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$107+ Cheap flights from Caribbean Islands 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 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Jun 24 — Jul 11
Tue 6/24
Tue 7/1
1 adult, Economy
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Cheap flight deals from Caribbean Islands to Illinois

Keep the following information in mind while searching for Caribbean Islands to Illinois flight deals. Data was last updated June 19, 2025.

Round-trip from

$185
(Priceline)

One-way from

$107
(Priceline)
From Caribbean Islands to Illinois
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One-way flight from Caribbean Islands to Illinois
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Find flight deals from Caribbean Islands to Illinois

Cheapest flights from Caribbean Islands to Illinois
Explore the most affordable flight options available from Caribbean Islands to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 19, 2025.

This Priceline deal was found by Cheapflights users on 6/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/28:15 amSJU - MDW
1 stop12h 15mFrontier
Sat 7/129:12 pmMDW - SJU
1 stop28h 27mFrontier
Deal found 6/17$185
This Priceline deal was found by Cheapflights users on 6/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/154:43 pmSJU - ORD
1 stop15h 21mMultiple Airlines
Wed 7/1611:28 amORD - SJU
1 stop14h 11mMultiple Airlines
Deal found 6/17$197
This SmartFares deal was found by Cheapflights users on 6/17. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/113:50 pmSJU - ORD
1 stop16h 14mSpirit Airlines
Mon 7/145:05 amORD - SJU
1 stop15h 04mSpirit Airlines
Deal found 6/17$207
This Priceline deal was found by Cheapflights users on 6/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/13:40 amSJU - ORD
1 stop7h 37mFrontier
Sat 7/1212:20 pmORD - SJU
1 stop11h 07mFrontier
Deal found 6/17$212
This FlightHub deal was found by Cheapflights users on 6/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/99:30 amSJU - STL
1 stop15h 17mFrontier
Wed 7/165:40 pmSTL - SJU
1 stop14h 24mFrontier
Deal found 6/17$219
This American Airlines deal was found by Cheapflights users on 6/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/317:54 amSJU - STL
1 stop17h 05mAmerican Airlines
Tue 8/126:00 amSTL - SJU
1 stop15h 49mAmerican Airlines
Deal found 6/17$224
This Delta deal was found by Cheapflights users on 6/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/157:30 amSJU - STL
1 stop9h 36mDelta
Sat 9/67:00 amSTL - SJU
1 stop8h 36mDelta
Deal found 6/17$229
This Trip.com deal was found by Cheapflights users on 6/18. 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 7/301:37 amSJU - STL
1 stop9h 15mMultiple Airlines
Tue 8/125:40 pmSTL - SJU
1 stop7h 59mMultiple Airlines
Deal found 6/18$271
This SmartFares deal was found by Cheapflights users on 6/18. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/281:37 amSJU - STL
2 stops33h 52mSpirit Airlines
Fri 8/810:47 amSTL - SJU
1 stop23h 45mSpirit Airlines
Deal found 6/18$273
This American Airlines deal was found by Cheapflights users on 6/18. 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 7/93:31 pmPUJ - ORD
Nonstop5h 05mAmerican Airlines
Wed 8/135:54 pmORD - PUJ
1 stop16h 11mAmerican Airlines
Deal found 6/18$284
This Southwest deal was found by Cheapflights users on 6/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/315:00 amSJU - STL
1 stop7h 05mSouthwest
Tue 8/129:45 amSTL - SJU
1 stop11h 45mSouthwest
Deal found 6/19$295
This Cheapflightsfares deal was found by Cheapflights users on 6/16. 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.
Wed 6/2512:07 pmMBJ - ORD
1 stop11h 38mSpirit Airlines
Mon 6/307:39 pmORD - MBJ
1 stop15h 23mSpirit Airlines
Deal found 6/16$300

Cheapflights Fare Finder

Customize your flight search to find flights from Caribbean Islands 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 June 19, 2025.
Use the filters below to find and compare flights from Caribbean Islands to Illinois that are best for you.

Fly from

Caribbean Islands

Fly to

Illinois

Route

Depart

Return

Price

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Wed 7/2

8:15 am-7:30 pm

1 stop12h 15m

Chicago Midway

Sat 7/12

9:12 pm-2:39 am

1 stop28h 27m

$185

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 7/15

4:43 pm-7:04 am

1 stop15h 21m

Chicago O'Hare Intl

Wed 7/16

11:28 am-2:39 am

1 stop14h 11m

$197

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 7/11

3:50 pm-7:04 am

1 stop16h 14m

Chicago O'Hare Intl

Mon 7/14

5:05 am-9:09 pm

1 stop15h 04m

$207

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 7/1

3:40 am-10:17 am

1 stop7h 37m

Chicago O'Hare Intl

Sat 7/12

12:20 pm-12:27 am

1 stop11h 07m

$212

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Wed 7/9

9:30 am-11:47 pm

1 stop15h 17m

Lambert-St Louis

Wed 7/16

5:40 pm-9:04 am

1 stop14h 24m

$219

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Thu 7/31

7:54 am-11:59 pm

1 stop17h 05m

Lambert-St Louis

Tue 8/12

6:00 am-10:49 pm

1 stop15h 49m

$224

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Fri 8/15

7:30 am-4:06 pm

1 stop9h 36m

Lambert-St Louis

Sat 9/6

7:00 am-4:36 pm

1 stop8h 36m

$229

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Wed 7/30

1:37 am-9:52 am

1 stop9h 15m

Lambert-St Louis

Tue 8/12

5:40 pm-2:39 am

1 stop7h 59m

$271

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Mon 7/28

1:37 am-10:29 am

2 stops33h 52m

Lambert-St Louis

Fri 8/8

10:47 am-11:32 am

1 stop23h 45m

$273

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Wed 7/9

3:31 pm-7:36 pm

Nonstop5h 05m

Chicago O'Hare Intl

Wed 8/13

5:54 pm-11:05 am

1 stop16h 11m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/17

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

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

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

Currently, August is the cheapest month in which you can book a flight from Caribbean Islands to Illinois (average of $245). Flying from Caribbean Islands 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 EPX to IL?

Find hourly flight availability from Caribbean Islands 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 June 19, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Caribbean Islands to Illinois as you normally would.

Weekly flight availability from Caribbean Islands to Illinois

Explore weekly flight availability from Caribbean Islands 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 June 19, 2025.

The most flights from zzEPX 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 June 19, 2025.
Read reviews from past customers who have flown Delta, Southwest and Copa Airlines from Caribbean Islands to Illinois. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Southwest
8.0
Very good
4,280 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Copa Airlines
7.5
Good
1,455 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Aeromexico
7.5
Good
1,714 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,810 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Caribbean Islands 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 Islands to Illinois one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $107. Users have also found prices from $110 and $113 on Southwest and Spirit Airlines, respectively.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Caribbean Islands 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 Islands to Illinois?

    Currently, August is the cheapest month in which you can book a flight from Caribbean Islands to Illinois (average of $245). Flying from Caribbean Islands 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 Islands 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 Islands to Illinois

Discover the top 6 airlines that operate flights from Caribbean Islands 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 June 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$135Average$328FlexibilityNo cancel feeOn-time65%
FrontierCheapest$137Average$293FlexibilityNo cancel feeOn-time62%
DeltaCheapest$172Average$438FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$217Average$526FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$495FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$329Average$560FlexibilityNo cancel feeOn-time71%

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