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Illinois

$106+ 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 12/23. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Cheap flight deals from Caribbean to Illinois

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

Round-trip from

$196
(Frontier)

One-way from

$106
(Kiwi.com)

Popular in

August

Cheapest in

January

Average price

$339

Good round-trip deal

$195 or less

Good one-way deal

$171 or less
From Caribbean to Illinois
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One-way flight from Caribbean to Illinois
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Highest demand for flights based on searches. 1% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Caribbean to Illinois.
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Price to beat on a one-way flight from Caribbean to Illinois.
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Find 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 October 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Thu 12/410:42 amSJU - ORD
1 stop9h 54mMultiple Airlines
Sun 12/77:41 pmORD - SJU
1 stop11h 56mMultiple Airlines
Deal found 10/28$193
This Frontier deal was found by Cheapflights users on 10/28. 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.
Thu 12/410:42 amSJU - MDW
1 stop13h 11mFrontier
Mon 12/86:15 amMDW - SJU
1 stop6h 56mFrontier
Deal found 10/28$196
This Priceline deal was found by Cheapflights users on 10/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/63:37 pmSJU - ORD
1 stop10h 50mSpirit Airlines
Mon 11/178:00 amORD - SJU
Nonstop4h 36mSpirit Airlines
Deal found 10/27$203
This Expedia deal was found by Cheapflights users on 10/27. 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.
Thu 11/133:37 pmSJU - ORD
1 stop10h 50mSpirit Airlines
Mon 11/178:00 amORD - SJU
Nonstop4h 36mSpirit Airlines
Deal found 10/27$211
This Booking.com deal was found by Cheapflights users on 10/28. 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.
Thu 12/44:31 pmSJU - MDW
1 stop7h 41mFrontier
Sun 12/72:59 pmMDW - SJU
1 stop16h 38mFrontier
Deal found 10/28$215
This Cheapflightsfares deal was found by Cheapflights users on 10/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/48:45 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Mon 12/85:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 10/27$217
This Priceline deal was found by Cheapflights users on 10/26. 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.
Fri 12/58:45 pmSJU - ORD
Nonstop5h 14mSpirit Airlines
Mon 12/85:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 10/26$218
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/227:15 amSJU - ORD
1 stop29h 40mMultiple Airlines
Tue 1/67:30 amORD - SJU
1 stop14h 19mMultiple Airlines
Deal found 10/27$219
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Thu 12/410:42 amSJU - ORD
1 stop9h 54mMultiple Airlines
Mon 12/85:45 amORD - SJU
Nonstop4h 41mMultiple Airlines
Deal found 10/28$220
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/54:52 pmSJU - ORD
Nonstop5h 28mUnited Airlines
Tue 12/91:05 pmORD - SJU
1 stop7h 17mUnited Airlines
Deal found 10/28$223
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/243:54 amSJU - ORD
1 stop15h 06mMultiple Airlines
Mon 1/56:05 pmORD - SJU
1 stop16h 54mMultiple Airlines
Deal found 10/27$224
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/46:38 pmSJU - STL
1 stop7h 04mDelta
Mon 12/86:00 amSTL - SJU
1 stop6h 14mDelta
Deal found 10/27$225

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 October 28, 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

Fri 2/6

2:15 pm-10:59 pm

1 stop10h 44m

Chicago O'Hare Intl

Mon 2/9

2:20 pm-9:00 pm

Nonstop4h 40m

$223

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/29

2:05 am-9:40 am

1 stop9h 35m

Chicago O'Hare Intl

Mon 2/2

2:20 pm-9:00 pm

Nonstop4h 40m

$223

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Thu 12/4

2:36 pm-9:28 pm

2 stops8h 52m

Lambert-St Louis

Sun 12/7

5:02 am-10:05 pm

1 stop15h 03m

$225

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 12/5

7:00 am-11:55 am

1 stop6h 55m

Chicago Midway

Mon 12/8

6:00 am-2:14 pm

1 stop6h 14m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Fri 1/23

6:15 am-12:01 pm

1 stop7h 46m

Chicago Midway

Tue 2/3

12:48 pm-8:57 pm

1 stop6h 09m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 1/21

5:50 pm-11:39 pm

1 stop7h 49m

Chicago O'Hare Intl

Sun 1/25

7:50 pm-6:11 am

1 stop8h 21m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 12/4

7:19 am-5:46 pm

1 stop12h 27m

Chicago O'Hare Intl

Mon 12/8

5:30 am-2:14 pm

1 stop6h 44m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 12/5

6:38 pm-12:01 am

1 stop7h 23m

Chicago O'Hare Intl

Mon 12/8

5:30 am-2:14 pm

1 stop6h 44m

$227

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 11/19

6:17 pm-11:42 am

1 stop19h 25m

Chicago Midway

Thu 11/27

6:05 am-1:06 am

1 stop17h 01m

$237

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 2/19

7:00 am-12:55 pm

1 stop7h 55m

Chicago Midway

Tue 2/24

6:50 am-7:05 pm

2 stops10h 15m

$252

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

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, December is the cheapest month in which you can book a flight from Caribbean to Illinois (average of $113). Flying from Caribbean 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 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 October 28, 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 35% 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.

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 October 28, 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
7,994 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
Delta
7.9
Good
7,994 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
United Airlines
7.4
Good
9,001 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
Spirit Airlines
6.3
Okay
8,116 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
Frontier
5.8
Fair
3,124 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!

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 6h 55m. Caribbean and Illinois are separated by a distance of 2057 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 United Airlines, which is currently one of the cheapest options available, starting at $109. Southwest flights start at $113 while deals on Delta start at $113 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, December is the cheapest month in which you can book a flight from Caribbean to Illinois (average of $113). Flying from Caribbean 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 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 to Illinois

Discover the top 6 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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$137Average$336FlexibilityNo cancel feeOn-time65%
FrontierCheapest$139Average$312FlexibilityNo cancel feeOn-time62%
DeltaCheapest$162Average$579FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$269Average$533FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$334Average$574FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$384Average$523FlexibilityNo cancel feeOn-time63%

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