Cheap flights from Chicago to Pensacola

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Check our current prices for flights from Chicago to Pensacola. Please note that we also give you historical search data for this city connection. These are all airfares that people found in the past, in order to find more current flight information from Chicago to Pensacola, you will need to run a search below.

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From $305 / RT details

Book your flight now with FlyFar and save!

Cheap Pensacola airfares from $305/RT are provided by FlyFar. Outbound flight is leaving on 09/25/2019, 03:30 pm from Chicago Midway (MDW) airport and arrives at Pensacola Regional (PNS) at 08:35 pm. The flight time is 5 hours and 5 minutes. The Returning flight departes on 10/01/2019, 07:50 am (other return dates are also available). Date posted: 24 Aug 2019

Price evolution for flights From Chicago To Pensacola

Price overview for flights from Chicago to Pensacola

Recent Deals on Flights from Chicago to Pensacola:Roundtrip / Oneway

  • $305Major Airline flight Major Airline 
    FromToDepartureTime
    Chicago, IL (MDW)Pensacola, FL (PNS)09/25/201903:30 pm
    Pensacola, FL (PNS)Chicago, IL (MDW)10/01/201907:50 am
    flyfar.ca check price
  • $305Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)Pensacola, FL (PNS)09/25/201903:30 pm
    Pensacola, FL (PNS)Chicago, IL (MDW)10/01/201907:50 am
    flightnetwork.com check price
  • $305Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)Pensacola, FL (PNS)09/18/201903:30 pm
    Pensacola, FL (PNS)Chicago, IL (MDW)09/30/201907:50 am
    flightnetwork.com check price
  • $305Major Airline flight Major Airline 
    FromToDepartureTime
    Chicago, IL (MDW)Pensacola, FL (PNS)09/18/201903:30 pm
    Pensacola, FL (PNS)Chicago, IL (MDW)09/30/201907:50 am
    flyfar.ca check price
  • $328United Airlines flight United Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Pensacola, FL (PNS)09/01/201912:20 pm
    Pensacola, FL (PNS)Chicago, IL (ORD)09/08/201906:45 pm
    flightnetwork.com check price
  • $200Major Airline flight Major Airline 
    FromToDepartureTime
    Chicago, IL (MDW)Pensacola, FL (PNS)09/02/201906:25 am
    flyfar.ca check price
  • $200Southwest Airlines flight Southwest Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)Pensacola, FL (PNS)09/02/201906:25 am
    flightnetwork.com check price
  • $312Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Pensacola, FL (PNS)09/02/201907:02 am
    cheapoair.com check price
  • $426Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Pensacola, FL (PNS)09/02/201907:02 am
    cheapoair.com check price
  • $437Jetblue Airways flight Jetblue Airways 
    FromToDepartureTime
    Chicago, IL (ORD)Pensacola, FL (PNS)09/02/201907:02 am
    flyfar.ca check price
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Know what to do when flying to Pensacola?

Pensacola Travel Guide Pensacola abounds with sights, sounds, and things to do. Whether you're a historian or just plain folk, Pensacola is an enjoyable and relaxed city with an array of entertainment choices that's also remarkably well organized for visitors [...]
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