Caribbean Islands

$90+ 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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Dec 23 — Dec 301
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Cheap flight deals from Illinois to Caribbean Islands

Discover tips and strategies to find the most affordable flight options for your journey from Illinois (USIL) to Caribbean Islands (zzEPX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 18, 2024.

Round-trip from

$161
(Kiwi.com)

One-way from

$90
(Trip.com)
From Illinois to Caribbean Islands
One-way flight from Illinois to Caribbean Islands

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 December 18, 2024.

This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Tue 12/311:47 pmORD - SJU
1 stop8h 54mMultiple Airlines
Tue 1/149:26 pmSJU - ORD
Nonstop5h 25mMultiple Airlines
Deal found 12/17$191
This Cheapflightsfares deal was found by Cheapflights users on 12/17. 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 12/311:00 pmORD - SJU
Nonstop4h 36mSpirit Airlines
Tue 1/149:26 pmSJU - ORD
Nonstop5h 25mSpirit Airlines
Deal found 12/17$209
This Frontier deal was found by Cheapflights users on 12/18. 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.
Mon 12/304:41 pmORD - SJU
1 stop11h 49mFrontier
Sat 1/189:15 pmSJU - ORD
1 stop14h 37mFrontier
Deal found 12/18$278
This FlightHub deal was found by Cheapflights users on 12/17. 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.
Mon 12/309:16 amMDW - SJU
1 stop9h 54mFrontier
Sat 1/189:15 pmSJU - MDW
1 stop14h 47mFrontier
Deal found 12/17$288
This Kiwi.com deal was found by Cheapflights users on 12/18. 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.
Tue 12/316:10 amORD - PUJ
Nonstop4h 29mFrontier
Tue 12/316:45 pmPUJ - ORD
Nonstop5h 14mFrontier
Deal found 12/18$315
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Tue 12/315:11 pmORD - STT
1 stop15h 28mSpirit Airlines
Thu 1/911:51 amSTT - ORD
1 stop10h 22mSpirit Airlines
Deal found 12/16$379
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Tue 12/316:39 pmORD - PUJ
1 stop17h 31mAmerican Airlines
Thu 1/95:40 pmPUJ - ORD
1 stop17h 05mAmerican Airlines
Deal found 12/17$383
This CheapOair deal was found by Cheapflights users on 12/17. 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.
Tue 12/316:10 amORD - PUJ
Nonstop4h 29mMultiple Airlines
Sun 1/124:50 pmPUJ - ORD
1 stop8h 42mMultiple Airlines
Deal found 12/17$408
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Tue 12/316:39 pmORD - SJU
1 stop16h 55mAmerican Airlines
Sun 7/273:15 pmSJU - ORD
Nonstop5h 10mAmerican Airlines
Deal found 12/17$420
This Southwest deal was found by Cheapflights users on 12/17. 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.
Tue 12/3111:55 amMDW - SJU
2 stops10h 50mSouthwest
Tue 1/146:00 amSJU - MDW
2 stops12h 50mSouthwest
Deal found 12/17$434
This Booking.com deal was found by Cheapflights users on 12/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/278:25 amMDW - PUJ
1 stop26h 24mFrontier
Mon 12/301:59 pmPUJ - MDW
1 stop27h 12mFrontier
Deal found 12/17$447
This CheapOair deal was found by Cheapflights users on 12/17. 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.
Tue 12/313:31 pmORD - MBJ
1 stop21h 14mSpirit Airlines
Wed 1/221:16 pmMBJ - ORD
1 stop7h 57mSpirit Airlines
Deal found 12/17$451

Find flights from Illinois to Caribbean Islands within your budget

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 December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 1/8

3:31 pm-1:25 am

1 stop7h 54m

San Juan Luis Munoz Marin Intl

Fri 1/17

9:26 pm-12:51 am

Nonstop5h 25m

$161

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 1/23

6:50 am-12:36 am

1 stop15h 46m

San Juan Luis Munoz Marin Intl

Sun 1/26

6:55 pm-4:23 pm

1 stop23h 28m

$162

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Fri 1/17

6:45 am-1:59 am

1 stop17h 14m

San Juan Luis Munoz Marin Intl

Thu 1/23

9:49 pm-2:42 pm

1 stop18h 53m

$162

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/27

1:44 pm-8:21 pm

Nonstop4h 37m

San Juan Luis Munoz Marin Intl

Mon 2/3

6:00 am-10:16 pm

1 stop18h 16m

$163

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/12

11:15 am-10:22 pm

1 stop9h 07m

San Juan Luis Munoz Marin Intl

Wed 1/22

2:05 am-9:40 am

1 stop9h 35m

$234

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 1/25

5:11 am-3:45 pm

1 stop8h 34m

Punta Cana

Fri 1/31

6:10 pm-9:27 pm

Nonstop5h 17m

$249

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Tue 1/28

5:31 pm-9:41 pm

2 stops26h 10m

San Juan Luis Munoz Marin Intl

Sun 2/2

10:09 pm-3:43 pm

2 stops19h 34m

$249

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 1/29

6:10 am-1:00 pm

Nonstop4h 50m

Punta Cana

Fri 1/31

6:10 pm-9:27 pm

Nonstop5h 17m

$255

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Thu 2/27

4:13 pm-2:00 pm

1 stop19h 47m

Punta Cana

Mon 3/3

3:10 pm-7:32 am

1 stop18h 22m

$257

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/27

12:25 pm-9:38 pm

1 stop7h 13m

San Juan Luis Munoz Marin Intl

Sat 2/1

6:00 am-12:14 pm

1 stop8h 14m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

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.

Travel insights for flights from Illinois to Caribbean Islands

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

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 March is currently the most expensive (average of $334). 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 December 18, 2024.

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 December 18, 2024.

The most flights from USIL to zzEPX are scheduled on a Monday (10 on average). You will have fewer flight options on Thursday, 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 December 18, 2024.
Read through reviews of airlines operating flights from Illinois to Caribbean Islands, such as United Airlines, Spirit Airlines and American Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.1
Very good
4,848 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.1
Very good
4,848 reviews
8.1
Very good
4,848 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
8,604 reviews
8.1
Very good
4,848 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
9,552 reviews
8.1
Very good
4,848 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.7
Good
1,723 reviews
8.1
Very good
4,848 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.4
Good
9,059 reviews
8.1
Very good
4,848 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Frontier, which is currently one of the cheapest options available, starting at $90. Spirit Airlines flights start at $93 while deals on United Airlines start at $113 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 March is currently the most expensive (average of $334). 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.

Top 9 airlines flying from Illinois to Caribbean Islands

Discover the top 9 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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$65Average$361FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$137Average$489FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$159Average$356FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$194Average$675FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$254Average$623FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$304Average$632FlexibilityNo cancel feeOn-time63%
DeltaCheapest$307Average$624FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$379Average$496FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$514Average$753FlexibilityNo cancel feeOn-time67%
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