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$87+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
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 January 27, 2026.

This Trip.com deal was found by Cheapflights users on 1/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/55:01 am
SJU
-
ORD
1 stop8h 48m
JetBlue
Mon 3/912:41 pm
ORD
-
SJU
1 stop7h 43m
JetBlue
Deal found 1/25$120
This Trip.com deal was found by Cheapflights users on 1/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/273:05 pm
SJU
-
ORD
1 stop9h 54m
JetBlue
Mon 3/212:41 pm
ORD
-
SJU
1 stop9h 48m
JetBlue
Deal found 1/25$137
This Trip.com deal was found by Cheapflights users on 1/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/119:25 am
SJU
-
ORD
1 stop12h 06m
JetBlue
Wed 2/1810:00 am
ORD
-
SJU
1 stop10h 53m
JetBlue
Deal found 1/26$142
This Trip.com deal was found by Cheapflights users on 1/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:25 pm
SJU
-
ORD
1 stop10h 26m
JetBlue
Tue 4/288:31 am
ORD
-
SJU
1 stop8h 59m
JetBlue
Deal found 1/25$146
This Trip.com deal was found by Cheapflights users on 1/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/61:44 pm
SJU
-
ORD
1 stop11h 16m
JetBlue
Tue 3/1012:39 pm
ORD
-
SJU
1 stop7h 45m
JetBlue
Deal found 1/25$148
This JetBlue deal was found by Cheapflights users on 1/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/173:26 am
SJU
-
ORD
1 stop8h 59m
JetBlue
Tue 3/246:45 am
ORD
-
SJU
1 stop9h 38m
JetBlue
Deal found 1/27$151
This Trip.com deal was found by Cheapflights users on 1/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/612:32 pm
SJU
-
ORD
Nonstop5h 16m
Multiple Airlines
Tue 3/1012:39 pm
ORD
-
SJU
1 stop7h 45m
Multiple Airlines
Deal found 1/25$154
This Expedia deal was found by Cheapflights users on 1/26. 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.
Sat 2/71:22 pm
SJU
-
ORD
Nonstop5h 15m
Multiple Airlines
Wed 2/2512:59 pm
ORD
-
SJU
1 stop9h 30m
Multiple Airlines
Deal found 1/26$156
This Trip.com deal was found by Cheapflights users on 1/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2712:32 pm
SJU
-
ORD
Nonstop5h 16m
Multiple Airlines
Mon 3/212:41 pm
ORD
-
SJU
1 stop9h 48m
Multiple Airlines
Deal found 1/25$157
This Priceline deal was found by Cheapflights users on 1/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/71:22 pm
SJU
-
ORD
Nonstop5h 15m
Spirit Airlines
Wed 2/2512:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/26$161
This Priceline deal was found by Cheapflights users on 1/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/245:25 pm
SJU
-
ORD
1 stop24h 27m
Multiple Airlines
Tue 3/312:17 pm
ORD
-
SJU
Nonstop4h 32m
Multiple Airlines
Deal found 1/26$163
This Trip.com deal was found by Cheapflights users on 1/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/233:26 am
SJU
-
ORD
1 stop8h 59m
JetBlue
Mon 3/3011:10 am
ORD
-
SJU
1 stop9h 18m
JetBlue
Deal found 1/24$164

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 January 27, 2026.

Round-trip from

$120
(Trip.com)

One-way from

$87
(Mytrip)

Popular in

December

Cheapest in

February

Average price

$301

Good round-trip deal

$160 or less

Good one-way deal

$187 or less
From Caribbean to Illinois
Search Deals
One-way flight from Caribbean to Illinois
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 27, 2026.
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

Thu 2/19

7:54 pm-3:18 pm

1 stop21h 24m

Chicago O'Hare Intl

Mon 2/23

3:50 pm-9:54 am

1 stop16h 04m

$165

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 5/1

11:59 pm-9:48 am

1 stop10h 49m

Chicago O'Hare Intl

Mon 5/4

3:15 pm-2:07 am

1 stop9h 52m

$169

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Mon 5/4

11:59 pm-9:48 am

1 stop10h 49m

Chicago O'Hare Intl

Thu 5/7

10:35 am-9:01 pm

1 stop9h 26m

$171

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Mon 4/20

3:19 pm-11:19 pm

1 stop9h 00m

Lambert-St Louis

Sat 4/25

4:55 pm-2:01 am

1 stop8h 06m

$182

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 3/17

3:26 am-11:25 am

1 stop8h 59m

Chicago O'Hare Intl

Mon 3/23

12:20 pm-10:51 pm

1 stop9h 31m

$183

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Sat 5/2

11:59 pm-9:48 am

1 stop10h 49m

Chicago O'Hare Intl

Wed 5/6

3:15 pm-12:07 am

1 stop7h 52m

$183

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 4/21

11:59 pm-7:41 am

1 stop8h 42m

Chicago O'Hare Intl

Sat 4/25

8:31 am-6:30 pm

1 stop8h 59m

$191

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 2/27

1:44 pm-10:59 pm

1 stop11h 15m

Chicago O'Hare Intl

Mon 3/2

12:41 pm-12:29 am

1 stop9h 48m

$192

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 4/24

12:22 pm-4:37 pm

Nonstop5h 15m

Chicago O'Hare Intl

Tue 4/28

12:22 pm-5:54 pm

Nonstop4h 32m

$198

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Thu 2/26

5:25 pm-11:59 pm

1 stop8h 34m

Lambert-St Louis

Mon 3/2

3:49 pm-12:43 am

1 stop6h 54m

$203

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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, February is the cheapest month in which you can book a flight from Caribbean to Illinois (average of $118). Flying from Caribbean to Illinois in December is currently the most expensive (average of $157). 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 January 27, 2026.

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 55% 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 January 24, 2026.

Travelers seeking maximum savings on their Caribbean to Illinois flight should consider departing on Friday evenings 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 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 January 27, 2026.

The most flights from 0CB to USIL are scheduled on a Monday (12 on average). You will have fewer flight options on Saturday, 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 January 27, 2026.
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
8,120 reviews

Overall

7.9

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

7.9

Entertainment

7.8

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
8,120 reviews
Delta
7.9
Good
8,120 reviews

Overall

7.9

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

7.9

Entertainment

7.8

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
9,206 reviews
Delta
7.9
Good
8,120 reviews

Overall

7.9

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

7.9

Entertainment

7.8

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
11,198 reviews
Delta
7.9
Good
8,120 reviews

Overall

7.9

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

7.9

Entertainment

7.8

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
8,384 reviews
Delta
7.9
Good
8,120 reviews

Overall

7.9

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

7.9

Entertainment

7.8

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
5.7
Fair
3,056 reviews
Delta
7.9
Good
8,120 reviews

Overall

7.9

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

7.9

Entertainment

7.8

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 8h 07m. Caribbean and Illinois are separated by a distance of 2116 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 $74. Frontier flights start at $92 while deals on Spirit Airlines start at $94 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, February is the cheapest month in which you can book a flight from Caribbean to Illinois (average of $118). Flying from Caribbean to Illinois in December is currently the most expensive (average of $157). 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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$116Average$626FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$118Average$316FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$131Average$201FlexibilityNo cancel feeOn-time62%
FrontierCheapest$137Average$351FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$256Average$525FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$258Average$542FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$392Average$548FlexibilityNo cancel feeOn-time63%

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