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Basseterre

$251+ Cheap flights from Illinois to Basseterre (SKB)

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 12/30. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SKB
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Illinois to Basseterre

Cheapest flights from Illinois to Basseterre
Explore the most affordable flight options available from Illinois to Basseterre. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/17. 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.
Tue 12/235:00 amORD - SKB
1 stop7h 27mAmerican Airlines
Wed 1/213:47 pmSKB - ORD
1 stop10h 43mAmerican Airlines
Deal found 12/17$892
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/297:26 pmORD - SKB
1 stop17h 01mAmerican Airlines
Thu 1/15:29 pmSKB - ORD
1 stop17h 18mAmerican Airlines
Deal found 12/16$971
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/1510:05 pmORD - SKB
2 stops38h 15mAmerican Airlines
Sat 12/205:29 pmSKB - ORD
2 stops16h 00mAmerican Airlines
Deal found 12/15$1,024
This American Airlines deal was found by Cheapflights users on 12/15. 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.
Sun 12/215:05 amSTL - SKB
1 stop9h 24mAmerican Airlines
Fri 1/25:29 pmSKB - STL
2 stops17h 06mAmerican Airlines
Deal found 12/15$1,551
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/317:00 amORD - SKB
1 stop7h 29mAmerican Airlines
Sat 1/34:24 pmSKB - ORD
1 stop20h 56mAmerican Airlines
Deal found 12/17$1,555
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Sat 12/208:35 pmORD - SKB
1 stop17h 54mAmerican Airlines
Sat 1/34:24 pmSKB - ORD
1 stop20h 56mAmerican Airlines
Deal found 12/17$1,843
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Tue 12/235:00 amORD - SKB
1 stop7h 27mAmerican Airlines
Sun 1/45:29 pmSKB - ORD
1 stop10h 04mAmerican Airlines
Deal found 12/17$2,020
This Delta deal was found by Cheapflights users on 12/17. 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.
Sat 12/206:00 amMDW - SKB
1 stop7h 13mDelta
Sat 1/32:53 pmSKB - MDW
1 stop9h 29mDelta
Deal found 12/17$3,403

Find flight deals from Illinois to Basseterre

Keep the following information in mind while searching for Illinois to Basseterre flight deals. Data was last updated December 18, 2025.

Round-trip from

$463
(Expedia)

One-way from

$251
(American Airlines)

Popular in

August

Cheapest in

July

Average price

$1,645
From Illinois to Basseterre Robert Bradshaw Intl
Search Deals
One-way flight from Illinois to Basseterre Robert Bradshaw Intl
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($148 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 13% potential price decrease ($118 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to Basseterre 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 December 18, 2025.
Use the filters below to find and compare flights from Illinois to Basseterre that are best for you.

Fly from

Illinois

Fly to

Basseterre

Route

Depart

Return

Price

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 1/24

9:40 am-2:13 pm

1 stop26h 33m

Basseterre Robert Bradshaw Intl

Tue 1/27

3:20 pm-7:36 pm

1 stop30h 16m

$463

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Tue 1/20

7:30 pm-2:47 pm

1 stop17h 17m

Basseterre Robert Bradshaw Intl

Tue 1/27

3:47 pm-11:08 pm

1 stop9h 21m

$524

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 1/24

7:48 pm-2:47 pm

2 stops16h 59m

Basseterre Robert Bradshaw Intl

Tue 1/27

3:47 pm-7:22 am

2 stops17h 35m

$529

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 2/7

7:48 pm-2:47 pm

2 stops16h 59m

Basseterre Robert Bradshaw Intl

Sat 2/14

5:30 pm-7:20 am

2 stops15h 50m

$529

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 2/21

5:45 am-4:30 pm

1 stop8h 45m

Basseterre Robert Bradshaw Intl

Sat 2/28

5:30 pm-7:20 am

2 stops15h 50m

$529

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Tue 3/3

5:00 am-2:17 pm

1 stop7h 17m

Basseterre Robert Bradshaw Intl

Mon 3/9

2:23 pm-10:55 am

1 stop21h 32m

$536

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 4/18

7:17 pm-1:10 pm

1 stop16h 53m

Basseterre Robert Bradshaw Intl

Sat 4/25

4:06 pm-7:10 am

2 stops16h 04m

$565

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Sat 4/18

6:00 am-2:08 pm

1 stop7h 08m

Basseterre Robert Bradshaw Intl

Sat 4/25

1:53 pm-9:45 pm

1 stop8h 52m

$590

EvansvilleBasseterre

EVV - SKB

EVVSKB

Evansville Dress Regional

Tue 1/13

4:51 pm-2:47 pm

2 stops19h 56m

Basseterre Robert Bradshaw Intl

Tue 1/20

3:47 pm-11:37 am

2 stops21h 50m

$596

St. LouisBasseterre

STL - SKB

STLSKB

Lambert-St Louis

Sat 3/7

3:31 pm-1:23 pm

2 stops19h 52m

Basseterre Robert Bradshaw Intl

Thu 3/12

2:23 pm-9:15 am

2 stops19h 52m

$633

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 17 results
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Best time to book a flight from Illinois to Basseterre

Have a flexible travel schedule? Discover the best time to fly to Basseterre 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.

Cheapflights Insights

Everything you need to know about your flight from Illinois to Basseterre

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

Currently, May is the cheapest month in which you can book a flight from Illinois to Basseterre (average of $465). Flying from Illinois to Basseterre in August is currently the most expensive (average of $737). 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.

Related info for your journey

Find useful and relevant information for your journey from Illinois to Basseterre. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Basseterre from Illinois?

    For a flight from Illinois to Basseterre, you will be flying into Robert Bradshaw Intl. Basseterre Robert Bradshaw Intl (SKB) is just 1.1 mi from the center of the city.

  • How long is the flight from Illinois to Basseterre?

    For as low as $590, JetBlue can have you in Basseterre from Illinois in 7h 08m. Illinois and Basseterre are separated by a distance of 2245 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most popular routes from Illinois to Basseterre?

    Most travelers choose Chicago O'Hare Intl - Basseterre Robert Bradshaw Intl, Lambert-St Louis - Basseterre Robert Bradshaw Intl or Chicago Midway - Basseterre Robert Bradshaw Intl when deciding on the best route from Illinois to Basseterre.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Illinois to Basseterre 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 Illinois to Basseterre?

    Currently, May is the cheapest month in which you can book a flight from Illinois to Basseterre (average of $465). Flying from Illinois to Basseterre in August is currently the most expensive (average of $737). 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 Basseterre

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Illinois to Basseterre

Discover the top airline that operate flights from Illinois to Basseterre. 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$488Average$737FlexibilityNo cancel feeOn-time71%

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