All airlines flying from San Antonio (SAT) to Chicago Midway (MDW).

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Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Mon,Thu,Fri 14:15 San Antonio (SAT) A 16:50 Chicago Midway (MDW)
Southwest Airlines WN 245 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Effective 2026-08-06 through 2026-09-28
Tue,Wed 14:45 San Antonio (SAT) A 17:15 Chicago Midway (MDW)
Southwest Airlines WN 457 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2026-03-10 through 2026-04-01
Mon,Thu,Fri 15:25 San Antonio (SAT) A 17:55 Chicago Midway (MDW)
Southwest Airlines WN 457 Non-stop Boeing 737-700 (Scimitar Winglets) 2:30 Effective 2026-03-05 through 2026-04-06
Sat 15:25 San Antonio (SAT) A 17:55 Chicago Midway (MDW)
Southwest Airlines WN 457 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2026-03-07 through 2026-04-04
Sun 15:30 San Antonio (SAT) A 18:00 Chicago Midway (MDW)
Southwest Airlines WN 457 Non-stop Boeing 737-800 (73H) 2:30 Effective 2026-03-08 through 2026-04-05
Tue,Wed,Sat 09:20 San Antonio (SAT) A 11:50 Chicago Midway (MDW)
Southwest Airlines WN 1590 Non-stop Boeing 737-800 (73H) 2:30 Effective 2026-03-07 through 2026-04-04
Mon,Thu,Fri 09:25 San Antonio (SAT) A 11:55 Chicago Midway (MDW)
Southwest Airlines WN 1590 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2026-03-05 through 2026-04-06
Sun 09:30 San Antonio (SAT) A 12:00 Chicago Midway (MDW)
Southwest Airlines WN 1590 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2026-03-08 through 2026-04-05
Mon,Thu,Fri 14:40 San Antonio (SAT) A 17:15 Chicago Midway (MDW)
Southwest Airlines WN 2170 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Effective 2026-04-09 through 2026-06-01
Fri 16:25 San Antonio (SAT) A 19:00 Chicago Midway (MDW)
Southwest Airlines WN 2278 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Operates only on 2026-01-02
Sun 16:40 San Antonio (SAT) A 19:20 Chicago Midway (MDW)
Southwest Airlines WN 2278 Non-stop Boeing 737 MAX 8 (7M8) 2:40 Operates only on 2026-01-04
Mon 06:10 San Antonio (SAT) A 08:45 Chicago Midway (MDW)
Southwest Airlines WN 2634 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Operates only on 2026-01-05
Wed,Thu 14:30 San Antonio (SAT) A 17:05 Chicago Midway (MDW)
Southwest Airlines WN 2634 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Valid until 2026-01-01
Sat 11:50 San Antonio (SAT) A 14:25 Chicago Midway (MDW)
Southwest Airlines WN 2743 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-04-11 through 2026-05-30
Tue,Wed 14:35 San Antonio (SAT) A 17:10 Chicago Midway (MDW)
Southwest Airlines WN 2743 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-04-07 through 2026-06-03
Sun 15:05 San Antonio (SAT) A 17:40 Chicago Midway (MDW)
Southwest Airlines WN 2743 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Effective 2026-04-12 through 2026-05-17
Sun 15:05 San Antonio (SAT) A 17:40 Chicago Midway (MDW)
Southwest Airlines WN 2743 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Operates only on 2026-05-31
Mon,Tue,Fri,Sun 05:10 San Antonio (SAT) A 07:45 Chicago Midway (MDW)
Southwest Airlines WN 2827 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Valid until 2026-01-04
Sat 06:05 San Antonio (SAT) A 08:40 Chicago Midway (MDW)
Southwest Airlines WN 2827 Non-stop Boeing 737-800 (73H) 2:35 Valid until 2026-01-03
Sun 14:25 San Antonio (SAT) A 17:00 Chicago Midway (MDW)
Southwest Airlines WN 3224 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Operates only on 2026-05-24
Sun 15:25 San Antonio (SAT) A 18:00 Chicago Midway (MDW)
Southwest Airlines WN 3361 Non-stop Boeing 737-800 (73H) 2:35 Effective 2026-06-07 through 2026-08-02
Sat 17:15 San Antonio (SAT) A 19:50 Chicago Midway (MDW)
Southwest Airlines WN 3384 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Operates only on 2026-01-03
Sat 06:00 San Antonio (SAT) A 08:35 Chicago Midway (MDW)
Southwest Airlines WN 3464 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-01-10 through 2026-02-07
Sat 06:55 San Antonio (SAT) A 09:30 Chicago Midway (MDW)
Southwest Airlines WN 3464 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Effective 2026-02-14 through 2026-02-28
Sun 07:00 San Antonio (SAT) A 09:35 Chicago Midway (MDW)
Southwest Airlines WN 3464 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-08-09 through 2026-09-27
Mon-Fri 14:10 San Antonio (SAT) A 16:45 Chicago Midway (MDW)
Southwest Airlines WN 3464 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-01-06 through 2026-01-14
Tue-Fri,Sun 14:10 San Antonio (SAT) A 16:45 Chicago Midway (MDW)
Southwest Airlines WN 3464 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-01-18 through 2026-01-23
Mon-Fri 14:10 San Antonio (SAT) A 16:45 Chicago Midway (MDW)
Southwest Airlines WN 3464 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-01-26 through 2026-02-04
Tue,Wed,Sun 14:10 San Antonio (SAT) A 16:45 Chicago Midway (MDW)
Southwest Airlines WN 3464 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-02-08 through 2026-02-11
Tue,Wed 14:10 San Antonio (SAT) A 16:45 Chicago Midway (MDW)
Southwest Airlines WN 3464 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-02-18 through 2026-03-04
Thu,Fri,Sun 14:35 San Antonio (SAT) A 17:10 Chicago Midway (MDW)
Southwest Airlines WN 3464 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-01-11 through 2026-01-16
Mon,Sun 14:35 San Antonio (SAT) A 17:10 Chicago Midway (MDW)
Southwest Airlines WN 3464 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-01-19 through 2026-01-25
Sun 14:35 San Antonio (SAT) A 17:10 Chicago Midway (MDW)
Southwest Airlines WN 3464 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Operates only on 2026-02-01
Mon,Thu,Fri 14:40 San Antonio (SAT) A 17:15 Chicago Midway (MDW)
Southwest Airlines WN 3464 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-02-05 through 2026-02-09
Tue,Thu,Sun 14:40 San Antonio (SAT) A 17:15 Chicago Midway (MDW)
Southwest Airlines WN 3464 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-02-15 through 2026-02-19
Mon 14:40 San Antonio (SAT) A 17:15 Chicago Midway (MDW)
Southwest Airlines WN 3464 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-02-23 through 2026-03-02
Mon,Thu,Fri 15:55 San Antonio (SAT) A 18:30 Chicago Midway (MDW)
Southwest Airlines WN 3464 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 15:55 San Antonio (SAT) A 18:30 Chicago Midway (MDW)
Southwest Airlines WN 3464 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-02-20 through 2026-03-01
Mon,Thu,Fri 05:00 San Antonio (SAT) A 07:35 Chicago Midway (MDW)
Southwest Airlines WN 3503 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Effective 2026-08-06 through 2026-09-28
Sat 11:10 San Antonio (SAT) A 13:45 Chicago Midway (MDW)
Southwest Airlines WN 3503 Non-stop Boeing 737-800 (73H) 2:35 Effective 2026-08-08 through 2026-09-26
Sun 14:30 San Antonio (SAT) A 17:05 Chicago Midway (MDW)
Southwest Airlines WN 3503 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Effective 2026-08-09 through 2026-09-27
Tue,Wed 14:35 San Antonio (SAT) A 17:10 Chicago Midway (MDW)
Southwest Airlines WN 3503 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-08-04 through 2026-09-30
Mon,Thu,Fri 06:25 San Antonio (SAT) A 09:00 Chicago Midway (MDW)
Southwest Airlines WN 3583 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-06-04 through 2026-08-03
Sun 06:50 San Antonio (SAT) A 09:25 Chicago Midway (MDW)
Southwest Airlines WN 3583 Non-stop Boeing 737-800 (73H) 2:35 Effective 2026-06-07 through 2026-08-02
Tue,Wed 09:20 San Antonio (SAT) A 11:55 Chicago Midway (MDW)
Southwest Airlines WN 3583 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-06-09 through 2026-07-29
Sat 09:25 San Antonio (SAT) A 12:00 Chicago Midway (MDW)
Southwest Airlines WN 3583 Non-stop Boeing 737-700 (Scimitar Winglets) 2:35 Effective 2026-06-06 through 2026-08-01
Tue,Wed 14:00 San Antonio (SAT) A 16:40 Chicago Midway (MDW)
Southwest Airlines WN 3584 Non-stop Boeing 737-800 (73H) 2:40 Effective 2026-06-09 through 2026-07-29
Sat 14:15 San Antonio (SAT) A 16:50 Chicago Midway (MDW)
Southwest Airlines WN 3584 Non-stop Boeing 737-800 (73H) 2:35 Effective 2026-06-06 through 2026-08-01
Mon,Thu,Fri 15:20 San Antonio (SAT) A 17:55 Chicago Midway (MDW)
Southwest Airlines WN 3584 Non-stop Boeing 737-800 (73H) 2:35 Effective 2026-06-04 through 2026-08-03
Wed,Thu 06:40 San Antonio (SAT) A 09:15 Chicago Midway (MDW)
Southwest Airlines WN 3591 Non-stop Boeing 737-800 (73H) 2:35 Valid until 2026-01-01
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All airlines flying from San Antonio (SAT) to Chicago Midway (MDW).
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Select flight date:
FLIGHT SCHEDULE
Direct Flights:

Effective 2026-08-06 through 2026-09-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-03-10 through 2026-04-01
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-03-05 through 2026-04-06
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:30, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-03-07 through 2026-04-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-03-08 through 2026-04-05
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:30, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-03-07 through 2026-04-04
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:30, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-03-05 through 2026-04-06
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-03-08 through 2026-04-05
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-04-09 through 2026-06-01
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Operates only on 2026-01-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 2:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Operates only on 2026-01-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:40, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Operates only on 2026-01-05
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Valid until 2026-01-01
Mon
-
Tue
-
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-04-11 through 2026-05-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-04-07 through 2026-06-03
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-04-12 through 2026-05-17
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Operates only on 2026-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Valid until 2026-01-04
Mon
Tue
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Valid until 2026-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:35, non-stop
Boeing 737-800 (73H)

Direct Flights:

Operates only on 2026-05-24
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-06-07 through 2026-08-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:35, non-stop
Boeing 737-800 (73H)

Direct Flights:

Operates only on 2026-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-01-10 through 2026-02-07
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-02-14 through 2026-02-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-08-09 through 2026-09-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-01-06 through 2026-01-14
Mon
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-01-18 through 2026-01-23
Mon
-
Tue
Wed
Thu
Fri
Sat
-
Sun
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-01-26 through 2026-02-04
Mon
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-02-08 through 2026-02-11
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-02-18 through 2026-03-04
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-01-11 through 2026-01-16
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-01-19 through 2026-01-25
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Operates only on 2026-02-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-02-05 through 2026-02-09
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-02-15 through 2026-02-19
Mon
-
Tue
Wed
-
Thu
Fri
-
Sat
-
Sun
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-02-23 through 2026-03-02
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-02-12 through 2026-02-16
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-02-20 through 2026-03-01
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-08-06 through 2026-09-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-08-08 through 2026-09-26
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:35, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-08-09 through 2026-09-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-08-04 through 2026-09-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-06-04 through 2026-08-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-06-07 through 2026-08-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:35, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-06-09 through 2026-07-29
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-06-06 through 2026-08-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-06-09 through 2026-07-29
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:40, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-06-06 through 2026-08-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:35, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-06-04 through 2026-08-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:35, non-stop
Boeing 737-800 (73H)

Direct Flights:

Valid until 2026-01-01
Mon
-
Tue
-
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:35, non-stop
Boeing 737-800 (73H)
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  • A domestic route departing from the San Antonio airport (SAT) and arriving at Chicago Midway airport (MDW).
  • The flight distance is 1036 miles, or 1667 km.
  • The timezone of both the departure and the arrival airports is UTC-6 . Current time at both airports is (loading...).
  • For direct flights, the flight time varies between 2:30 and 2:40.