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$86+ Cheap flights from Caribbean Islands to Illinois

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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheap flight deals from Caribbean Islands to Illinois

Cheapest flights from Caribbean Islands to Illinois
Explore the most affordable flight options available from Caribbean Islands to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 28, 2025.

This FlightHub deal was found by Cheapflights users on 12/26. 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.
Fri 12/266:28 pmSJU - ORD
1 stop8h 02mSpirit Airlines
Sun 1/45:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 12/26$223
This Kiwi.com deal was found by Cheapflights users on 12/26. 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 12/276:28 pmSJU - ORD
1 stop8h 02mMultiple Airlines
Wed 1/79:34 amORD - SJU
1 stop15h 39mMultiple Airlines
Deal found 12/26$251
This Kiwi.com deal was found by Cheapflights users on 12/26. 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 12/276:28 pmSJU - ORD
1 stop8h 02mMultiple Airlines
Fri 1/97:20 amORD - SJU
1 stop14h 24mMultiple Airlines
Deal found 12/26$254
This JetBlue deal was found by Cheapflights users on 12/26. 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 12/262:21 pmSJU - ORD
1 stop9h 43mJetBlue
Tue 1/69:35 amORD - SJU
1 stop7h 48mJetBlue
Deal found 12/26$260
This Kiwi.com deal was found by Cheapflights users on 12/26. 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 12/276:28 pmSJU - ORD
1 stop8h 02mMultiple Airlines
Thu 1/83:32 pmORD - SJU
1 stop7h 27mMultiple Airlines
Deal found 12/26$265
This Kiwi.com deal was found by Cheapflights users on 12/26. 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.
Fri 12/266:49 pmPUJ - ORD
Nonstop5h 10mFrontier
Fri 1/27:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 12/26$267
This JetBlue deal was found by Cheapflights users on 12/26. 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 12/262:21 pmSJU - ORD
1 stop9h 43mJetBlue
Sun 1/46:45 amORD - SJU
1 stop10h 04mJetBlue
Deal found 12/26$274
This JetBlue deal was found by Cheapflights users on 12/26. 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.
Sat 12/272:20 pmSJU - ORD
1 stop9h 44mJetBlue
Mon 1/56:45 amORD - SJU
1 stop7h 41mJetBlue
Deal found 12/26$277
This Expedia deal was found by Cheapflights users on 12/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:49 pmPUJ - ORD
Nonstop5h 10mMultiple Airlines
Mon 1/55:45 amORD - PUJ
Nonstop4h 45mMultiple Airlines
Deal found 12/26$279
This Cheapflightsfares deal was found by Cheapflights users on 12/26. 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 12/266:49 pmPUJ - ORD
Nonstop5h 10mFrontier
Sun 1/47:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 12/26$282
This Kiwi.com deal was found by Cheapflights users on 12/26. 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 12/276:28 pmSJU - ORD
1 stop8h 02mSpirit Airlines
Wed 1/75:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 12/26$284
This Expedia deal was found by Cheapflights users on 12/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Sat 1/108:27 pmORD - SJU
1 stop10h 27mMultiple Airlines
Deal found 12/27$286

Find flight deals from Caribbean Islands to Illinois

Keep the following information in mind while searching for Caribbean Islands to Illinois flight deals. Data was last updated December 28, 2025.

Round-trip from

$163
(eDestinos)

One-way from

$86
(Priceline)
From Caribbean Islands to Illinois
Search Deals
One-way flight from Caribbean Islands to Illinois
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean Islands to Illinois 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 28, 2025.
Use the filters below to find and compare flights from Caribbean Islands to Illinois that are best for you.

Fly from

Caribbean Islands

Fly to

Illinois

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 2/25

5:10 am-12:04 pm

1 stop8h 54m

Chicago O'Hare Intl

Wed 3/4

12:59 pm-12:29 am

1 stop9h 30m

$168

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 1/13

1:22 pm-4:37 pm

Nonstop5h 15m

Chicago O'Hare Intl

Wed 1/21

7:45 am-6:05 pm

1 stop8h 20m

$169

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 2/27

11:52 am-6:08 pm

1 stop8h 16m

Chicago O'Hare Intl

Sun 3/1

6:40 am-5:58 pm

1 stop9h 18m

$171

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Sat 1/24

4:36 pm-11:33 pm

1 stop8h 57m

Lambert-St Louis

Sat 1/31

5:42 pm-9:54 am

1 stop14h 12m

$176

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Thu 1/29

4:36 pm-11:33 pm

1 stop8h 57m

Lambert-St Louis

Mon 2/2

10:16 am-11:59 pm

1 stop11h 43m

$180

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 1/29

4:22 pm-10:19 pm

1 stop7h 57m

Chicago Midway

Mon 2/2

1:00 pm-11:59 pm

1 stop8h 59m

$180

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/19

4:25 pm-2:26 pm

1 stop24h 01m

Chicago Midway

Mon 2/23

9:22 pm-12:43 am

1 stop25h 21m

$180

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Mon 2/23

3:53 am-3:52 pm

1 stop13h 59m

Chicago O'Hare Intl

Mon 3/2

2:13 pm-2:25 am

1 stop10h 12m

$180

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 2/6

9:25 am-7:31 pm

1 stop12h 06m

Chicago O'Hare Intl

Tue 2/10

9:40 am-7:23 pm

1 stop7h 43m

$182

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/15

11:06 am-7:36 pm

1 stop10h 30m

Chicago O'Hare Intl

Mon 1/19

10:15 am-7:26 pm

1 stop7h 11m

$190

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/26

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

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

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

Currently, August is the cheapest month in which you can book a flight from Caribbean Islands to Illinois (average of $121). Flying from Caribbean Islands to Illinois in June is currently the most expensive (average of $175). 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 EPX to IL?

Find hourly flight availability from Caribbean Islands to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 28, 2025.

One of the essential ways to save on airfare from Caribbean Islands to Illinois is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 51% on airfare.

What is the cheapest day to fly from Caribbean Islands to Illinois?

Use this chart to determine the cheapest time to fly round-trip from Caribbean Islands to Illinois. Price data was last updated on December 27, 2025.

Travelers seeking maximum savings on their Caribbean Islands to Illinois flight should consider departing on Thursday afternoons when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Caribbean Islands to Illinois

Explore weekly flight availability from Caribbean Islands to Illinois. 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 28, 2025.

The most flights from zzEPX to USIL are scheduled on a Monday (12 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (12 on average).

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated December 28, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Caribbean Islands to Illinois to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,018 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,018 reviews
Delta
7.9
Good
8,018 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,114 reviews
Delta
7.9
Good
8,018 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,071 reviews
Delta
7.9
Good
8,018 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,210 reviews
Delta
7.9
Good
8,018 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Frontier
5.8
Fair
3,064 reviews
Delta
7.9
Good
8,018 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Caribbean Islands to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Caribbean Islands to Illinois?

    JetBlue, Frontier, and Spirit Airlines can get you from Caribbean Islands to Illinois in just under 7h 41m. Your travel time can differ by up to 1h 16m. The distance from Caribbean Islands to Illinois is about 1947 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Caribbean Islands to Illinois one-way?

    For one-way options, check prices for JetBlue. According to our data, you can fly for as low as $71. Users have also found prices from $85 and $94 on Frontier and Spirit Airlines, respectively.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Caribbean Islands to Illinois (average of $121). Flying from Caribbean Islands to Illinois in June is currently the most expensive (average of $175). 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 Caribbean Islands to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Caribbean Islands to Illinois

Discover the top 7 airlines that operate flights from Caribbean Islands to Illinois. 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 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$120Average$228FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$137Average$329FlexibilityNo cancel feeOn-time65%
FrontierCheapest$138Average$349FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$626FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$254Average$556FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$277Average$542FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$392Average$551FlexibilityNo cancel feeOn-time63%

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