Illinois

$60+ 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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
janv. 26 — févr. 21
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Cheap flight deals from Caribbean to Illinois

Discover tips and strategies to find the most affordable flight options for your journey from Caribbean (0CB) to Illinois (USIL). 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 janvier 21, 2025.

Round-trip from

$118
(eDestinos)

One-way from

$60
(eDestinos)

Good round-trip deal

$309 or less

Good one-way deal

$188 or less
From Caribbean to Illinois
One-way flight from Caribbean to Illinois
Price to beat on a round-trip flight from Caribbean to Illinois.
Price to beat on a one-way flight from Caribbean to Illinois.

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 janvier 21, 2025.

This eDestinos deal was found by Cheapflights users on 1/20. 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.
jeu. 2/64:51 pmSJU - STL
1 stop8h 40mFrontier
mar. 2/255:20 pmSTL - SJU
1 stop14h 29mFrontier
Deal found 1/20$118
This eDestinos deal was found by Cheapflights users on 1/21. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 2/207:57 pmSJU - ORD
Nonstop5h 23mSpirit Airlines
lun. 2/2412:55 pmORD - SJU
Nonstop4h 31mSpirit Airlines
Deal found 1/21$136
This FlightHub deal was found by Cheapflights users on 1/21. 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.
sam. 2/89:15 pmSJU - MDW
1 stop14h 47mFrontier
lun. 2/1011:33 amMDW - SJU
1 stop12h 46mFrontier
Deal found 1/21$140
This Priceline deal was found by Cheapflights users on 1/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 2/276:35 amSJU - ORD
1 stop8h 45mFrontier
mar. 3/43:14 pmORD - SJU
1 stop16h 35mFrontier
Deal found 1/21$140
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 2/218:31 pmSJU - ORD
Nonstop5h 24mMultiple Airlines
lun. 2/247:08 pmORD - SJU
1 stop12h 41mMultiple Airlines
Deal found 1/21$142
This OneTravel deal was found by Cheapflights users on 1/20. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 2/133:49 amSJU - STL
1 stop21h 54mMultiple Airlines
mar. 2/184:00 pmSTL - SJU
1 stop29h 22mMultiple Airlines
Deal found 1/20$211
This United Airlines deal was found by Cheapflights users on 1/21. 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.
mer. 2/52:05 amSJU - ORD
1 stop9h 35mUnited Airlines
dim. 2/98:50 amORD - SJU
1 stop10h 38mUnited Airlines
Deal found 1/21$245
This eDestinos deal was found by Cheapflights users on 1/20. 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.
jeu. 1/306:19 pmSDQ - ORD
1 stop7h 13mSpirit Airlines
jeu. 2/66:55 amORD - SDQ
1 stop8h 19mSpirit Airlines
Deal found 1/20$246
This Priceline deal was found by Cheapflights users on 1/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/42:48 pmMBJ - ORD
1 stop8h 15mSpirit Airlines
mar. 3/115:10 amORD - MBJ
1 stop5h 52mSpirit Airlines
Deal found 1/20$248
This Cheapflightsfares deal was found by Cheapflights users on 1/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 1/306:54 pmPUJ - ORD
Nonstop5h 17mFrontier
mar. 2/46:10 amORD - PUJ
Nonstop4h 50mFrontier
Deal found 1/21$251
This American Airlines deal was found by Cheapflights users on 1/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 2/126:15 amSJU - STL
2 stops12h 05mAmerican Airlines
mer. 2/196:00 amSTL - SJU
1 stop15h 54mAmerican Airlines
Deal found 1/20$265
This Southwest deal was found by Cheapflights users on 1/20. 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.
jeu. 2/206:05 amSJU - MDW
1 stop10h 40mSouthwest
lun. 2/241:25 pmMDW - SJU
2 stops9h 25mSouthwest
Deal found 1/20$310

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 janvier 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

jeu. 2/6

4:51 pm-11:31 pm

1 stop8h 40m

Lambert-St Louis

mar. 2/25

5:20 pm-9:49 am

1 stop14h 29m

$118

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jeu. 2/20

7:57 pm-11:20 pm

Nonstop5h 23m

Chicago O'Hare Intl

lun. 2/24

12:55 pm-7:26 pm

Nonstop4h 31m

$136

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

jeu. 2/27

6:35 am-1:20 pm

1 stop8h 45m

Chicago O'Hare Intl

mar. 3/4

3:14 pm-9:49 am

1 stop16h 35m

$140

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

ven. 2/21

8:31 pm-11:55 pm

Nonstop5h 24m

Chicago O'Hare Intl

lun. 2/24

7:08 pm-9:49 am

1 stop12h 41m

$142

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

mar. 3/4

7:59 pm-3:13 pm

1 stop21h 14m

Chicago Midway

mar. 3/11

7:25 am-9:44 am

1 stop25h 19m

$144

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

jeu. 2/13

3:49 am-11:43 pm

1 stop21h 54m

Lambert-St Louis

mar. 2/18

4:00 pm-11:22 pm

1 stop29h 22m

$211

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mer. 2/5

2:05 am-9:40 am

1 stop9h 35m

Chicago O'Hare Intl

dim. 2/9

8:50 am-9:28 pm

1 stop10h 38m

$245

Montego BayChicago

MBJ - ORD

MBJORD

Montego Bay Sangster Intl

mar. 3/4

2:48 pm-10:03 pm

1 stop8h 15m

Chicago O'Hare Intl

mar. 3/11

5:10 am-11:02 am

1 stop5h 52m

$248

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

mer. 2/12

6:15 am-4:20 pm

2 stops12h 05m

Lambert-St Louis

mer. 2/19

6:00 am-11:54 pm

1 stop15h 54m

$265

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

mer. 5/14

5:08 pm-9:14 pm

Nonstop5h 06m

Chicago O'Hare Intl

mer. 5/21

6:20 am-11:55 am

Nonstop4h 35m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

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 $320). 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 janvier 21, 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 janvier 21, 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 janvier 21, 2025.
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.1
Very good
4,662 reviews
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
8,521 reviews
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
9,706 reviews
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.8
Good
381 reviews
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.7
Good
1,662 reviews
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $60. Spirit Airlines flights start at $70 while deals on Southwest start at $118 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 $320). 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.

Top 8 airlines flying from Caribbean to Illinois

Discover the top 8 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 janvier 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$124Average$284FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$140Average$338FlexibilityNo cancel feeOn-time65%
DeltaCheapest$187Average$466FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$196Average$545FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$220Average$386FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$274Average$460FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$327Average$558FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$400Average$568FlexibilityNo cancel feeOn-time70%
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