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$57+ 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
nov. 26 — dic. 31
mar. 11/26
mar. 12/3
1 adult, Economy
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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 noviembre 21, 2024.

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 noviembre 21, 2024.

This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/53:03 pmSJU - STL
1 stop10h 21mFrontier
lun. 12/95:02 pmSTL - SJU
1 stop24h 29mFrontier
Deal found 11/20$152
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/61:55 pmSJU - MDW
1 stop12h 25mFrontier
lun. 12/97:25 amMDW - SJU
1 stop16h 32mFrontier
Deal found 11/20$158
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/184:43 pmSJU - ORD
Nonstop5h 30mSpirit Airlines
jue. 1/21:00 pmORD - SJU
Nonstop4h 36mSpirit Airlines
Deal found 11/20$158
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.
vie. 12/62:17 pmSJU - ORD
Nonstop5h 30mMultiple Airlines
lun. 12/94:58 pmORD - SJU
1 stop7h 04mMultiple Airlines
Deal found 11/20$161
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/2410:01 pmSJU - ORD
1 stop13h 23mFrontier
jue. 1/22:19 pmORD - SJU
1 stop8h 22mFrontier
Deal found 11/20$168
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/68:35 amSJU - ORD
Nonstop5h 19mUnited Airlines
lun. 12/92:20 pmORD - SJU
Nonstop4h 35mUnited Airlines
Deal found 11/20$221
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/55:05 pmSJU - STL
1 stop8h 19mMultiple Airlines
lun. 12/911:31 amSTL - SJU
1 stop23h 06mMultiple Airlines
Deal found 11/20$231
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/65:25 amSJU - MDW
2 stops17h 37mMultiple Airlines
lun. 12/98:15 amMDW - SJU
2 stops31h 28mMultiple Airlines
Deal found 11/20$238
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/215:00 pmPUJ - ORD
Nonstop5h 31mFrontier
mar. 1/146:10 amORD - PUJ
Nonstop4h 29mFrontier
Deal found 11/20$252
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.
sáb. 12/214:50 pmPUJ - ORD
1 stop20h 14mMultiple Airlines
vie. 1/106:20 amORD - PUJ
Nonstop4h 29mMultiple Airlines
Deal found 11/19$301
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/126:10 amSJU - MDW
1 stop10h 05mSouthwest
lun. 12/1611:55 amMDW - SJU
2 stops10h 50mSouthwest
Deal found 11/20$312
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/279:13 pmSJU - STL
1 stop21h 49mSpirit Airlines
jue. 1/24:27 pmSTL - SJU
1 stop25h 55mSpirit Airlines
Deal found 11/20$340

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 2,629,791 searches. Data last updated noviembre 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

jue. 12/5

3:03 pm-11:24 pm

1 stop10h 21m

Lambert-St Louis

lun. 12/9

5:02 pm-7:31 pm

1 stop24h 29m

$152

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mié. 12/18

4:43 pm-8:13 pm

Nonstop5h 30m

Chicago O'Hare Intl

jue. 1/2

1:00 pm-7:36 pm

Nonstop4h 36m

$158

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

vie. 12/6

1:55 pm-12:20 am

1 stop12h 25m

Chicago Midway

lun. 12/9

7:25 am-1:57 am

1 stop16h 32m

$158

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 12/6

2:17 pm-5:47 pm

Nonstop5h 30m

Chicago O'Hare Intl

lun. 12/9

4:58 pm-2:02 am

1 stop7h 04m

$161

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

mar. 12/24

10:01 pm-9:24 am

1 stop13h 23m

Chicago O'Hare Intl

jue. 1/2

2:19 pm-12:41 am

1 stop8h 22m

$168

San JuanChicago

SJU - MDW

SJUMDW

San Juan Luis Munoz Marin Intl

jue. 1/23

4:50 pm-6:01 pm

1 stop27h 11m

Chicago Midway

lun. 1/27

6:15 am-3:19 pm

2 stops31h 04m

$200

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

vie. 1/31

6:10 pm-9:27 pm

Nonstop5h 17m

Chicago O'Hare Intl

mié. 2/5

6:10 am-1:00 pm

Nonstop4h 50m

$200

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

vie. 12/6

8:35 am-11:54 am

Nonstop5h 19m

Chicago O'Hare Intl

lun. 12/9

2:20 pm-8:55 pm

Nonstop4h 35m

$221

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

jue. 12/5

5:05 pm-11:24 pm

1 stop8h 19m

Lambert-St Louis

lun. 12/9

11:31 am-12:37 pm

1 stop23h 06m

$231

San JuanSt. Louis

SJU - STL

SJUSTL

San Juan Luis Munoz Marin Intl

jue. 2/6

2:25 pm-11:46 pm

2 stops11h 21m

Lambert-St Louis

mar. 2/11

6:00 am-5:30 pm

2 stops9h 30m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

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, September is the cheapest month in which you can book a flight from Caribbean to Illinois (average of $232). Flying from Caribbean to Illinois in June is currently the most expensive (average of $308). 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 noviembre 21, 2024.

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 noviembre 21, 2024.

The most flights from 0CB to USIL 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 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 noviembre 21, 2024.
Southwest
8.1
Very good
5,015 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

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

Southwest
8.1
Very good
5,015 reviews
Southwest
8.1
Very good
5,015 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

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

Delta
8.0
Very good
8,759 reviews
Southwest
8.1
Very good
5,015 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

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

Alaska Airlines
8.0
Very good
9,458 reviews
Southwest
8.1
Very good
5,015 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Entertainment

7.7

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
5,015 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

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

Aeromexico
7.5
Good
2,004 reviews
Southwest
8.1
Very good
5,015 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Overall

8.1

Entertainment

7.7

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 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 $57. Spirit Airlines flights start at $85 while deals on United Airlines start at $101 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, September is the cheapest month in which you can book a flight from Caribbean to Illinois (average of $232). Flying from Caribbean to Illinois in June is currently the most expensive (average of $308). 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 Caribbean to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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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 2,629,791 searches. Data last updated noviembre 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$120Average$300FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$148Average$347FlexibilityNo cancel feeOn-time65%
DeltaCheapest$182Average$472FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$195Average$509FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$220Average$379FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$303Average$557FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$400Average$521FlexibilityNo cancel feeOn-time70%
JetBlueCheapest$467Average$619FlexibilityNo cancel feeOn-time62%
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