Boston (BOS) to Chicago (MDW) flights
One airline flies nonstop from Boston (BOS) to Chicago (MDW): Southwest Airlines. The two airports are 857 miles (1,379 km) apart. There are also 31 ways to fly it with one stop, through Detroit, Buffalo and Rochester and more.
Airlines flying nonstop from BOS to MDW
- Southwest AirlinesNot in an allianceWho books it
BOS to MDW with one stop
31 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Buffalo (BUF)JetBlue Airways, Delta Air Lines and 1 more, then Southwest Airlines
- Via Rochester (ROC)American Airlines, then Southwest Airlines
- Via Cleveland (CLE)JetBlue Airways and Delta Air Lines, then Southwest Airlines
- Via Toronto (YTZ)Porter Airlines the whole way
- Via Grand Rapids (GRR)Allegiant Air, then Southwest Airlines
- Via Pittsburgh (PIT)JetBlue Airways and Delta Air Lines, then Southwest Airlines
- Via New York (LGA)American Airlines and Delta Air Lines, then Southwest Airlines
- Via Columbus (CMH)Delta Air Lines and American Airlines, then Southwest Airlines
- Via Milwaukee (MKE)Southwest Airlines the whole way+1
- Via Philadelphia (PHL)American Airlines, JetBlue Airways and 1 more, then Southwest Airlines
- Via Baltimore (BWI)Southwest Airlines the whole way
- Via Indianapolis (IND)Delta Air Lines, American Airlines and 1 more, then Southwest Airlines
- Via Washington (DCA)American Airlines, JetBlue Airways and 1 more, then Southwest Airlines
- Via Cincinnati (CVG)Delta Air Lines and American Airlines, then Southwest Airlines
BOS to MDW: common questions
Which airlines fly nonstop from BOS to MDW?
Southwest Airlines flies nonstop from Boston (BOS) to Chicago (MDW).
How far is Boston from Chicago by plane?
Boston (BOS) and Chicago (MDW) are 857 miles (1,379 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does BOS to MDW cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for BOS to MDW with taxes and fees.
Where can I connect between Boston and Chicago?
The most direct connections are through Detroit (DTW), Buffalo (BUF), Rochester (ROC), Cleveland (CLE) and Toronto (YTZ). On 10 of them the same airline flies both flights, for example Delta Air Lines through Detroit.
More routes
Routes are scheduled nonstop flights. The route data is refreshed monthly; this list was last checked November 11, 2026. Seasonal routes and new launches can be missing or end early, so confirm with the airline before you book. Distances are great-circle, the shortest path between the two airports.