Airlines with flights from Norfolk to Chicago
There are two airlines with scheduled flights between ORF and MDW. Southwest is the only airline with non-stop flights from Norfolk International to Midway International Airport and the flight time is 2 hours and 10 minutes.
Choose airline
Schedules
Non-stop with Southwest Airlines
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Total flight time: 2 hours and 10 minutes
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Low-cost airline
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Chicago is a Southwest Airlines focus city (Operating base).
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17 flights per week
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Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
ORF
Direct
MDW
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN2834
07:05
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----
07:05
07:05
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WN3078
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07:50
07:50
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----
----
----
WN3732
----
----
----
----
----
----
08:05
WN1371
----
----
----
----
----
08:15
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WN3149
----
----
----
----
----
----
11:35
WN2031
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11:40
11:40
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----
----
----
WN938
----
----
----
----
----
13:10
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WN3187
15:30
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----
15:30
15:30
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WN1338
----
----
----
----
----
18:35
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WN2224
----
19:00
19:00
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----
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----
WN1039
19:15
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----
19:15
19:15
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WN3135
----
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19:20
The timetable & schedule information was updated at 2026-04-21
Via Baltimore with Southwest Airlines
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Total flight time: 3h 40m - 8h 25m.
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Low-cost airline
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Chicago is a Southwest Airlines focus city (Operating base).
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111 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
ORF
Via BWI
MDW
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN3183
WN4217
WN4217
06:00
----
----
06:00
06:00
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05:50
WN3183
WN2794
WN2794
----
----
----
----
----
06:00
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WN3183
WN1139
WN1139
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06:05
06:05
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----
----
----
WN4904
WN435
WN435
09:55
----
----
09:55
09:55
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----
WN1396
WN800
WN800
----
----
----
----
----
09:55
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WN4904
WN2475
WN2475
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10:05
10:05
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----
----
----
WN4904
WN655
WN655
----
----
----
----
----
----
10:05
WN3185
WN961
WN961
12:15
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----
12:15
12:15
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----
WN2583
WN1107
WN1107
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12:25
12:25
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----
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----
WN3185
WN5047
WN5047
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----
----
----
----
----
13:25
WN1665
WN997
WN997
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15:00
15:00
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WN1192
WN998
WN998
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----
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15:10
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WN2848
WN998
WN998
16:30
16:30
16:30
16:30
16:30
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WN4904
WN999
WN999
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----
----
----
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17:40
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WN1665
WN999
WN999
18:10
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----
18:10
18:10
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----
The timetable & schedule information was updated at 2026-04-21
Via Detroit with Delta Air Lines
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Total flight time: 3h 43m - 4h 09m.
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Sky Team Alliance
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38 flights per week
ORF
Via DTW
MDW
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
DL1079
DL4684
DL4684
06:05
06:05
06:05
06:05
06:05
06:05
06:05
The timetable & schedule information was updated at 2026-04-21
Via Nashville with Southwest Airlines
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Total flight time: 4h 00m - 8h 05m.
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Low-cost airline
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Chicago is a Southwest Airlines focus city (Operating base).
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21 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
ORF
Via BNA
MDW
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN2131
WN578
WN578
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18:55
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WN2082
WN578
WN578
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----
----
----
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19:45
The timetable & schedule information was updated at 2026-04-21
Via Atlanta with Delta Air Lines
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Total flight time: 4h 29m - 6h 40m.
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Sky Team Alliance
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145 flights per week
ORF
Via ATL
MDW
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
DL2966
DL1063
DL1063
05:15
05:15
05:15
05:15
05:15
06:00
05:15
DL1364
DL1063
DL1063
06:20
06:20
06:20
06:20
06:20
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06:20
DL1338
DL2417
DL2417
08:00
08:00
08:00
08:00
08:00
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08:00
DL2755
DL2417
DL2417
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----
----
----
----
10:58
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DL2755
DL1728
DL1728
12:34
12:34
12:34
12:34
12:34
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12:34
DL1101
DL1076
DL1076
16:43
16:43
16:43
16:43
16:43
16:54
16:43
DL2329
DL1076
DL1076
18:17
18:17
18:17
18:17
18:17
18:17
18:17
The timetable & schedule information was updated at 2026-04-21

There are two airlines with scheduled flights between ORF and MDW. Southwest is the only airline with non-stop flights from Norfolk International to Midway International Airport and the flight time is 2 hours and 10 minutes.