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Caribbean

$57+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Nov 5 — Nov 121
1 adult
Tue 11/5
Tue 11/12
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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 October 31, 2024.

This Frontier deal was found by Cheapflights users on 10/29. 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.
Sun 12/812:36 pmMDW - SJU
1 stop11h 56mFrontier
Fri 12/135:03 pmSJU - MDW
1 stop9h 17mFrontier
Deal found 10/29$168
This FlightHub deal was found by Cheapflights users on 10/30. 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 16mMultiple Airlines
Wed 12/112:17 pmSJU - ORD
Nonstop5h 30mMultiple Airlines
Deal found 10/30$169
This FareScan deal was found by Cheapflights users on 10/31. 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 12/39:10 pmORD - SJU
1 stop12h 51mSpirit Airlines
Tue 12/1010:34 amSJU - ORD
1 stop11h 41mSpirit Airlines
Deal found 10/31$171
This FlightHub deal was found by Cheapflights users on 10/30. 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.
Thu 11/146:30 amORD - SJU
1 stop17h 19mFrontier
Sun 11/1710:12 pmSJU - ORD
1 stop15h 40mFrontier
Deal found 10/30$175
This eDestinos deal was found by Cheapflights users on 10/30. 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.
Tue 12/39:34 amMDW - SJU
2 stops16h 00mMultiple Airlines
Wed 12/116:20 amSJU - MDW
1 stop7h 22mMultiple Airlines
Deal found 10/30$200
This Mytrip deal was found by Cheapflights users on 10/31. 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.
Sat 11/165:00 amORD - PUJ
1 stop8h 46mMultiple Airlines
Wed 11/204:37 pmPUJ - ORD
Nonstop5h 28mMultiple Airlines
Deal found 10/31$287
This Mytrip deal was found by Cheapflights users on 10/29. 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.
Thu 11/1411:10 amORD - STT
2 stops21h 38mSpirit Airlines
Tue 11/1911:43 amSTT - ORD
1 stop8h 58mSpirit Airlines
Deal found 10/29$287
This Cheapflightsfares deal was found by Cheapflights users on 10/31. 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.
Sat 12/76:00 amORD - PUJ
Nonstop4h 29mFrontier
Thu 12/126:45 pmPUJ - ORD
Nonstop5h 14mFrontier
Deal found 10/31$288
This JetBlue deal was found by Cheapflights users on 10/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/88:51 amORD - SJU
1 stop7h 44mJetBlue
Tue 12/107:00 amSJU - ORD
1 stop10h 53mJetBlue
Deal found 10/30$289
This Booking.com deal was found by Cheapflights users on 10/30. 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.
Sun 12/812:36 pmMDW - PUJ
1 stop20h 55mFrontier
Fri 12/132:30 pmPUJ - MDW
2 stops34h 59mFrontier
Deal found 10/30$324
This American Airlines deal was found by Cheapflights users on 10/30. 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 12/97:00 amORD - PUJ
1 stop7h 05mAmerican Airlines
Thu 12/125:50 pmPUJ - ORD
1 stop8h 24mAmerican Airlines
Deal found 10/30$336
This United Airlines deal was found by Cheapflights users on 10/30. 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 12/910:43 amORD - PUJ
Nonstop4h 28mUnited Airlines
Mon 12/165:25 pmPUJ - ORD
1 stop7h 55mUnited Airlines
Deal found 10/30$339

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 2,570,725 searches. Data last updated October 31, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sun 1/5

5:52 pm-2:21 am

1 stop6h 29m

$83

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 12/10

8:02 pm-5:43 pm

1 stop19h 41m

$89

ChicagoSan Juan

MDW - SJU

MDWSJU

Chicago Midway

Sat 11/9

2:52 pm-1:52 am

1 stop9h 00m

$100

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 12/7

8:51 am-7:19 pm

1 stop8h 28m

$143

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 12/9

5:10 am-4:45 pm

1 stop9h 35m

$160

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 1/1

6:20 am-4:52 pm

1 stop8h 32m

$165

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/26

4:01 pm-2:38 am

1 stop8h 37m

$84

ChicagoOranjestad

ORD - AUA

ORDAUA

Chicago O'Hare Intl

Wed 1/29

1:35 pm-10:00 am

1 stop18h 25m

$172

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 11/11

10:43 am-5:11 pm

Nonstop4h 28m

$176

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 1/22

7:30 am-9:40 pm

2 stops12h 10m

$192

Flights are sorted by cheapest first

Deals found on 10/30

Showing 1-10 of 60 results
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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 October 31, 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.

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 October 31, 2024.
Southwest
8.1
Very good
5,116 reviews

Boarding

8.3

Food

7.2

Overall

8.1

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

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

Southwest
8.1
Very good
5,116 reviews
Southwest
8.1
Very good
5,116 reviews

Boarding

8.3

Food

7.2

Overall

8.1

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

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

Delta
8.0
Very good
8,835 reviews
Southwest
8.1
Very good
5,116 reviews

Boarding

8.3

Food

7.2

Overall

8.1

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

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

Alaska Airlines
8.0
Very good
9,420 reviews
Southwest
8.1
Very good
5,116 reviews

Boarding

8.3

Food

7.2

Overall

8.1

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

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

Copa Airlines
7.8
Good
1,885 reviews
Southwest
8.1
Very good
5,116 reviews

Boarding

8.3

Food

7.2

Overall

8.1

Entertainment

7.7

Comfort

8.1

Crew

8.7

Reviews

1 / 10

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

JetBlue
7.5
Good
3,514 reviews
Southwest
8.1
Very good
5,116 reviews

Boarding

8.3

Food

7.2

Overall

8.1

Entertainment

7.7

Comfort

8.1

Crew

8.7

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.

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

    Yes, there are multiple flights from Illinois to Caribbean for under $200. The cheapest flight booked recently is on Spirit Airlines for just $126, but on average you can expect to pay $277.

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

    Cheapflights has at least 19 direct flights from Illinois to Caribbean under $200. A good price for a nonstop flight from Illinois to Caribbean is less than $518.

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

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

  • What days are nonstop flights available from Illinois to Caribbean?

    Days when nonstop flights are available for this flight are: Sunday, Thursday, Friday, Saturday.

  • How many flights depart from Illinois to Caribbean on average per day?

    Per day, 2 flights depart from Illinois to Caribbean on average.
    Morning (6am - Noon) - 100% of flight departures

  • How long is the flight from Illinois to Caribbean?

    There are many flights that can get you from Illinois to Caribbean in 4h 28m. Fly via Spirit Airlines, Frontier, or United Airlines to get the fastest option. The distance from Illinois to Caribbean is about 2085 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 ($57), Spirit Airlines ($68), and JetBlue ($143).

  • 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), Nassau Intl Airport (NAS) are some additional IATA codes for airports related to your trip.

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

    The amount of baggage you can bring on your Illinois to Caribbean 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 with specific airlines?

    Yes, Cheapflights allows you to browse and filter Illinois to Caribbean 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 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.

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

    Many airlines flying from Illinois to Caribbean 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?

    Yes, you can often find last-minute deals on Illinois to Caribbean 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 flight deals updated?

    The Illinois to Caribbean flight deals you see on this page were last updated on 10/31.

  • 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

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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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Hobby to LaGuardia flights

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 2,570,725 searches. Data last updated October 31, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$117Average$354FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$159Average$398FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$173Average$564FlexibilityNo cancel feeOn-time62%
DeltaCheapest$204Average$642FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$267Average$566FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$268Average$620FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$284Average$679FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$379Average$524FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$526Average$880FlexibilityNo cancel feeOn-time67%
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