Chicago (MDW) to Boston (BOS) flights
One airline flies nonstop from Chicago (MDW) to Boston (BOS): 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 MDW to BOS
- Southwest AirlinesNot in an allianceWho books it
MDW to BOS 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)Southwest Airlines, then JetBlue Airways, Delta Air Lines and 1 more
- Via Rochester (ROC)Southwest Airlines, then American Airlines
- Via Cleveland (CLE)Southwest Airlines, then JetBlue Airways and Delta Air Lines
- Via Grand Rapids (GRR)Southwest Airlines, then Allegiant Air
- Via Toronto (YTZ)Porter Airlines the whole way
- Via Pittsburgh (PIT)Southwest Airlines, then JetBlue Airways and Delta Air Lines
- Via New York (LGA)Southwest Airlines, then American Airlines and Delta Air Lines
- Via Columbus (CMH)Southwest Airlines, then Delta Air Lines and American Airlines
- Via Milwaukee (MKE)Southwest Airlines the whole way+1
- Via Philadelphia (PHL)Southwest Airlines, then American Airlines, JetBlue Airways and 1 more
- Via Baltimore (BWI)Southwest Airlines the whole way
- Via Indianapolis (IND)Southwest Airlines, then Delta Air Lines, American Airlines and 1 more
- Via Washington (DCA)Southwest Airlines, then American Airlines, JetBlue Airways and 1 more
- Via Cincinnati (CVG)Southwest Airlines, then Delta Air Lines and American Airlines
MDW to BOS: common questions
Which airlines fly nonstop from MDW to BOS?
Southwest Airlines flies nonstop from Chicago (MDW) to Boston (BOS).
How far is Chicago from Boston by plane?
Chicago (MDW) and Boston (BOS) 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 MDW to BOS cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for MDW to BOS with taxes and fees.
Where can I connect between Chicago and Boston?
The most direct connections are through Detroit (DTW), Buffalo (BUF), Rochester (ROC), Cleveland (CLE) and Grand Rapids (GRR). 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.