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$64+ 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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Sep 24 — Oct 11
From?
To?
Tue 9/24
Tue 10/1
1 adult, Economy
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Find cheap flights from Illinois to Caribbean Islands with Cheapflights

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Cheap Illinois to Caribbean Islands flights in September & October 2024

Find cheap flight options from Illinois to Caribbean Islands specifically for the months of September and October 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,082,863 searches. Prices were last updated on September 19, 2024.
These are some of the best deals we've found on flights to Caribbean Islands in 2024 at this time. Check back in a little while for more flight options.
This CheapOair deal was found by Cheapflights users on 9/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/174:46 pmORD - SJU
1 stop10h 02mFrontier
Tue 10/2210:18 amSJU - ORD
1 stop26h 48mFrontier
Deal found 9/19$165
This CheapOair deal was found by Cheapflights users on 9/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/38:56 amMDW - SJU
1 stop16h 00mFrontier
Wed 10/93:32 pmSJU - MDW
1 stop27h 27mFrontier
Deal found 9/19$165
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Thu 10/317:05 amORD - SJU
1 stop17h 01mMultiple Airlines
Mon 11/44:07 pmSJU - ORD
Nonstop5h 19mMultiple Airlines
Deal found 9/19$166
This FareScan deal was found by Cheapflights users on 9/18. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/198:28 amORD - SJU
Nonstop4h 45mSpirit Airlines
Tue 10/227:17 pmSJU - ORD
1 stop22h 31mSpirit Airlines
Deal found 9/18$174
This eDestinos deal was found by Cheapflights users on 9/18. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/52:53 pmMDW - SJU
2 stops27h 20mMultiple Airlines
Sat 10/128:30 pmSJU - MDW
1 stop15h 14mMultiple Airlines
Deal found 9/18$192
This Southwest deal was found by Cheapflights users on 9/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/291:25 pmMDW - SJU
1 stop7h 55mSouthwest
Wed 11/135:35 amSJU - MDW
2 stops8h 40mSouthwest
Deal found 9/18$220
This United Airlines deal was found by Cheapflights users on 9/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/212:20 pmORD - SJU
1 stop8h 37mUnited Airlines
Fri 9/271:05 amSJU - ORD
1 stop7h 29mUnited Airlines
Deal found 9/18$250
This Booking.com deal was found by Cheapflights users on 9/19. 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 10/48:03 pmMDW - PUJ
1 stop12h 18mFrontier
Sat 10/121:33 pmPUJ - MDW
1 stop22h 22mFrontier
Deal found 9/19$253
This FareScan deal was found by Cheapflights users on 9/18. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/265:25 amORD - STT
2 stops27h 20mSpirit Airlines
Fri 11/110:35 amSTT - ORD
1 stop23h 58mSpirit Airlines
Deal found 9/18$272

Illinois to Caribbean Islands 2024 flight deals

Discover exclusive flight deals for travel between Illinois and Caribbean Islands in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,082,863 searches. Data last updated September 19, 2024.
These are some of the best deals we've found on flights to Caribbean Islands in 2024 at this time. Check back in a little while for more flight options.
This CheapOair deal was found by Cheapflights users on 9/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/174:46 pmORD - SJU
1 stop10h 02mFrontier
Thu 10/245:52 pmSJU - ORD
1 stop26h 29mFrontier
Deal found 9/19$165
This CheapOair deal was found by Cheapflights users on 9/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/38:56 amMDW - SJU
1 stop16h 00mFrontier
Wed 10/93:32 pmSJU - MDW
1 stop27h 27mFrontier
Deal found 9/19$165
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Thu 10/317:05 amORD - SJU
1 stop17h 01mMultiple Airlines
Mon 11/44:07 pmSJU - ORD
Nonstop5h 19mMultiple Airlines
Deal found 9/19$166
This Cheapflightsfares deal was found by Cheapflights users on 9/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/297:30 amORD - SJU
1 stop9h 56mSpirit Airlines
Sun 11/34:07 pmSJU - ORD
Nonstop5h 19mSpirit Airlines
Deal found 9/19$187
This eDestinos deal was found by Cheapflights users on 9/18. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/52:53 pmMDW - SJU
2 stops27h 20mMultiple Airlines
Sat 10/128:30 pmSJU - MDW
1 stop15h 14mMultiple Airlines
Deal found 9/18$192
This Southwest deal was found by Cheapflights users on 9/19. 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 11/712:35 pmMDW - SJU
2 stops10h 10mSouthwest
Thu 11/1411:40 amSJU - MDW
1 stop9h 50mSouthwest
Deal found 9/19$220
This United Airlines deal was found by Cheapflights users on 9/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/212:20 pmORD - SJU
1 stop8h 37mUnited Airlines
Fri 9/271:05 amSJU - ORD
1 stop7h 29mUnited Airlines
Deal found 9/18$250
This Booking.com deal was found by Cheapflights users on 9/19. 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 10/48:03 pmMDW - PUJ
1 stop12h 18mFrontier
Sat 10/121:33 pmPUJ - MDW
1 stop22h 22mFrontier
Deal found 9/19$253
This FareScan deal was found by Cheapflights users on 9/18. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/265:25 amORD - STT
2 stops27h 20mSpirit Airlines
Fri 11/110:35 amSTT - ORD
1 stop23h 58mSpirit Airlines
Deal found 9/18$272

Illinois to Caribbean Islands flights leaving soon

Find last-minute flight options from Illinois to Caribbean Islands for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,082,863 searches. Data last updated September 19, 2024.
Check out these flights departing soon from Illinois to Caribbean Islands. Tip: verify your flight details before completing your reservation.
This Trip.com deal was found by Cheapflights users on 9/18. 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 9/258:35 amORD - SJU
1 stop7h 22mMultiple Airlines
Wed 10/26:30 pmSJU - ORD
1 stop22h 11mMultiple Airlines
Deal found 9/18$186
This Frontier deal was found by Cheapflights users on 9/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/281:40 pmORD - SJU
1 stop13h 35mFrontier
Sat 10/128:30 pmSJU - ORD
1 stop11h 59mFrontier
Deal found 9/19$208
This Frontier deal was found by Cheapflights users on 9/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/282:53 pmMDW - SJU
1 stop12h 22mFrontier
Thu 10/311:43 amSJU - MDW
1 stop13h 19mFrontier
Deal found 9/18$208
This eDestinos deal was found by Cheapflights users on 9/18. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2612:53 pmORD - SJU
1 stop8h 04mSpirit Airlines
Mon 10/710:46 pmSJU - ORD
1 stop12h 12mSpirit Airlines
Deal found 9/18$224
This Southwest deal was found by Cheapflights users on 9/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/267:40 amMDW - SJU
2 stops11h 05mSouthwest
Wed 10/210:55 amSJU - MDW
2 stops10h 20mSouthwest
Deal found 9/18$267
This Frontier deal was found by Cheapflights users on 9/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/282:53 pmMDW - PUJ
2 stops20h 40mFrontier
Sat 10/510:35 amPUJ - MDW
2 stops14h 15mFrontier
Deal found 9/19$294
This United Airlines deal was found by Cheapflights users on 9/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/277:35 amORD - SJU
1 stop12h 00mUnited Airlines
Mon 9/301:05 amSJU - ORD
1 stop8h 29mUnited Airlines
Deal found 9/18$297
This FareScan deal was found by Cheapflights users on 9/18. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/265:30 amORD - STT
3 stops31h 15mSpirit Airlines
Wed 10/210:35 amSTT - ORD
1 stop11h 21mSpirit Airlines
Deal found 9/18$343
This FareScan deal was found by Cheapflights users on 9/18. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/295:20 amORD - PUJ
1 stop8h 42mSpirit Airlines
Fri 10/41:58 pmPUJ - ORD
1 stop11h 34mSpirit Airlines
Deal found 9/18$351

One-way flights to Caribbean Islands from Illinois

Search for one-way flight options from Illinois to Caribbean Islands. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,082,863 searches. Data last updated September 19, 2024.
Take a look at some of the one-way flights we've detected from Illinois to Caribbean Islands. For those needing a return trip from Illinois, there is a search form available above.
This Frontier deal was found by Cheapflights users on 9/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/176:54 pmMDW - SJU
1 stop7h 54mFrontier
Deal found 9/18$64
This CheapOair deal was found by Cheapflights users on 9/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/212:00 pmORD - SJU
1 stop19h 27mFrontier
Deal found 9/19$81
This FareScan deal was found by Cheapflights users on 9/19. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/188:22 amORD - SJU
1 stop26h 29mSpirit Airlines
Deal found 9/19$82
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/76:15 amORD - PUJ
Nonstop4h 32mFrontier
Deal found 9/18$96
This eDestinos deal was found by Cheapflights users on 9/18. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/510:49 amORD - SJU
2 stops22h 59mMultiple Airlines
Deal found 9/18$108
This eDestinos deal was found by Cheapflights users on 9/19. 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.
Wed 10/3011:54 amMDW - SJU
1 stop11h 13mMultiple Airlines
Deal found 9/19$108
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Tue 10/225:00 amORD - PUJ
1 stop9h 00mSpirit Airlines
Deal found 9/19$110
This Southwest deal was found by Cheapflights users on 9/19. 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.
Tue 11/191:10 pmMDW - SJU
1 stop9h 20mSouthwest
Deal found 9/19$110
This FareScan deal was found by Cheapflights users on 9/18. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/124:20 pmORD - STT
1 stop16h 25mSpirit Airlines
Deal found 9/18$116

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 3,082,863 searches. Data last updated September 19, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$116 - $385

Route

Depart

Return

Price

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 10/5

1 stop13h 35m

San Juan Luis Munoz Marin Intl

Sat 10/12

1 stop11h 59m

$116

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Thu 11/7

1 stop8h 43m

San Juan Luis Munoz Marin Intl

Thu 11/14

1 stop11h 42m

$128

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 10/21

1 stop15h 36m

San Juan Luis Munoz Marin Intl

Thu 10/31

1 stop10h 55m

$149

Chicago O'Hare IntlSan Juan Luis Munoz Marin Intl

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 10/1

1 stop7h 22m

San Juan Luis Munoz Marin Intl

Fri 10/4

1 stop12h 12m

$180

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Sat 10/5

2 stops27h 20m

San Juan Luis Munoz Marin Intl

Sat 10/12

1 stop15h 14m

$192

Chicago MidwaySan Juan Luis Munoz Marin Intl

MDW - SJU

MDWSJU

Chicago Midway

Tue 10/29

1 stop10h 15m

San Juan Luis Munoz Marin Intl

Wed 11/13

1 stop10h 55m

$220

Chicago O'Hare IntlPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 12/8

1 stop9h 35m

Punta Cana

Thu 12/12

Nonstop5h 15m

$303

Chicago O'Hare IntlPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 10/27

1 stop6h 23m

Punta Cana

Sat 11/2

1 stop8h 34m

$349

Chicago O'Hare IntlPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 10/28

Nonstop4h 28m

Punta Cana

Wed 11/6

Nonstop5h 10m

$385

Flights are sorted by cheapest first

Deals found on 9/18

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, October is the cheapest month in which you can book a flight from Illinois to Caribbean Islands (average of $92). Flying from Illinois to Caribbean Islands in June is currently the most expensive (average of $192). 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 September 19, 2024.

It’s optimal to fly from Illinois to Caribbean Islands at noon. By choosing this option you can save up to 74% on the cost of your flight, compared to a flight in the morning.

What is the cheapest day to fly from Illinois to Caribbean Islands?

Use this chart to determine the cheapest time to fly round-trip from Illinois to Caribbean Islands. Price data was last updated on February 4, 2024.

Travelers seeking maximum savings on their Illinois to Caribbean Islands flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Find deals

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 September 19, 2024.

The most flights from USIL to zzEPX are scheduled on a Monday (4 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (1 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 September 19, 2024.
Read through reviews of airlines operating flights from Illinois to Caribbean Islands, such as Delta, Frontier and Spirit Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.2
Very good
5,315 reviews

Comfort

8.1

Overall

8.2

Food

7.3

Boarding

8.3

Crew

8.7

Entertainment

7.8

Reviews

1 / 10

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

Southwest
8.2
Very good
5,315 reviews
Southwest
8.2
Very good
5,315 reviews

Comfort

8.1

Overall

8.2

Food

7.3

Boarding

8.3

Crew

8.7

Entertainment

7.8

Reviews

1 / 10

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

Delta
8.0
Very good
9,069 reviews
Southwest
8.2
Very good
5,315 reviews

Comfort

8.1

Overall

8.2

Food

7.3

Boarding

8.3

Crew

8.7

Entertainment

7.8

Reviews

1 / 10

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

Alaska Airlines
8.0
Very good
9,367 reviews
Southwest
8.2
Very good
5,315 reviews

Comfort

8.1

Overall

8.2

Food

7.3

Boarding

8.3

Crew

8.7

Entertainment

7.8

Reviews

1 / 10

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

Copa Airlines
7.8
Good
2,024 reviews
Southwest
8.2
Very good
5,315 reviews

Comfort

8.1

Overall

8.2

Food

7.3

Boarding

8.3

Crew

8.7

Entertainment

7.8

Reviews

1 / 10

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

JetBlue
7.5
Good
3,672 reviews
Southwest
8.2
Very good
5,315 reviews

Comfort

8.1

Overall

8.2

Food

7.3

Boarding

8.3

Crew

8.7

Entertainment

7.8

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.

  • Can I find flights from Illinois to Caribbean Islands for under $200 on Cheapflights?

    Yes, there are multiple flights from Illinois to Caribbean Islands for under $200. The cheapest flight booked recently is on Frontier for just $116, but on average you can expect to pay $262.

  • Are there nonstop flights from Illinois to Caribbean Islands for under $200 on Cheapflights?

    Cheapflights has at least 18 direct flights from Illinois to Caribbean Islands under $200. A good price for a nonstop flight from Illinois to Caribbean Islands is less than $512.

  • Are there last-minute flights available from Illinois to Caribbean Islands for under $200?

    There are currently 20+ open flights from Illinois to Caribbean Islands within the next 7 days for less than $200.

  • 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 $64. Spirit Airlines flights start at $82 while deals on Southwest start at $110 one-way.

  • What does ORD to SJU mean?

    ORD and SJU are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. ORD to SJU refers to a flight route from Chicago O'Hare Intl Airport to San Juan Luis Munoz Marin Intl Airport. Punta Cana Airport (PUJ), Santo Domingo Las Americas Airport (SDQ), Montego Bay Sangster Intl Airport (MBJ), Oranjestad Reina Beatrix Airport (AUA), Santiago de los Caballeros Airport (STI) are other airports near this flight route and their unique identifiers/IATA codes.

  • Can I find deals for flights from Illinois to Caribbean Islands that include extra baggage allowance?

    The amount of baggage you can bring on your Illinois to Caribbean Islands flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Illinois to Caribbean Islands with specific airlines?

    Yes, Cheapflights allows you to browse and filter Illinois to Caribbean Islands flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Illinois to Caribbean Islands that allow pets onboard?

    Many airlines flying from Illinois to Caribbean Islands offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Illinois to Caribbean Islands?

    Yes, you can often find last-minute deals on Illinois to Caribbean Islands flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Illinois to Caribbean Islands flight deals updated?

    The Illinois to Caribbean Islands flight deals you see on this page were last updated on 9/19.

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

    Currently, October is the cheapest month in which you can book a flight from Illinois to Caribbean Islands (average of $92). Flying from Illinois to Caribbean Islands in June is currently the most expensive (average of $192). 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.

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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 3,082,863 searches. Data last updated September 19, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$117Average$353FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$155Average$392FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$173Average$515FlexibilityNo cancel feeOn-time62%
DeltaCheapest$194Average$632FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$267Average$414FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$271Average$626FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$284Average$677FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$379Average$524FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$587Average$993FlexibilityNo cancel feeOn-time67%
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