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A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Chicago to Pensacola:
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Looking for direct flights from Chicago to Pensacola? We've got you covered! Skip the hassle of layovers and enjoy a non-stop journey to sunny Pensacola. Experience the convenience of a direct flight that takes you from the Windy City straight to the beautiful beaches of the Florida Panhandle. With multiple airlines offering this route, finding the perfect flight is just a click away. If direct flights aren't available for your chosen dates, fret not. There are alternative routes with convenient connections. Connect through major hubs like Atlanta or Dallas, and reach Pensacola in no time. Although these routes may involve a layover, they allow for greater flexibility and can often be more budget-friendly. Whether you prefer a non-stop adventure or don't mind a short layover, our air ticket search website provides you with all the options to make your journey from Chicago to Pensacola seamless and enjoyable. Start your search today!
Unable to find information about the schedule of direct flights from
Chicago — Pensacola
02/15/2026
Departure
Direct flight
UA2672
starting at $164
Chicago — Pensacola
03/26/2026
Departure
Direct flight
AA3706
starting at $215
Flights from Chicago to Pensacola are operated by several airlines — United Airlines, American Airlines, and Spirit Airlines. This allows passengers to flexibly choose flights based on departure time, cost, and additional services. The minimum ticket price starts at $118, making this destination accessible to travelers with different budgets. We help compare all available options in real time, so you can book tickets at the best value for money. The service ensures transparent search and lets you book affordable flights in just a few clicks.
The cheapest one-way flight from Chicago to Pensacola departs on 02/15/2026, is operated by Spirit Airlines and costs $118
The cheapest roundtrip flight from Chicago to Pensacola departs on 04/24/2026, is operated by Spirit Airlines and costs $132
Fastest flight from Chicago to Pensacola takes 6h 58m
There are direct flights on this route 2 days a week: Su and Th
The distance between Chicago and Pensacola is 1274km (790 miles). Chicago and Pensacola are in the same time zone
We couldn't find any special offers for flights from Chicago to Pensacola
The cheapest flight ticket from Chicago to Pensacola according to data for the last 48 hours costs $118
Often the best time to buy tickets from Chicago to Pensacola is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Chicago to Pensacola can be found flying in these months: February.
The fastest flights from Chicago to Pensacola start from 6 hours 58 minutes in the air.
The following airlines operate direct flights on the route Chicago — Pensacola: United Airlines, American Airlines
We carefully collect statistics on the search and pricing of airlines and, based on these data, we make an assumption about future prices. Thus, you can better understand which season is the cheapest to fly from Chicago to Pensacola