Cheap flights from MDW to SKB (Midway Intl. to Robert L. Bradshaw Intl.)
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Cheap Flights from MDW to SKB starting at $429 One Way, $678 Round Trip
Prices starting at $678 for return flights and $429 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
$678 Roundtrip, found 3 hours ago
$678
Roundtrip
found 3 hours ago
MDW
Chicago
SKB
St. Kitts
$690 Roundtrip, found 6 days ago
$690
Roundtrip
found 6 days ago
MDW
Chicago
SKB
St. Kitts
$798 Roundtrip, found 6 days ago
$798
Roundtrip
found 6 days ago
MDW
Chicago
SKB
St. Kitts
$812 Roundtrip, found 6 days ago
$812
Roundtrip
found 6 days ago
MDW
Chicago
SKB
St. Kitts
$888 Roundtrip, found 6 days ago
$888
Roundtrip
found 6 days ago
Hotel Ideas near Robert L. Bradshaw Intl.
Airport Hotels near Robert L. Bradshaw Intl.
Koi Resort Saint Kitts, Curio Collection by Hilton
100 Koi Resort Drive, Basseterre
$143 nightly
The price is $159 total per night from Oct 29 to Oct 30
$159 total
Oct 29 - Oct 30
Total with taxes and fees
Stay at this 4-star spa resort in Basseterre. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the clean ...
8.2/10 Very Good! (423 reviews)
I had two treatments at the spa and as usual tney were exceptional
Reviewed on Oct 17, 2025
St Kitts Marriott Beach Resort, Casino & Spa
858 Frigate Bay Road, Frigate Bay, Basseterre, St. Kitts
$242 nightly
The price is $268 total per night from Nov 3 to Nov 4
$268 total
Nov 3 - Nov 4
Total with taxes and fees
Stay at this 4.5-star luxury resort in Basseterre. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (1,010 reviews)
Lovely property close to restaurants, bars, beach and supermarkets. Great location. Beautiful property with great amenities also
Reviewed on Oct 23, 2025
Sugar Bay Club Suites & Hotel
Basseterre, Frigate Bay, Basseterre, St. Kitts
$131 nightly
The price is $146 total per night from Oct 31 to Nov 1
$146 total
Oct 31 - Nov 1
Total with taxes and fees
Stay at this 3-star beach hotel in Basseterre. Enjoy free WiFi, 2 outdoor pools, and 5 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
7.8/10 Good! (437 reviews)
Budget friendly and very cozy.
Reviewed on Aug 27, 2025
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, Frigate Bay, Basseterre, St. Kitts
$242 nightly
The price is $268 total per night from Nov 3 to Nov 4
$268 total
Nov 3 - Nov 4
Total with taxes and fees
Stay at this 4.5-star luxury resort in Basseterre. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (1,010 reviews)
Lovely property close to restaurants, bars, beach and supermarkets. Great location. Beautiful property with great amenities also
Reviewed on Oct 23, 2025
Koi Resort Saint Kitts, Curio Collection by Hilton
100 Koi Resort Drive, Basseterre
$143 nightly
The price is $159 total per night from Oct 29 to Oct 30
$159 total
Oct 29 - Oct 30
Total with taxes and fees
Stay at this 4-star spa resort in Basseterre. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the clean ...
8.2/10 Very Good! (423 reviews)
I had two treatments at the spa and as usual tney were exceptional
Reviewed on Oct 17, 2025
Royal St. Kitts Hotel
406 Zenway Blvd, Frigate Bay, Basseterre, St. Kitts
$209 nightly
The price is $231 total per night from Nov 25 to Nov 26
$231 total
Nov 25 - Nov 26
Total with taxes and fees
Stay at this 4-star golf hotel in Basseterre. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (503 reviews)
Everything was great
Reviewed on Oct 23, 2025
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, Fortlands, Basseterre
Stay at this 4.5-star luxury hotel in Basseterre. Enjoy free WiFi, free parking, and 2 restaurants. Popular attractions The War Memorial and National Museum ...
Comfortable stay
The room was large & cleaned everyday. Staff was friendly & helped get the bags to the room. On checkin there was only 1 towel & 1 water in the room but after a phone call housekeeping quickly brought the 2nd. Tishan is an excellent front desk rep. Super friendly, thorough & helpful. My booking said ...
Reviewed on Mar 9, 2020
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, Frigate Bay, Basseterre, St. Kitts
$131 nightly
The price is $146 total per night from Oct 31 to Nov 1
$146 total
Oct 31 - Nov 1
Total with taxes and fees
Stay at this 3-star beach hotel in Basseterre. Enjoy free WiFi, 2 outdoor pools, and 5 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
7.8/10 Good! (437 reviews)
Budget friendly and very cozy.
Reviewed on Aug 27, 2025
Timothy Beach Resort
Frigate Bay, Basseterre, St. Kitts
$139 nightly
The price is $154 total per night from Oct 27 to Oct 28
$154 total
Oct 27 - Oct 28
Total with taxes and fees
Stay at this 3-star beach hotel in Basseterre. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular ...
8.2/10 Very Good! (480 reviews)
Massive bed, good air con. Friendly staff.
Reviewed on Oct 11, 2025
Bird Rock Beach Hotel
South Pelican Drive, P.O. Box 227, Basseterre, St. Kitts
$90 nightly
The price is $100 total per night from Nov 5 to Nov 6
$100 total
Nov 5 - Nov 6
Total with taxes and fees
Stay at this 3.5-star beach hotel in Basseterre. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Frigate Bay Beach and Frigate Bay are ...
6.2/10 (316 reviews)
Beautiful
Reviewed on May 30, 2025
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, Frigate Bay, Basseterre, St. Kitts
$242 nightly
The price is $268 total per night from Nov 3 to Nov 4
$268 total
Nov 3 - Nov 4
Total with taxes and fees
Stay at this 4.5-star luxury resort in Basseterre. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (1,010 reviews)
Families like: Outdoor pools, babysitting, on the beach, cribs
Travelers say...
Lovely property close to restaurants, bars, beach and supermarkets. Great location. Beautiful property with great amenities also
Reviewed on Oct 23, 2025
Luxury Villa, Panoramic, Ocean, Mountain Views, Turtle Beach, Grill, Pool!
Basseterre
Book a stay at this business-friendly vacation home in Basseterre. Enjoy free WiFi, private pools, and a garden. Our guests praise the helpful staff in our reviews. ...
9.6/10 Exceptional! (82 reviews)
Best stay ever! Property was clean and the views were immaculate. Owners provided plenty of information to help us plan our stay on the island and was very responsive. Loved waking up here each day. Absolutely wonderful family getaway!
Reviewed on Aug 24, 2025
Sugar Bay Club Suites & Hotel
Basseterre, Frigate Bay, Basseterre, St. Kitts
$131 nightly
The price is $146 total per night from Oct 31 to Nov 1
$146 total
Oct 31 - Nov 1
Total with taxes and fees
Stay at this 3-star beach hotel in Basseterre. Enjoy free WiFi, 2 outdoor pools, and 5 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
7.8/10 Good! (437 reviews)
Families like: Outdoor pools, babysitting, bicycle rentals, cribs
Travelers say...
Budget friendly and very cozy.
Reviewed on Aug 27, 2025
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 | |
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Number Of Airlines Serving | |
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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)
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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.