Boston (BOS) to Chicago (MDW) flights
Nonstop from Boston Logan International to Chicago Midway International Airport: distance, flying time, which airlines fly it and how often.
Distance
858 mi, great circle
Flying time
typical, gate to gate
Flights a day
average, November 2026
Airlines
passenger airlines
Airlines flying BOS to MDW
Also in the data (cargo, charter or a foreign airline on a domestic route): NetJets Aviation.
Route map
The shortest path over the Earth's surface. Actual tracks vary with winds and airspace. Map © OpenStreetMap contributors.
Cheapest recent fare
Fares found in recent searches load here. You can also compare BOS to MDW fares by month.
Both directions
- Chicago Midway International Airport (MDW) · we don't have MDW's route list yet
- All nonstop routes from Boston (BOS)
- BOS to MDW on the flight-path tool
Frequently asked questions
How long is the flight from Boston to Chicago?
About 2h 29m gate to gate for the 1,381 km (858 mile) trip, estimated from distance. Schedules vary by airline and season, and winds can add or save time.
Which airlines fly nonstop from BOS to MDW?
Southwest Airlines, with about 6 flights a day between them in our data (AeroDataBox, November 2026).