Flights from Chicago to Pensacola, United States

Did you mean flights from Pensacola to Chicago?

Chicago to Pensacola Last modified: Feb 7, 2023 12:01 -05:00

We've scanned 2,618 round trip itineraries and found the cheapest flights to Pensacola. 00 & !! frequently offer the best deals to Pensacola flights, or select your preferred carrier below to see the cheapest days to fly.

00
CHIPNS
Tue 2/21
nonstop
PNSCHI
Tue 2/28
nonstop
$160
!!
CHIPNS
Mon 4/17
nonstop
PNSCHI
Thu 4/20
nonstop
$221

How Much is a Flight from Chicago to Pensacola?

We have collected flight cost data from across the web for travel from Chicago to Pensacola, and have found the average flight price for this trip to be $212.

Where To Buy Cheap Flights from Chicago to Pensacola?

The best way to find a great deal on airfare is to search multiple sites. When you run a search on FareCompare, we search multiple sites and fare sources all at once so you don't have to - which is why we think FareCompare is the best place to find cheap tickets. Airlines can adjust prices for tickets from Chicago to Pensacola based on the day and time that you decide to book your flight. We have collected data from all airlines, and have found that Tuesdays, Wednesdays, and Saturdays are often the best days to book flights. If you'd like to learn more, read our article about the best time to buy airline tickets.

How far in advance should I book tickets from Chicago to Pensacola?

The chart below shows up-to-date information regarding how far in advance to book your flight from Chicago to Pensacola.

Non Stop versus Connecting
Advanced PurchaseNon StopConnecting
< 7 days $236 $496
7-14 days $160 $690
14-21 days $162 $658
21-30 days $160 $418
30-60 days $178 $397
60-90 days $214 $581
90+ days $286 $587

Cheapest Day To Fly from Chicago to Pensacola

We've examined 5,236 itinerary searches that we've seen for departures in the next 90 days and found that the cheapest day to fly from Chicago to Pensacola is Tuesday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$162$160$163$257$160$416$161

Compare Flight Prices from Chicago to Pensacola by Month

Low priced flights are most commonly available by purchasing between one and three months in advance. International or holiday flights may need to be purchased even further in advance. The chart below shows the cheapest flight prices by month for Chicago to Pensacola flights.

Month Origin Destination Carrier Depart Date Return Date Stops Price
February Chicago Pensacola 00 2/21/23 2/28/23 0 $160
March Chicago Pensacola 00 3/3/23 3/8/23 0 $160
April Chicago Pensacola 00 4/4/23 4/11/23 0 $178
May Chicago Pensacola 00 5/1/23 5/5/23 0 $214
June Chicago Pensacola 00 6/13/23 6/27/23 0 $343
July Chicago Pensacola 00 7/12/23 7/17/23 0 $369
August Chicago Pensacola 00 8/12/23 8/19/23 0 $404
September Chicago Pensacola 00 9/11/23 9/16/23 0 $342

Cheap Last Minute Flights from Chicago to Pensacola

Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from Chicago to Pensacola. The chart below shows the best last minute deals and cheap flights this weekend we could find.

Next 30 Days

SunMonTueWedThuFriSat
22 23 24 25 26 27 28
$158
29 30 31 1 2 3 4
$158
5 6 7 8 9 10 11
$236
12 13 14 15 16 17 18
$236 $449
19 20 21 22 23 24 25
$449 $257
26 27 28 1 2 3 4
$257 $142
5 6 7 8 9 10 11
$142

Connecting Flights vs Direct Flights from Chicago to Pensacola

Flights between some cities may be significantly cheaper if you choose a multi-stop airline ticket. Although these connecting flights sacrifice some convenience, on average, travelers save 20%-60% when they choose to fly multi-stop versus a direct flight.

The average price for connecting flights from Chicago to Pensacola is $581.

The average price for direct flights from Chicago to Pensacola is $285.

The chart below shows up to date information regarding non-stop flights from Chicago to Pensacola.

Weekly Direct Flights from Chicago to Pensacola - By Carrier
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
United 1 1 1 1 1 1 1 06:35 06:35

One Way Flights vs Round Trip Flights from Chicago to Pensacola

We have found that there is often no price difference between buying a round trip flight versus a one way flight. Increased flexibility is the main benefit when it comes to buying a one way flight from Chicago to Pensacola. However, booking a round trip flight can be a simpler process. You can compare round trip and one way flights by using our flight comparison.

The average price for one way flights from Chicago to Pensacola is $251.

The average price for round trip flights from Chicago to Pensacola is $295.

Chicago to Pensacola Flight Questions

Below are some common questions that asked about this flight route:

Question: How long is the flight from Chicago to Pensacola?
Answer: The average Chicago to Pensacola flight time is 2 hours and 20 minutes.
Question: How far is Pensacola from Chicago?
Answer: The distance from Chicago to Pensacola is 795 miles (1,279 kilometers).
Question: How common are direct flights from Chicago to Pensacola?
Answer: There are 7 direct flights from Chicago to Pensacola.
Question: What are the most popular Chicago airlines for direct flights from Chicago to Pensacola?
Answer: United Airlines provides 100% of the non-stop flights between Chicago and Pensacola.

Chicago to Pensacola Airports

These are the major commercial airports we're currently monitoring in Chicago and Pensacola. If your route includes a city with multiple airports, you may be able to find substantial savings by choosing an alternate airport.

Farecompare Research Tools

FareCompare's Flight Schedule Search Tool helps you find information about airline schedule filings, including flight numbers, depart times, and travel distance.

Cheap Flights from Chicago to Pensacola