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$81+ 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 3/26. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Feb 27 — Mar 61
Thu 2/27
Thu 3/6
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 February 22, 2025.

Round-trip from

$167
(Cheapflightsfares)

One-way from

$81
(FlightHub)

Popular in

December

Cheapest in

April

Average price

$372

Good round-trip deal

$283 or less

Good one-way deal

$170 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 ($69 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 February 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 February 22, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/14:15 pmORD - SJU
1 stop9h 36mMultiple Airlines
Tue 5/610:25 amSJU - ORD
1 stop8h 16mMultiple Airlines
Deal found 2/22$167
This Cheapflightsfares deal was found by Cheapflights users on 2/22. 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.
Wed 5/146:00 amORD - SJU
1 stop17h 12mSpirit Airlines
Thu 5/298:59 pmSJU - ORD
Nonstop4h 59mSpirit Airlines
Deal found 2/22$169
This Frontier deal was found by Cheapflights users on 2/20. 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 5/21:19 pmMDW - SJU
1 stop12h 32mFrontier
Mon 5/510:46 amSJU - MDW
1 stop14h 01mFrontier
Deal found 2/20$170
This Frontier deal was found by Cheapflights users on 2/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/81:30 pmORD - SJU
1 stop10h 10mFrontier
Sat 3/155:25 amSJU - ORD
1 stop7h 45mFrontier
Deal found 2/22$171
This Mytrip deal was found by Cheapflights users on 2/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/47:07 amORD - STT
2 stops28h 46mSpirit Airlines
Tue 3/1111:11 amSTT - ORD
2 stops25h 25mSpirit Airlines
Deal found 2/21$263
This Delta deal was found by Cheapflights users on 2/21. 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.
Sat 3/12:00 pmORD - SJU
1 stop7h 59mDelta
Wed 3/56:17 pmSJU - ORD
1 stop7h 32mDelta
Deal found 2/21$271
This Delta deal was found by Cheapflights users on 2/21. 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.
Fri 4/2512:48 pmMDW - SJU
1 stop9h 27mDelta
Mon 4/287:15 amSJU - MDW
1 stop11h 44mDelta
Deal found 2/21$271
This American Airlines deal was found by Cheapflights users on 2/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/286:35 pmORD - SJU
1 stop15h 14mAmerican Airlines
Mon 3/34:44 pmSJU - ORD
1 stop9h 33mAmerican Airlines
Deal found 2/21$296
This Frontier deal was found by Cheapflights users on 2/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/239:12 pmMDW - PUJ
1 stop10h 39mFrontier
Thu 5/293:05 pmPUJ - MDW
1 stop9h 50mFrontier
Deal found 2/21$303
This Kiwi.com deal was found by Cheapflights users on 2/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/66:10 amORD - PUJ
Nonstop4h 50mFrontier
Tue 3/115:54 pmPUJ - ORD
Nonstop5h 20mFrontier
Deal found 2/21$304
This CheapOair deal was found by Cheapflights users on 2/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/285:10 amORD - PUJ
1 stop8h 32mMultiple Airlines
Fri 5/23:07 pmPUJ - ORD
1 stop9h 04mMultiple Airlines
Deal found 2/21$306
This FlightHub deal was found by Cheapflights users on 2/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/65:10 amORD - PUJ
1 stop8h 32mSpirit Airlines
Wed 5/144:03 pmPUJ - ORD
1 stop29h 37mSpirit Airlines
Deal found 2/22$307

Find flights from Illinois to Caribbean within your budget

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 February 22, 2025.

Fly from

Illinois

Fly to

Caribbean

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 5/1

8:45 am-2:34 am

1 stop16h 49m

San Juan Luis Munoz Marin Intl

Thu 5/8

4:46 pm-8:50 pm

Nonstop5h 04m

$167

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 3/11

9:25 am-11:38 pm

1 stop13h 13m

San Juan Luis Munoz Marin Intl

Fri 3/14

6:00 am-10:36 am

Nonstop5h 36m

$168

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 5/2

1:19 pm-2:51 am

1 stop12h 32m

San Juan Luis Munoz Marin Intl

Mon 5/5

10:46 am-11:47 pm

1 stop14h 01m

$170

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 3/8

1:30 pm-1:40 am

1 stop10h 10m

San Juan Luis Munoz Marin Intl

Thu 3/13

5:45 am-6:54 pm

1 stop14h 09m

$171

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Tue 3/4

7:07 am-1:53 pm

2 stops28h 46m

Saint Thomas Island Cyril E King

Tue 3/11

11:11 am-11:36 am

2 stops25h 25m

$263

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 3/1

2:00 pm-11:59 pm

1 stop7h 59m

San Juan Luis Munoz Marin Intl

Wed 3/5

6:17 pm-11:49 pm

1 stop7h 32m

$271

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 4/25

12:48 pm-11:15 pm

1 stop9h 27m

San Juan Luis Munoz Marin Intl

Mon 4/28

7:15 am-5:59 pm

1 stop11h 44m

$271

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 2/28

6:35 pm-11:49 am

1 stop15h 14m

San Juan Luis Munoz Marin Intl

Mon 3/3

4:44 pm-12:17 am

1 stop9h 33m

$296

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 5/23

9:12 pm-8:51 am

1 stop10h 39m

Punta Cana

Thu 5/29

3:05 pm-11:55 pm

1 stop9h 50m

$303

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Thu 3/6

6:10 am-1:00 pm

Nonstop4h 50m

Punta Cana

Tue 3/11

5:54 pm-10:14 pm

Nonstop5h 20m

$304

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

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.

Travel insights for flights from Illinois to Caribbean

Get recent, data-driven insights about flights from Illinois to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $363). 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 February 22, 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 February 22, 2025.

The most flights from USIL to 0CB are scheduled on a Friday (9 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 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 February 22, 2025.
Southwest
8.1
Very good
4,396 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,396 reviews
Southwest
8.1
Very good
4,396 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,203 reviews
Southwest
8.1
Very good
4,396 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,702 reviews
Southwest
8.1
Very good
4,396 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Copa Airlines
7.6
Good
1,502 reviews
Southwest
8.1
Very good
4,396 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,754 reviews
Southwest
8.1
Very good
4,396 reviews

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 ($81), Frontier ($83), and United Airlines ($131).

  • 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 March is currently the most expensive (average of $363). 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 February 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$366FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$151Average$347FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$194Average$694FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$226Average$638FlexibilityNo cancel feeOn-time69%
Copa AirlinesCheapest$226Average$524FlexibilityNo cancel feeOn-time70%
JetBlueCheapest$293Average$509FlexibilityNo cancel feeOn-time62%
DeltaCheapest$293Average$678FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$332Average$678FlexibilityNo cancel feeOn-time63%
Air CanadaCheapest$335Average$779FlexibilityNo cancel feeOn-time67%
AviancaCheapest$1,422Average$1,422FlexibilityNo cancel feeOn-time71%
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