Cheap flights from MDW to SKB (Midway Intl. to Robert L. Bradshaw Intl.)
Earn rewards on top of your airline miles with Orbitz Rewards
Many airlines offer flexible change policies
Sign up to receive text alerts about your trip
Cheap Flights from MDW to SKB starting at $393 One Way, $1,947 Round Trip
Prices starting at $1,947 for return flights and $393 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.
MDW
Chicago
SKB
St. Kitts
$1,947 Roundtrip, found 6 days ago
$1,947
Roundtrip
found 6 days ago
MDW
Chicago
SKB
St. Kitts
$2,125 Roundtrip, found 6 days ago
$2,125
Roundtrip
found 6 days ago
MDW
Chicago
SKB
St. Kitts
$2,140 Roundtrip, found 6 days ago
$2,140
Roundtrip
found 6 days ago
MDW
Chicago
SKB
St. Kitts
$2,173 Roundtrip, found 3 days ago
$2,173
Roundtrip
found 3 days ago
MDW
Chicago
SKB
St. Kitts
$2,173 Roundtrip, found 7 hours ago
$2,173
Roundtrip
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
858 Frigate Bay Road Basseterre St. Kitts
$205 nightly
The price is $232 total per night from Sep 7 to Sep 8
$232 total
Sep 7 - Sep 8
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! (1,006 reviews)
"All was good"
Reviewed on Aug 20, 2026
Koi Resort Saint Kitts, Curio Collection by Hilton
100 Koi Resort Drive Basseterre
$143 nightly
The price is $159 total per night from Aug 27 to Aug 28
$159 total
Aug 27 - Aug 28
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 ...
8.4/10 Very Good! (553 reviews)
"If your island traveling..do not book this through Expedia!! In the event your flight gets cancelled and you can’t make it here they will KEEP your money, they are also VERY RUDE!!"
Reviewed on Aug 19, 2026
St. Kitts Castle Premium Suites
Second Round About Frigate Bay Basseterre Basseterre
$141 nightly
The price is $158 total per night from Aug 21 to Aug 22
$158 total
Aug 21 - Aug 22
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
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
858 Frigate Bay Road Basseterre St. Kitts
$205 nightly
The price is $232 total per night from Sep 7 to Sep 8
$232 total
Sep 7 - Sep 8
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! (1,006 reviews)
"All was good"
Reviewed on Aug 20, 2026
Koi Resort Saint Kitts, Curio Collection by Hilton
100 Koi Resort Drive Basseterre
$143 nightly
The price is $159 total per night from Aug 27 to Aug 28
$159 total
Aug 27 - Aug 28
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 ...
8.4/10 Very Good! (553 reviews)
"If your island traveling..do not book this through Expedia!! In the event your flight gets cancelled and you can’t make it here they will KEEP your money, they are also VERY RUDE!!"
Reviewed on Aug 19, 2026
Royal St. Kitts Hotel
406 Zenway Blvd Basseterre St. Kitts
$151 nightly
The price is $168 total per night from Sep 20 to Sep 21
$168 total
Sep 20 - Sep 21
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! (628 reviews)
"My recent stay at the Royal St. Kitts Hotel in Frigate Bay was an absolute dream from start to finish! If you are planning a trip to St. Kitts, this resort is an unmatched sanctuary of comfort, luxury, and authentic Caribbean hospitality. Why You Will Love It: Stunning Grounds: The property is a ..."
Reviewed on Aug 17, 2026
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
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 ...
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
Basseterre Basseterre St. Kitts
$128 nightly
The price is $144 total per night from Sep 19 to Sep 20
$144 total
Sep 19 - Sep 20
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 ...
Timothy Beach Resort
Frigate Bay Basseterre St. Kitts
$129 nightly
The price is $143 total per night from Aug 21 to Aug 22
$143 total
Aug 21 - Aug 22
Total with taxes and fees
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 ...
Bird Rock Beach Hotel
South Pelican Drive Basseterre St. Kitts
$105 nightly
The price is $116 total per night from Aug 21 to Aug 22
$116 total
Aug 21 - Aug 22
Total with taxes and fees
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 ...
6.4/10 (337 reviews)
"My experience at this property did not meet expectations, and I would not recommend staying here. The property did not appear to match what was advertised or shown in the photos. The room and overall conditions were not what I expected. There were bugs present, the bed was uncomfortable, and the ..."
Reviewed on Aug 19, 2026
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
858 Frigate Bay Road Basseterre St. Kitts
$205 nightly
The price is $232 total per night from Sep 7 to Sep 8
$232 total
Sep 7 - Sep 8
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! (1,006 reviews)
Families like: Outdoor pools, babysitting, close to beach, cribs
Travelers say...
"All was good"
Reviewed on Aug 20, 2026
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! (128 reviews)
"Wonderful week! Once American Airlines allowed us to get there."
Reviewed on Aug 9, 2026
Sugar Bay Club Suites & Hotel
Basseterre Basseterre St. Kitts
$128 nightly
The price is $144 total per night from Sep 19 to Sep 20
$144 total
Sep 19 - Sep 20
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 ...
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.
MDW to SKB Route Info
Origin Airport | |
|---|---|
Destination Airport | |
Number Of Airlines Serving | |
Distance | |
Shortest Flight Departure Time | |
Shortest Flight Departure Date |
- Airport Locations
- More Popular Flights
- Top Trending
- Flights from Other Cities
- Flights From Other Airports
- Great Travel Ideas
MDW Address & GPS
Address:
5700 South Cicero
Chicago IL, 60638
United States
IATA Code:
MDW
Longitude:
-87.740871
Latitude:
41.788136
Time Zone:
America/Chicago
SKB Address & GPS
Address:
Saint Kitts ,
St. Kitts and Nevis
IATA Code:
SKB
Longitude:
-62.71397
Latitude:
17.310843
Time Zone:
America/St_Kitts
Other Flights from Midway Intl. Airport (MDW)
Other Flights to Robert L. Bradshaw Intl. Airport (SKB)
- O'Hare Intl. Airport (ORD)
- Chicago Executive Airport (PWK)
- Dupage Airport (DPA)
- Kenosha Regional Airport (ENW)
- South Bend Intl. Airport (SBN)
- Greater Rockford Airport (RFD)
- General Mitchell Intl. Airport (MKE)
- Waukesha County Airport (UES)
- Goshen Municipal Airport (GSH)
- Purdue University Airport (LAF)
Top Trending
Hotels
- Farmstay Orlando
- Hotels with Hot Tubs in Kingsport
- Hotels near Port of Charleston
- Hotels with Hot Tubs in Meadville
- Home2 Suites by Hilton Orlando at Flamingo Crossings
- Hotels with Hot Tubs in Beaumont
- Cabin Rentals Statesboro
- Cabin Rentals Brainerd
- Villas Brunei
- Caribbean Resort & Villas
- Little Sur Inn
- The Penthouse at Pacific Winds: Oceanfront Paradise
- Hotels with Waterslides in Northwest Montana - Glacier National Park
- Ogunquit River Inn & Suites
- Motels Groveland
- Teton Valley Motel
Flights
Cruises
Packages
Frequently asked questions
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.