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$58+ Cheap flights from Caribbean 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
ene. 11 — ene. 181
dom. 1/11
dom. 1/18
1 adult, Economy
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Cheap flight deals from Caribbean to Illinois

Cheapest flights from Caribbean to Illinois
Explore the most affordable flight options available from Caribbean to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on diciembre 12, 2025.

This JetBlue deal was found by Cheapflights users on 12/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/262:21 pmSJU - ORD
1 stop9h 43mJetBlue
vie. 1/26:45 amORD - SJU
1 stop10h 04mJetBlue
Deal found 12/10$170
This Kiwi.com deal was found by Cheapflights users on 12/11. 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.
sáb. 12/136:50 pmPUJ - ORD
Nonstop5h 10mFrontier
lun. 12/157:10 amORD - PUJ
Nonstop4h 37mFrontier
Deal found 12/11$179
This Frontier deal was found by Cheapflights users on 12/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/214:21 pmSJU - ORD
1 stop8h 03mFrontier
jue. 1/86:07 pmORD - SJU
1 stop10h 27mFrontier
Deal found 12/11$185
This Cheapflightsfares deal was found by Cheapflights users on 12/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/258:08 pmSJU - ORD
Nonstop5h 17mSpirit Airlines
mar. 1/65:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 12/10$187
This Cheapflightsfares deal was found by Cheapflights users on 12/11. 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.
jue. 12/258:08 pmSJU - ORD
Nonstop5h 17mSpirit Airlines
lun. 1/59:09 pmORD - SJU
1 stop18h 14mSpirit Airlines
Deal found 12/11$191
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
jue. 12/258:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
lun. 1/56:05 pmORD - SJU
1 stop18h 13mMultiple Airlines
Deal found 12/10$197
This Expedia deal was found by Cheapflights users on 12/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/297:15 amSJU - ORD
1 stop29h 40mFrontier
mar. 1/65:29 pmORD - SJU
1 stop28h 48mFrontier
Deal found 12/10$201
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
vie. 12/268:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
mié. 1/75:29 pmORD - SJU
1 stop7h 21mMultiple Airlines
Deal found 12/10$202
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
mié. 12/248:08 pmSJU - ORD
Nonstop5h 17mSpirit Airlines
mar. 1/65:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 12/10$203
This Frontier deal was found by Cheapflights users on 12/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/257:00 amSJU - ORD
1 stop13h 33mFrontier
jue. 1/17:57 pmORD - SJU
1 stop8h 37mFrontier
Deal found 12/11$204
This Frontier deal was found by Cheapflights users on 12/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/265:22 pmSJU - ORD
1 stop9h 23mFrontier
mié. 1/75:29 pmORD - SJU
1 stop7h 21mFrontier
Deal found 12/10$205
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
mié. 12/247:30 amSJU - ORD
1 stop13h 03mMultiple Airlines
lun. 1/55:45 amORD - SJU
Nonstop4h 41mMultiple Airlines
Deal found 12/10$211

Find flight deals from Caribbean to Illinois

Keep the following information in mind while searching for Caribbean to Illinois flight deals. Data was last updated diciembre 12, 2025.

Round-trip from

$148
(Frontier)

One-way from

$58
(Frontier)

Popular in

December

Cheapest in

February

Average price

$431

Good round-trip deal

$184 or less

Good one-way deal

$140 or less
From Caribbean to Illinois
Search Deals
One-way flight from Caribbean to Illinois
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Caribbean to Illinois.
Search Deals
Price to beat on a one-way flight from Caribbean to Illinois.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean 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 diciembre 12, 2025.
Use the filters below to find and compare flights from Caribbean to Illinois that are best for you.

Fly from

Caribbean

Fly to

Illinois

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 2/5

11:06 am-7:31 pm

1 stop10h 25m

Chicago O'Hare Intl

dom. 2/8

7:45 am-6:02 pm

1 stop8h 17m

$179

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mar. 4/14

5:40 am-12:50 pm

1 stop8h 10m

Chicago O'Hare Intl

sáb. 4/18

1:45 pm-1:47 am

1 stop11h 02m

$182

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 1/23

12:55 pm-10:49 pm

1 stop11h 54m

Chicago O'Hare Intl

lun. 1/26

5:40 am-3:12 pm

1 stop7h 32m

$183

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mar. 4/7

12:17 pm-4:43 pm

Nonstop5h 26m

Chicago O'Hare Intl

mar. 4/14

1:45 pm-1:47 am

1 stop11h 02m

$204

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

jue. 1/22

4:40 pm-11:46 pm

1 stop9h 06m

Chicago O'Hare Intl

lun. 1/26

5:15 am-3:35 pm

1 stop8h 20m

$213

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mié. 1/21

6:00 am-9:35 am

Nonstop5h 35m

Chicago O'Hare Intl

sáb. 1/24

3:00 pm-9:39 pm

Nonstop4h 39m

$220

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mar. 3/24

1:30 am-10:05 am

1 stop9h 35m

Chicago O'Hare Intl

dom. 3/29

10:56 am-11:23 pm

1 stop11h 27m

$220

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mar. 12/23

8:08 pm-11:25 pm

Nonstop5h 17m

Chicago O'Hare Intl

lun. 1/5

5:45 am-12:26 pm

Nonstop4h 41m

$222

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

jue. 1/15

8:20 am-11:12 pm

1 stop16h 52m

Lambert-St Louis

lun. 1/19

6:00 am-5:03 pm

2 stops9h 03m

$230

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

lun. 2/2

11:15 am-11:33 pm

1 stop14h 18m

Lambert-St Louis

vie. 2/6

5:42 pm-3:26 pm

1 stop19h 44m

$236

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

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

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

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

Currently, May is the cheapest month in which you can book a flight from Caribbean to Illinois (average of $120). Flying from Caribbean to Illinois in June is currently the most expensive (average of $174). 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 CB to IL?

Find hourly flight availability from Caribbean 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 diciembre 12, 2025.

A simple way to save on the total cost of your ticket is to fly from Caribbean to Illinois in the evening. If you’re flexible enough to do this you can expect to save up to 41% on your trip compared to booking a flight in the afternoon.

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

Use this chart to determine the cheapest time to fly round-trip from Caribbean to Illinois. Price data was last updated on December 16, 2024.

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

Weekly flight availability from Caribbean to Illinois

Explore weekly flight availability from Caribbean 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 diciembre 12, 2025.

The most flights from 0CB 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 (7 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 diciembre 12, 2025.
See what other customers who have flown with Delta, United Airlines, and American Airlines from Caribbean to Illinois have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,008 reviews

Comfort

7.9

Boarding

8.1

Food

7.3

Crew

8.5

Entertainment

7.9

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

Comfort

7.9

Boarding

8.1

Food

7.3

Crew

8.5

Entertainment

7.9

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
9,095 reviews
Delta
7.9
Good
8,008 reviews

Comfort

7.9

Boarding

8.1

Food

7.3

Crew

8.5

Entertainment

7.9

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
11,050 reviews
Delta
7.9
Good
8,008 reviews

Comfort

7.9

Boarding

8.1

Food

7.3

Crew

8.5

Entertainment

7.9

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
8,179 reviews
Delta
7.9
Good
8,008 reviews

Comfort

7.9

Boarding

8.1

Food

7.3

Crew

8.5

Entertainment

7.9

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
3,084 reviews
Delta
7.9
Good
8,008 reviews

Comfort

7.9

Boarding

8.1

Food

7.3

Crew

8.5

Entertainment

7.9

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 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 to Illinois?

    Departing from Caribbean to Illinois will take you 9h 06m. Caribbean and Illinois are separated by a distance of 2302 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    To fly one-way, consider booking your trip with JetBlue, which is currently one of the cheapest options available, starting at $62. Frontier flights start at $69 while deals on Spirit Airlines start at $82 one-way.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Caribbean 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 to Illinois?

    Currently, May is the cheapest month in which you can book a flight from Caribbean to Illinois (average of $120). Flying from Caribbean to Illinois in June is currently the most expensive (average of $174). 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 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 to Illinois

Discover the top 7 airlines that operate flights from Caribbean 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 diciembre 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$120Average$256FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$137Average$329FlexibilityNo cancel feeOn-time65%
FrontierCheapest$138Average$349FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$600FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$272Average$555FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$274Average$506FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$341Average$521FlexibilityNo cancel feeOn-time63%

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