Airlines with flights from Chicago to Boston

There are two airlines with scheduled flights between MDW and BOS. Southwest is the only airline with non-stop flights from Midway International Airport to Logan Airport and the flight time is 2 hours and 15 minutes.

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Choose airline

Schedules

Southwest Airlines

Non-stop with Southwest Airlines

  • Total flight time: 2 hours and 15 minutes
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 34 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
Direct
BOS
 
Flight
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Aug 3
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WN4611
07:40
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WN3473
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WN3315
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WN1405
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WN1165
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11:25
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WN573
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WN562
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WN4716
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WN1181
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WN232
19:35
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - BOS

The timetable & schedule information was updated at 2026-04-21

Delta Air Lines

Via Detroit with Delta Air Lines

  • Total flight time: 3h 52m - 6h 03m.
  • Sky Team Alliance
  • Boston is a Delta Air Lines hub.
  • 94 flights per week
MDW
 
Via DTW
 
BOS
 
Flight
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Aug 3
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DL4674
DL1171
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DL4688
DL1707
13:16
13:16
13:16
13:16
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13:16
DL4690
DL1187
18:58
18:58
18:58
18:58
18:58
18:35
18:58
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - BOS

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

Via Baltimore with Southwest Airlines

  • Total flight time: 3h 55m - 8h 35m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 189 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
 
Via BWI
 
BOS
 
Flight
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WN211
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WN1058
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WN856
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WN232
WN1058
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WN1695
WN737
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WN646
WN1910
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WN908
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WN856
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WN777
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WN892
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WN2689
WN1222
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18:00
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - BOS

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

Via Saint Louis with Southwest Airlines

  • Total flight time: 4h 20m - 6h 45m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 55 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
 
Via STL
 
BOS
 
Flight
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Aug 3
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WN2837
WN3808
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WN3891
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WN1538
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08:15
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WN3808
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WN2144
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WN3892
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WN3809
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WN1643
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15:10
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WN126
WN982
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16:40
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WN4254
WN982
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17:50
WN2904
WN4724
18:00
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - BOS

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

Via Nashville with Southwest Airlines

  • Total flight time: 4h 40m - 8h 50m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 101 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
 
Via BNA
 
BOS
 
Flight
Mon
Aug 3
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Aug 4
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WN508
WN2957
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WN4560
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WN2957
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WN1409
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WN4372
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WN120
WN1187
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08:00
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WN1187
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08:15
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WN442
WN4208
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WN485
WN671
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WN1257
WN4372
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WN671
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WN392
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WN392
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WN3869
WN459
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WN1794
WN392
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18:00
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - BOS

The timetable & schedule information was updated at 2026-04-21

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