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$103+ 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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
ago. 9 — ago. 161
sáb. 8/9
sáb. 8/16
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 agosto 4, 2025.

Round-trip from

$205
(Delta)

One-way from

$103
(United Airlines)
From Caribbean Islands to Illinois
Search Deals
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 agosto 4, 2025.

This Delta deal was found by Cheapflights users on 8/3. 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.
jue. 10/237:15 amSJU - STL
1 stop9h 40mDelta
lun. 10/276:00 amSTL - SJU
1 stop9h 33mDelta
Deal found 8/3$205
This Cheapflightsfares deal was found by Cheapflights users on 8/3. 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.
sáb. 8/307:40 pmSJU - ORD
Nonstop5h 03mSpirit Airlines
mar. 9/26:56 amORD - SJU
1 stop16h 01mSpirit Airlines
Deal found 8/3$220
This Mytrip deal was found by Cheapflights users on 8/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/123:40 amSJU - ORD
1 stop7h 34mMultiple Airlines
sáb. 9/136:44 pmORD - SJU
1 stop15h 20mMultiple Airlines
Deal found 8/4$232
This Frontier deal was found by Cheapflights users on 8/2. 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.
sáb. 8/303:21 pmSJU - MDW
1 stop8h 47mFrontier
sáb. 9/610:51 amMDW - SJU
1 stop12h 08mFrontier
Deal found 8/2$238
This Priceline deal was found by Cheapflights users on 8/3. 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.
mié. 9/35:05 pmSDQ - ORD
1 stop7h 54mSpirit Airlines
sáb. 9/65:05 amORD - SDQ
1 stop8h 37mSpirit Airlines
Deal found 8/3$240
This Cheapflightsfares deal was found by Cheapflights users on 8/3. 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.
sáb. 9/63:19 pmPUJ - ORD
1 stop8h 29mSpirit Airlines
sáb. 9/135:05 amORD - PUJ
1 stop8h 09mSpirit Airlines
Deal found 8/3$250
This eDestinos deal was found by Cheapflights users on 8/3. 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.
jue. 8/143:40 amSJU - ORD
1 stop29h 27mFrontier
lun. 8/185:00 pmORD - SJU
1 stop8h 39mFrontier
Deal found 8/3$252
This Priceline deal was found by Cheapflights users on 8/2. 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.
jue. 8/143:40 amSJU - STL
1 stop21h 07mFrontier
mar. 8/198:00 amSTL - SJU
1 stop10h 08mFrontier
Deal found 8/2$254
This Frontier deal was found by Cheapflights users on 8/2. 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.
vie. 9/193:32 amBQN - ORD
1 stop12h 45mFrontier
vie. 10/38:49 pmORD - BQN
1 stop13h 07mFrontier
Deal found 8/2$258
This American Airlines deal was found by Cheapflights users on 8/2. 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.
vie. 9/263:05 pmSJU - STL
1 stop19h 09mAmerican Airlines
vie. 10/36:00 amSTL - SJU
2 stops11h 15mAmerican Airlines
Deal found 8/2$278
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
mar. 10/1412:10 pmMBJ - ORD
1 stop11h 35mSpirit Airlines
mar. 10/215:05 amORD - MBJ
1 stop6h 00mSpirit Airlines
Deal found 8/3$286
This United Airlines deal was found by Cheapflights users on 8/3. 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.
mié. 10/221:05 amSJU - STL
2 stops10h 44mUnited Airlines
lun. 10/276:15 amSTL - SJU
1 stop8h 21mUnited Airlines
Deal found 8/3$295

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 agosto 4, 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 JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

jue. 10/23

7:15 am-3:55 pm

1 stop9h 40m

Lambert-St Louis

lun. 10/27

6:00 am-4:33 pm

1 stop9h 33m

$205

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

sáb. 8/30

7:40 pm-11:43 pm

Nonstop5h 03m

Chicago O'Hare Intl

mar. 9/2

6:56 am-11:57 pm

1 stop16h 01m

$220

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

sáb. 8/30

3:21 pm-11:08 pm

1 stop8h 47m

Chicago Midway

sáb. 9/6

10:51 am-11:59 pm

1 stop12h 08m

$238

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 8/21

8:00 pm-9:22 am

1 stop14h 22m

Chicago O'Hare Intl

lun. 8/25

5:10 am-2:26 pm

1 stop8h 16m

$240

Santo DomingoChicago

SDQ - ORD

SDQORD

Santo Domingo Las Americas

mié. 9/3

5:05 pm-11:59 pm

1 stop7h 54m

Chicago O'Hare Intl

sáb. 9/6

5:05 am-2:42 pm

1 stop8h 37m

$240

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

sáb. 9/6

3:19 pm-10:48 pm

1 stop8h 29m

Chicago O'Hare Intl

sáb. 9/13

5:05 am-2:14 pm

1 stop8h 09m

$250

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jue. 8/14

3:40 am-8:07 am

1 stop29h 27m

Chicago O'Hare Intl

lun. 8/18

5:00 pm-2:39 am

1 stop8h 39m

$252

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

jue. 8/14

3:40 am-11:47 pm

1 stop21h 07m

Lambert-St Louis

mar. 8/19

8:00 am-7:08 pm

1 stop10h 08m

$254

AguadillaChicago

BQN - ORD

BQNORD

Aguadilla Borinquen

vie. 9/19

3:32 am-3:17 pm

1 stop12h 45m

Chicago O'Hare Intl

vie. 10/3

8:49 pm-10:56 am

1 stop13h 07m

$258

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

jue. 8/14

5:45 pm-9:53 pm

Nonstop5h 08m

Chicago O'Hare Intl

lun. 8/18

6:45 am-12:25 pm

Nonstop4h 40m

$262

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/4

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 agosto 4, 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 agosto 4, 2025.

The most flights from zzEPX to USIL are scheduled on a Saturday (10 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (6 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 agosto 4, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Caribbean Islands to Illinois to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,987 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,912 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.2
Good
2,915 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 United Airlines. According to our data, you can fly for as low as $103. Users have also found prices from $109 and $113 on American Airlines and Frontier, 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 agosto 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$130Average$310FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$136Average$293FlexibilityNo cancel feeOn-time65%
DeltaCheapest$162Average$440FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$218Average$575FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$480FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$329Average$524FlexibilityNo cancel feeOn-time71%

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