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Direct flights from Boston to Chicago

Airlines Schedules

BOS - MDW route map All flights from BOS to MDW non-stop. There are direct flights from Boston Logan International Airport (BOS), Massachusetts, USA to Chicago Midway International (MDW), Illinois, USA with Southwest Airlines. 32 weekly departures are currently scheduled on this route. Departure times range from 05:50 to 22:50 depending on the schedule period. The flight distance is 863 miles (1389 km). Flight time ranges from 2 hours and 30 minutes to 3 hours.

BOS
Boston Logan Airport
USABoston , USA
MDW
Chicago Midway
USAChicago , USA
BOS
Boston Logan Airport
USABoston , USA
Chicago Midway
USAChicago , USA
MDW
Flight time 2h 30min to 3h 0min
Updated Aug 31, 2026
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Airlines with non-stop routes:

Southwest Airlines Low-cost carrier

Departure times vary between 05:50 and 22:50 • From Terminal B
S
M
T
W
T
F
S
Sun
Mon
Tue
Wed
Thu
Fri
Sat
32 flights/week
32 flights/week
Weekday-labels: HAS FLIGHTS UPCOMING NO FLIGHTS
View all flight dates
Flight schedule from Boston to Chicago with Southwest Airlines

This is a weekly direct flight schedule for Southwest Airlines. Use the arrows or click on the date to change week. Click on any flight departure time to show more information and check availability.

 
Flight
Mon
Sep 28
Tue
Sep 29
Wed
Sep 30
Thu
Oct 1
Fri
Oct 2
Sat
Oct 3
Sun
Oct 4
WN4305
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05:50
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WN805
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05:50
07:40
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WN4568
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06:10
WN1955
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07:05
07:05
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WN744
07:30
07:30
07:30
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WN1346
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09:40
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WN1645
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10:05
10:05
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WN806
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10:40
WN2421
12:40
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WN807
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13:10
13:10
13:25
14:50
WN746
18:40
15:20
15:20
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WN672
15:55
19:15
19:15
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WN4233
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18:35
18:35
16:20
18:45
WN2799
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16:50
16:50
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WN3183
20:20
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WN909
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22:00
22:00
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WN1383
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22:50

The timetable & schedule information was updated at 2026-08-31

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Boston to Chicago scheduled departures

Select a date to see every published non-stop departure between BOS and MDW.

Friday
Fri
Sep 25
5 flights(5)
Saturday
Sat
Sep 26
4 flights(4)
Sunday
Sun
Sep 27
5 flights(5)
Monday
Mon
Sep 28
5 flights(5)
Tuesday
Tue
Sep 29
4 flights(4)
Wednesday
Wed
Sep 30
4 flights(4)
Thursday
Thu
Oct 01
6 flights(6)
Time
Airline
Flight
07:30
Southwest Airlines Southwest Airlines
WN744
12:40
Southwest Airlines Southwest Airlines
WN2421
15:55
Southwest Airlines Southwest Airlines
WN672
18:40
Southwest Airlines Southwest Airlines
WN746
20:20
Southwest Airlines Southwest Airlines
WN3183
07:05
Southwest Airlines Southwest Airlines
WN744
08:40
Southwest Airlines Southwest Airlines
WN175
13:00
Southwest Airlines Southwest Airlines
WN4298
15:25
Southwest Airlines Southwest Airlines
WN3480
07:30
Southwest Airlines Southwest Airlines
WN744
09:25
Southwest Airlines Southwest Airlines
WN1585
13:55
Southwest Airlines Southwest Airlines
WN4657
17:35
Southwest Airlines Southwest Airlines
WN3738
21:10
Southwest Airlines Southwest Airlines
WN2662
07:30
Southwest Airlines Southwest Airlines
WN744
12:40
Southwest Airlines Southwest Airlines
WN2421
15:55
Southwest Airlines Southwest Airlines
WN672
18:40
Southwest Airlines Southwest Airlines
WN746
20:20
Southwest Airlines Southwest Airlines
WN3183
07:30
Southwest Airlines Southwest Airlines
WN744
10:05
Southwest Airlines Southwest Airlines
WN1645
15:20
Southwest Airlines Southwest Airlines
WN746
19:15
Southwest Airlines Southwest Airlines
WN672
07:30
Southwest Airlines Southwest Airlines
WN744
10:05
Southwest Airlines Southwest Airlines
WN1645
15:20
Southwest Airlines Southwest Airlines
WN746
19:15
Southwest Airlines Southwest Airlines
WN672
05:50
Southwest Airlines Southwest Airlines
WN4305
07:05
Southwest Airlines Southwest Airlines
WN1955
13:10
Southwest Airlines Southwest Airlines
WN807
16:50
Southwest Airlines Southwest Airlines
WN2799
18:35
Southwest Airlines Southwest Airlines
WN4233
22:00
Southwest Airlines Southwest Airlines
WN909
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BOS-MDW flight route
Route map from Boston, BOS to Chicago, MDW. The distance is 863 miles or 1389 km.
Boston - Chicago direct flight map
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BOS - MDW route facts

  • Distance
    863 miles (1389 km)
  • Flight time
    2 hours and 30 minutes to 3 hours
  • Airline
    Southwest Southwest
  • Airline alliances
    Low-cost carrier
  • Cabins
    Economy
  • Departure terminals
    Terminal B
  • Aircraft
    Boeing 737MAX 8 Passenger, Boeing 737-700 Passenger (Scimitar Winglets) and Boeing 737-800 (winglets) Passenger/BBJ2

Route FAQ

Southwest Airlines operates non-stop flights from BOS to MDW with 32 weekly departures.

Scheduled flight time from BOS to MDW ranges from 2 hours and 30 minutes to 3 hours. The route covers 863 miles (1389 km).

32 weekly departures are currently scheduled on this route, with published departure times ranging from 05:50 to 22:50 depending on the schedule period.

Departure terminal: Terminal B.

Economy are currently scheduled on non-stop flights for this route.
Direct flights from Boston to IL, USA
From Boston to Chicago

ORD Chicago O Hare International
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