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Caribbean Islands

$93+ Cheap flights from Illinois 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Apr 9 — Apr 161
Wed 4/9
Wed 4/16
1 adult, Economy
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Cheap flight deals from Illinois to Caribbean Islands

Keep the following information in mind while searching for Illinois to Caribbean Islands flight deals. Data was last updated April 4, 2025.

Round-trip from

$188
(Cheapflightsfares)

One-way from

$93
(eDestinos)

Popular in

December

Cheapest in

August

Average price

$312
From Illinois to Caribbean Islands
Search Deals
One-way flight from Illinois to Caribbean Islands
Search Deals
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 April 2025
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Find flight deals from Illinois to Caribbean Islands

Cheapest flights from Illinois to Caribbean Islands
Explore the most affordable flight options available from Illinois to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 4, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/3. 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 4/138:45 amORD - SJU
1 stop14h 01mSpirit Airlines
Fri 4/189:30 pmSJU - ORD
1 stop11h 34mSpirit Airlines
Deal found 4/3$180
This Southwest deal was found by Cheapflights users on 4/3. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/31:25 pmSTL - SJU
Nonstop4h 25mSouthwest
Sat 5/103:20 pmSJU - STL
1 stop7h 40mSouthwest
Deal found 4/3$205
This United Airlines deal was found by Cheapflights users on 4/3. 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.
Sat 4/268:00 amSTL - SJU
2 stops11h 38mUnited Airlines
Wed 4/307:45 amSJU - STL
1 stop9h 02mUnited Airlines
Deal found 4/3$219
This CheapOair deal was found by Cheapflights users on 4/3. 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 4/119:54 amORD - SJU
1 stop14h 56mMultiple Airlines
Fri 4/189:30 pmSJU - ORD
1 stop11h 34mMultiple Airlines
Deal found 4/3$238
This American Airlines deal was found by Cheapflights users on 4/4. 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 5/36:15 amSTL - SJU
1 stop16h 54mAmerican Airlines
Tue 5/65:25 amSJU - STL
1 stop16h 33mAmerican Airlines
Deal found 4/4$286
This FlightHub deal was found by Cheapflights users on 4/3. 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 5/109:14 pmORD - STT
2 stops17h 16mSpirit Airlines
Sat 5/1710:52 amSTT - ORD
1 stop14h 13mSpirit Airlines
Deal found 4/3$297
This CheapOair deal was found by Cheapflights users on 4/4. 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 4/132:16 pmMDW - SJU
1 stop18h 29mFrontier
Fri 4/182:20 pmSJU - MDW
1 stop26h 55mFrontier
Deal found 4/4$298
This CheapOair deal was found by Cheapflights users on 4/4. 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.
Sat 5/35:45 pmSTL - SJU
1 stop13h 51mFrontier
Fri 5/93:56 amSJU - STL
1 stop21h 10mFrontier
Deal found 4/4$298
This Frontier deal was found by Cheapflights users on 4/3. 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 4/178:10 amORD - SJU
1 stop11h 09mFrontier
Sun 4/205:55 amSJU - ORD
1 stop10h 11mFrontier
Deal found 4/3$308
This Frontier deal was found by Cheapflights users on 4/3. 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 7/256:45 amORD - PUJ
Nonstop4h 40mFrontier
Tue 7/295:54 pmPUJ - ORD
Nonstop5h 08mFrontier
Deal found 4/3$313
This Delta deal was found by Cheapflights users on 4/3. 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 6/103:43 pmSTL - SJU
1 stop6h 08mDelta
Tue 6/176:15 amSJU - STL
1 stop7h 22mDelta
Deal found 4/3$313
This American Airlines deal was found by Cheapflights users on 4/4. 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 4/285:10 amORD - PUJ
1 stop6h 40mAmerican Airlines
Sat 5/34:40 pmPUJ - ORD
1 stop17h 09mAmerican Airlines
Deal found 4/4$314

Cheapflights Fare Finder

Customize your flight search to find flights from Illinois 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 April 4, 2025.
Use the filters below to find and compare flights from Illinois to Caribbean Islands that are best for you.

Fly from

Illinois

Fly to

Caribbean Islands

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 4/29

11:53 am-11:39 pm

1 stop10h 46m

San Juan Luis Munoz Marin Intl

Fri 5/2

12:54 am-8:35 am

1 stop8h 41m

$188

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Sat 5/3

1:25 pm-6:50 pm

Nonstop4h 25m

San Juan Luis Munoz Marin Intl

Sat 5/10

3:20 pm-10:00 pm

1 stop7h 40m

$205

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Sat 4/26

8:00 am-8:38 pm

2 stops11h 38m

San Juan Luis Munoz Marin Intl

Wed 4/30

7:45 am-3:47 pm

1 stop9h 02m

$219

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 5/1

11:53 am-11:39 pm

1 stop10h 46m

San Juan Luis Munoz Marin Intl

Mon 5/5

10:46 am-11:11 pm

1 stop13h 25m

$250

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Sat 5/3

6:15 am-12:09 am

1 stop16h 54m

San Juan Luis Munoz Marin Intl

Tue 5/6

5:25 am-8:58 pm

1 stop16h 33m

$286

ChicagoSaint Thomas Island

ORD - STT

ORDSTT

Chicago O'Hare Intl

Sat 5/10

9:14 pm-3:30 pm

2 stops17h 16m

Saint Thomas Island Cyril E King

Sat 5/17

10:52 am-12:05 am

1 stop14h 13m

$297

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 4/13

2:16 pm-9:45 am

1 stop18h 29m

San Juan Luis Munoz Marin Intl

Fri 4/18

2:20 pm-4:15 pm

1 stop26h 55m

$298

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Sat 5/3

5:45 pm-8:36 am

1 stop13h 51m

San Juan Luis Munoz Marin Intl

Fri 5/9

3:56 am-12:06 am

1 stop21h 10m

$298

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

Sun 4/20

5:55 am-3:06 pm

1 stop10h 11m

$308

St. LouisSan Juan

STL - SJU

STLSJU

Lambert-St Louis

Tue 6/10

3:43 pm-10:51 pm

1 stop6h 08m

San Juan Luis Munoz Marin Intl

Tue 6/17

6:15 am-12:37 pm

1 stop7h 22m

$313

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/4

Showing 1-10 of 60 results
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Best time to book a flight from Illinois to Caribbean Islands

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

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

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

Find hourly flight availability from Illinois 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 April 4, 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 Islands as you normally would.

Weekly flight availability from Illinois to Caribbean Islands

Explore weekly flight availability from Illinois 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 April 4, 2025.

The most flights from USIL to zzEPX are scheduled on a Wednesday (10 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 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 April 4, 2025.
Read through reviews of airlines operating flights from Illinois to Caribbean Islands, such as Delta, Alaska Airlines and Southwest. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,897 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Comfort

8.0

Crew

8.5

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
7,897 reviews
Delta
8.0
Very good
7,897 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Comfort

8.0

Crew

8.5

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
9,836 reviews
Delta
8.0
Very good
7,897 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Comfort

8.0

Crew

8.5

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
4,276 reviews
Delta
8.0
Very good
7,897 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Comfort

8.0

Crew

8.5

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
7.6
Good
1,402 reviews
Delta
8.0
Very good
7,897 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Comfort

8.0

Crew

8.5

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.
SWISS
7.5
Good
1,574 reviews
Delta
8.0
Very good
7,897 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Food

7.3

Comfort

8.0

Crew

8.5

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 Illinois 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 Illinois to Caribbean Islands one-way?

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $93. Southwest flights start at $100 while deals on Frontier start at $103 one-way.

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

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

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

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

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

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

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

Discover the top 10 airlines that operate flights from Illinois 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 April 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$350FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$144Average$340FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$194Average$688FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$226Average$667FlexibilityNo cancel feeOn-time69%
Copa AirlinesCheapest$226Average$537FlexibilityNo cancel feeOn-time70%
DeltaCheapest$235Average$655FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$293Average$587FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$335Average$754FlexibilityNo cancel feeOn-time67%
SouthwestCheapest$342Average$673FlexibilityNo cancel feeOn-time63%
AviancaCheapest$397Average$953FlexibilityNo cancel feeOn-time71%

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