Boston to Chicago (BOS–MDW) — Airlines, Schedules & Connections
No flights match your filters.
No nonstop flights on this route. connecting options below.
BOS–MDW is served by 2 airlines with nonstop service. Southwest Airlines and SGX lead the route. The flight covers 858 miles in approximately 2h 9m. Beyond nonstop, 184 hubs offer 1-stop connections.
Airline Landscape
| Airline | Freq/wk | Aircraft | Duration | Dep OTP | Alliance | Codeshares |
|---|---|---|---|---|---|---|
| WN Southwest Airlines | 28 | 737, 73H, 7M8, 7S7, B38M | 2h32-2h45 | – | – | |
| SGX SGX | 0 | – | – | – | – |
Weekly Schedule Pattern
Connection Landscape
Other ways to reach Chicago from Boston
| Metric | BOS→MDW | BED→MDW | ORH→MDW |
|---|---|---|---|
| Distance from BOS | – | 16 mi | 45 mi |
| Nonstop airlines | 2 | 6 | 2 |
| Weekly flights | 29 | 1 | 1 |
| Flight time | 2h 9m | 1h 50m | 2h 2m |
| Departure OTP | 84% | – | – |
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 SGX and Southwest Airlines. With 29 weekly departures, this is a heavily served route.
BOS to MDW Flight Duration and Schedule
Nonstop flight time from BOS to MDW ranges from 2 hours 9 minutes to 2 hours 45 minutes. The route covers a distance of 858 miles (1,381 km). There are approximately 29 weekly flights outbound and 29 return, totaling 58 flights per week in both directions.
Connecting Options and Alternatives
184 one-stop connections are available, with the fastest taking approximately 3 hours via WST. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Bedford (BED), Worcester (ORH) and Manchester (MHT).