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$74+ Cheap flights from Caribbean 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap flight deals from Caribbean to Illinois

Keep the following information in mind while searching for Caribbean to Illinois flight deals. Data was last updated February 20, 2025.

Round-trip from

$137
(Kiwi.com)

One-way from

$74
(FlightHub)

Popular in

December

Cheapest in

January

Average price

$302

Good round-trip deal

$257 or less

Good one-way deal

$171 or less
From Caribbean to Illinois
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One-way flight from Caribbean to Illinois
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High demand for flights, 2% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from Caribbean to Illinois.
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Price to beat on a one-way flight from Caribbean to Illinois.
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Find flight deals from Caribbean to Illinois

Cheapest flights from Caribbean to Illinois
Explore the most affordable flight options available from Caribbean to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Thu 4/246:35 amSJU - ORD
Nonstop5h 23mMultiple Airlines
Mon 4/284:30 pmORD - SJU
1 stop9h 19mMultiple Airlines
Deal found 2/20$137
This eDestinos deal was found by Cheapflights users on 2/20. 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.
Tue 3/113:38 amSJU - ORD
1 stop7h 01mSpirit Airlines
Mon 3/178:46 pmORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 2/20$138
This Flightnetwork deal was found by Cheapflights users on 2/20. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/111:20 amSJU - MDW
1 stop12h 20mFrontier
Mon 5/51:19 pmMDW - SJU
1 stop12h 32mFrontier
Deal found 2/20$143
This Flightnetwork deal was found by Cheapflights users on 2/20. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/111:20 amSJU - ORD
1 stop20h 46mFrontier
Mon 5/54:15 pmORD - SJU
1 stop9h 36mFrontier
Deal found 2/20$148
This FlightHub deal was found by Cheapflights users on 2/19. 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.
Wed 3/129:35 pmSJU - STL
1 stop27h 14mFrontier
Wed 3/195:24 pmSTL - SJU
1 stop27h 12mFrontier
Deal found 2/19$156
This Mytrip deal was found by Cheapflights users on 2/20. 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.
Fri 3/76:45 pmSJU - STL
1 stop16h 24mSpirit Airlines
Tue 3/115:38 pmSTL - SJU
2 stops19h 29mSpirit Airlines
Deal found 2/20$206
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 4/225:50 pmPUJ - ORD
Nonstop5h 18mFrontier
Mon 4/286:20 amORD - PUJ
Nonstop4h 36mFrontier
Deal found 2/19$210
This Cheapflightsfares deal was found by Cheapflights users on 2/19. 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.
Wed 3/1912:07 pmMBJ - ORD
1 stop6h 43mSpirit Airlines
Wed 3/267:21 pmORD - MBJ
1 stop15h 41mSpirit Airlines
Deal found 2/19$263
This Priceline deal was found by Cheapflights users on 2/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/225:50 pmPUJ - ORD
Nonstop5h 18mMultiple Airlines
Mon 4/285:10 amORD - PUJ
1 stop8h 32mMultiple Airlines
Deal found 2/19$266
This Delta deal was found by Cheapflights users on 2/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/66:15 amSJU - MDW
1 stop7h 44mDelta
Mon 3/109:54 amMDW - SJU
1 stop9h 16mDelta
Deal found 2/18$271
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/264:15 pmSJU - ORD
1 stop9h 34mDelta
Sun 3/211:15 amORD - SJU
1 stop10h 31mDelta
Deal found 2/20$271
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Wed 3/1211:36 amSJU - STL
2 stops10h 05mAmerican Airlines
Wed 3/198:49 amSTL - SJU
2 stops10h 35mAmerican Airlines
Deal found 2/19$290

Find flights from Caribbean to Illinois within your budget

Customize your flight search to find flights from Caribbean 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 February 20, 2025.

Fly from

Caribbean

Fly to

Illinois

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 4/24

6:35 am-10:58 am

Nonstop5h 23m

Chicago O'Hare Intl

Mon 4/28

4:30 pm-2:49 am

1 stop9h 19m

$137

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 3/11

3:38 am-9:39 am

1 stop7h 01m

Chicago O'Hare Intl

Mon 3/17

8:46 pm-2:27 am

Nonstop4h 41m

$138

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 5/1

11:20 am-10:40 pm

1 stop12h 20m

Chicago Midway

Mon 5/5

1:19 pm-2:51 am

1 stop12h 32m

$143

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 5/1

11:20 am-7:06 am

1 stop20h 46m

Chicago O'Hare Intl

Mon 5/5

4:15 pm-2:51 am

1 stop9h 36m

$148

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Wed 3/12

9:35 pm-11:49 pm

1 stop27h 14m

Lambert-St Louis

Wed 3/19

5:24 pm-9:36 pm

1 stop27h 12m

$156

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

Fri 3/7

6:45 pm-9:09 am

1 stop16h 24m

Lambert-St Louis

Tue 3/11

5:38 pm-2:07 pm

2 stops19h 29m

$206

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Tue 4/22

5:50 pm-10:08 pm

Nonstop5h 18m

Chicago O'Hare Intl

Mon 4/28

6:20 am-11:56 am

Nonstop4h 36m

$210

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

Wed 3/19

12:07 pm-6:50 pm

1 stop6h 43m

Chicago O'Hare Intl

Wed 3/26

7:21 pm-11:02 am

1 stop15h 41m

$263

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Tue 4/22

5:50 pm-10:08 pm

Nonstop5h 18m

Chicago O'Hare Intl

Mon 4/28

5:10 am-2:42 pm

1 stop8h 32m

$266

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

Thu 3/6

6:15 am-11:59 am

1 stop7h 44m

Chicago Midway

Mon 3/10

9:54 am-8:10 pm

1 stop9h 16m

$271

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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

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

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

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

Currently, August is the cheapest month in which you can book a flight from Caribbean to Illinois (average of $245). Flying from Caribbean 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 CB to IL?

Find hourly flight availability from Caribbean 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 February 20, 2025.

When flying from Caribbean to Illinois, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Caribbean to Illinois

Explore weekly flight availability from Caribbean 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 February 20, 2025.

The most flights from 0CB to USIL are scheduled on a Monday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Illinois by month

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

In terms of precipitation, rainfall in Illinois ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Illinois when rainfall is around 1.7 in.

Temperature in Illinois by month

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

If weather is an important factor for your trip to Illinois, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 February 20, 2025.
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Air Transat
7.8
Good
380 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Copa Airlines
7.6
Good
1,510 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $74. Spirit Airlines flights start at $76 while deals on American Airlines start at $131 one-way.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Caribbean 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 to Illinois?

    Currently, August is the cheapest month in which you can book a flight from Caribbean to Illinois (average of $245). Flying from Caribbean 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Caribbean to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Caribbean to Illinois

Discover the top 7 airlines that operate flights from Caribbean 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$137Average$304FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$139Average$312FlexibilityNo cancel feeOn-time65%
DeltaCheapest$182Average$445FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$213Average$568FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$220Average$386FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$314Average$575FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$400Average$568FlexibilityNo cancel feeOn-time70%
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