$249 Cheap Flights from Chicago (ORD) to Basseterre (SKB)

View $249 flight on Sat, May 17, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Chicago to Basseterre (ORD-SKB)

Prices were available within the past 7 days and start at $249 for one-way flights and $546 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Sat, May 17 - Tue, May 27
ORD
Chicago
SKB
St. Kitts
$546 Roundtrip, found 5 days ago
$546
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sat, May 17 from Chicago to St. Kitts, returning Tue, May 27, priced at $546 found 5 days ago
JetBlue Airways
Wed, May 14 - Tue, May 27
ORD
Chicago
SKB
St. Kitts
$555 Roundtrip, found 5 days ago
$555
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Wed, May 14 from Chicago to St. Kitts, returning Tue, May 27, priced at $555 found 5 days ago
JetBlue Airways
Sat, May 31 - Tue, Jun 17
ORD
Chicago
SKB
St. Kitts
$559 Roundtrip, found 5 days ago
$559
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sat, May 31 from Chicago to St. Kitts, returning Tue, Jun 17, priced at $559 found 5 days ago
JetBlue Airways
Wed, Jun 4 - Tue, Jun 17
ORD
Chicago
SKB
St. Kitts
$564 Roundtrip, found 4 days ago
$564
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Wed, Jun 4 from Chicago to St. Kitts, returning Tue, Jun 17, priced at $564 found 4 days ago
JetBlue Airways
Sat, May 31 - Sun, Jun 15
ORD
Chicago
SKB
St. Kitts
$570 Roundtrip, found 5 days ago
$570
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sat, May 31 from Chicago to St. Kitts, returning Sun, Jun 15, priced at $570 found 5 days ago
JetBlue Airways
Wed, Jun 4 - Sun, Jun 15
ORD
Chicago
SKB
St. Kitts
$575 Roundtrip, found 4 days ago
$575
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Wed, Jun 4 from Chicago to St. Kitts, returning Sun, Jun 15, priced at $575 found 4 days ago
American Airlines
Sun, Nov 2 - Fri, Dec 19
ORD
Chicago
SKB
St. Kitts
$618 Roundtrip, found 14 hours ago
$618
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Sun, Nov 2 from Chicago to St. Kitts, returning Fri, Dec 19, priced at $618 found 14 hours ago
United
Sun, Jul 20 - Mon, Jul 28
ORD
Chicago
SKB
St. Kitts
$656 Roundtrip, found 6 hours ago
$656
Roundtrip
found 6 hours ago
Select United flight, departing Sun, Jul 20 from Chicago to St. Kitts, returning Mon, Jul 28, priced at $656 found 6 hours ago
Delta
Sat, Jul 26 - Sat, Aug 2
ORD
Chicago
SKB
St. Kitts
$668 Roundtrip, found 1 day ago
$668
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Jul 26 from Chicago to St. Kitts, returning Sat, Aug 2, priced at $668 found 1 day ago
Air Canada
Fri, Jan 16 - Sat, Jan 24
ORD
Chicago
SKB
St. Kitts
$1,344 Roundtrip, found 2 days ago
$1,344
Roundtrip
found 2 days ago
Select Air Canada flight, departing Fri, Jan 16 from Chicago to St. Kitts, returning Sat, Jan 24, priced at $1,344 found 2 days ago

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.
*Available to One Key members.