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Caribbean Islands

$88+ Cheap flights from Illinois to Caribbean Islands

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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
nov. 26 — dic. 31
mar. 11/26
mar. 12/3
1 adult, Economy
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Cheap flight deals from Illinois to Caribbean Islands

Discover tips and strategies to find the most affordable flight options for your journey from Illinois (USIL) to Caribbean Islands (zzEPX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated noviembre 21, 2024.

Find flight deals from Illinois to Caribbean Islands

Cheapest flights from Illinois to Caribbean Islands
Explore the most affordable flight options available from Illinois to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on noviembre 21, 2024.

This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
sáb. 12/71:00 pmORD - SJU
Nonstop4h 36mSpirit Airlines
jue. 12/122:17 pmSJU - ORD
Nonstop5h 30mSpirit Airlines
Deal found 11/20$170
This Trip.com deal was found by Cheapflights users on 11/20. 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.
lun. 12/167:25 amMDW - SJU
1 stop16h 32mFrontier
vie. 12/206:00 amSJU - MDW
1 stop9h 06mFrontier
Deal found 11/20$174
This FlightHub deal was found by Cheapflights users on 11/21. 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.
dom. 12/89:35 amORD - SJU
1 stop26h 19mFrontier
jue. 12/125:05 pmSJU - ORD
1 stop18h 49mFrontier
Deal found 11/21$175
This Justfly.com deal was found by Cheapflights users on 11/20. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/89:35 amORD - SJU
1 stop26h 19mMultiple Airlines
jue. 12/122:17 pmSJU - ORD
Nonstop5h 30mMultiple Airlines
Deal found 11/20$177
This United Airlines deal was found by Cheapflights users on 11/21. 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.
lun. 12/92:20 pmORD - SJU
Nonstop4h 35mUnited Airlines
vie. 12/132:05 amSJU - ORD
1 stop10h 48mUnited Airlines
Deal found 11/21$226
This eDestinos deal was found by Cheapflights users on 11/20. 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.
lun. 12/98:15 amMDW - SJU
2 stops31h 28mMultiple Airlines
sáb. 12/143:20 amSJU - MDW
2 stops45h 25mMultiple Airlines
Deal found 11/20$254
This FlightHub deal was found by Cheapflights users on 11/21. 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.
mié. 12/46:00 amORD - PUJ
Nonstop4h 29mFrontier
mié. 12/115:00 pmPUJ - ORD
Nonstop5h 31mFrontier
Deal found 11/21$269
This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
vie. 12/136:07 pmORD - PUJ
1 stop15h 24mMultiple Airlines
mié. 12/182:35 pmPUJ - ORD
1 stop7h 38mMultiple Airlines
Deal found 11/20$281
This FlightHub deal was found by Cheapflights users on 11/20. 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.
vie. 12/136:48 pmMDW - PUJ
1 stop14h 43mFrontier
vie. 12/201:59 pmPUJ - MDW
1 stop11h 15mFrontier
Deal found 11/20$301
This Southwest deal was found by Cheapflights users on 11/20. 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.
sáb. 12/712:25 pmMDW - SJU
2 stops10h 05mSouthwest
mar. 12/106:10 amSJU - MDW
2 stops10h 00mSouthwest
Deal found 11/20$312
This FlightHub deal was found by Cheapflights users on 11/20. 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.
vie. 12/137:45 pmORD - STT
1 stop15h 38mSpirit Airlines
vie. 1/1711:46 amSTT - ORD
1 stop13h 16mSpirit Airlines
Deal found 11/20$324
This Mytrip deal was found by Cheapflights users on 11/20. 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.
lun. 12/239:25 pmORD - STT
3 stops35h 14mMultiple Airlines
mar. 12/3111:44 amSTT - ORD
1 stop10h 07mMultiple Airlines
Deal found 11/20$337

Find flights from Illinois to Caribbean Islands within your budget

Customize your flight search to find flights from Illinois to Caribbean Islands 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 2,612,795 searches. Data last updated noviembre 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

sáb. 12/7

1:00 pm-7:36 pm

Nonstop4h 36m

San Juan Luis Munoz Marin Intl

jue. 12/12

2:17 pm-5:47 pm

Nonstop5h 30m

$170

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

dom. 2/2

4:18 pm-10:37 am

1 stop16h 19m

San Juan Luis Munoz Marin Intl

jue. 2/6

9:49 pm-9:52 am

1 stop14h 03m

$173

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

vie. 2/21

12:26 pm-1:18 am

1 stop10h 52m

San Juan Luis Munoz Marin Intl

lun. 2/24

4:00 am-7:15 pm

1 stop17h 15m

$173

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mié. 1/8

8:14 pm-11:18 am

1 stop13h 04m

San Juan Luis Munoz Marin Intl

mié. 1/15

4:49 pm-1:50 pm

1 stop23h 01m

$174

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

lun. 12/9

2:20 pm-8:55 pm

Nonstop4h 35m

San Juan Luis Munoz Marin Intl

vie. 12/13

2:05 am-9:43 am

1 stop9h 38m

$226

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

sáb. 1/11

7:35 am-1:57 am

2 stops40h 22m

San Juan Luis Munoz Marin Intl

mié. 1/15

8:43 pm-6:26 pm

2 stops23h 43m

$241

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

mié. 1/15

1:20 pm-12:40 am

1 stop9h 20m

San Juan Luis Munoz Marin Intl

jue. 1/23

2:55 pm-7:45 pm

1 stop6h 50m

$257

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

mié. 12/4

6:00 am-12:29 pm

Nonstop4h 29m

Punta Cana

mié. 12/11

5:00 pm-8:31 pm

Nonstop5h 31m

$265

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

sáb. 1/25

5:10 am-3:49 pm

1 stop8h 39m

Punta Cana

mar. 1/28

6:54 pm-10:11 pm

Nonstop5h 17m

$268

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

lun. 1/13

5:10 am-3:49 pm

1 stop8h 39m

Punta Cana

sáb. 1/18

4:54 pm-11:02 pm

1 stop8h 08m

$297

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

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

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

Travel insights for flights from Illinois to Caribbean Islands

Get recent, data-driven insights about flights from Illinois to Caribbean Islands including ideal travel times, pricing trends, and more.

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

Currently, September is the cheapest month in which you can book a flight from Illinois to Caribbean Islands (average of $254). Flying from Illinois to Caribbean Islands in March is currently the most expensive (average of $335). 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 IL to EPX?

Find hourly flight availability from Illinois to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated noviembre 21, 2024.

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

Weekly flight availability from Illinois to Caribbean Islands

Explore weekly flight availability from Illinois to Caribbean Islands. 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 noviembre 21, 2024.

The most flights from USIL to zzEPX are scheduled on a Thursday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 on average).

Rainfall in Caribbean Islands by month

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

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

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

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Caribbean Islands. Reviews last updated noviembre 21, 2024.
Read through reviews of airlines operating flights from Illinois to Caribbean Islands, such as Spirit Airlines, Frontier and Southwest. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,005 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,755 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,464 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

KLM
7.8
Good
1,349 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Copa Airlines
7.8
Good
1,779 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Related info for your journey

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $88. Spirit Airlines flights start at $91 while deals on United Airlines start at $105 one-way.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Illinois to Caribbean Islands (average of $254). Flying from Illinois to Caribbean Islands in March is currently the most expensive (average of $335). 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 Illinois to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 9 airlines flying from Illinois to Caribbean Islands

Discover the top 9 airlines that operate flights from Illinois to Caribbean Islands. 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 2,612,795 searches. Data last updated noviembre 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$65Average$352FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$137Average$521FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$166Average$354FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$194Average$674FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$267Average$618FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$275Average$660FlexibilityNo cancel feeOn-time63%
DeltaCheapest$319Average$620FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$379Average$518FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$514Average$872FlexibilityNo cancel feeOn-time67%
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