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$105+ 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 5/17. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 April 17, 2025.

Round-trip from

$216
(eDestinos)

One-way from

$105
(United Airlines)

Popular in

March

Cheapest in

January

Average price

$339

Good round-trip deal

$212 or less

Good one-way deal

$194 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. 9% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 17, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/17. 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 4/259:30 pmSJU - ORD
1 stop11h 34mSpirit Airlines
Tue 4/297:00 pmORD - SJU
1 stop12h 26mSpirit Airlines
Deal found 4/17$208
This Cheapflightsfares deal was found by Cheapflights users on 4/17. 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 5/15:54 pmPUJ - ORD
Nonstop5h 06mFrontier
Mon 5/56:10 amORD - PUJ
Nonstop4h 41mFrontier
Deal found 4/17$239
This CheapOair deal was found by Cheapflights users on 4/17. 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.
Fri 4/259:30 pmSJU - ORD
1 stop11h 34mMultiple Airlines
Sun 4/276:30 amORD - SJU
1 stop12h 11mMultiple Airlines
Deal found 4/17$248
This FlightHub deal was found by Cheapflights users on 4/16. 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.
Wed 5/71:34 pmKIN - ORD
2 stops19h 21mSpirit Airlines
Wed 5/145:05 amORD - KIN
1 stop7h 24mSpirit Airlines
Deal found 4/16$268
This eDestinos deal was found by Cheapflights users on 4/17. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/303:56 amSJU - STL
1 stop21h 10mFrontier
Fri 5/95:55 pmSTL - SJU
1 stop24h 35mFrontier
Deal found 4/17$270
This Flightnetwork deal was found by Cheapflights users on 4/16. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/13:56 amSJU - MDW
1 stop9h 28mFrontier
Sun 5/1110:55 amMDW - SJU
1 stop12h 10mFrontier
Deal found 4/16$287
This eDestinos deal was found by Cheapflights users on 4/17. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/216:00 pmSJU - ORD
1 stop15h 22mFrontier
Mon 5/265:14 pmORD - SJU
1 stop8h 18mFrontier
Deal found 4/17$288
This Booking.com deal was found by Cheapflights users on 4/17. 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 5/19:25 amSJU - STL
1 stop8h 50mMultiple Airlines
Fri 5/95:55 pmSTL - SJU
1 stop7h 56mMultiple Airlines
Deal found 4/17$289
This American Airlines deal was found by Cheapflights users on 4/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/72:12 pmPUJ - ORD
1 stop10h 59mAmerican Airlines
Sun 5/115:00 amORD - PUJ
1 stop7h 10mAmerican Airlines
Deal found 4/16$289
This Cheapflightsfares deal was found by Cheapflights users on 4/16. 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.
Tue 6/1012:07 pmMBJ - ORD
1 stop10h 57mSpirit Airlines
Wed 6/255:05 amORD - MBJ
1 stop5h 57mSpirit Airlines
Deal found 4/16$291
This Kiwi.com deal was found by Cheapflights users on 4/17. 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 5/112:39 pmPUJ - ORD
1 stop11h 53mMultiple Airlines
Wed 5/77:25 amORD - PUJ
Nonstop4h 50mMultiple Airlines
Deal found 4/17$295
This Delta deal was found by Cheapflights users on 4/16. 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 9/42:39 pmSJU - STL
1 stop10h 00mDelta
Sun 9/711:51 amSTL - SJU
1 stop9h 21mDelta
Deal found 4/16$304

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 April 17, 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 5/2

6:35 am-10:58 am

Nonstop5h 23m

Chicago O'Hare Intl

Mon 5/5

8:04 am-1:45 pm

Nonstop4h 41m

$216

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 5/1

5:54 pm-10:00 pm

Nonstop5h 06m

Chicago O'Hare Intl

Mon 5/5

6:10 am-11:51 am

Nonstop4h 41m

$239

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Wed 4/30

3:56 am-12:06 am

1 stop21h 10m

Lambert-St Louis

Fri 5/9

5:55 pm-7:30 pm

1 stop24h 35m

$270

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 5/8

3:56 am-11:32 pm

1 stop20h 36m

Chicago O'Hare Intl

Sun 5/11

4:15 pm-2:51 am

1 stop9h 36m

$270

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Mon 5/5

6:00 am-6:29 pm

1 stop13h 29m

Chicago O'Hare Intl

Mon 5/12

11:30 am-5:16 pm

Nonstop4h 46m

$275

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 5/16

1:34 pm-12:05 am

1 stop10h 31m

Chicago O'Hare Intl

Tue 5/20

5:05 am-12:29 pm

1 stop7h 24m

$284

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/1

3:56 am-12:24 pm

1 stop9h 28m

Chicago Midway

Sun 5/11

10:55 am-12:05 am

1 stop12h 10m

$287

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 5/7

2:12 pm-12:11 am

1 stop10h 59m

Chicago O'Hare Intl

Sun 5/11

5:00 am-1:10 pm

1 stop7h 10m

$289

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Thu 5/1

9:25 am-5:15 pm

1 stop8h 50m

Lambert-St Louis

Fri 5/9

5:55 pm-2:51 am

1 stop7h 56m

$289

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Tue 6/10

12:07 pm-11:04 pm

1 stop10h 57m

Chicago O'Hare Intl

Wed 6/25

5:05 am-11:02 am

1 stop5h 57m

$291

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

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, August is the cheapest month in which you can book a flight from Caribbean to Illinois (average of $245). Flying from Caribbean to Illinois in March is currently the most expensive (average of $321). 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 April 17, 2025.

When flying from Caribbean to Illinois, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 April 17, 2025.

The most flights from 0CB to USIL are scheduled on a Monday (9 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (9 on average).

Rainfall in Illinois by month

Plan your trip to Illinois by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Illinois ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Illinois when rainfall is around 1.7 in.

Temperature in Illinois by month

Plan your trip to Illinois by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Illinois, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 17, 2025.
Delta
8.0
Very good
7,916 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,916 reviews
Delta
8.0
Very good
7,916 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Southwest
8.0
Very good
4,280 reviews
Delta
8.0
Very good
7,916 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Copa Airlines
7.6
Good
1,409 reviews
Delta
8.0
Very good
7,916 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
LATAM Airlines
7.5
Good
1,761 reviews
Delta
8.0
Very good
7,916 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Avelo Airlines
7.5
Good
Delta
8.0
Very good
7,916 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

  • 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 $105. Spirit Airlines flights start at $118 while deals on American Airlines start at $131 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, August is the cheapest month in which you can book a flight from Caribbean to Illinois (average of $245). Flying from Caribbean to Illinois in March is currently the most expensive (average of $321). 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

Browse thousands of different options on Cheapflights for your next trip

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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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$137Average$278FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$138Average$321FlexibilityNo cancel feeOn-time65%
DeltaCheapest$172Average$438FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$214Average$552FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$528FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$309Average$569FlexibilityNo cancel feeOn-time71%

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