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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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Round-trip from

$196
(CheapOair)

One-way from

$103
(FlightHub)

Popular in

December

Cheapest in

August

Average price

$334
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 May 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 May 1, 2025.

This CheapOair deal was found by Cheapflights users on 4/30. 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.
Sun 5/258:17 amORD - SJU
1 stop10h 45mSpirit Airlines
Thu 5/298:12 pmSJU - ORD
1 stop13h 38mSpirit Airlines
Deal found 4/30$196
This FlightHub deal was found by Cheapflights users on 4/30. 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.
Sat 5/174:35 pmORD - SJU
1 stop17h 10mMultiple Airlines
Tue 5/203:56 amSJU - ORD
1 stop29h 26mMultiple Airlines
Deal found 4/30$255
This CheapOair deal was found by Cheapflights users on 4/30. 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.
Sun 5/46:10 amORD - PUJ
Nonstop4h 41mMultiple Airlines
Fri 5/912:42 pmPUJ - ORD
1 stop11h 47mMultiple Airlines
Deal found 4/30$285
This eDestinos deal was found by Cheapflights users on 4/30. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/305:10 amORD - SJU
1 stop9h 05mFrontier
Mon 6/23:40 amSJU - ORD
1 stop21h 56mFrontier
Deal found 4/30$288
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 5/306:45 amORD - PUJ
Nonstop4h 41mFrontier
Tue 6/35:54 pmPUJ - ORD
Nonstop5h 11mFrontier
Deal found 4/29$289
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Sun 5/115:00 amORD - PUJ
1 stop9h 49mAmerican Airlines
Thu 5/153:16 pmPUJ - ORD
Nonstop5h 20mAmerican Airlines
Deal found 4/30$295
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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.
Tue 5/205:05 amORD - PUJ
1 stop8h 12mSpirit Airlines
Sat 5/2412:42 pmPUJ - ORD
1 stop8h 21mSpirit Airlines
Deal found 4/30$298
This Frontier deal was found by Cheapflights users on 4/30. 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.
Thu 5/81:19 pmMDW - SJU
1 stop9h 46mFrontier
Wed 5/143:56 amSJU - MDW
1 stop9h 28mFrontier
Deal found 4/30$298
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2712:41 pmORD - STT
2 stops23h 55mSpirit Airlines
Tue 6/32:41 pmSTT - ORD
2 stops19h 09mSpirit Airlines
Deal found 4/30$304
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 5/245:05 amORD - AUA
1 stop8h 35mSpirit Airlines
Sat 5/313:45 pmAUA - ORD
1 stop18h 05mSpirit Airlines
Deal found 4/30$325
This Delta deal was found by Cheapflights users on 4/30. 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.
Mon 8/116:00 amMDW - PUJ
1 stop6h 17mDelta
Fri 8/151:10 pmPUJ - MDW
1 stop9h 37mDelta
Deal found 4/30$335
This Trip.com deal was found by Cheapflights users on 4/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/212:15 pmMDW - SJU
1 stop12h 35mMultiple Airlines
Wed 6/42:54 pmSJU - MDW
1 stop8h 44mMultiple Airlines
Deal found 4/30$337

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 May 1, 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

Sun 5/25

8:17 am-8:02 pm

1 stop10h 45m

San Juan Luis Munoz Marin Intl

Thu 5/29

8:12 pm-8:50 am

1 stop13h 38m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 5/17

4:35 pm-10:45 am

1 stop17h 10m

San Juan Luis Munoz Marin Intl

Tue 5/20

3:56 am-8:22 am

1 stop29h 26m

$255

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 5/4

6:10 am-11:51 am

Nonstop4h 41m

Punta Cana

Fri 5/9

12:42 pm-11:29 pm

1 stop11h 47m

$285

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 5/30

5:10 am-3:15 pm

1 stop9h 05m

San Juan Luis Munoz Marin Intl

Mon 6/2

3:40 am-12:36 am

1 stop21h 56m

$288

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 5/30

6:45 am-12:26 pm

Nonstop4h 41m

Punta Cana

Tue 6/3

5:54 pm-10:05 pm

Nonstop5h 11m

$289

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 5/11

5:00 am-3:49 pm

1 stop9h 49m

Punta Cana

Thu 5/15

3:16 pm-7:36 pm

Nonstop5h 20m

$295

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 5/20

5:05 am-2:17 pm

1 stop8h 12m

Punta Cana

Sat 5/24

12:42 pm-8:03 pm

1 stop8h 21m

$298

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 5/8

1:19 pm-12:05 am

1 stop9h 46m

San Juan Luis Munoz Marin Intl

Wed 5/14

3:56 am-12:24 pm

1 stop9h 28m

$298

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Tue 5/27

12:41 pm-1:36 pm

2 stops23h 55m

Saint Thomas Island Cyril E King

Tue 6/3

2:41 pm-8:50 am

2 stops19h 09m

$304

ChicagoOranjestad

ORD - AUA

ORDAUA

Chicago O'Hare Intl

Sat 5/24

5:05 am-2:40 pm

1 stop8h 35m

Oranjestad Reina Beatrix

Sat 5/31

3:45 pm-8:50 am

1 stop18h 05m

$325

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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 May 1, 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 May 1, 2025.

The most flights from CHI to zzEPX are scheduled on a Monday (9 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (4 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 May 1, 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
7,934 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.3

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
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.3

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
9,968 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.3

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
4,294 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.3

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
7.5
Good
1,414 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.3

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.
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.3

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 $104 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 O'Hare Intl - Montego Bay Sangster 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 $757, our data indicates the cheapest price to be $133. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $211.

  • 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$375FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$142Average$363FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$193Average$542FlexibilityNo cancel feeOn-time70%
DeltaCheapest$216Average$668FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$226Average$642FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$293Average$487FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$335Average$648FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$335Average$768FlexibilityNo cancel feeOn-time67%
SouthwestCheapest$345Average$674FlexibilityNo cancel feeOn-time63%
AviancaCheapest$397Average$953FlexibilityNo cancel feeOn-time71%

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