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Cheap flights Chicago to Pensacola

1 passenger, economy

There are no nonstop flights from Chicago to Pensacola. With a connection, the trip takes from 4 hours 40 minutes. Distance: 1269 km. Tickets from C$190 (departure 12 November).

Prices updated on 23 October at 10:53

See also: Pensacola — ChicagoFlights from ChicagoFlights to Pensacola

Cheap flights Chicago to Pensacola

Compare prices, duration and stops

Frontier Airlines
F9 1483 Best price
06:30
O'Hare International Airport (ORD)
Thu, 12 Nov
8h 3min
1 stop
14:33
Pensacola (PNS)
Thu, 12 Nov
C$190
Southwest Airlines
WN 2589
11:20
Chicago Midway International Airport (MDW)
Fri, 26 Mar
4h 40min
1 stop
16:00
Pensacola (PNS)
Fri, 26 Mar
C$345

Low price calendar

From
To
October 2026 — no data Fri, 23 Oct · One way

Prices as of 23 October, 11:05 Moscow time

Cheap flights Chicago to Pensacola

Southwest Airlines
Southwest Airlines
Fri
Price from
C$345

Popular destinations from Chicago

All →
CHI
Chicago — Philadelphia
United States → United States
PHL
from
C$34
CHI
Chicago — Fort Lauderdale
United States → United States
FLL
from
C$43
CHI
Chicago — Baltimore
United States → United States
BWI
from
C$47
CHI
Chicago — Denver
United States → United States
DEN
from
C$54
CHI
Chicago — Washington
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WAS
from
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CHI
Chicago — Miami
United States → United States
MIA
from
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CHI
Chicago — Burlington
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BRL
from
C$73
CHI
Chicago — Phoenix
United States → United States
PHX
from
C$78

Popular destinations to Pensacola

All →
ORL
Orlando — Pensacola
United States → United States
PNS
from
C$84
FLL
Fort Lauderdale — Pensacola
United States → United States
PNS
from
C$118
RDU
Raleigh — Pensacola
United States → United States
PNS
from
C$180
HOU
Houston — Pensacola
United States → United States
PNS
from
C$187
TPA
Tampa — Pensacola
United States → United States
PNS
from
C$190
TYS
Knoxville — Pensacola
United States → United States
PNS
from
C$209
PHL
Philadelphia — Pensacola
United States → United States
PNS
from
C$210
CLT
Charlotte — Pensacola
United States → United States
PNS
from
C$210
LAX
Los Angeles — Pensacola
United States → United States
PNS
from
C$212

Flights from Chicago to cities near Pensacola

Cheaper than Pensacola right now: New Orleans — from C$124, C$67 less. The cities are 300 km apart.

City Distance Direct Flights Airlines Price from
PensacolaPNS — 022
Fort Walton BeachVPS 63 km 011
Panama CityECP 134 km 042
New OrleansMSY 300 km 11304 C$67 cheaper direct from C$137

Distance is a straight line between the cities. Prices are the lowest one-way fares.

Cheap flights Chicago to Pensacola

Price from
C$190
Average price
C$252
Flight time
4 hours 40 minutes
Distance
1 269 km
Рейсов в неделю
2
Airlines
2
Most frequent flight
F9 1483

Prices as of 23 October, 10:53 Moscow time

Airports on the Chicago — Pensacola route

From → to Flights Direct Airlines Price from
O'Hare International AirportORD PensacolaPNS Cheapest
101
Chicago Midway International AirportMDW PensacolaPNS
101

Departure airports · Chicago

Arrival airports · Pensacola

  • PensacolaPNS

Passenger reviews

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Frequently Asked Questions

Based on the tickets found, there are no nonstop flights from Chicago to Pensacola — you will need to fly with a connection. Tickets with a connection start at C$190. The journey takes from 4 hours 40 minutes.
The average ticket price Chicago Pensacola is C$252. The cheapest ticket costs C$190, operated by Frontier Airlines, flight F9 1483, departing Chicago on 12 November at 06:30, arriving Pensacola on 12 November at 14:33. Prices as of 23 October.
There are no nonstop flights. With a connection: from 4 hours 40 minutes, usually about 5 hours.
Flights from Chicago to Pensacola depart from these airports: O'Hare International Airport (ORD), Chicago Midway International Airport (MDW). Most flights depart from O'Hare International Airport. Arrival: Pensacola (PNS).
Tickets from Chicago to Pensacola are sold by: Frontier Airlines, Southwest Airlines. All flights have connections.
The distance from Chicago to Pensacola is 1269 km.