Great-circle route BOS ↔ MDW. Faint dots are other airports, for geographic context. Download this map — free to reuse with a link back to this page.
Frequencies below are per direction, from our most recent schedule sample.
| Direction | Frequency | Days | Airlines |
|---|---|---|---|
| BOS → MDW Boston to Chicago |
34/wk | Daily | Southwest Airlines |
| MDW → BOS Chicago to Boston |
34/wk | Daily | Southwest Airlines |
Where a direction shows “—” we track it as an operating nonstop but hold no schedule sample for it — we would rather show nothing than guess.
In 2025, airlines reported 382,507 passengers on 2,605 flights between BOS and MDW — about 1,049 a day — filling 87% of the 437,347 seats flown. Southwest Airlines Co. carried the most passengers (100%).
Source: US DOT T-100 segment reports — actual airline-reported traffic, scheduled service only, both directions combined. Cargo and charter flights excluded.
Southwest Airlines is the only airline flying the BOS–MDW nonstop.
Recent scheduled departures on this route have used the Boeing 737, Boeing 737-800.
Aircraft assignments change by season and by time of day.
The distance between General Edward Lawrence Logan International Airport and Chicago Midway International Airport is 858 miles, or 1,381 kilometres.
| Great-circle distance | 858 mi |
| Kilometres | 1,381 km |
| Nautical miles | 746 nmi |
Measured airport to airport. The actual track is longer — aircraft follow airways, avoid restricted airspace and route around weather.
Yes. Southwest Airlines flies the route nonstop, with about 68 departures a week across both directions. The route is in our live nonstop dataset, last seeded 2026-07-07.
About 2h 17m in the air. That is a great-circle estimate from the 858-mile distance, not a scheduled block time — an airline's published time will differ by roughly 15 to 45 minutes depending on routing, winds and taxi.
About 34 a week from Boston to Chicago and 34 a week from Chicago to Boston, from our most recent schedule sample.
Southwest Airlines.
In 2025, airlines reported 382,507 passengers on 2,605 scheduled flights between BOS and MDW — about 1,049 a day — filling 87% of the seats flown. Source: US DOT T-100 segment reports, both directions combined.
Recent scheduled departures have used the Boeing 737, Boeing 737-800. Assignments change by season and by time of day.
