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($39 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Caribbean.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Caribbean.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 29, 2026.
Use the filters below to find and compare flights from Chicago to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 9/11

3:15 pm-11:10 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Fri 9/18

2:35 pm-10:25 pm

2 stops8h 50m

$274

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 9/8

12:45 pm-10:05 pm

2 stops8h 20m

San Juan Luis Munoz Marin Intl

Tue 9/15

10:30 am-5:40 pm

1 stop8h 10m

$274

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 9/13

8:05 pm-9:10 am

1 stop12h 05m

San Juan Luis Munoz Marin Intl

Sat 9/19

5:55 am-1:05 pm

2 stops8h 10m

$300

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 9/9

1:29 pm-11:49 pm

1 stop9h 20m

San Juan Luis Munoz Marin Intl

Wed 9/16

2:59 pm-8:56 pm

1 stop6h 57m

$316

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 8/28

11:15 am-8:05 pm

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Fri 9/4

6:30 am-3:35 pm

1 stop10h 05m

$316

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 8/26

9:40 am-9:05 pm

1 stop10h 25m

San Juan Luis Munoz Marin Intl

Mon 8/31

8:55 pm-9:25 am

1 stop13h 30m

$316

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Wed 9/9

9:40 am-6:10 pm

1 stop7h 30m

San Juan Luis Munoz Marin Intl

Wed 9/16

1:45 pm-9:00 pm

1 stop8h 15m

$316

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 9/27

8:05 pm-9:10 am

1 stop12h 05m

San Juan Luis Munoz Marin Intl

Wed 9/30

10:30 am-5:40 pm

1 stop8h 10m

$326

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 9/28

6:40 am-4:49 pm

1 stop9h 09m

San Juan Luis Munoz Marin Intl

Mon 10/12

7:15 am-5:03 pm

1 stop10h 48m

$331

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 9/11

8:55 am-2:44 pm

Nonstop4h 49m

San Juan Luis Munoz Marin Intl

Sat 9/19

3:56 pm-8:05 pm

Nonstop5h 09m

$355

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 60 resultsSorted by cheapest first
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6

Best time to book a flight from Chicago to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Caribbean

What is the cheapest month to book a flight from Chicago to Caribbean?

Currently, August is the cheapest month in which you can book a flight from Chicago to Caribbean (average of $442). Flying from Chicago to Caribbean in December is currently the most expensive (average of $611). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to CB?

Find hourly flight availability from Chicago to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 29, 2026.

One of the essential ways to save on airfare from Chicago to Caribbean is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 34% on airfare.

Weekly flight availability from Chicago to Caribbean

Explore weekly flight availability from Chicago to Caribbean. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 29, 2026.

The most flights from CHI to 0CB are scheduled on a Wednesday (10 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (9 on average).

How far ahead should I book a flight from Chicago to Caribbean?

The best time to book flights from Chicago to Caribbean is 48 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest day to fly from Chicago to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Caribbean. Price data was last updated on July 25, 2026.

Travelers seeking maximum savings on their Chicago to Caribbean flight should consider departing on Sunday evenings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated July 29, 2026.
Read reviews from past customers who have flown United Airlines,American Airlines, andJetBlue from Chicago to Caribbean. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
10,051 reviews

Crew

8.1

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
United Airlines
7.4
Good
10,051 reviews
United Airlines
7.4
Good
10,051 reviews

Crew

8.1

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
American Airlines
7.1
Good
11,842 reviews
United Airlines
7.4
Good
10,051 reviews

Crew

8.1

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
JetBlue
7.1
Good
3,028 reviews
United Airlines
7.4
Good
10,051 reviews

Crew

8.1

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
Frontier
5.6
Fair
2,747 reviews
United Airlines
7.4
Good
10,051 reviews

Crew

8.1

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Ruth,Dec 2024

ORD - AMS

United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!

Related info for your journey

Find useful and relevant information for your journey from Chicago to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Caribbean?

    There are many flights that can get you from Chicago to Caribbean in 4h 49m. Fly via Southwest, Delta, or United Airlines to get the fastest option. The distance between Chicago and Caribbean is about 2073 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Chicago to Caribbean one-way?

    $75 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on Frontier and Arajet, with prices starting from $86 and $100, respectively.

  • What are the most popular routes from Chicago to Caribbean?

    The most popular flight routes from Chicago to Caribbean are Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl, Chicago O'Hare Intl - Punta Cana and Chicago Midway - San Juan Luis Munoz Marin Intl.

  • What are the most reliable airlines from Chicago to Caribbean?

    The top 3 most reliable airlines when flying from Chicago to Caribbean are Air Canada (83%), United Airlines (83%) and Air New Zealand (83%).

  • What are the cheapest flights from Chicago to Caribbean?

    Looking for the cheapest flight from Chicago to Caribbean? While on average our users pay $880, our data indicates the cheapest price to be $74. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $265.

  • Can I find deals for flights from Chicago to Caribbean that include hotel bookings?

    Yes. In addition to deals on Chicago to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Caribbean.

  • Can I find deals for business class flights from Chicago to Caribbean?

    Yes. Cheapflights offers flight deals from Chicago to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Caribbean?

    Currently, August is the cheapest month in which you can book a flight from Chicago to Caribbean (average of $442). Flying from Chicago to Caribbean in December is currently the most expensive (average of $611). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Chicago to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 9 airlines flying from Chicago to Caribbean

Discover the top 9 airlines that operate flights from Chicago to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$91Average$586FlexibilityNo cancel feeOn-time62%
DeltaCheapest$118Average$538FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$119Average$440FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$175Average$528FlexibilityNo cancel feeOn-time67%
ArajetCheapest$218Average$370FlexibilityNo cancel feeOn-timeN/A
Hahn AirCheapest$228Average$486FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$261Average$590FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$302Average$608FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$346Average$691FlexibilityNo cancel feeOn-time63%

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