Chicago to Boston (MDW–BOS) — 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.
MDW–BOS is served by 2 airlines with nonstop service. Southwest Airlines and Delta Air Lines lead the route. The flight covers 858 miles in approximately 2h 20m. Beyond nonstop, 1-stop connecting options are also available.
Airline Landscape
| Airline | Freq/wk | Aircraft | Duration | Dep OTP | Alliance | Codeshares |
|---|---|---|---|---|---|---|
| WN Southwest Airlines | 36 | 737, 738, 73H, 7M8, 7S7, B38M | 1h57-2h20 | – | – | |
| DL Delta Air Lines | 0 | – | – | SkyTeam | – |
Weekly Schedule Pattern
Connection Landscape
On-Time Performance
Other ways to reach Boston from Chicago
| Metric | MDW→BOS | ORD→BOS | GYY→BOS |
|---|---|---|---|
| Distance from MDW | – | 15 mi | 21 mi |
| Nonstop airlines | 2 | 27 | 2 |
| Weekly flights | 36 | 463 | – |
| Flight time | 2h 20m | 2h 7m | 1h 48m |
| Departure OTP | 100% | – | – |
Travel Essentials
MDW: CDT · BOS: EDT
When it's 6:00 PM in Chicago, it's 7:00 PM in Boston.
Silver Line SL1 (free from Logan) runs to South Station in 15–20 minutes, connecting to the Red Line subway and Amtrak services. The Massport Shuttle connects all Logan terminals and the remote parking areas; it's also the transfer between terminals. Water taxi to Long Wharf (downtown) is $12 and runs seasonally; check weather and schedule.Taxis to downtown Boston cost $30–45 (tunnel toll included in meter). Ride-hails pick up at designated zones; follow the Logan app directions to avoid the main curb chaos. MBTA Blue Line (Airport station, free shuttle from terminals) reaches downtown in 10 minutes but requires a separate transfer. Amtrak Acela to New York departs from South Station (2.5h, from $49).
Humid continental climate with significant maritime influence. Winters (December–March) bring regular Nor'easters. These coastal storms that dump heavy snow and produce high winds, frequently closing Logan for hours and causing mass cancellations. Ice storms hit several times each winter. BOS is one of the most weather-disrupted major US airports in winter.
Summers are warm (22–29°C) with humidity and afternoon thunderstorms causing July–August delays. Hurricane remnants reach New England in September–October. Spring and fall are mild (8–18°C) but unpredictable. Logan's harbor location means it runs windier than inland readings suggest. Factor this into small aircraft routing.
MDW–BOS Quick Facts
Frequently Asked Questions
Flights from MDW to BOS
Chicago Midway International Airport (MDW) and Boston Logan International Airport (BOS) are connected by nonstop service from Southwest Airlines and Delta Air Lines. With 36 weekly departures, this is a heavily served route.
MDW to BOS Flight Duration and Schedule
Nonstop flight time from MDW to BOS is about 2 hours 20 minutes gate to gate. The route covers a distance of 858 miles (1,381 km). There are approximately 36 weekly flights outbound and 39 return, totaling 75 flights per week in both directions.
Connecting Options and Alternatives
1-stop connecting options are also available, commonly via Pittsburgh, Detroit Metropolitan Wayne County and Baltimore/Washington International Thurgood Marshall. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Chicago (ORD), Gary (GYY) and South Bend (SBN).