Chicago to Basseterre (MDW–SKB) — Airlines, Schedules & Connections
No flights match your filters.
No scheduled airline flights on this route — it's flown by charter / private operators (). No nonstop flights on this route. connecting options below.
Most recently operated nonstop flights — the month shown is when each was last scheduled. Most destinations remain reachable with a connection.
No discontinued nonstop flights on record for this route.
While no nonstop service exists between MDW and SKB, 1-stop connecting options are available.
Connection Landscape
On-Time Performance
Travel Essentials
MDW: CDT · SKB: AST
When it's 6:00 PM in Chicago, it's 7:00 PM in Basseterre.
US passport holders enter St Kitts and Nevis visa-free for up to 90 days. No advance application is needed. Passport must be valid for the duration of the stay. A return or onward ticket and proof of accommodation are required. At Robert L. Bradshaw International Airport (SKB) on St Kitts, immigration stamps your passport after a brief interview about your travel plans.
The 90-day stay can be extended at the Immigration Department in Basseterre. St Kitts and Nevis is a dual-island federation: St Kitts is the larger island (68 square miles) with the capital Basseterre, while Nevis (36 square miles) sits 2 miles across a channel called The Narrows. The ferry between Basseterre and Charlestown, Nevis takes 45 minutes and costs XCD 25 ($9.25) one way. Brimstone Hill Fortress, a UNESCO World Heritage Site on St Kitts, is one of the best-preserved colonial fortifications in the Americas. The St Kitts Scenic Railway circles the island in 3 hours using tracks originally built for the sugar cane industry.
Direct flights from Miami (MIA) to St Kitts run about 3 hours 15 minutes on American Airlines. New York JFK has seasonal direct service. Charlotte (CLT) and Atlanta (ATL) also connect to SKB. St Kitts and Nevis uses the Eastern Caribbean dollar (XCD), pegged at XCD 2.70 per $1. US dollars are accepted everywhere on both islands. ATMs in Basseterre and Charlestown dispense XCD. Card payments work at hotels and restaurants. Taxis are not metered: fixed rates are set by the government and posted at the airport. Basseterre to Frigate Bay costs XCD 35 ($13). Nevis has a quieter, less developed feel with small plantation inn hotels and fewer crowds than St Kitts.
MDW–SKB Quick Facts
Frequently Asked Questions
Connecting Options and Alternatives
1-stop connecting options are also available, commonly via Hartsfield Jackson Atlanta, Luis Munoz Marin and Charlotte Douglas. Two-stop connections are also available via intermediate hubs.