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Caribbean

$88+ Cheap flights from Illinois to Caribbean

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 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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Cheap flight deals from Illinois to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from Illinois (USIL) to Caribbean (0CB). 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 November 20, 2024.

Find flight deals from Illinois to Caribbean

Cheapest flights from Illinois to Caribbean
Explore the most affordable flight options available from Illinois to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 20, 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.
Sat 12/71:00 pmORD - SJU
Nonstop4h 36mSpirit Airlines
Wed 12/112:17 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.
Mon 12/167:25 amMDW - SJU
1 stop16h 32mFrontier
Thu 12/193:59 amSJU - MDW
1 stop7h 32mFrontier
Deal found 11/20$174
This FlightHub deal was found by Cheapflights users on 11/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/66:07 pmORD - SJU
1 stop21h 16mFrontier
Tue 12/246:00 amSJU - ORD
1 stop29h 24mFrontier
Deal found 11/18$175
This FlightHub deal was found by Cheapflights users on 11/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/85:25 amORD - SJU
2 stops12h 57mMultiple Airlines
Thu 12/127:16 pmSJU - ORD
1 stop16h 38mMultiple Airlines
Deal found 11/19$176
This United Airlines deal was found by Cheapflights users on 11/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/92:20 pmORD - SJU
Nonstop4h 35mUnited Airlines
Mon 12/162:05 amSJU - ORD
1 stop8h 54mUnited Airlines
Deal found 11/19$216
This eDestinos deal was found by Cheapflights users on 11/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1512:36 pmMDW - SJU
2 stops35h 21mMultiple Airlines
Wed 1/224:53 pmSJU - MDW
2 stops27h 33mMultiple Airlines
Deal found 11/19$240
This Booking.com deal was found by Cheapflights users on 11/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/136:07 pmORD - PUJ
1 stop15h 24mFrontier
Mon 12/1612:46 pmPUJ - ORD
1 stop11h 52mFrontier
Deal found 11/19$270
This Booking.com deal was found by Cheapflights users on 11/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/136:48 pmMDW - PUJ
1 stop14h 43mFrontier
Mon 12/1612:46 pmPUJ - MDW
1 stop26h 23mFrontier
Deal found 11/19$270
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/116:00 amORD - PUJ
Nonstop4h 29mMultiple Airlines
Wed 12/182:35 pmPUJ - ORD
1 stop7h 38mMultiple Airlines
Deal found 11/19$280
This Southwest deal was found by Cheapflights users on 11/19. 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 12/121:30 pmMDW - SJU
1 stop9h 15mSouthwest
Sat 12/147:20 amSJU - MDW
2 stops8h 50mSouthwest
Deal found 11/19$297
This FlightHub deal was found by Cheapflights users on 11/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/35:15 pmORD - STT
2 stops15h 36mSpirit Airlines
Fri 12/62:18 pmSTT - ORD
1 stop8h 40mSpirit Airlines
Deal found 11/18$324
This American Airlines deal was found by Cheapflights users on 11/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/94:28 pmORD - PUJ
1 stop17h 22mAmerican Airlines
Thu 12/123:30 pmPUJ - ORD
Nonstop5h 15mAmerican Airlines
Deal found 11/19$363

Find flights from Illinois to Caribbean within your budget

Customize your flight search to find flights from Illinois to Caribbean 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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

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Fly to

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Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 12/7

1:00 pm-7:36 pm

Nonstop4h 36m

San Juan Luis Munoz Marin Intl

Wed 12/18

4:43 pm-8:13 pm

Nonstop5h 30m

$170

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Mon 12/16

7:25 am-1:57 am

1 stop16h 32m

San Juan Luis Munoz Marin Intl

Fri 12/20

6:00 am-1:06 pm

1 stop9h 06m

$174

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 12/6

6:07 pm-5:23 pm

1 stop21h 16m

San Juan Luis Munoz Marin Intl

Tue 12/24

6:00 am-9:24 am

1 stop29h 24m

$175

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 12/8

5:25 am-8:22 pm

2 stops12h 57m

San Juan Luis Munoz Marin Intl

Thu 12/12

7:16 pm-9:54 am

1 stop16h 38m

$176

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 2/2

1:20 pm-12:50 am

2 stops9h 30m

San Juan Luis Munoz Marin Intl

Wed 2/5

2:55 pm-7:45 pm

1 stop6h 50m

$210

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 12/9

2:20 pm-8:55 pm

Nonstop4h 35m

San Juan Luis Munoz Marin Intl

Mon 12/16

2:05 am-8:59 am

1 stop8h 54m

$216

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Thu 1/9

3:04 pm-6:02 pm

1 stop24h 58m

San Juan Luis Munoz Marin Intl

Sat 1/25

8:00 am-11:29 pm

2 stops17h 29m

$239

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 1/13

5:10 am-3:49 pm

1 stop8h 39m

Punta Cana

Fri 1/17

6:10 pm-9:27 pm

Nonstop5h 17m

$268

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 1/31

8:12 pm-10:40 am

1 stop12h 28m

Punta Cana

Tue 2/4

6:54 pm-10:11 pm

Nonstop5h 17m

$269

ChicagoPunta Cana

MDW - PUJ

MDWPUJ

Chicago Midway

Fri 12/13

6:48 pm-11:31 am

1 stop14h 43m

Punta Cana

Mon 12/16

12:46 pm-1:09 pm

1 stop26h 23m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

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Best time to book a flight from Illinois to Caribbean

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

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

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

Currently, September is the cheapest month in which you can book a flight from Illinois to Caribbean (average of $254). Flying from Illinois to Caribbean 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 CB?

Find hourly flight availability from Illinois to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 20, 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 as you normally would.

Weekly flight availability from Illinois to Caribbean

Explore weekly flight availability from Illinois to Caribbean. 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 November 20, 2024.

The most flights from USIL to 0CB are scheduled on a Wednesday (7 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 on average).

Rainfall in Caribbean by month

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

In terms of precipitation, rainfall in Caribbean 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 when rainfall is around 2.2 in.

Temperature in Caribbean by month

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

If weather is an important factor for your trip to Caribbean, 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

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated November 20, 2024.
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Crew

8.7

Boarding

8.2

Food

7.2

Reviews

1 / 10

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

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Crew

8.7

Boarding

8.2

Food

7.2

Reviews

1 / 10

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

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Crew

8.7

Boarding

8.2

Food

7.2

Reviews

1 / 10

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

KLM
7.8
Good
1,350 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Crew

8.7

Boarding

8.2

Food

7.2

Reviews

1 / 10

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

Copa Airlines
7.8
Good
1,785 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Crew

8.7

Boarding

8.2

Food

7.2

Reviews

1 / 10

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

United Airlines
7.4
Good
9,171 reviews
Southwest
8.1
Very good
5,014 reviews

Overall

8.1

Entertainment

7.7

Comfort

8.1

Crew

8.7

Boarding

8.2

Food

7.2

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. 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 one-way?

    The cheapest airlines for a one-way flight from Illinois to Caribbean are Frontier ($88), Spirit Airlines ($91), and United Airlines ($105).

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Illinois to Caribbean 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?

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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Illinois to Caribbean

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

Discover the top 9 airlines that operate flights from Illinois to Caribbean. 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 2,629,791 searches. Data last updated November 20, 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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