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 $141 / RT details

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Cheap Pensacola airfares from $141/RT are provided by Cheapoair.com. Outbound flight is leaving on 03/05/2025, 07:05 am from Chicago Midway (MDW) airport and arrives at Pensacola Regional (PNS) at 04:23 pm. The flight time is 9 hours and 18 minutes. The Returning flight departes on 03/11/2025, 03:17 pm (other return dates are also available). Date posted: 16 Feb 2025

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

  • $141Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)Pensacola, FL (PNS)03/05/202507:05 am
    Pensacola, FL (PNS)Chicago, IL (MDW)03/11/202503:17 pm
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  • $147Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Pensacola, FL (PNS)03/05/202506:45 am
    Pensacola, FL (PNS)Chicago, IL (ORD)03/11/202503:17 pm
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  • $718Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Pensacola, FL (PNS)03/11/202508:00 am
    Pensacola, FL (PNS)Chicago, IL (ORD)03/26/202508:10 pm
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  • $997Multiple Airlines flight Multiple Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Pensacola, FL (PNS)03/11/202508:00 am
    Pensacola, FL (PNS)Chicago, IL (ORD)03/26/202508:46 am
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  • $71Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Pensacola, FL (PNS)03/05/202506:45 am
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  • $81Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Pensacola, FL (PNS)04/02/202502:53 pm
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  • $82Spirit Airlines flight Spirit Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Pensacola, FL (PNS)04/18/202507:49 pm
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  • $130Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)Pensacola, FL (PNS)03/05/202507:05 am
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  • $136Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)Pensacola, FL (PNS)04/02/202506:40 am
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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 [...]
Pensacola History Pensacola is the county-seat of Escambia County, which represents the western extremity of Florida (the closest settlements in Florida are Fort Walton Beach and Valparaiso resorts). Pensacola history is almost as old as the discovery of the New [...]
Pensacola Sightseeing The city of Pensacola is one of the very famous tourist hot spots in the state of Florida, United State of America. Pensacola Sights have become very famous in the last years due to the continuous involvement of the local government in [...]
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