Flight Schedules
Last Updated: Thu, 2 May, 2024
-
Depart
Earliest
- Earliest
- Latest
-
Arrive
- Earliest
- Latest
-
Airline
Filter by Airline
All
-
Total Duration
- Shortest
- Longest
-
Stopover
All
-
Availability
- M
- T
- W
- T
- F
- S
- S
-
07:35 - 11:10PNS - MDW
-
07:35 (PNS)Pensacola Municipal Airport
-
11:10 (MDW)Chicago Midway Airport
-
Southwest Airlines (WN 2119)Boeing 737 700 - 3h 35m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
-
11:00 - 13:10PNS - MDW
-
11:00 (PNS)Pensacola Municipal Airport
-
13:10 (MDW)Chicago Midway Airport
-
Southwest Airlines (WN 3052)Boeing 737 700 - 2h 10m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 700
-
13:53 - 16:35PNS - ORD
-
13:53 (PNS)Pensacola Municipal Airport
-
16:35 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 1980)Boeing 737 800 - 2h 42m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
14:00 - 16:15PNS - MDW
-
14:00 (PNS)Pensacola Municipal Airport
-
16:15 (MDW)Chicago Midway Airport
-
Southwest Airlines (WN 3052)Boeing 737 700 - 2h 15m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
-
16:40 - 21:30PNS - ORD
-
16:40 (PNS)Pensacola Municipal Airport
-
21:30 (ORD)Chicago O'Hare International Airport
-
Southwest Airlines (WN 3633)Boeing 737 700 - 4h 50m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
Connecting Flights
-
07:35 - 09:00PNS - BNA11:00 - 12:45BNA - ORD
-
07:35 (PNS)Pensacola Municipal Airport11:00 (BNA)Nashville Airport
-
09:00 (BNA)Nashville Airport12:45 (ORD)Chicago O'Hare International Airport
-
Southwest Airlines (WN 2119)Boeing 737 700 Southwest Airlines (WN 3624)Boeing 737 800 - 5h 10m (2h)
- BNA Nashville 2h
-
- -
- -
- -
- -
- -
- -
- S
-
08:00 - 09:25PNS - BNA12:55 - 14:30BNA - MDW
-
08:00 (PNS)Pensacola Municipal Airport12:55 (BNA)Nashville Airport
-
09:25 (BNA)Nashville Airport14:30 (MDW)Chicago Midway Airport
-
Southwest Airlines (WN 5789)Boeing 737 700 Southwest Airlines (WN 5597)Boeing 737 800 - 6h 30m (3h 30m)
- BNA Nashville 3h 30m
-
- -
- -
- -
- -
- -
- S
- -
-
08:00 - 09:25PNS - BNA10:15 - 12:00BNA - ORD
-
08:00 (PNS)Pensacola Municipal Airport10:15 (BNA)Nashville Airport
-
09:25 (BNA)Nashville Airport12:00 (ORD)Chicago O'Hare International Airport
-
Southwest Airlines (WN 5789)Boeing 737 700 Southwest Airlines (WN 3624)Boeing 737 700 - 4h (50m)
- BNA Nashville 50m
-
- -
- -
- -
- -
- -
- S
- -
-
08:20 - 09:45PNS - BNA12:30 - 14:15BNA - ORD
-
08:20 (PNS)Pensacola Municipal Airport12:30 (BNA)Nashville Airport
-
09:45 (BNA)Nashville Airport14:15 (ORD)Chicago O'Hare International Airport
-
Southwest Airlines (WN 5789)Boeing 737 700 Southwest Airlines (WN 3623)Boeing 737 700 - 5h 55m (2h 45m)
- BNA Nashville 2h 45m
-
- M
- -
- -
- T
- F
- -
- -
-
13:35 - 13:50CMH - MDW08:20 - 09:45PNS - BNA
-
13:35 (CMH)Columbus Port Columbus Intl Airport08:20 (PNS)Pensacola Municipal Airport
-
13:50 (MDW)Chicago Midway Airport09:45 (BNA)Nashville Airport
-
Southwest Airlines (WN 6025)Boeing 737 Max 8 Passenger Southwest Airlines (WN 5789)Boeing 737 700 - 5h 30m (1h 30m)
- MDW Chicago 1h 30m
-
- M
- -
- -
- T
- F
- -
- -
-
09:40 - 11:30PNS - DAL12:40 - 15:00DAL - ORD
-
09:40 (PNS)Pensacola Municipal Airport12:40 (DAL)Dallas/Fort Worth Love Field Airport
-
11:30 (DAL)Dallas/Fort Worth Love Field Airport15:00 (ORD)Chicago O'Hare International Airport
-
Southwest Airlines (WN 3944)Boeing 737 700 Southwest Airlines (WN 4903)Boeing 737 Max 8 Passenger - 5h 20m (1h 10m)
- DAL Dallas 1h 10m
-
- -
- -
- -
- -
- -
- -
- S
-
09:40 - 11:30PNS - DAL14:00 - 16:10DAL - MDW
-
09:40 (PNS)Pensacola Municipal Airport14:00 (DAL)Dallas/Fort Worth Love Field Airport
-
11:30 (DAL)Dallas/Fort Worth Love Field Airport16:10 (MDW)Chicago Midway Airport
-
Southwest Airlines (WN 3944)Boeing 737 700 Southwest Airlines (WN 473)Boeing 737 Max 8 Passenger - 6h 30m (2h 30m)
- DAL Dallas 2h 30m
-
- -
- -
- -
- -
- -
- -
- S
-
10:05 - 11:55PNS - DAL12:50 - 15:00DAL - MDW
-
10:05 (PNS)Pensacola Municipal Airport12:50 (DAL)Dallas/Fort Worth Love Field Airport
-
11:55 (DAL)Dallas/Fort Worth Love Field Airport15:00 (MDW)Chicago Midway Airport
-
Southwest Airlines (WN 3944)Boeing 737 700 Southwest Airlines (WN 473)Boeing 737 Max 8 Passenger - 4h 55m (55m)
- DAL Dallas 55m
-
- -
- -
- -
- -
- -
- S
- -
-
10:30 - 12:15PNS - DAL14:45 - 16:55DAL - MDW
-
10:30 (PNS)Pensacola Municipal Airport14:45 (DAL)Dallas/Fort Worth Love Field Airport
-
12:15 (DAL)Dallas/Fort Worth Love Field Airport16:55 (MDW)Chicago Midway Airport
-
Southwest Airlines (WN 3944)Boeing 737 800 Southwest Airlines (WN 5380)Boeing 737 Max 8 Passenger - 6h 25m (2h 30m)
- DAL Dallas 2h 30m
-
- -
- T
- W
- -
- -
- -
- -
-
11:45 - 13:10PNS - BNA16:10 - 17:55BNA - ORD
-
11:45 (PNS)Pensacola Municipal Airport16:10 (BNA)Nashville Airport
-
13:10 (BNA)Nashville Airport17:55 (ORD)Chicago O'Hare International Airport
-
Southwest Airlines (WN 5789)Boeing 737 700 Southwest Airlines (WN 510)Boeing 737 Max 8 Passenger - 6h 10m (3h)
- BNA Nashville 3h
-
- -
- -
- -
- -
- -
- -
- S
-
11:55 - 13:45PNS - STL17:10 - 18:15STL - MDW
-
11:55 (PNS)Pensacola Municipal Airport17:10 (STL)St Louis Lambert Intl Airport
-
13:45 (STL)St Louis Lambert Intl Airport18:15 (MDW)Chicago Midway Airport
-
Southwest Airlines (WN 3627)Boeing 737 700 Southwest Airlines (WN 3244)Boeing 737 800 - 6h 20m (3h 25m)
- STL Saint Louis 3h 25m
-
- -
- -
- -
- -
- -
- S
- -
-
12:30 - 13:55PNS - BNA16:45 - 18:20BNA - MDW
-
12:30 (PNS)Pensacola Municipal Airport16:45 (BNA)Nashville Airport
-
13:55 (BNA)Nashville Airport18:20 (MDW)Chicago Midway Airport
-
Southwest Airlines (WN 1167)Boeing 737 800 Southwest Airlines (WN 2261)Boeing 737 Max 8 Passenger - 5h 50m (2h 50m)
- BNA Nashville 2h 50m
-
- -
- T
- W
- -
- -
- -
- -
-
12:30 - 13:55PNS - BNA14:40 - 16:25BNA - ORD
-
12:30 (PNS)Pensacola Municipal Airport14:40 (BNA)Nashville Airport
-
13:55 (BNA)Nashville Airport16:25 (ORD)Chicago O'Hare International Airport
-
Southwest Airlines (WN 1167)Boeing 737 800 Southwest Airlines (WN 3624)Boeing 737 800 - 3h 55m (45m)
- BNA Nashville 45m
-
- -
- T
- W
- -
- -
- -
- -
-
12:40 - 14:05PNS - BNA14:40 - 16:25BNA - ORD
-
12:40 (PNS)Pensacola Municipal Airport14:40 (BNA)Nashville Airport
-
14:05 (BNA)Nashville Airport16:25 (ORD)Chicago O'Hare International Airport
-
Southwest Airlines (WN 10)Boeing 737 700 Southwest Airlines (WN 3624)Boeing 737 800 - 3h 45m (35m)
- BNA Nashville 35m
-
- M
- -
- -
- T
- F
- -
- -
-
12:40 - 14:05PNS - BNA15:10 - 16:40BNA - MDW
-
12:40 (PNS)Pensacola Municipal Airport15:10 (BNA)Nashville Airport
-
14:05 (BNA)Nashville Airport16:40 (MDW)Chicago Midway Airport
-
Southwest Airlines (WN 10)Boeing 737 700 Southwest Airlines (WN 2934)Boeing 737 700 - 4h (1h 05m)
- BNA Nashville 1h 05m
-
- M
- -
- -
- T
- F
- -
- -
-
12:40 - 14:05PNS - BNA17:00 - 18:35BNA - MDW
-
12:40 (PNS)Pensacola Municipal Airport17:00 (BNA)Nashville Airport
-
14:05 (BNA)Nashville Airport18:35 (MDW)Chicago Midway Airport
-
Southwest Airlines (WN 10)Boeing 737 700 Southwest Airlines (WN 2261)Boeing 737 800 - 5h 55m (2h 55m)
- BNA Nashville 2h 55m
-
- M
- -
- -
- T
- F
- -
- -
-
16:00 - 17:55PNS - DAL18:50 - 20:55DAL - MDW
-
16:00 (PNS)Pensacola Municipal Airport18:50 (DAL)Dallas/Fort Worth Love Field Airport
-
17:55 (DAL)Dallas/Fort Worth Love Field Airport20:55 (MDW)Chicago Midway Airport
-
Southwest Airlines (WN 1086)Boeing 737 700 Southwest Airlines (WN 2885)Boeing 737 800 - 4h 55m (55m)
- DAL Dallas 55m
-
- -
- -
- -
- -
- -
- S
- -
-
16:40 - 18:35PNS - DAL20:45 - 22:50DAL - MDW
-
16:40 (PNS)Pensacola Municipal Airport20:45 (DAL)Dallas/Fort Worth Love Field Airport
-
18:35 (DAL)Dallas/Fort Worth Love Field Airport22:50 (MDW)Chicago Midway Airport
-
Southwest Airlines (WN 3633)Boeing 737 700 Southwest Airlines (WN 3084)Boeing 737 Max 8 Passenger - 6h 10m (2h 10m)
- DAL Dallas 2h 10m
-
- -
- -
- -
- -
- -
- -
- S
-
17:10 - 18:35PNS - BNA21:30 - 23:00BNA - MDW
-
17:10 (PNS)Pensacola Municipal Airport21:30 (BNA)Nashville Airport
-
18:35 (BNA)Nashville Airport23:00 (MDW)Chicago Midway Airport
-
Southwest Airlines (WN 675)Boeing 737 800 Southwest Airlines (WN 3046)Boeing 737 Max 8 Passenger - 5h 50m (2h 55m)
- BNA Nashville 2h 55m
-
- -
- T
- W
- -
- -
- -
- -
-
17:10 - 18:35PNS - BNA19:45 - 21:30BNA - ORD
-
17:10 (PNS)Pensacola Municipal Airport19:45 (BNA)Nashville Airport
-
18:35 (BNA)Nashville Airport21:30 (ORD)Chicago O'Hare International Airport
-
Southwest Airlines (WN 675)Boeing 737 800 Southwest Airlines (WN 3625)Boeing 737 Max 8 Passenger - 4h 20m (1h 10m)
- BNA Nashville 1h 10m
-
- -
- T
- W
- -
- -
- -
- -
-
17:10 - 18:35PNS - BNA19:20 - 20:55BNA - MDW
-
17:10 (PNS)Pensacola Municipal Airport19:20 (BNA)Nashville Airport
-
18:35 (BNA)Nashville Airport20:55 (MDW)Chicago Midway Airport
-
Southwest Airlines (WN 675)Boeing 737 800 Southwest Airlines (WN 6066)Boeing 737 700 - 3h 45m (45m)
- BNA Nashville 45m
-
- -
- T
- W
- -
- -
- -
- -
-
18:20 - 20:00PNS - HOU20:50 - 23:25HOU - MDW
-
18:20 (PNS)Pensacola Municipal Airport20:50 (HOU)Houston Hobby Airport
-
20:00 (HOU)Houston Hobby Airport23:25 (MDW)Chicago Midway Airport
-
Southwest Airlines (WN 5097)Boeing 737 700 Southwest Airlines (WN 3115)Boeing 737 Max 8 Passenger - 5h 05m (50m)
- HOU Houston 50m
-
- -
- -
- -
- -
- -
- S
- -
-
18:35 - 20:00+ 1PNS - BNA22:40 - 00:10+ 1BNA - MDW
-
18:35 (PNS)Pensacola Municipal Airport22:40 (BNA)Nashville Airport
-
20:00 (BNA)Nashville Airport + 100:10 (MDW)Chicago Midway Airport
-
Southwest Airlines (WN 1167)Boeing 737 700 Southwest Airlines (WN 5212)Boeing 737 700 - 5h 35m (2h 40m)
- BNA Nashville 2h 40m
-
- -
- -
- -
- -
- -
- -
- S
-
18:35 - 20:00PNS - BNA20:35 - 22:10BNA - MDW
-
18:35 (PNS)Pensacola Municipal Airport20:35 (BNA)Nashville Airport
-
20:00 (BNA)Nashville Airport22:10 (MDW)Chicago Midway Airport
-
Southwest Airlines (WN 1167)Boeing 737 700 Southwest Airlines (WN 3046)Boeing 737 800 - 3h 35m (35m)
- BNA Nashville 35m
-
- -
- -
- -
- -
- -
- -
- S
-
18:50 - 20:30+ 1PNS - HOU21:35 - 00:05+ 1HOU - MDW
-
18:50 (PNS)Pensacola Municipal Airport21:35 (HOU)Houston Hobby Airport
-
20:30 (HOU)Houston Hobby Airport + 100:05 (MDW)Chicago Midway Airport
-
Southwest Airlines (WN 5097)Boeing 737 800 Southwest Airlines (WN 3115)Boeing 737 800 - 5h 15m (1h 05m)
- HOU Houston 1h 05m
-
- M
- -
- -
- T
- F
- -
- -
No Schedules
Sorry, there are no schedules matching your filters. Try removing one.
reset
What’s the fastest flight time from Pensacola to Chicago?
The fastest flight time for direct flights from Pensacola to Chicago is 2 hours 10 minutes. Check latest flight schedules & prices on Wego.
What’s the most popular airline flying from Pensacola to Chicago?
The most popular airline flying from Pensacola to Chicago is American Airlines. Find the latest flight deals on Wego.
How far is Chicago from Pensacola?
The flight distance between Pensacola and Chicago is 1274km. Check all available flights on Wego.
When is the earliest and latest flight of the day?
The earliest flight of the day departs at 07:35. The last flight of the day departs at 07:35. See the full list of flight times on Wego.
How many airlines offer direct flights from Pensacola to Chicago?
There are 2 airlines that offer direct flights from Pensacola to Chicago. Find out the list of airlines on Wego.
All Airports in Pensacola
All Airports in Chicago
Popular Airlines flying from Pensacola to Chicago
Popular destinations from Chicago
Popular destinations from Pensacola
Popular Hotels in Chicago
- Clarion Inn Elmhurst - Oak Brook near I-88, I-290, I-294
- The Royal Sonesta Chicago Downtown
- Club Quarters Hotel, Central Loop, Chicago
- The Ritz-Carlton, Chicago
- Fairmont Chicago at Millennium Park Gold Experience
- Swissôtel Chicago
- Pendry Chicago
- Hotel Felix Chicago
- Hotel Saint Clair
- Best Western River North Hotel