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$101+ 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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
May 3 — May 101
Sat 5/3
Sat 5/10
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 April 28, 2025.

Round-trip from

$195
(Cheapflightsfares)

One-way from

$101
(Mytrip)

Popular in

December

Cheapest in

August

Average price

$352

Good round-trip deal

$321 or less

Good one-way deal

$166 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. 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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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 April 28, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/245:05 amORD - SJU
1 stop13h 02mSpirit Airlines
Fri 5/308:12 pmSJU - ORD
1 stop13h 38mSpirit Airlines
Deal found 4/28$195
This CheapOair deal was found by Cheapflights users on 4/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/235:10 amORD - SJU
1 stop9h 05mMultiple Airlines
Fri 5/308:12 pmSJU - ORD
1 stop13h 38mMultiple Airlines
Deal found 4/28$229
This United Airlines deal was found by Cheapflights users on 4/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/119:23 amORD - PUJ
Nonstop4h 42mUnited Airlines
Thu 5/151:50 pmPUJ - ORD
Nonstop5h 05mUnited Airlines
Deal found 4/28$290
This American Airlines deal was found by Cheapflights users on 4/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/54:44 pmORD - PUJ
1 stop17h 00mAmerican Airlines
Thu 5/153:16 pmPUJ - ORD
Nonstop5h 20mAmerican Airlines
Deal found 4/28$295
This Priceline deal was found by Cheapflights users on 4/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/27:35 pmORD - STT
1 stop13h 22mSpirit Airlines
Fri 6/62:41 pmSTT - ORD
1 stop9h 48mSpirit Airlines
Deal found 4/27$295
This eDestinos deal was found by Cheapflights users on 4/28. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/65:36 amORD - PUJ
1 stop8h 06mSpirit Airlines
Wed 5/143:22 pmPUJ - ORD
1 stop8h 42mSpirit Airlines
Deal found 4/28$297
This Frontier deal was found by Cheapflights users on 4/27. 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.
Sun 5/48:30 amMDW - SJU
1 stop10h 14mFrontier
Wed 5/73:56 amSJU - MDW
1 stop9h 28mFrontier
Deal found 4/27$298
This Frontier deal was found by Cheapflights users on 4/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/154:15 pmORD - SJU
1 stop6h 50mFrontier
Mon 5/1910:46 amSJU - ORD
1 stop13h 25mFrontier
Deal found 4/28$308
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Sat 5/174:35 pmORD - PUJ
1 stop18h 12mMultiple Airlines
Sat 5/2412:42 pmPUJ - ORD
1 stop12h 22mMultiple Airlines
Deal found 4/28$311
This JetBlue deal was found by Cheapflights users on 4/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/304:03 pmORD - SJU
1 stop8h 46mJetBlue
Tue 6/38:00 amSJU - ORD
1 stop11h 36mJetBlue
Deal found 4/27$324
This Cheapflightsfares deal was found by Cheapflights users on 4/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/225:05 amORD - AUA
1 stop8h 35mSpirit Airlines
Thu 5/293:45 pmAUA - ORD
1 stop9h 20mSpirit Airlines
Deal found 4/28$330
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/127:10 amORD - PUJ
1 stop6h 22mDelta
Mon 8/182:42 pmPUJ - ORD
1 stop7h 39mDelta
Deal found 4/27$335

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 April 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

Sat 5/24

5:05 am-7:07 pm

1 stop13h 02m

San Juan Luis Munoz Marin Intl

Fri 5/30

8:12 pm-8:50 am

1 stop13h 38m

$195

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 5/23

5:10 am-3:15 pm

1 stop9h 05m

San Juan Luis Munoz Marin Intl

Fri 5/30

8:12 pm-8:50 am

1 stop13h 38m

$229

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 5/11

9:23 am-3:05 pm

Nonstop4h 42m

Punta Cana

Thu 5/15

1:50 pm-5:55 pm

Nonstop5h 05m

$290

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

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Mon 6/2

7:35 pm-9:57 am

1 stop13h 22m

Saint Thomas Island Cyril E King

Fri 6/6

2:41 pm-11:29 pm

1 stop9h 48m

$295

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 5/4

8:30 am-7:44 pm

1 stop10h 14m

San Juan Luis Munoz Marin Intl

Thu 5/8

10:46 am-11:39 pm

1 stop13h 53m

$298

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 5/5

4:15 pm-2:51 am

1 stop9h 36m

San Juan Luis Munoz Marin Intl

Mon 5/12

6:00 am-6:29 pm

1 stop13h 29m

$299

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 5/18

5:05 am-2:17 pm

1 stop8h 12m

Punta Cana

Wed 5/28

3:22 pm-11:04 pm

1 stop8h 42m

$303

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 5/17

4:35 pm-11:47 am

1 stop18h 12m

Punta Cana

Sat 5/24

12:42 pm-12:04 am

1 stop12h 22m

$311

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 5/30

4:03 pm-1:49 am

1 stop8h 46m

San Juan Luis Munoz Marin Intl

Tue 6/3

8:00 am-6:36 pm

1 stop11h 36m

$324

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

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 April 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 April 28, 2025.

The most flights from CHI to 0CB are scheduled on a Saturday (10 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 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 April 28, 2025.
Delta
8.0
Very good
7,929 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Entertainment

7.9

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
7,929 reviews
Delta
8.0
Very good
7,929 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Entertainment

7.9

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
9,961 reviews
Delta
8.0
Very good
7,929 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Entertainment

7.9

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
4,292 reviews
Delta
8.0
Very good
7,929 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Entertainment

7.9

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
1,410 reviews
Delta
8.0
Very good
7,929 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Entertainment

7.9

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
1,766 reviews
Delta
8.0
Very good
7,929 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Entertainment

7.9

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. 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?

    $101 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 United Airlines and Southwest, with prices starting from $116 and $116, 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 United Airlines (88%), American Airlines (83%) and Air Canada (82%).

  • What are the cheapest flights from Chicago to Caribbean?

    Looking for the cheapest flight from Chicago to Caribbean? 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 $188.

  • 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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Midway to Cancún flights
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O'Hare Intl to Reagan-National flights
Midway to LaGuardia flights
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Midway to Seattle flights
O'Hare Intl to Ontario flights
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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 April 28, 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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