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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 KSh16 691 (departure 12 November).

Prices updated on 24 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
Chicago O'Hare International Airport (ORD)
Thu, 12 Nov
8h 3min
1 stop
14:33
Pensacola (PNS)
Thu, 12 Nov
KSh16 691
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
KSh30 245

Low price calendar

From
To
October 2026 — no data Sun, 25 Oct · One way

Prices as of 24 October, 11:05 Moscow time

Cheap flights Chicago to Pensacola

Southwest Airlines
Southwest Airlines
Fri
Price from
KSh30 245

Popular destinations from Chicago

All →
CHI
Chicago — Philadelphia
United States → United States
PHL
from
KSh3 418
CHI
Chicago — Fort Lauderdale
United States → United States
FLL
from
KSh3 765
CHI
Chicago — Baltimore
United States → United States
BWI
from
KSh4 163
CHI
Chicago — Denver
United States → United States
DEN
from
KSh4 714
CHI
Chicago — Washington
United States → United States
WAS
from
KSh5 583
CHI
Chicago — Miami
United States → United States
MIA
from
KSh6 320
CHI
Chicago — Burlington
United States → United States
BRL
from
KSh6 404
CHI
Chicago — Phoenix
United States → United States
PHX
from
KSh6 844

Popular destinations to Pensacola

All →
ORL
Orlando — Pensacola
United States → United States
PNS
from
KSh7 107
FLL
Fort Lauderdale — Pensacola
United States → United States
PNS
from
KSh10 354
RDU
Raleigh — Pensacola
United States → United States
PNS
from
KSh15 767
HOU
Houston — Pensacola
United States → United States
PNS
from
KSh16 405
TPA
Tampa — Pensacola
United States → United States
PNS
from
KSh16 636
WAS
Washington — Pensacola
United States → United States
PNS
from
KSh18 013
PHL
Philadelphia — Pensacola
United States → United States
PNS
from
KSh18 420
LAX
Los Angeles — Pensacola
United States → United States
PNS
from
KSh18 576
IND
Indianapolis — Pensacola
United States → United States
PNS
from
KSh18 715

Flights from Chicago to cities near Pensacola

Cheaper than Pensacola right now: New Orleans — from KSh10 833, KSh5 858 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 KSh5 858 cheaper direct from KSh12 053

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

Cheap flights Chicago to Pensacola

Price from
KSh16 691
Average price
KSh22 088
Flight time
4 hours 40 minutes
Distance
1 269 km
Рейсов в неделю
2
Airlines
2
Most frequent flight
F9 1483

Prices as of 24 October, 10:53 Moscow time

Airports on the Chicago — Pensacola route

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

Departure airports · Chicago

Arrival airports · Pensacola

  • PensacolaPNS

Passenger reviews

No reviews for this route yet

Internet abroad

eSIM · United States

All plans

change

3 GB

data

30

days

KSh1 101

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2 GB

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15

days

KSh1 530

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5 GB

data

30

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KSh1 713

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3 GB

data

30

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KSh1 958

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5 GB

data

30

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KSh2 753

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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 KSh16 691. The journey takes from 4 hours 40 minutes.
The average ticket price Chicago Pensacola is KSh22 088. The cheapest ticket costs KSh16 691, 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 24 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: Chicago O'Hare International Airport (ORD), Chicago Midway International Airport (MDW). Most flights depart from Chicago 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.