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$101+ 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 6/6. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Round-trip from

$188
(eDestinos)

One-way from

$101
(CheapOair)

Popular in

March

Cheapest in

January

Average price

$262

Good round-trip deal

$212 or less

Good one-way deal

$186 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 ($30 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 May 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 May 1, 2025.

This eDestinos deal was found by Cheapflights users on 4/29. 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.
Thu 5/298:12 pmSJU - ORD
1 stop13h 38mSpirit Airlines
Thu 6/511:30 amORD - SJU
Nonstop4h 46mSpirit Airlines
Deal found 4/29$188
This Delta deal was found by Cheapflights users on 4/29. 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.
Wed 7/307:30 amSJU - STL
1 stop9h 48mDelta
Tue 8/1211:51 amSTL - SJU
1 stop9h 21mDelta
Deal found 4/29$209
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Tue 5/65:54 pmPUJ - ORD
Nonstop5h 06mFrontier
Sun 5/116:10 amORD - PUJ
Nonstop4h 41mFrontier
Deal found 4/29$234
This Booking.com deal was found by Cheapflights users on 4/30. 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 5/83:56 amSJU - ORD
1 stop20h 36mMultiple Airlines
Sat 5/177:47 amORD - SJU
1 stop16h 07mMultiple Airlines
Deal found 4/30$244
This eDestinos deal was found by Cheapflights users on 4/29. 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 5/73:56 amSJU - ORD
1 stop20h 36mFrontier
Sun 5/114:15 pmORD - SJU
1 stop6h 50mFrontier
Deal found 4/29$270
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 5/86:00 amSJU - MDW
1 stop7h 24mFrontier
Mon 5/126:15 amMDW - SJU
1 stop7h 32mFrontier
Deal found 4/29$292
This Booking.com deal was found by Cheapflights users on 5/1. 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 5/85:54 pmPUJ - ORD
Nonstop5h 06mMultiple Airlines
Tue 5/135:05 amORD - PUJ
1 stop8h 12mMultiple Airlines
Deal found 5/1$293
This Frontier deal was found by Cheapflights users on 4/29. 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.
Fri 5/92:34 pmSJU - STL
1 stop10h 40mFrontier
Tue 5/135:45 pmSTL - SJU
1 stop8h 06mFrontier
Deal found 4/29$298
This American Airlines deal was found by Cheapflights users on 4/30. 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 8/203:50 pmSJU - STL
1 stop8h 09mAmerican Airlines
Wed 8/276:00 amSTL - SJU
2 stops11h 15mAmerican Airlines
Deal found 4/30$300
This CheapOair deal was found by Cheapflights users on 4/29. 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 5/92:34 pmSJU - STL
1 stop10h 40mMultiple Airlines
Sun 5/1110:10 amSTL - SJU
1 stop7h 57mMultiple Airlines
Deal found 4/29$306
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Wed 7/161:50 pmPUJ - ORD
Nonstop5h 05mUnited Airlines
Wed 8/69:23 amORD - PUJ
Nonstop4h 42mUnited Airlines
Deal found 4/30$313
This eDestinos deal was found by Cheapflights users on 5/1. 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.
Thu 5/812:42 pmPUJ - ORD
1 stop11h 47mSpirit Airlines
Tue 5/135:05 amORD - PUJ
1 stop8h 12mSpirit Airlines
Deal found 5/1$316

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 May 1, 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

Thu 5/29

8:12 pm-8:50 am

1 stop13h 38m

Chicago O'Hare Intl

Thu 6/5

11:30 am-5:16 pm

Nonstop4h 46m

$188

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Wed 7/30

7:30 am-4:18 pm

1 stop9h 48m

Lambert-St Louis

Tue 8/12

11:51 am-10:12 pm

1 stop9h 21m

$209

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 7/16

5:08 pm-9:16 pm

Nonstop5h 08m

Chicago O'Hare Intl

Wed 8/13

6:45 am-12:25 pm

Nonstop4h 40m

$234

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

Sat 5/17

7:47 am-12:54 am

1 stop16h 07m

$244

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 5/7

3:56 am-11:32 pm

1 stop20h 36m

Chicago O'Hare Intl

Sun 5/11

4:15 pm-12:05 am

1 stop6h 50m

$270

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/8

6:00 am-12:24 pm

1 stop7h 24m

Chicago Midway

Mon 5/12

6:15 am-2:47 pm

1 stop7h 32m

$292

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Wed 8/20

3:50 pm-8:04 am

1 stop17h 14m

Lambert-St Louis

Wed 8/27

5:18 am-6:15 pm

1 stop11h 57m

$300

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 7/16

5:08 pm-9:16 pm

Nonstop5h 08m

Chicago O'Hare Intl

Wed 8/6

8:00 am-3:08 pm

1 stop6h 08m

$303

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Tue 5/13

3:56 am-12:06 am

1 stop21h 10m

Lambert-St Louis

Sat 5/17

5:45 pm-8:36 am

1 stop13h 51m

$308

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 5/28

3:22 pm-11:04 pm

1 stop8h 42m

Chicago O'Hare Intl

Wed 6/25

5:05 am-2:10 pm

1 stop8h 05m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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 May 1, 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 May 1, 2025.

The most flights from 0CB to USIL are scheduled on a Monday (9 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (4 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 May 1, 2025.
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

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
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

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
Alaska Airlines
8.0
Very good
9,968 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

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
4,294 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

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
7.5
Good
1,414 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

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
Aeromexico
7.5
Good
1,698 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

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 Spirit Airlines, which is currently one of the cheapest options available, starting at $101. Delta flights start at $105 while deals on American Airlines start at $110 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

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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$137Average$292FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$324FlexibilityNo cancel feeOn-time65%
DeltaCheapest$172Average$438FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$215Average$556FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$504FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$326Average$561FlexibilityNo cancel feeOn-time71%

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