Flights from Boston (BOS) to Chicago/Midway (MDW)

Flight Boston(BOS) to Midway(MDW)
CHANGE DIRECTION

Logan International Airport Chicago Midway International Airport
BOS : Boston , United States MDW : Chicago , United States
UTC-4(DST) UTC-5(DST)

Boston to Chicago/Midway Flights

Find updated flight schedules, timetable, distance, aircraft types, Map, Transfer for routes from Boston (BOS) to Chicago/Midway (MDW).

Change Direction(MDW to BOS)

Flight Schedules Boston to Midway

This route is operated by Southwest Airlines. This is the first direct flight from Boston to Chicago/Midway.

Change Direction(MDW to BOS)

Flight Duration: Approximately 2 hours 30 minutes to 3 hours (Direct Flights)

Flight No. Departure Time Arrival Time Duration Airfare
WN2650 05:15 06:45 2h30m Trip.com PRICES HIS Prices Expedia PRICES skyticket PRICES
Flight schedules as of September 01, 2025, 06:01 AM(OAG data). Schedules may change without notice, so please check with airlines before booking. Refer to FlyTeam's terms of use before proceeding. Some airlines and flight numbers may not be displayed.

The last direct flight from Boston to Midway is the final flight at 21:40 by Southwest Airlines WN1779.

All Flight Schdules(BOS to MDW)

From Boston (BOS) to Chicago/Midway (MDW) Flights Info

Duration(Flight time)

From Boston to Midway
2 hours 30 minutes to 3 hours
From Midway to Boston
2 hours 10 minutes to 2 hours 25 minutes

Distance

From Midway to Boston
Approx. 860 miles
Approx. 1,380 Km
This is different from mileage credits in airline loyalty programs.

Boston to Chicago Map

Logan International Airport Logan International Airport
Chicago Midway International Airport Chicago Midway International Airport

Type of aircrafts (BOS to MDW)

Below is a list of the aircraft types and airlines operating on this route. (Direct flights only)

* All links below lead to Japanese pages.

Boeing 737-700 *

Boeing 737-800 *

Boeing 737 MAX 8 *

Transfer / Cities with One-Stop Flights

This list shows cities where you can connect for one-stop flights between Boston and Chicago. Direct flights operate on each segment, with the shortest flight durations listed. This is a great resource for travelers planning multi-city itineraries.

Detroit (DTW)
BOS 2h3m DTW 1h5m MDW
1h43m 1h4m
Buffalo (BUF)
BOS 1h32m BUF 1h35m MDW
1h20m 1h25m
Rochester (ROC)
BOS 1h30m ROC 1h45m MDW
1h19m 1h30m
Cleveland (CLE)
BOS 1h59m CLE 1h15m MDW
1h39m 1h10m
Grand Rapids (GRR)
BOS 2h6m GRR 55分 MDW
2h0m 50分
Chicago (ORD)
BOS 2h44m ORD 45分 MDW
2h12m 45分
Pittsburgh (PIT)
BOS 1h45m PIT 1h25m MDW
1h32m 1h20m
La Guardia (LGA)
BOS 1h2m LGA 2h20m MDW
59分 2h0m
Newark (EWR)
BOS 1h13m EWR 2h25m MDW
1h9m 1h50m
Columbus (CMH)
BOS 2h10m CMH 1h10m MDW
1h52m 1h10m

FAQ : Boston to Chicago/Midway

How far is it from Boston to Chicago?
The distance between Boston (BOS) to Chicago/Midway (MDW) is approximately 860 miles(1,380km) by air.
Which airlines operate at from Boston(BOS) to Midway(MDW)?
Currently, this route is served by Southwest Airlines (Japanese). You can check flight schedules for this route at Boston to Midway Flight Schedules and Midway to Boston Flight Schedules
What aircraft types are flying on the Boston (BOS) to Chicago/Midway (MDW) route?
The Boston – Midway route is operated by Boeing 737-700 , Boeing 737-800 , Boeing 737 MAX 8 aircraft types.
What is the time difference between Boston to Chicago?
The time difference between Logan International Airport(Boston) and Chicago Midway International Airport(Chicago) is -1 hour. Chicago is 1 hour behind Boston.Boston is currently observing daylight saving time (DST) from March 9, 2025 to November 2, 2025.Chicago is currently observing daylight saving time (DST) from March 9, 2025 to November 2, 2025.