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$81+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
1 adult, Economy
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Cheap flight deals from Chicago to Caribbean

Keep the following information in mind while searching for Chicago to Caribbean flight deals. Data was last updated March 28, 2025.

Round-trip from

$180
(eDestinos)

One-way from

$81
(Cheapflightsfares)

Popular in

December

Cheapest in

August

Average price

$430

Good round-trip deal

$266 or less

Good one-way deal

$151 or less
From Chicago (CHI) to Caribbean
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One-way flight from Chicago (CHI) to Caribbean
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Highest demand for flights based on searches. 16% potential increase in price ($70 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Caribbean.
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Price to beat on a one-way flight from Chicago (CHI) to Caribbean.
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Find 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 March 28, 2025.

This eDestinos deal was found by Cheapflights users on 3/26. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/238:04 amORD - SJU
Nonstop4h 41mSpirit Airlines
Wed 4/306:35 amSJU - ORD
Nonstop5h 23mSpirit Airlines
Deal found 3/26$180
This Kiwi.com deal was found by Cheapflights users on 3/26. 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.
Fri 5/27:47 pmORD - STT
1 stop13h 13mSpirit Airlines
Sat 5/1010:52 amSTT - ORD
1 stop14h 32mSpirit Airlines
Deal found 3/26$261
This CheapOair deal was found by Cheapflights users on 3/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/178:10 amORD - SJU
1 stop11h 09mMultiple Airlines
Thu 4/246:35 amSJU - ORD
Nonstop5h 23mMultiple Airlines
Deal found 3/27$264
This Frontier deal was found by Cheapflights users on 3/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/49:54 amORD - SJU
1 stop7h 37mFrontier
Tue 4/82:55 amSJU - ORD
1 stop8h 45mFrontier
Deal found 3/27$296
This Frontier deal was found by Cheapflights users on 3/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/312:46 pmMDW - SJU
1 stop12h 04mFrontier
Sun 4/63:14 amSJU - MDW
1 stop10h 14mFrontier
Deal found 3/27$296
This American Airlines deal was found by Cheapflights users on 3/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/165:15 amORD - PUJ
1 stop7h 45mAmerican Airlines
Sun 7/204:55 pmPUJ - ORD
1 stop8h 02mAmerican Airlines
Deal found 3/27$319
This Kiwi.com deal was found by Cheapflights users on 3/27. 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.
Sun 5/114:15 pmORD - PUJ
2 stops21h 02mMultiple Airlines
Thu 5/155:54 pmPUJ - ORD
Nonstop5h 06mMultiple Airlines
Deal found 3/27$320
This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/115:05 amORD - PUJ
1 stop8h 12mSpirit Airlines
Thu 5/1512:42 pmPUJ - ORD
1 stop8h 21mSpirit Airlines
Deal found 3/27$324
This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/266:20 amORD - PUJ
Nonstop4h 36mFrontier
Tue 4/295:50 pmPUJ - ORD
Nonstop5h 18mFrontier
Deal found 3/27$331
This Delta deal was found by Cheapflights users on 3/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/106:15 amORD - PUJ
1 stop8h 51mDelta
Mon 4/141:45 pmPUJ - ORD
1 stop9h 21mDelta
Deal found 3/26$335
This Delta deal was found by Cheapflights users on 3/25. 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 4/206:04 amMDW - PUJ
1 stop6h 11mDelta
Thu 4/242:40 pmPUJ - MDW
1 stop8h 42mDelta
Deal found 3/25$335
This Mytrip deal was found by Cheapflights users on 3/25. 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.
Sat 4/2611:45 amORD - STT
2 stops21h 15mMultiple Airlines
Sat 5/312:29 pmSTT - ORD
3 stops26h 46mMultiple Airlines
Deal found 3/25$337

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 March 28, 2025.
Use the filters below to find and compare flights from Chicago to Caribbean that are best for you.

Fly from

Chicago

Fly to

Caribbean

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 4/23

8:04 am-1:45 pm

Nonstop4h 41m

San Juan Luis Munoz Marin Intl

Wed 4/30

6:35 am-10:58 am

Nonstop5h 23m

$180

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Fri 5/2

7:47 pm-10:00 am

1 stop13h 13m

Saint Thomas Island Cyril E King

Sat 5/10

10:52 am-12:24 am

1 stop14h 32m

$261

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 4/17

8:10 am-8:19 pm

1 stop11h 09m

San Juan Luis Munoz Marin Intl

Thu 4/24

6:35 am-10:58 am

Nonstop5h 23m

$264

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 4/7

9:50 am-6:28 pm

1 stop7h 38m

San Juan Luis Munoz Marin Intl

Tue 4/8

2:55 am-10:40 am

1 stop8h 45m

$296

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 4/25

6:15 am-3:22 pm

1 stop8h 07m

San Juan Luis Munoz Marin Intl

Fri 5/2

6:00 am-5:28 pm

1 stop12h 28m

$296

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 7/16

5:15 am-2:00 pm

1 stop7h 45m

Punta Cana

Sun 7/20

4:55 pm-11:57 pm

1 stop8h 02m

$319

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 5/11

4:15 pm-2:17 pm

2 stops21h 02m

Punta Cana

Thu 5/15

5:54 pm-10:00 pm

Nonstop5h 06m

$320

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 4/26

1:26 pm-10:02 pm

1 stop7h 36m

San Juan Luis Munoz Marin Intl

Tue 4/29

3:28 am-12:13 pm

1 stop9h 45m

$324

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 5/11

5:05 am-2:17 pm

1 stop8h 12m

Punta Cana

Thu 5/15

12:42 pm-8:03 pm

1 stop8h 21m

$324

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 4/26

6:20 am-11:56 am

Nonstop4h 36m

Punta Cana

Tue 4/29

5:50 pm-10:08 pm

Nonstop5h 18m

$331

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/28

Showing 1-10 of 60 results
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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, September is the cheapest month in which you can book a flight from Chicago to Caribbean (average of $254). Flying from Chicago to Caribbean 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 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 March 28, 2025.

When flying from Chicago to Caribbean, 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

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 March 28, 2025.

The most flights from CHI to 0CB are scheduled on a Thursday (10 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Caribbean by month

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

In terms of precipitation, rainfall in Caribbean 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 when rainfall is around 2.2 in.

Temperature in Caribbean by month

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

If weather is an important factor for your trip to Caribbean, 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

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 March 28, 2025.
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very good
4,274 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,897 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Alaska Airlines
8.0
Very good
9,798 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Air Transat
7.8
Good
381 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Copa Airlines
7.5
Good
1,395 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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.

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

    $81 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 American Airlines, with prices starting from $132 and $138, 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 Spirit Airlines (91%), Air Canada (91%) and Air New Zealand (91%).

  • What are the cheapest flights from Chicago to Caribbean?

    Looking for the cheapest flight from Chicago to Caribbean? While on average our users pay $841, our data indicates the cheapest price to be $69. The most popular route (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), is priced around $180.

  • 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, September is the cheapest month in which you can book a flight from Chicago to Caribbean (average of $254). Flying from Chicago to Caribbean 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

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

Discover the top 10 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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$352FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$144Average$339FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$193Average$540FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$226Average$641FlexibilityNo cancel feeOn-time69%
DeltaCheapest$235Average$660FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$293Average$510FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$332Average$637FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$335Average$779FlexibilityNo cancel feeOn-time67%
SouthwestCheapest$342Average$680FlexibilityNo cancel feeOn-time63%
AviancaCheapest$397Average$953FlexibilityNo cancel feeOn-time71%
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