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Caribbean Islands

$103+ Cheap flights from Chicago (CHI) to Caribbean Islands

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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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Cheap flight deals from Chicago to Caribbean Islands

Keep the following information in mind while searching for Chicago to Caribbean Islands flight deals. Data was last updated April 24, 2025.

Round-trip from

$202
(Cheapflightsfares)

One-way from

$103
(FlightHub)

Popular in

December

Cheapest in

August

Average price

$352
From Chicago (CHI) to Caribbean Islands
Search Deals
One-way flight from Chicago (CHI) to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($67 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Chicago to Caribbean Islands

Cheapest flights from Chicago to Caribbean Islands
Explore the most affordable flight options available from Chicago to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 24, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/107:47 amORD - SJU
1 stop16h 07mSpirit Airlines
Thu 5/151:33 amSJU - ORD
1 stop18h 44mSpirit Airlines
Deal found 4/22$196
This Booking.com deal was found by Cheapflights users on 4/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/104:35 pmORD - SJU
1 stop17h 10mMultiple Airlines
Thu 5/1510:46 amSJU - ORD
1 stop13h 25mMultiple Airlines
Deal found 4/23$238
This Cheapflightsfares deal was found by Cheapflights users on 4/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/26:15 amMDW - SJU
1 stop7h 32mFrontier
Thu 5/86:00 amSJU - MDW
1 stop7h 24mFrontier
Deal found 4/23$294
This Frontier deal was found by Cheapflights users on 4/23. 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.
Fri 5/29:00 amORD - SJU
1 stop8h 47mFrontier
Sun 5/410:46 amSJU - ORD
1 stop13h 25mFrontier
Deal found 4/23$298
This CheapOair deal was found by Cheapflights users on 4/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/206:10 amORD - PUJ
Nonstop4h 41mMultiple Airlines
Sat 5/243:22 pmPUJ - ORD
1 stop9h 43mMultiple Airlines
Deal found 4/23$299
This American Airlines deal was found by Cheapflights users on 4/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/32:53 pmORD - PUJ
1 stop19h 25mAmerican Airlines
Fri 5/94:53 pmPUJ - ORD
1 stop19h 16mAmerican Airlines
Deal found 4/23$304
This Cheapflightsfares deal was found by Cheapflights users on 4/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/256:45 amORD - PUJ
Nonstop4h 40mFrontier
Wed 7/305:08 pmPUJ - ORD
Nonstop5h 08mFrontier
Deal found 4/23$307
This Delta deal was found by Cheapflights users on 4/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/316:00 amORD - SJU
1 stop9h 50mDelta
Fri 9/122:28 pmSJU - ORD
1 stop10h 25mDelta
Deal found 4/21$307
This Cheapflightsfares deal was found by Cheapflights users on 4/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/105:05 amORD - PUJ
1 stop8h 12mSpirit Airlines
Thu 5/1512:42 pmPUJ - ORD
1 stop11h 47mSpirit Airlines
Deal found 4/23$308
This Cheapflightsfares deal was found by Cheapflights users on 4/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/257:47 amORD - STT
1 stop6h 43mSpirit Airlines
Sat 5/313:49 pmSTT - ORD
1 stop9h 16mSpirit Airlines
Deal found 4/23$311
This Delta deal was found by Cheapflights users on 4/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/36:04 amMDW - PUJ
1 stop6h 11mDelta
Tue 5/62:40 pmPUJ - MDW
1 stop8h 42mDelta
Deal found 4/23$335
This Delta deal was found by Cheapflights users on 4/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/157:10 amORD - PUJ
1 stop6h 22mDelta
Wed 7/231:10 pmPUJ - ORD
1 stop11h 45mDelta
Deal found 4/22$335

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Caribbean Islands 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 April 24, 2025.
Use the filters below to find and compare flights from Chicago to Caribbean Islands that are best for you.

Fly from

Chicago

Fly to

Caribbean Islands

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/10

7:47 am-12:54 am

1 stop16h 07m

San Juan Luis Munoz Marin Intl

Thu 5/15

1:33 am-7:17 pm

1 stop18h 44m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/10

4:35 pm-10:45 am

1 stop17h 10m

San Juan Luis Munoz Marin Intl

Thu 5/15

10:46 am-11:11 pm

1 stop13h 25m

$238

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 5/2

6:15 am-2:47 pm

1 stop7h 32m

San Juan Luis Munoz Marin Intl

Thu 5/8

6:00 am-12:24 pm

1 stop7h 24m

$294

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 5/2

4:15 pm-12:05 am

1 stop6h 50m

San Juan Luis Munoz Marin Intl

Mon 5/5

6:00 am-6:29 pm

1 stop13h 29m

$298

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 5/20

6:10 am-11:51 am

Nonstop4h 41m

Punta Cana

Sat 5/24

3:22 pm-12:05 am

1 stop9h 43m

$299

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 5/3

2:53 pm-11:18 am

1 stop19h 25m

Punta Cana

Fri 5/9

4:53 pm-11:09 am

1 stop19h 16m

$304

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 5/10

5:05 am-2:17 pm

1 stop8h 12m

Punta Cana

Thu 5/15

12:42 pm-11:29 pm

1 stop11h 47m

$308

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 5/30

6:45 am-12:26 pm

Nonstop4h 41m

Punta Cana

Thu 6/5

5:54 pm-10:03 pm

Nonstop5h 09m

$310

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sun 5/25

7:47 am-3:30 pm

1 stop6h 43m

Saint Thomas Island Cyril E King

Sat 5/31

3:49 pm-12:05 am

1 stop9h 16m

$311

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Sat 5/3

6:04 am-1:15 pm

1 stop6h 11m

Punta Cana

Tue 5/6

2:40 pm-10:22 pm

1 stop8h 42m

$335

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands

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

Currently, September is the cheapest month in which you can book a flight from Chicago to Caribbean Islands (average of $254). Flying from Chicago to Caribbean Islands in December is currently the most expensive (average of $336). 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 EPX?

Find hourly flight availability from Chicago to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 24, 2025.

When flying from Chicago to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Chicago to Caribbean Islands

Explore weekly flight availability from Chicago to Caribbean Islands. 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 April 24, 2025.

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

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated April 24, 2025.
Peruse reviews from past customers who have flown with Delta, Alaska Airlines and Southwest from Chicago to Caribbean Islands to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,920 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,920 reviews
Delta
8.0
Very good
7,920 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Alaska Airlines
8.0
Very good
9,918 reviews
Delta
8.0
Very good
7,920 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Southwest
8.0
Very good
4,286 reviews
Delta
8.0
Very good
7,920 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Copa Airlines
7.6
Good
1,411 reviews
Delta
8.0
Very good
7,920 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
LATAM Airlines
7.5
Good
1,765 reviews
Delta
8.0
Very good
7,920 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

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

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

    $103 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and United Airlines, with prices starting from $105 and $116, respectively.

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

    When deciding which route to take from Chicago to Caribbean Islands consider Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl, Chicago O'Hare Intl - Punta Cana or Chicago Midway - San Juan Luis Munoz Marin Intl as they are the most popular.

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

    No one likes to see their flight delayed. When booking a flight from Chicago to Caribbean Islands consider choosing United Airlines (88%), American Airlines (83%) or Air Canada (82%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Caribbean Islands?

    Looking for the cheapest flight from Chicago to Caribbean Islands? While on average our users pay $805, our data indicates the cheapest price to be $117. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $189.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Caribbean Islands 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 Islands?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Caribbean Islands (average of $254). Flying from Chicago to Caribbean Islands in December is currently the most expensive (average of $336). 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 Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 10 airlines flying from Chicago to Caribbean Islands

Discover the top 10 airlines that operate flights from Chicago to Caribbean Islands. 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$374FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$142Average$362FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$193Average$537FlexibilityNo cancel feeOn-time70%
DeltaCheapest$222Average$658FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$226Average$643FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$293Average$502FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$331Average$648FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$335Average$780FlexibilityNo cancel feeOn-time67%
SouthwestCheapest$343Average$675FlexibilityNo cancel feeOn-time63%
AviancaCheapest$397Average$953FlexibilityNo cancel feeOn-time71%

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