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 $553 One Way, $1,965 Round Trip
Prices starting at $1,965 for return flights and $553 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
$1,965 Roundtrip, found 6 days ago
$1,965
Roundtrip
found 6 days ago
MDW
Chicago
SKB
St. Kitts
$2,193 Roundtrip, found 6 days ago
$2,193
Roundtrip
found 6 days ago
MDW
Chicago
SKB
St. Kitts
$2,196 Roundtrip, just found
$2,196
Roundtrip
just found
MDW
Chicago
SKB
St. Kitts
$2,205 Roundtrip, found 6 days ago
$2,205
Roundtrip
found 6 days ago
MDW
Chicago
SKB
St. Kitts
$2,436 Roundtrip, just found
$2,436
Roundtrip
just found
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 Jul 13 to Jul 14
$232 total
Jul 13 - Jul 14
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! (1,000 reviews)
"I loved the entire property. I felt like i was on a cruise because of the stairway and lay out then I look outside and see that we’re not moving. I loooved that there were 3 pools. The food in all the places was yummy. Breakfast buffet was the best. Everyone was pleasant and helpful. I give 8/10 ..."
Reviewed on Jun 24, 2026
Koi Resort Saint Kitts, Curio Collection by Hilton
100 Koi Resort Drive Basseterre
$143 nightly
The price is $159 total per night from Jul 8 to Jul 9
$159 total
Jul 8 - Jul 9
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! (535 reviews)
"Amazing stay. Food at hotel was great."
Reviewed on Jun 27, 2026
Sugar Bay Club Suites & Hotel
Basseterre Basseterre St. Kitts
$152 nightly
The price is $171 total per night from Jun 30 to Jul 1
$171 total
Jun 30 - Jul 1
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 ...
7.8/10 Good! (471 reviews)
"Friendly customer service, clean rooms."
Reviewed on Jun 26, 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 Jul 13 to Jul 14
$232 total
Jul 13 - Jul 14
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! (1,000 reviews)
"I loved the entire property. I felt like i was on a cruise because of the stairway and lay out then I look outside and see that we’re not moving. I loooved that there were 3 pools. The food in all the places was yummy. Breakfast buffet was the best. Everyone was pleasant and helpful. I give 8/10 ..."
Reviewed on Jun 24, 2026
Koi Resort Saint Kitts, Curio Collection by Hilton
100 Koi Resort Drive Basseterre
$143 nightly
The price is $159 total per night from Jul 8 to Jul 9
$159 total
Jul 8 - Jul 9
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! (535 reviews)
"Amazing stay. Food at hotel was great."
Reviewed on Jun 27, 2026
Sugar Bay Club Suites & Hotel
Basseterre Basseterre St. Kitts
$152 nightly
The price is $171 total per night from Jun 30 to Jul 1
$171 total
Jun 30 - Jul 1
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 ...
7.8/10 Good! (471 reviews)
"Friendly customer service, clean rooms."
Reviewed on Jun 26, 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
$152 nightly
The price is $171 total per night from Jun 30 to Jul 1
$171 total
Jun 30 - Jul 1
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 ...
7.8/10 Good! (471 reviews)
"Friendly customer service, clean rooms."
Reviewed on Jun 26, 2026
Timothy Beach Resort
Frigate Bay Basseterre St. Kitts
$129 nightly
The price is $143 total per night from Jul 1 to Jul 2
$143 total
Jul 1 - Jul 2
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 ...
8.4/10 Very Good! (517 reviews)
"This was my second time staying here. I love the friendly, local feel compared to high end "American" style resorts. This small resort is on the Caribben side of the island with much calmer and pleasant waters than the Atlantic side. No meals are included but there is a reasonable restaurant/bar ..."
Reviewed on Jun 24, 2026
Bird Rock Beach Hotel
South Pelican Drive Basseterre St. Kitts
$105 nightly
The price is $116 total per night from Jun 30 to Jul 1
$116 total
Jun 30 - Jul 1
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 (332 reviews)
"Helpful staff."
Reviewed on Jun 29, 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 Jul 13 to Jul 14
$232 total
Jul 13 - Jul 14
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! (1,000 reviews)
Families like: Outdoor pools, babysitting, on the beach, cribs
Travelers say...
"I loved the entire property. I felt like i was on a cruise because of the stairway and lay out then I look outside and see that we’re not moving. I loooved that there were 3 pools. The food in all the places was yummy. Breakfast buffet was the best. Everyone was pleasant and helpful. I give 8/10 ..."
Reviewed on Jun 24, 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! (124 reviews)
"Like many previous reviews articulated, this house’ view is tremendously good value and a lovely, quiet place to spend a holiday. We never got tired of watching the beautiful ocean so close by along with the backdrop of Nevis. Dinners outside were wonderful and the house is as listed: large, clean, ..."
Reviewed on Jun 18, 2026
Sugar Bay Club Suites & Hotel
Basseterre Basseterre St. Kitts
$152 nightly
The price is $171 total per night from Jun 30 to Jul 1
$171 total
Jun 30 - Jul 1
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 ...
7.8/10 Good! (471 reviews)
Families like: Outdoor pools, babysitting, bicycle rentals, laundry
Travelers say...
"Friendly customer service, clean rooms."
Reviewed on Jun 26, 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.
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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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.