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$69+ 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Dez 12 — Dez 191
Fr 12/12
Fr 12/19
1 adult, Economy
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Find 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 November 12, 2025.

This Expedia deal was found by Cheapflights users on 11/11. 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.
Mi 12/33:55 amSJU - STL
1 stop20h 38mFrontier
Mo 12/83:30 pmSTL - SJU
1 stop9h 20mFrontier
Deal found 11/11$168
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Do 12/111:59 amSJU - ORD
1 stop12h 41mMultiple Airlines
Mo 12/155:40 amORD - SJU
Nonstop4h 41mMultiple Airlines
Deal found 11/11$185
This Priceline deal was found by Cheapflights users on 11/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 12/54:10 amSJU - ORD
2 stops13h 37mMultiple Airlines
So 12/76:00 amORD - SJU
1 stop12h 08mMultiple Airlines
Deal found 11/11$191
This Mytrip deal was found by Cheapflights users on 11/10. 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.
Fr 12/58:45 pmSJU - ORD
Nonstop5h 14mMultiple Airlines
Mo 12/82:26 pmORD - SJU
1 stop10h 24mMultiple Airlines
Deal found 11/10$193
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Fr 12/193:55 amSJU - MDW
1 stop19h 09mFrontier
So 1/46:00 amMDW - SJU
1 stop17h 37mFrontier
Deal found 11/11$195
This Priceline deal was found by Cheapflights users on 11/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 12/56:50 pmPUJ - ORD
Nonstop5h 10mFrontier
Fr 12/127:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 11/12$196
This Cheapflightsfares deal was found by Cheapflights users on 11/11. 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.
Sa 11/2211:55 amSJU - ORD
1 stop13h 34mSpirit Airlines
Fr 11/2811:40 amORD - SJU
1 stop8h 10mSpirit Airlines
Deal found 11/11$196
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Sa 11/223:59 amSJU - ORD
1 stop8h 14mFrontier
Sa 11/295:20 amORD - SJU
1 stop8h 30mFrontier
Deal found 11/11$197
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Do 11/2011:55 amSJU - ORD
1 stop13h 18mSpirit Airlines
Mo 11/245:00 amORD - SJU
1 stop13h 27mSpirit Airlines
Deal found 11/10$198
This CheapOair deal was found by Cheapflights users on 11/12. 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.
Do 12/48:45 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Mo 12/87:10 amORD - SJU
1 stop15h 35mSpirit Airlines
Deal found 11/12$199
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Mo 11/245:19 pmSJU - ORD
1 stop28h 02mMultiple Airlines
Fr 11/2811:40 amORD - SJU
1 stop8h 10mMultiple Airlines
Deal found 11/11$201
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Do 12/183:54 amSJU - ORD
1 stop15h 06mMultiple Airlines
Sa 1/104:46 pmORD - SJU
1 stop29h 45mMultiple Airlines
Deal found 11/11$202

Cheap 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 November 12, 2025.

Round-trip from

$138
(Priceline)

One-way from

$69
(Frontier)
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 November 12, 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 JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Do 2/19

11:05 am-10:33 pm

1 stop13h 28m

Lambert-St Louis

Mo 2/23

5:11 pm-2:50 am

1 stop7h 39m

$153

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fr 12/19

3:55 am-9:04 pm

1 stop19h 09m

Chicago Midway

So 1/4

6:00 am-1:37 am

1 stop17h 37m

$195

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fr 12/12

8:45 pm-11:59 pm

Nonstop5h 14m

Chicago O'Hare Intl

Mo 12/15

5:40 am-12:21 pm

Nonstop4h 41m

$198

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Mo 11/24

7:09 pm-5:15 pm

1 stop24h 06m

Chicago Midway

Mi 11/26

5:30 pm-9:12 pm

1 stop25h 42m

$206

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Do 1/22

4:52 pm-8:20 pm

Nonstop5h 28m

Chicago O'Hare Intl

Mo 1/26

2:20 pm-9:00 pm

Nonstop4h 40m

$216

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Mi 1/28

7:00 am-5:45 pm

1 stop12h 45m

Chicago O'Hare Intl

Mi 2/4

7:01 am-4:52 pm

1 stop7h 51m

$226

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Do 3/5

3:55 am-1:47 pm

1 stop11h 52m

Chicago Midway

Di 3/10

3:10 pm-1:50 am

1 stop9h 40m

$226

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Do 3/5

9:37 pm-9:58 pm

1 stop26h 21m

Chicago Midway

Mo 3/9

8:00 am-12:45 am

1 stop15h 45m

$226

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Do 12/4

3:55 am-10:39 pm

1 stop20h 44m

Chicago Midway

Mo 12/8

3:10 pm-2:50 am

1 stop9h 40m

$226

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Do 12/4

12:49 pm-9:47 pm

2 stops10h 58m

Lambert-St Louis

Mo 12/8

8:13 am-10:09 pm

1 stop11h 56m

$230

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

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, January is the cheapest month in which you can book a flight from Caribbean Islands to Illinois (average of $116). Flying from Caribbean Islands to Illinois in June is currently the most expensive (average of $193). 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 November 12, 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 35% 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 16, 2024.

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. Sunday afternoons 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 November 12, 2025.

The most flights from zzEPX to USIL are scheduled on a Monday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 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 November 12, 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
8,008 reviews

Boarding

8.1

Food

7.3

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

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
8,008 reviews
Delta
7.9
Good
8,008 reviews

Boarding

8.1

Food

7.3

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

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
9,014 reviews
Delta
7.9
Good
8,008 reviews

Boarding

8.1

Food

7.3

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

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
11,049 reviews
Delta
7.9
Good
8,008 reviews

Boarding

8.1

Food

7.3

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

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
8,137 reviews
Delta
7.9
Good
8,008 reviews

Boarding

8.1

Food

7.3

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

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
3,113 reviews
Delta
7.9
Good
8,008 reviews

Boarding

8.1

Food

7.3

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

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?

    Frontier, Spirit Airlines, and United Airlines can get you from Caribbean Islands to Illinois in just under 5h 14m. Your travel time can differ by up to 8h 14m. The distance from Caribbean Islands to Illinois is about 2073 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 United Airlines. According to our data, you can fly for as low as $108. Users have also found prices from $109 and $113 on Spirit Airlines and Delta, 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, January is the cheapest month in which you can book a flight from Caribbean Islands to Illinois (average of $116). Flying from Caribbean Islands to Illinois in June is currently the most expensive (average of $193). 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 6 airlines flying from Caribbean Islands to Illinois

Discover the top 6 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 November 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$137Average$335FlexibilityNo cancel feeOn-time65%
FrontierCheapest$139Average$312FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$562FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$269Average$520FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$334Average$576FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$384Average$523FlexibilityNo cancel feeOn-time63%

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