starting at $183
starting at $251
starting at $94
starting at $163
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Fly from Pensacola to Chicago with confidence — our search scans over 700 airlines, 50+ agencies and more than 5 top booking systems to uncover the best prices, schedules and travel conditions for your trip. Compare nonstop and connecting options in seconds and book the itinerary that fits your budget and timing.
Fly nonstop from Pensacola to Chicago for the quickest, most convenient way to get between the Gulf Coast and the Windy City—less hassle, no layovers, and more time for what matters. While connecting options can sometimes be cheaper, a direct flight saves hours and delivers greater comfort, making it a smart choice for business trips or weekend getaways.
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Pensacola to Chicago:
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Answers to questions about the route that travelers are most interested in.
We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.
The route Pensacola — Chicago is served by many carriers — 4 in total, including United Airlines, Southwest Airlines, Frontier Airlines, and Spirit Airlines. This gives passengers wide opportunities: from finding the lowest fare (from $94) to selecting flights by schedule or service class. Our service aggregates data from multiple booking systems so you can compare offers in one place. This saves time and money: no need to check dozens of sites — just pick the right option and book online.
starting at $183
starting at $251
starting at $94
starting at $163
Pensacola — Chicago
02/11/2026
Departure
Direct flight
UA3532
starting at $183
Pensacola — Chicago
02/12/2026
Departure
Direct flight
UA2005
starting at $183
Pensacola — Chicago
02/15/2026
Departure
Direct flight
WN309
starting at $251
Unable to find information about the schedule of direct flights from
Pensacola International Airport (PNS) is a small regional hub serving northwest Florida and parts of southern Alabama, typically handling a mix of legacy carriers and low-cost airlines on mainly domestic routes with occasional seasonal connections. The airport is about 7–12 miles from downtown Pensacola (roughly 15–25 minutes by car depending on traffic). Ground transport options usually include rental cars, app-based rideshares and taxis, plus limited shuttle services; fares to the city center commonly fall in a modest range compared with larger metros, and drive times are generally short. Pros: compact terminals and quick walk times make connections convenient; cons: fewer nonstop destinations and limited late-night service can mean longer or pricier connections for some itineraries.
Chicago is served primarily by O'Hare International (ORD), a major international hub handling numerous long-haul and domestic flights—especially from legacy carriers—while Midway (MDW) operates as a smaller, cost-sensitive airport favored by low-cost and leisure carriers for domestic routes. O'Hare is roughly 17 miles northwest of downtown (travel times can be 30–60+ minutes depending on traffic); options include the CTA Blue Line train (about 45–55 minutes, low to moderate fares), prepaid airport shuttles, taxis, and rideshares. Midway sits about 10 miles southwest (typically 20–40 minutes by road) with CTA Orange Line service (roughly 25–35 minutes) and local buses. Fares vary by mode and time of day; trains and buses are usually cheapest, while taxis/rideshares cost more. O'Hare’s scale offers many amenities and international connections but can feel crowded and involve longer walks or waits; Midway is generally quicker to navigate and can be easier for domestic connections but has fewer long-haul options and amenities.
The cheapest one-way flight from Pensacola to Chicago departs on 02/12/2026, is operated by Frontier Airlines and costs $94
The cheapest roundtrip flight from Pensacola to Chicago departs on 02/14/2026, is operated by American Airlines and costs $122
Fastest flight from Pensacola to Chicago takes 6h 27m
There are direct flights on this route 3 days a week: Su, We, and Th
The distance between Pensacola and Chicago is 1274km (790 miles). Pensacola and Chicago are in the same time zone
We couldn't find any special offers for flights from Pensacola to Chicago
The cheapest flight ticket from Pensacola to Chicago according to data for the last 48 hours costs $94
Often the best time to buy tickets from Pensacola to Chicago is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Pensacola to Chicago can be found flying in these months: February.
The fastest flights from Pensacola to Chicago start from 6 hours 27 minutes in the air.
The following airlines operate direct flights on the route Pensacola — Chicago: United Airlines, Southwest 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 Pensacola to Chicago