Cheap flights from Pensacola to Chicago from $79
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Pensacola to Chicago departing on 8/4. 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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Delta flights from Pensacola to Chicago
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How to get the cheapest flight ticket from Pensacola to Chicago
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 Chicago?
The month of February is, on average, the cheapest month to fly to Chicago from Pensacola, with most prices found around $279. If you’re not able to fly to Chicago in February, then September is your next best option. Flight prices from Pensacola to Chicago during September average around $286.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $427. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Pensacola to Chicago for around $671.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Pensacola to Chicago during this time can be as low as $307. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $540.
What is the cheapest Pensacola to Chicago flight route?
Fly from Pensacola to Chicago Midway for the best Pensacola - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Pensacola when booking 25 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $344 when searching 25 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Pensacola for as low as $196 on momondo.
What cabin class options are available on Pensacola to Chicago flights?
There are 4 cabin classes available to choose from on Pensacola to Chicago 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 Pensacola to Chicago flights?
No. A direct flight is the cheapest option for a flight between Pensacola to Chicago.
How have Pensacola to Chicago flight prices changed over time?
As of June 2025, prices for Pensacola to Chicago flights are approximately 36% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from Pensacola to Chicago?
Southwest, United Airlines, and Delta are the most popular carriers operating from Pensacola to Chicago
What airlines fly to Chicago?
United Airlines, Delta and American Airlines are the top three most popular airlines that fly to Chicago from Pensacola according to our data. United Airlines is the first choice among our users, with 37% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Pensacola to Chicago on average per day?
As of June 2025, 5 flights take off from Pensacola and land in Chicago each day. The most common flight departure time for this route is 2:00PM, with 78% of daily flights taking off in the afternoon.
How many flights depart from Pensacola to Chicago on average per week?
As of June 2025, 39 flights take off from Pensacola and land in Chicago each week. The most common flight departure day for this route is Mon, with 15% of weekly flights taking off on this day.
When to book flights from Pensacola to Chicago
Cheap Pensacola to Chicago (PNS to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Pensacola to Chicago
How far is Pensacola to Chicago by plane?
A flight from Pensacola to Chicago will travel around 791.2 mi. 2h 15m is a normal flight duration for this route.
When did momondo last update prices for flights from Pensacola Airport to Chicago?
Prices for flights from Pensacola Airport to Chicago were last updated today.
How many operators does momondo search for flights from Pensacola Airport to Chicago?
As of June 2025, there are 5 operators available to choose from for flights from Pensacola Airport to Chicago.
How old do you have to be to fly from Pensacola Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Pensacola Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Pensacola to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Pensacola to Chicago is Airbus A320-100/200, representing 26.91% of all bookings. The subsequent popular models are Airbus A319 at 17.49%, Airbus A320neo at 9.87%, and Boeing 737-800 Passenger/BBJ2 (winglets) at 9.87%.
What is the most popular airline from Pensacola to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Pensacola to Chicago is United Airlines (43% of total bookings). The next most popular airlines are Delta (20%), Southwest (16%), and American Airlines (13%).
Best airlines flying from Pensacola to Chicago
Compare and see reviews for airlines that fly from Pensacola to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $98 | Free Cancellation | Rating 6.3 8,052 reviews | |||
| PriceFrom $192 | Free Cancellation | Rating 8.0 4,287 reviews | |||
| PriceFrom $196 | Free Cancellation | Rating 8.0 7,950 reviews | |||
| PriceFrom $228 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $238 | Free Cancellation | Rating 7.4 8,790 reviews |
Southwest Flights From Pensacola to Chicago
Southwest is one of the most popular airlines flying from Pensacola to Chicago, operating 5 flights/week on average for this route. A good Southwest flight deal for Pensacola to Chicago starts from $192 round-trip, up to an average price of $377. Our users have rated Southwest at 8.0/10.
United Airlines Flights From Pensacola to Chicago
$238 is the best United Airlines flight deal from Pensacola to Chicago found on momondo over the last 72 hours. The average United Airlines ticket price found was closer to $403, however, with flight time and availability significantly affecting the price. United Airlines (7.4/10 from 8,790 user reviews) flies into Chicago from Pensacola 13 times in an average week so prices can vary.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Pensacola to Chicago?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Pensacola.
Can I find flights from Pensacola to Chicago with flexible booking policies on momondo?
momondo does allow users to show only those flights to Chicago from Pensacola which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Pensacola to Chicago?
momondo helps you find the best flight between Pensacola and Chicago 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 Pensacola to Chicago right now. Can momondo alert me if prices change?
If you are not ready to book a flight from Pensacola to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.