Boston to Chicago (BOS–MDW) — 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.
BOS–MDW is served by 3 airlines with nonstop service. Southwest Airlines and Delta Air Lines lead the route. The flight covers 858 miles in approximately 2h 36m. Beyond nonstop, 1-stop connecting options are also available.
Airline Landscape
| Airline | Freq/wk | Aircraft | Duration | Dep OTP | Alliance | Codeshares |
|---|---|---|---|---|---|---|
| WN Southwest Airlines | 39 | 738, 73H, 7M8, 7S7 | 2h29-3h31 | – | – | |
| DL Delta Air Lines | 1 | – | – | SkyTeam | – | |
| SGX SGX | 0 | – | – | – | – |
Weekly Schedule Pattern
Connection Landscape
On-Time Performance
Other ways to reach Chicago from Boston
| Metric | BOS→MDW | BED→MDW | ORH→MDW |
|---|---|---|---|
| Distance from BOS | – | 16 mi | 45 mi |
| Nonstop airlines | 3 | 10 | 2 |
| Weekly flights | 39 | 2 | 1 |
| Flight time | 2h 36m | 1h 52m | 1h 47m |
| Departure OTP | 58% | – | – |
Travel Essentials
BOS: EDT · MDW: CDT
When it's 6:00 PM in Boston, it's 5:00 PM in Chicago.
MBTA Silver Line SL1 bus runs from South Station (Red Line, Amtrak) through the Ted Williams Tunnel to all Logan terminals; free from the airport, $2.40 inbound. Journey from South Station takes 15–20 minutes depending on traffic. The Blue Line Aquarium station connects to a free water taxi ($12) across the harbor to Logan; scenic but weather-dependent.Taxis from downtown Boston cost $30–45 with the Ted Williams Tunnel toll included. Ride-hails are comparable. The Sumner and Ted Williams tunnels both serve the airport; check traffic before departing, as both frequently back up. Logan is only 3 miles from downtown but tunnel congestion often extends that to 30+ minutes.
BOS–MDW Quick Facts
Frequently Asked Questions
Flights from BOS to MDW
Boston Logan International Airport (BOS) and Chicago Midway International Airport (MDW) are connected by nonstop service from Southwest Airlines and Delta Air Lines. With 39 weekly departures, this is a heavily served route.
BOS to MDW Flight Duration and Schedule
Nonstop flight time from BOS to MDW is about 2 hours 36 minutes gate to gate. The route covers a distance of 858 miles (1,381 km). There are approximately 39 weekly flights outbound and 36 return, totaling 75 flights per week in both directions.
Connecting Options and Alternatives
1-stop connecting options are also available, commonly via Buffalo Niagara, Cleveland Hopkins and Pittsburgh. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Bedford (BED), Worcester (ORH) and Manchester (MHT).