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Basseterre

$271+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SKB
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
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Cheap flight deals from Illinois to Basseterre

Keep the following information in mind while searching for Illinois to Basseterre flight deals. Data was last updated November 4, 2025.

Round-trip from

$524
(American Airlines)

One-way from

$271
(Expedia)

Popular in

August

Cheapest in

July

Average price

$741
From Illinois to Basseterre Robert Bradshaw Intl
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One-way flight from Illinois to Basseterre Robert Bradshaw Intl
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Highest demand for flights based on searches. 16% potential increase in price ($189 potential increase over avg. RT price).
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Cheapest flight prices on average. 14% potential price decrease ($122 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find 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 November 4, 2025.

This American Airlines deal was found by Cheapflights users on 11/3. 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 12/137:00 amORD - SKB
1 stop7h 19mAmerican Airlines
Thu 12/185:29 pmSKB - ORD
1 stop9h 14mAmerican Airlines
Deal found 11/3$524
This American Airlines deal was found by Cheapflights users on 11/4. 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.
Thu 12/47:07 pmORD - SKB
1 stop17h 13mAmerican Airlines
Mon 12/83:27 pmSKB - ORD
1 stop21h 40mAmerican Airlines
Deal found 11/4$536
This American Airlines deal was found by Cheapflights users on 11/2. 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 12/28:45 pmORD - SKB
2 stops15h 35mAmerican Airlines
Tue 12/93:27 pmSKB - ORD
2 stops17h 52mAmerican Airlines
Deal found 11/2$609
This American Airlines deal was found by Cheapflights users on 11/4. 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 12/1310:05 pmORD - SKB
2 stops14h 22mAmerican Airlines
Sat 12/205:29 pmSKB - ORD
2 stops16h 00mAmerican Airlines
Deal found 11/4$641
This American Airlines deal was found by Cheapflights users on 11/2. 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 12/95:10 amSTL - SKB
1 stop7h 17mAmerican Airlines
Tue 12/163:27 pmSKB - STL
1 stop10h 32mAmerican Airlines
Deal found 11/2$688
This American Airlines deal was found by Cheapflights users on 11/3. 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.
Thu 12/185:00 amORD - SKB
1 stop9h 29mAmerican Airlines
Thu 12/253:27 pmSKB - ORD
1 stop10h 26mAmerican Airlines
Deal found 11/3$706
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Thu 12/185:05 amSTL - SKB
1 stop7h 22mAmerican Airlines
Thu 12/253:27 pmSKB - STL
1 stop9h 08mAmerican Airlines
Deal found 11/2$758
This Mytrip deal was found by Cheapflights users on 11/2. 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.
Tue 12/22:01 pmORD - SKB
3 stops25h 44mMultiple Airlines
Tue 12/92:00 pmSKB - ORD
3 stops30h 36mMultiple Airlines
Deal found 11/2$764
This American Airlines deal was found by Cheapflights users on 11/4. 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.
Fri 12/195:05 amSTL - SKB
1 stop7h 22mAmerican Airlines
Fri 12/263:27 pmSKB - STL
1 stop9h 08mAmerican Airlines
Deal found 11/4$938
This Delta deal was found by Cheapflights users on 11/4. 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 11/4$2,197

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 November 4, 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

Mon 12/15

7:07 pm-2:27 pm

1 stop17h 20m

Basseterre Robert Bradshaw Intl

Sat 12/20

5:29 pm-12:43 am

1 stop9h 14m

$524

ChicagoBasseterre

ORD - SKB

ORDSKB

Chicago O'Hare Intl

Sat 12/13

5:00 am-2:07 pm

1 stop7h 07m

Basseterre Robert Bradshaw Intl

Thu 12/18

3:27 pm-10:59 pm

1 stop9h 32m

$524

St. LouisBasseterre

STL - SKB

STLSKB

Lambert-St Louis

Sun 1/25

3:30 pm-2:47 pm

2 stops21h 17m

Basseterre Robert Bradshaw Intl

Sat 1/31

5:35 pm-1:03 pm

2 stops21h 28m

$658

St. LouisBasseterre

STL - SKB

STLSKB

Lambert-St Louis

Wed 4/8

7:03 pm-1:10 pm

2 stops17h 07m

Basseterre Robert Bradshaw Intl

Wed 4/15

2:30 pm-9:25 am

2 stops19h 55m

$658

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

$678

St. LouisBasseterre

STL - SKB

STLSKB

Lambert-St Louis

Thu 1/29

3:37 pm-2:47 pm

2 stops21h 10m

Basseterre Robert Bradshaw Intl

Sat 2/7

5:35 pm-9:24 am

2 stops17h 49m

$683

St. LouisBasseterre

STL - SKB

STLSKB

Lambert-St Louis

Tue 12/9

5:10 am-2:27 pm

1 stop7h 17m

Basseterre Robert Bradshaw Intl

Tue 12/16

3:27 pm-11:59 pm

1 stop10h 32m

$688

St. LouisBasseterre

STL - SKB

STLSKB

Lambert-St Louis

Sun 2/15

6:20 pm-2:15 pm

1 stop17h 55m

Basseterre Robert Bradshaw Intl

Sun 2/22

3:15 pm-10:27 am

1 stop21h 12m

$699

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Sun 2/1

11:00 am-4:00 pm

3 stops27h 00m

Basseterre Robert Bradshaw Intl

Sun 2/8

9:45 am-1:09 pm

3 stops29h 24m

$1,318

ChicagoBasseterre

MDW - SKB

MDWSKB

Chicago Midway

Sat 12/20

6:00 am-3:13 pm

1 stop7h 13m

Basseterre Robert Bradshaw Intl

Sat 1/3

2:53 pm-10:22 pm

1 stop9h 29m

$2,197

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 28 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 July is currently the most expensive (average of $993). 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.

How much does it cost to fly round-trip from Illinois to Basseterre?

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 $678, American Airlines 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 cheapest airlines to fly from Illinois to Basseterre one-way?

    For one-way options, check prices for JetBlue. According to our data, you can fly for as low as $271. Users have also found prices from $410 and $429 on American Airlines and Delta, respectively.

  • 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 July is currently the most expensive (average of $993). 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 Basseterre

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Illinois to Basseterre

Discover the top 2 airlines 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 November 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$488Average$770FlexibilityNo cancel feeOn-time71%
DeltaCheapest$614Average$615FlexibilityNo cancel feeOn-timeN/A

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