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Cheap Flights from Pensacola (PNS) to Chicago (CHIA)

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Flight deals from Pensacola to Chicago

Looking for a cheap last-minute deal or the best return flight from Pensacola to Chicago? Find the lowest prices on one-way and return tickets right here.
Chicago.£119 per passenger.Departing Fri, 27 Feb, returning Mon, 2 Mar.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Pensacola on Fri, 27 Feb, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Mon, 2 Mar, arriving in Pensacola.Price includes taxes and charges.From £119, select.
Chicago.£123 per passenger.Departing Sat, 7 Mar, returning Tue, 17 Mar.Return flight with Frontier Airlines and Spirit Airlines.Outbound indirect flight with Frontier Airlines, departs from Pensacola on Sat, 7 Mar, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Tue, 17 Mar, arriving in Pensacola.Price includes taxes and charges.From £123, select.
Chicago.£135 per passenger.Departing Tue, 14 Apr, returning Thu, 16 Apr.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Pensacola on Tue, 14 Apr, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Thu, 16 Apr, arriving in Pensacola.Price includes taxes and charges.From £135, select.
Chicago.£135 per passenger.Departing Tue, 24 Mar, returning Sat, 11 Apr.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Pensacola on Tue, 24 Mar, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Sat, 11 Apr, arriving in Pensacola.Price includes taxes and charges.From £135, select.
Chicago.£135 per passenger.Departing Tue, 28 Apr, returning Mon, 18 May.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Pensacola on Tue, 28 Apr, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Mon, 18 May, arriving in Pensacola.Price includes taxes and charges.From £135, select.
Chicago.£135 per passenger.Departing Tue, 5 May, returning Mon, 18 May.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Pensacola on Tue, 5 May, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Mon, 18 May, arriving in Pensacola.Price includes taxes and charges.From £135, select.
Chicago.£138 per passenger.Departing Fri, 27 Feb, returning Sat, 28 Feb.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Pensacola on Fri, 27 Feb, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Sat, 28 Feb, arriving in Pensacola.Price includes taxes and charges.From £138, select.
Chicago.£140 per passenger.Departing Sat, 7 Mar, returning Tue, 17 Mar.Return flight with United.Outbound direct flight with United departs from Pensacola on Sat, 7 Mar, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Tue, 17 Mar, arriving in Pensacola.Price includes taxes and charges.From £140, 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 March.
Feb
from £138
Mar
from £123
Apr
from £135
May
from £135
Jun
from £157
Jul
from £197
Aug
from £152
Sep
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Oct
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Nov
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Dec
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Jan
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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.

Chicago Midway

9 miles from central Chicago
Closest
from £150
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Chicago O'Hare International

16 miles from central Chicago
Cheapest
from £119
Search flights

Chicago Dupage County

32 miles from central Chicago
Search flights

Chicago Rockford

78 miles from central Chicago
from £212
Search flights

Pensacola to Chicago: Flight information

The things to know before you go.
Cheapest flight found£119
Cheapest month to flyFebruary
Average flight time2 hrs, 30 mins
Most popular airlineQatar Airways
Average flights per week96

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 return flight from Pensacola to Chicago is £119. 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 30 minutes is the average flight time from Pensacola to Chicago.
Qatar Airways, United and Envoy Air fly direct from Pensacola to Chicago.
As of February 2026, there are 96 flights per week flying from Pensacola to Chicago.
The cheapest month to fly from Pensacola to Chicago is usually February.
If you're flying from Pensacola Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 15.8 miles away from the centre of Chicago. We've found flights into this airport from £119.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Pensacola Airport to Chicago on Friday, 27 February 2026.
Yes – the average flight time is 2 hours and 30 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 February, the average temperature is usually around -2°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, Spirit Airlines and United offer the cheapest flight tickets to Chicago.

Flying from Pensacola International Airport (PNS) to Chicago: what you need to know

  • The average length of a direct flight from Pensacola International Airport to Chicago is 2 hours 20 minutes.

  • Pensacola (the location of Pensacola International Airport) and Chicago follow the same timezone — UTC-5.

  • The busiest route is from Pensacola International Airport (PNS) to O'Hare International Airport (ORD). Choose from eight weekly services between these two airports. United Airlines offers a 10:23 departure between PNS and ORD.

  • Allow plenty of time to get on your PNS to Chicago flight. Generally, it's best to arrive at least two hours before international departures and an hour ahead for domestic flights.

  • Travelling during a peak time like school or public holidays? Expect longer lines at check-in and security. To give yourself peace of mind, arrive up to four hours before international flights and two hours before domestic departures.

  • You can book a direct Pensacola International Airport to Chicago ticket. Start your journey at PNS and touch down at O'Hare International Airport (ORD).

  • There's a good selection of carriers operating direct flights from Pensacola International Airport to Chicago, such as:

  • The journey from central Pensacola to PNS takes around 1 hour 40 minutes on public transport. If you ride-share, drive or take a cab, you'll cover the 4 miles in 15 minutes or so, depending on traffic conditions.

  • Catching an early flight from Pensacola International Airport to Chicago? Avoid the stress of rushing to the terminal (and sneak in some extra snooze time) by choosing one of these stays close to PNS:

  • Pensacola International Airport has an excellent on-time performance, so you're less likely to experience disruptions. Departures from PNS make it to their destination as scheduled 81.19% of the time.

  • PNS is located at 2430 Airport Boulevard.

How to find the cheapest flights from Pensacola International Airport (PNS) to Chicago

  • £54 is currently the best price for a one-way Pensacola International Airport to Chicago flight. A return plane ticket starts from £119. These prices may change depending on availability and demand.

  • Book one month before you want to fly. Pricing trends suggest that this is the ideal window for finding cheap flights from PNS to Chicago.

  • Organise your trip for May. That's the best month for scoring a bargain on Pensacola International Airport to Chicago tickets. If you're flexible on when you fly, use the 'Whole month' tool to find the cheapest price across every month.

  • Locking in a cheap flight from PNS to Chicago is easy with Price Alerts. Simply create one of these automatic notifications and we'll get in touch as soon as there's a better deal.

  • Find an affordable flight from Pensacola International Airport to Chicago with the help of our filters. Select your preferred duration, number of stops and airlines, then sort the results by 'Cheapest' for the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) is around 25 miles from the centre of Chicago. If you're opting for a ride-share or a cab, the drive will take roughly 35 minutes.

  • If you're taking public transport, expect a journey time of around 55 minutes.

  • If you're arriving on a late flight from Pensacola International Airport to Chicago, few things beat the convenience of staying near the terminal. Pick up your bags from the carousel and then be showered and sleeping soon after at one of these accommodation options near ORD:

  • Pick up an O'Hare International Airport rental car and discover Chicago and beyond with your own wheels. Routes Car Rentals, Dollar and Budget are top outlets you can book with here.

  • To get the lowest price, reserve your ride from O'Hare International Airport around four weeks in advance of your flight from PNS to Chicago.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Once your flight from Pensacola International Airport to Chicago has landed, you can reach the city centre in about 20 minutes by car. Central Chicago is roughly 12 miles from Chicago Midway International Airport (MDW).

  • Public transport will get you there in about 45 minutes.

  • After stepping off your PNS to Chicago flight, settle in at a hotel close to MDW. These are some comfortable accommodation options that'll help you get into relaxation mode:

  • Forget about public transport schedules or waiting forever for a cab. Grab a Chicago Midway International Airport rental car and let your trip unfold on your terms. Compare offers from Dollar, Hertz and Budget.

  • Snap up a deal by reserving your ride from MDW four weeks in advance. You can also expect to have a bigger selection of vehicles.

  • The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is about 85 miles from the centre of Chicago. It'll take you about 1 hour 25 minutes to get to the city centre in a cab or ride-share once you've hopped off your flight from Pensacola International Airport to Chicago.

  • If you use public transport, the journey takes about 4 hours 15 minutes.

  • Enjoy an unhurried start to your trip by checking in to a hotel near RFD after your PNS to Chicago flight. Unwind after a day of travel or just take a moment to get your bearings in a new destination at:

  • Be in the driver's seat of the next leg of your trip by picking up a Chicago Rockford International Airport rental car. Budget, Alamo and National make getting on the road smooth sailing.

  • Booking at least a few weeks in advance of your flight from Pensacola International Airport to Chicago is a good move. As well as better prices, you'll have a wider selection of vehicle makes and models at RFD.

  • The address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

  • Before you book your flights from Pensacola International Airport to Chicago, consider which time of year works best for you. High season in Chicago offers a bustling atmosphere and plenty of activities, while the off-season brings cheaper deals on hotels and fewer crowds.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC (59ºF) and 29ºC (84ºF). Lock in your Pensacola International Airport to Chicago plane ticket then if this is the type of weather you enjoy.

  • If you like cooler conditions, look for a cheap ticket from PNS to Chicago in January when temperatures average between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

  • Once you've booked your flight from Pensacola International Airport to Chicago, choose a hotel that puts you right where the action is. Make one of these options your base for exploring Chicago:

  • There are so many things to explore in this city it can be hard to know where to start. Art Institute of Chicago, Millennium Park and LandShark Beer Garden at Navy Pier are major attractions which should feature on any good Chicago itinerary.

Explore more of United States

  • Chicago is always a good idea, but there are so many other corners of United States you should also see. About 280 miles south-east of Chicago, a visit to Columbus will keep your itinerary packed. Start with attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Around 160 miles south-east of Chicago, Indianapolis is another favourite stop in United States. Experience this destination's highlights firsthand at The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

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.