Cheap flights from ORD to SKB (O'Hare Intl. to Robert L. Bradshaw Intl.)

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Cheap Flights from ORD to SKB starting at $304 One Way, $630 Round Trip

Prices starting at $630 for return flights and $304 for one-way flights to Robert L. Bradshaw Intl. were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Nov 27 - Fri, Dec 4
ORD
Chicago
SKB
St. Kitts
$630 Roundtrip, found 7 hours ago
$630
Roundtrip
found 7 hours ago
Select Air Canada flight, departing Fri, Nov 27 from Chicago to St. Kitts, returning Fri, Dec 4, priced at $630 found 7 hours ago
Tue, Feb 16 - Tue, Feb 23
ORD
Chicago
SKB
St. Kitts
$687 Roundtrip, found 1 day ago
$687
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Feb 16 from Chicago to St. Kitts, returning Tue, Feb 23, priced at $687 found 1 day ago
Tue, Feb 16 - Tue, Feb 23
ORD
Chicago
SKB
St. Kitts
$692 Roundtrip, found 1 day ago
$692
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Feb 16 from Chicago to St. Kitts, returning Tue, Feb 23, priced at $692 found 1 day ago
Tue, Feb 16 - Tue, Feb 23
ORD
Chicago
SKB
St. Kitts
$699 Roundtrip, found 1 day ago
$699
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Feb 16 from Chicago to St. Kitts, returning Tue, Feb 23, priced at $699 found 1 day ago
Fri, Nov 27 - Fri, Dec 4
ORD
Chicago
SKB
St. Kitts
$700 Roundtrip, found 7 hours ago
$700
Roundtrip
found 7 hours ago
Select Air Canada flight, departing Fri, Nov 27 from Chicago to St. Kitts, returning Fri, Dec 4, priced at $700 found 7 hours ago

Hotel Ideas near Robert L. Bradshaw Intl.

Airport Hotels near Robert L. Bradshaw Intl.

St Kitts Marriott Beach Resort, Casino & Spa

St Kitts Marriott Beach Resort, Casino & Spa

4.5 out of 5
858 Frigate Bay Road Basseterre St. Kitts
$196 nightly
The price is $222 total per night from Oct 11 to Oct 12
$222 total
Oct 11 - Oct 12
Total with taxes and fees
Book a stay at this luxury resort in Basseterre. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (1,001 reviews)
"I liked my sty here. The room was clean, no noise, fair pricing, and the location is near restaurants and stores in a walkable distance. I think the property is well-maintained. I’d suggest tightening up security because a couple of non-guests could easily walk around."

Reviewed on Sep 19, 2026

St Kitts Marriott Beach Resort, Casino & Spa
Koi Resort Saint Kitts, Curio Collection by Hilton

Koi Resort Saint Kitts, Curio Collection by Hilton

4 out of 5
100 Koi Resort Drive Basseterre
$164 nightly
The price is $182 total per night from Sep 28 to Sep 29
$182 total
Sep 28 - Sep 29
Total with taxes and fees
Book a stay at this spa resort in Basseterre. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the clean ...
Koi Resort Saint Kitts, Curio Collection by Hilton
St. Kitts Castle Premium Suites

St. Kitts Castle Premium Suites

4 out of 5
Second Round About Frigate Bay Basseterre Basseterre
$124 nightly
The price is $139 total per night from Sep 22 to Sep 23
$139 total
Sep 22 - Sep 23
Total with taxes and fees
Book a stay at this spa apartment in Basseterre. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Royal St. Kitts Golf Club and Warner ...
9/10 Wonderful! (2 reviews)
"The property was conveniently located and comfortable. We even received a complementary bottle of wine which was very thoughtful!"

Reviewed on Aug 18, 2026

St. Kitts Castle Premium Suites
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels In Basseterre

St Kitts Marriott Beach Resort, Casino & Spa

St Kitts Marriott Beach Resort, Casino & Spa

4.5 out of 5
858 Frigate Bay Road Basseterre St. Kitts
$196 nightly
The price is $222 total per night from Oct 11 to Oct 12
$222 total
Oct 11 - Oct 12
Total with taxes and fees
Book a stay at this luxury resort in Basseterre. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (1,001 reviews)
"I liked my sty here. The room was clean, no noise, fair pricing, and the location is near restaurants and stores in a walkable distance. I think the property is well-maintained. I’d suggest tightening up security because a couple of non-guests could easily walk around."

Reviewed on Sep 19, 2026

St Kitts Marriott Beach Resort, Casino & Spa
Koi Resort Saint Kitts, Curio Collection by Hilton

Koi Resort Saint Kitts, Curio Collection by Hilton

4 out of 5
100 Koi Resort Drive Basseterre
$164 nightly
The price is $182 total per night from Sep 28 to Sep 29
$182 total
Sep 28 - Sep 29
Total with taxes and fees
Book a stay at this spa resort in Basseterre. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the clean ...
Koi Resort Saint Kitts, Curio Collection by Hilton
Royal St. Kitts Hotel

Royal St. Kitts Hotel

4 out of 5
406 Zenway Blvd Basseterre St. Kitts
$150 nightly
The price is $166 total per night from Oct 21 to Oct 22
$166 total
Oct 21 - Oct 22
Total with taxes and fees
Book a stay at this golf hotel in Basseterre. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (639 reviews)
"Nice kitchen in our room made it easy to have supplies for convinced"

Reviewed on Sep 16, 2026

Royal St. Kitts Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Basseterre Hotels With Airport Transportation

Ocean Terrace Inn

Ocean Terrace Inn

4.5 out of 5
Wigley Avenue Basseterre
Book a stay at this luxury hotel in Basseterre. Enjoy free WiFi, free parking, and 2 restaurants. Popular attractions The War Memorial and National Museum are ...
Get rates
Ocean Terrace Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Low Priced Basseterre Hotels

Sugar Bay Club Suites & Hotel

Sugar Bay Club Suites & Hotel

3 out of 5
Basseterre Basseterre St. Kitts
The price is $157 total per night from Oct 20 to Oct 21
$157 total
per night
Oct 20 - Oct 21
Book a stay at this beach hotel in Basseterre. Enjoy free WiFi, 2 outdoor pools, and 5 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
Sugar Bay Club Suites & Hotel
Timothy Beach Resort

Timothy Beach Resort

3 out of 5
Frigate Bay Basseterre St. Kitts
The price is $143 total per night from Sep 22 to Sep 23
$143 total
per night
Sep 22 - Sep 23
Book a stay at this beach hotel in Basseterre. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (528 reviews)
"This is a very old property that shows its age. Buildings are just old and in need of remodel. They only provide 1 coffee packet for a 4 day stay WTH. No complimentary coffee in the lobby, restaurant was way overpriced and just palatable. Location is ok but the place needs work."

Reviewed on Sep 20, 2026

Timothy Beach Resort
Bird Rock Beach Hotel

Bird Rock Beach Hotel

3.5 out of 5
South Pelican Drive Basseterre St. Kitts
The price is $116 total per night from Sep 22 to Sep 23
$116 total
per night
Sep 22 - Sep 23
Book a stay at this beach hotel in Basseterre. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Frigate Bay Beach and Frigate Bay are located ...
Bird Rock Beach Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Basseterre

St Kitts Marriott Beach Resort, Casino & Spa

St Kitts Marriott Beach Resort, Casino & Spa

4.5 out of 5
858 Frigate Bay Road Basseterre St. Kitts
$196 nightly
The price is $222 total per night from Oct 11 to Oct 12
$222 total
Oct 11 - Oct 12
Total with taxes and fees
Book a stay at this luxury resort in Basseterre. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (1,001 reviews)

Families like: Outdoor pools, babysitting, close to beach, cribs

Travelers say...
"I liked my sty here. The room was clean, no noise, fair pricing, and the location is near restaurants and stores in a walkable distance. I think the property is well-maintained. I’d suggest tightening up security because a couple of non-guests could easily walk around."

Reviewed on Sep 19, 2026

St Kitts Marriott Beach Resort, Casino & Spa
Luxury Villa, Panoramic, Ocean, Mountain Views, Turtle Beach, Grill, Pool!

Luxury Villa, Panoramic, Ocean, Mountain Views, Turtle Beach, Grill, Pool!

Basseterre Caribbean
Stay at this vacation home in Basseterre. Enjoy free WiFi, private pools, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.8/10 Exceptional! (129 reviews)
"Our family loved our stay at Villa Alamandra! We traveled as a family of five with two kids (ages 6 and 11), my husband, and grandma. The villa is gorgeous, spacious, and immaculate. The pool is a major plus; it stays at a cool temperature which is perfect for a plunge after a long hot day at the ..."

Reviewed on Aug 23, 2026

Get rates
Luxury Villa, Panoramic, Ocean, Mountain Views, Turtle Beach, Grill, Pool!
Sugar Bay Club Suites & Hotel

Sugar Bay Club Suites & Hotel

3 out of 5
Basseterre Basseterre St. Kitts
$140 nightly
The price is $157 total per night from Oct 20 to Oct 21
$157 total
Oct 20 - Oct 21
Total with taxes and fees
Book a stay at this beach hotel in Basseterre. Enjoy free WiFi, 2 outdoor pools, and 5 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
Sugar Bay Club Suites & Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

ORD to SKB Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date

Frequently asked questions

Are there non-stop flights from O'Hare Intl. Airport (ORD) to Robert L. Bradshaw Intl. Airport?
With no direct flights operating on the route from O'Hare Intl. Airport (ORD) to SKB, your best option is to book with an airline that offers only one stopover. Accumulate those air miles with American Airlines, United Airlines or Delta Air Lines.
What is the shortest flight from O'Hare Intl. Airport (ORD) to Robert L. Bradshaw Intl. Airport?
Flying from O'Hare Intl. Airport (ORD) to SKB will take a minimum of 6 hours and 19 minutes. Enjoy a beverage and get stuck into that book — this is the perfect opportunity to relax.
How many hours flight from O'Hare Airport to Robert L. Bradshaw Intl. Airport?
From ORD to SKB, you'll be in your plane seat for about 6 hours and 24 minutes. Settle back, order a glass of wine and take out your noise-canceling earphones. It's time to binge-watch your favorite TV shows.
What airlines have the most flights from O'Hare Intl. Airport (ORD) to Robert L. Bradshaw Intl. Airport (SKB)?
At the moment, you won't find any direct flights from Chicago to Basseterre. However, you will find flights with one or more stops. Look on the bright side — use the break to stretch your legs or do a little souvenir shopping!

Map To Nearby Hotels

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.