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Cheap flights from Pensacola to Chicago

Compare Pensacola to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

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Flight deals from Pensacola to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from Pensacola to Chicago? Find the lowest prices on one-way and round-trip tickets right here.
Chicago.C$165 per passenger.Departing Thu, Jan 16, returning Sun, Jan 19.Round-trip flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from Pensacola on Thu, Jan 16, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Sun, Jan 19, arriving in Pensacola.Price includes taxes and charges.From C$165, select.
Chicago.C$192 per passenger.Departing Sun, Nov 17, returning Mon, Nov 18.Round-trip flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from Pensacola on Sun, Nov 17, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departing from Chicago O'Hare International on Mon, Nov 18, arriving in Pensacola.Price includes taxes and charges.From C$192, select.
Chicago.C$192 per passenger.Departing Thu, Dec 5, returning Sun, Dec 8.Round-trip flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from Pensacola on Thu, Dec 5, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departing from Chicago O'Hare International on Sun, Dec 8, arriving in Pensacola.Price includes taxes and charges.From C$192, select.
Chicago.C$199 per passenger.Departing Tue, Feb 18, returning Mon, Feb 24.Round-trip flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from Pensacola on Tue, Feb 18, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Mon, Feb 24, arriving in Pensacola.Price includes taxes and charges.From C$199, select.
Chicago.C$292 per passenger.Departing Thu, Nov 28, returning Sun, Dec 1.Round-trip flight with United.Outbound direct flight with United departing from Pensacola on Thu, Nov 28, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Sun, Dec 1, arriving in Pensacola.Price includes taxes and charges.From C$292, select.
Chicago.C$292 per passenger.Departing Thu, Jan 16, returning Sun, Jan 19.Round-trip flight with United.Outbound direct flight with United departing from Pensacola on Thu, Jan 16, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Sun, Jan 19, arriving in Pensacola.Price includes taxes and charges.From C$292, select.
Chicago.C$292 per passenger.Departing Fri, Feb 7, returning Mon, Feb 10.Round-trip flight with United.Outbound direct flight with United departing from Pensacola on Fri, Feb 7, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Mon, Feb 10, arriving in Pensacola.Price includes taxes and charges.From C$292, select.
Chicago.C$304 per passenger.Departing Sun, Dec 22, returning Thu, Jan 2.Round-trip flight with United.Outbound indirect flight with United, departing from Pensacola on Sun, Dec 22, arriving in Chicago O'Hare International.Inbound indirect flight with United, departing from Chicago O'Hare International on Thu, Jan 2, arriving in Pensacola.Price includes taxes and charges.From C$304, select.

Find the cheapest month to fly from Pensacola to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Pensacola to Chicago flights are currently cheapest in January.
Oct
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Nov
from C$192
Dec
from C$192
Jan
from C$165
Feb
from C$199
Mar
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Apr
from C$318
May
from C$422
Jun
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Jul
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Aug
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Sep
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Direct flights from Pensacola to Chicago

Alternative Pensacola to Chicago routes

Looking for the cheapest, fastest or easiest route from Pensacola to Chicago? You could fly into the following airports instead.

Pensacola to Chicago: Flight information

The things to know before you go.
Cheapest flight foundC$165
Cheapest month to flyJanuary
Average flight time2 hrs, 25 mins
Most popular airlineUnited
Average flights per week41

Finding cheap flights from Pensacola to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a round-trip flight from Pensacola to Chicago is C$165. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 24 minutes is the average flight time from Pensacola to Chicago.
United, Air New Zealand and SkyWest Airlines fly direct from Pensacola to Chicago.
There are 41 flights per week flying from Pensacola to Chicago, as of October 2024.
The cheapest month to fly from Pensacola to Chicago is usually October 2024.
If you're flying from Pensacola Airport, the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the center of Chicago. We've found flights to this airport from C$165.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Pensacola Airport to Chicago on Thursday, January 16, 2025.
Yes – the average flight time is 2 hours and 24 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In October, the average temperature is usually around 11°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Frontier Airlines and United offer the cheapest flight tickets to Chicago.

How to find cheap flights to Chicago from Pensacola

Looking for cheap tickets from Pensacola to Chicago? Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

  • Simply hit "search." From Delta Air Lines to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from Pensacola to Chicago. And with us, there are no hidden fees – what you see is what you pay.
  • Compare flight deals to Chicago from Pensacola from over 1,000 providers. Then choose the cheapest plane tickets or fastest journeys.
  • Flex your dates to find the best Pensacola–Chicago ticket prices. If you're flexible when it comes to your travel dates, use Skyscanner's "Whole month" tool to find the cheapest month, and even day to fly to Chicago from Pensacola.
  • Set up a Price Alert. You can easily track the fare of your cheap Pensacola–Chicago flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
  • Fly without stops. Only interested in direct flights between Pensacola and Chicago? Make sure to tick "Direct flights only" when performing a search. If there are direct flights available on the route, these will appear in the results.
  • Find the cheapest Business Class flights from Pensacola and Chicago. We scour the Internet for the best Business, Premium Economy and First Class flight fares to Chicago, too. Check the difference in price as you search – you might just stumble on a last-minute low fare. Note that not all cabin classes are available for every destination or airline.
  • Include nearby airports in your search. Widen your search for Pensacola to Chicago flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save the next time you travel.

    • Combine your flight to Chicago from Pensacola with hotels and car rental

    Once you've secured your cheap flight ticket from Pensacola to Chicago, discover the best prices and exclusive rates for hotels in Chicago or nearby. You can also compare hundreds of car rental companies at once so you get the best car rental price for your trip.


Plan the rest of your trip from Pensacola to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.