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Caribbean

$103+ Cheap flights from Illinois 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheap flight deals from Illinois to Caribbean

Keep the following information in mind while searching for Illinois to Caribbean 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

Good round-trip deal

$321 or less

Good one-way deal

$166 or less
From Illinois to Caribbean
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One-way flight from Illinois 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 May 2025
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Price to beat on a round-trip flight from Illinois to Caribbean.
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Price to beat on a one-way flight from Illinois to Caribbean.
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Find flight deals from Illinois to Caribbean

Cheapest flights from Illinois to Caribbean
Explore the most affordable flight options available from Illinois to Caribbean. 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 Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1210:10 amSTL - SJU
1 stop11h 13mDelta
Tue 7/156:15 amSJU - STL
1 stop11h 03mDelta
Deal found 4/29$209
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.
Sat 5/246:20 pmSTL - SJU
1 stop15h 44mAmerican Airlines
Tue 5/275:25 amSJU - STL
1 stop16h 33mAmerican Airlines
Deal found 4/28$244
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 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.
Sat 5/2410:10 amSTL - SJU
1 stop7h 57mSpirit Airlines
Sat 6/79:23 pmSJU - STL
1 stop12h 52mSpirit Airlines
Deal found 4/30$272
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/275:00 amSTL - SJU
1 stop8h 44mUnited Airlines
Tue 6/33:56 pmSJU - STL
1 stop7h 49mUnited Airlines
Deal found 4/29$274
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

Cheapflights Fare Finder

Customize your flight search to find flights from Illinois 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 May 1, 2025.
Use the filters below to find and compare flights from Illinois to Caribbean that are best for you.

Fly from

Illinois

Fly to

Caribbean

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

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Sat 7/12

10:10 am-10:23 pm

1 stop11h 13m

San Juan Luis Munoz Marin Intl

Tue 7/15

6:15 am-4:18 pm

1 stop11h 03m

$209

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Sat 5/24

6:20 pm-11:04 am

1 stop15h 44m

San Juan Luis Munoz Marin Intl

Tue 5/27

5:25 am-8:58 pm

1 stop16h 33m

$244

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

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Sat 5/24

10:10 am-7:07 pm

1 stop7h 57m

San Juan Luis Munoz Marin Intl

Sat 6/7

9:23 pm-9:15 am

1 stop12h 52m

$272

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Tue 5/27

5:00 am-2:44 pm

1 stop8h 44m

San Juan Luis Munoz Marin Intl

Tue 6/3

3:56 pm-10:45 pm

1 stop7h 49m

$274

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

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 Illinois to Caribbean

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

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

Currently, September is the cheapest month in which you can book a flight from Illinois to Caribbean (average of $254). Flying from Illinois 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 IL to CB?

Find hourly flight availability from Illinois 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 May 1, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Caribbean as you normally would.

Weekly flight availability from Illinois to Caribbean

Explore weekly flight availability from Illinois 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 May 1, 2025.

The most flights from USIL to 0CB 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 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 May 1, 2025.
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Copa Airlines
7.5
Good
1,415 reviews
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,922 reviews
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Related info for your journey

Find useful and relevant information for your journey from Illinois 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 Illinois to Caribbean one-way?

    The cheapest airlines for a one-way flight from Illinois to Caribbean are Spirit Airlines ($103), Frontier ($104), and Delta ($105).

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Illinois 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 Illinois to Caribbean?

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

Discover the top 10 airlines that operate flights from Illinois 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 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%
American AirlinesCheapest$194Average$683FlexibilityNo cancel feeOn-time71%
DeltaCheapest$216Average$662FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$226Average$671FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$293Average$487FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$335Average$768FlexibilityNo cancel feeOn-time67%
SouthwestCheapest$345Average$674FlexibilityNo cancel feeOn-time63%
AviancaCheapest$397Average$953FlexibilityNo cancel feeOn-time71%

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