$240 Cheap Flights from Chicago (ORD) to Basseterre (SKB)

View $240 flight on Fri, Apr 10, 2026Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Robert L. Bradshaw Intl. Airport (SKB)

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Cheap Flights from Chicago to Basseterre (ORD-SKB)

Prices were available within the past 7 days and start at $240 for one-way flights and $531 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Wed, Nov 5 - Thu, Nov 27
ORD
Chicago
SKB
St. Kitts
$531 Roundtrip, found 6 days ago
$531
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Wed, Nov 5 from Chicago to St. Kitts, returning Thu, Nov 27, priced at $531 found 6 days ago
JetBlue Airways
Wed, Aug 20 - Tue, Sep 2
ORD
Chicago
SKB
St. Kitts
$568 Roundtrip, found 6 days ago
$568
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Wed, Aug 20 from Chicago to St. Kitts, returning Tue, Sep 2, priced at $568 found 6 days ago
JetBlue Airways
Wed, Jul 30 - Tue, Aug 19
ORD
Chicago
SKB
St. Kitts
$574 Roundtrip, found 7 hours ago
$574
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Wed, Jul 30 from Chicago to St. Kitts, returning Tue, Aug 19, priced at $574 found 7 hours ago
JetBlue Airways
Sat, Nov 8 - Sat, Nov 15
ORD
Chicago
SKB
St. Kitts
$575 Roundtrip, found 1 day ago
$575
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Nov 8 from Chicago to St. Kitts, returning Sat, Nov 15, priced at $575 found 1 day ago
JetBlue Airways
Sat, Nov 15 - Thu, Dec 4
ORD
Chicago
SKB
St. Kitts
$586 Roundtrip, found 6 days ago
$586
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Sat, Nov 15 from Chicago to St. Kitts, returning Thu, Dec 4, priced at $586 found 6 days ago
JetBlue Airways
Wed, Nov 5 - Tue, Nov 25
ORD
Chicago
SKB
St. Kitts
$589 Roundtrip, found 6 days ago
$589
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Wed, Nov 5 from Chicago to St. Kitts, returning Tue, Nov 25, priced at $589 found 6 days ago
American Airlines
Tue, Mar 24 - Tue, Mar 31
ORD
Chicago
SKB
St. Kitts
$628 Roundtrip, found 6 hours ago
$628
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Tue, Mar 24 from Chicago to St. Kitts, returning Tue, Mar 31, priced at $628 found 6 hours ago
Air Canada
Fri, Nov 14 - Sat, Nov 22
ORD
Chicago
SKB
St. Kitts
$656 Roundtrip, found 8 hours ago
$656
Roundtrip
found 8 hours ago
Select Air Canada flight, departing Fri, Nov 14 from Chicago to St. Kitts, returning Sat, Nov 22, priced at $656 found 8 hours ago
Delta
Sat, May 2 - Sat, May 9
ORD
Chicago
SKB
St. Kitts
$678 Roundtrip, just found
$678
Roundtrip
just found
Select Delta flight, departing Sat, May 2 from Chicago to St. Kitts, returning Sat, May 9, priced at $678 just found
United
Fri, Nov 28 - Sat, Dec 13
ORD
Chicago
SKB
St. Kitts
$716 Roundtrip, found 6 days ago
$716
Roundtrip
found 6 days ago
Select United flight, departing Fri, Nov 28 from Chicago to St. Kitts, returning Sat, Dec 13, priced at $716 found 6 days ago

Find the cheapest month to fly from Chicago (ORD) to Basseterre (SKB)

September is typically the cheapest month to fly

From $481 - $966 per traveler.

Graph displaying average flight prices per month

Alternative airports near Basseterre

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Robert L. Bradshaw Intl. SKB. Cheapest option available. Flights from $878
SKB
Robert L. Bradshaw Intl.
Cheapest
Flights from $878
Flights from Chicago (ORD) to Basseterre (SKB)
Origin airport
O'Hare Intl.
Destination airport
Robert L. Bradshaw Intl.
Airlines serving
American Airlines, Delta, JetBlue Airways, United
Roundtrip price
$531
Distance
2261 mi

Chicago to Basseterre Flights

The cheapest times to fly from Chicago to Basseterre

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Basseterre are during the month of November. You can find some of the cheapest flights from Chicago to Basseterre with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Basseterre

Sunday is one of the best days to book for cheap flights from Chicago to Basseterre: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Basseterre

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Basseterre in 2025. You can also book with separate airlines for your outbound and return journeys, from $240 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Basseterre flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Basseterre airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Robert L. Bradshaw Intl. Airport (SKB) cost?
Discover the latest flight deals from ORD to SKB by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from ORD to SKB?
The cheapest flights from ORD to SKB are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from ORD to SKB?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from ORD to SKB. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from O'Hare Intl. Airport (ORD) to Robert L. Bradshaw Intl. Airport (SKB)?
Direct flights from O'Hare Intl. Airport (ORD) to Robert L. Bradshaw Intl. Airport (SKB) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel dates and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ORD to SKB?
Friday is typically the busiest day for flights, while Tuesday tends to be the quietest.* Keep in mind that flight schedules can change depending on various factors, such as the time of year and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Robert L. Bradshaw Intl. Airport (SKB)?
To avoid possible delays on the O'Hare Intl. Airport (ORD) to Robert L. Bradshaw Intl. Airport (SKB) route, aim to fly before 3 PM. Departures after this hour have a 22% higher chance of cancellation.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Robert L. Bradshaw Intl. Airport (SKB) last-minute?
Booking your flight from ORD to SKB just before your trip is generally more expensive. However, if you're flexible with your travel dates and times, you could score a cheap last-minute fare.
Is it cheaper to book an ORD to SKB flight and hotel package?
You'll generally save money by booking an ORD to SKB flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. After selecting your ideal accommodations and flights, consider other add-ons like activities, car rentals and tours.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Robert L. Bradshaw Intl. Airport (SKB)?
If you reserved your ORD to SKB flight in the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the ticket type you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal if you want more information.

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*Available to One Key members.