Cheap flights from Chicago to Pensacola from $89
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Pensacola departing on 7/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Spirit Airlines flights from Chicago to Pensacola
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How to get the cheapest flight ticket from Chicago to Pensacola
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Pensacola?
The cheapest month to fly to Pensacola from Chicago is in January. Flight prices, which tend to average around $298, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of January, then book flights to Pensacola from Chicago during April instead. Flights to Pensacola in April, while not as cheap as those in January, still average around $306.
What is the cheapest day to depart on your flight to Pensacola?
On average, the least expensive day to fly to Pensacola from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $332. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Friday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $464.
What is the cheapest time of day to depart on your flight to Pensacola?
The cheapest time of day to fly to Pensacola is in the afternoon when flights can be purchased for as low as $293. Flights to Pensacola are more costly in the morning, with an average ticket price of $413. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.
What is the cheapest Chicago to Pensacola flight route?
Fly from Chicago Midway to Pensacola for the best Chicago - Pensacola flight prices
How far in advance should I book a flight to Pensacola?
You are more likely to see cheaper flights to Pensacola from Chicago when booking 25 weeks ahead of your departure date. In general, you can expect to find flights to Pensacola for around $362 when searching 25 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Pensacola from Chicago for as low as $257 on momondo.
What cabin class options are available on Chicago to Pensacola flights?
There are 4 cabin classes available to choose from on Chicago to Pensacola flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Chicago to Pensacola flights?
You could potentially save up to 8% on your flight if you consider stops on a Chicago to Pensacola flight.
How have Chicago to Pensacola flight prices changed over time?
As of May 2025, prices for Chicago to Pensacola flights are approximately 2% more expensive when compared to flights at the same time last year.
What is the cheapest airline that flies from Chicago to Pensacola?
United Airlines, Southwest, and Spirit Airlines are the most popular carriers operating from Chicago to Pensacola
What airlines fly to Pensacola?
United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Pensacola from Chicago according to our data. United Airlines is the first choice among our users, with 43% of people opting to fly with this airline when traveling to Pensacola. Keep in mind that there are 6 different airlines that fly to Pensacola on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to Pensacola on average per day?
The number of flights available between Chicago and Pensacola is 2 per day as of May 2025. The most frequent departure time is 10:00AM, with 94% of daily flights leaving at noon.
How many flights depart from Chicago to Pensacola on average per week?
As of May 2025, there are 14 flights per week flying from Chicago to Pensacola. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.
When to book flights from Chicago to Pensacola
Cheap Chicago to Pensacola (CHI to PNS) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Pensacola
How far is Chicago to Pensacola by plane?
The distance between Chicago and Pensacola is about 791.2 mi. A reasonable flight in good conditions will take 2h 05m.
When did momondo last update prices for flights from Chicago to Pensacola Airport?
Prices for flights from Chicago to Pensacola Airport refresh daily.
How many operators does momondo search for flights from Chicago to Pensacola Airport?
As of May 2025, there are 5 operators available to choose from for flights from Chicago to Pensacola Airport.
How old do you have to be to fly from Chicago to Pensacola Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Pensacola Airport.
What documentation or ID do you need to fly to Pensacola Airport?
The travel and health documents required for your trip to Pensacola Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Pensacola Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to Pensacola?
Based on momondo bookings for flights between Chicago and Pensacola, the leading plane model is Airbus A320-100/200, making up 27.27% of the total bookings. Other popular models include Airbus A319 with 18.49%, Airbus A320neo with 10.62%, and Boeing 737-700 Passenger/BBJ1 (winglets) with 8.68%.
What is the most popular airline from Chicago to Pensacola?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago to Pensacola is United Airlines (48% of total bookings). The next most popular airlines are Southwest (17%), American Airlines (12%), and Delta (12%).
Best airlines flying from Chicago to Pensacola
Compare and see reviews for airlines that fly from Chicago to Pensacola with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $118 | Free Cancellation | Rating 6.3 8,011 reviews | |||
| PriceFrom $196 | Free Cancellation | Rating 8.0 7,957 reviews | |||
| PriceFrom $222 | Free Cancellation | Rating 8.0 4,286 reviews | |||
| PriceFrom $228 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $235 | Free Cancellation | Rating 7.4 8,756 reviews |
United Airlines Flights From Chicago to Pensacola
United Airlines is one of the most popular airlines flying from Chicago to Pensacola, operating 7 flights/week on average for this route. A good United Airlines flight deal for Chicago to Pensacola starts from $235 round-trip, up to an average price of $414. Our users have rated United Airlines at 7.4/10.
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Why should I use momondo to find a flight deal from Chicago to Pensacola?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Pensacola. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from Chicago to Pensacola with flexible booking policies on momondo?
All flight searches from Chicago to Pensacola on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Chicago to Pensacola?
momondo helps you find the best flight between Chicago and Pensacola by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
I’m not ready to book a flight from Chicago to Pensacola right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Pensacola, momondo offers a useful price alert feature which will track prices for flights to Pensacola from Chicago and alert you when they change.