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Cheap Flights from Pensacola to Chicago starting at S$ 77

We've found these cheap flights for you. You can book one-way or return flight tickets.

  • One way
  • Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Cheapest time to fly from Pensacola to Chicago

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the lowest average weekly prices of the corresponding route on Trip.com.
Cheapest Airlines flying from Pensacola to Chicago

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Frontier Airlines
From S$ 77
Spirit Airlines
From S$ 92
Delta Air Lines
From S$ 133
American Airlines
From S$ 140
United Airlines
From S$ 167
Silver Airways
From S$ 168
Southwest Airlines
From S$ 169
Breeze Airways
From S$ 278
ANA airlines

Find more flights and airlines

Alternative Routes from Pensacola to Chicago

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Pensacola to Chicago.

  • Cheapest
    Frontier Airlines
    PNS
    21:53
    27h 3m
    1 transfer
    ORD
    00:56
    Pensacola International Airport - O'Hare International Airport
    Sat, May 11Frontier Airlines
    S$ 77
  • Frontier Airlines
    PNS
    19:46
    12h 50m
    1 transfer
    MDW
    08:36
    Pensacola International Airport - Midway International Airport
    Wed, Apr 24Frontier Airlines
    S$ 93
  • Frontier Airlines
    PNS
    19:46
    12h 50m
    1 transfer
    MDW
    08:36
    Pensacola International Airport - Midway International Airport
    Wed, Apr 24Frontier Airlines
    S$ 93
    Find More Flights

Frequently Asked Questions

  • When to buy flight tickets from Pensacola (PNS) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Pensacola to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
  • How much is a flight from Pensacola (PNS) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around S$ 498.
  • How long is a flight from Pensacola (PNS) to Chicago (CHI)?

    It takes about 2 hours 56 minutes to fly from Pensacola (PNS) to Chicago (CHI).
  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
  • What are the most popular airlines that fly from Pensacola (PNS) to Chicago (CHI)?

    Airlines with flights from Pensacola (PNS) to Chicago (CHI): Qatar Airways, Southwest Airlines, Lufthansa, United Airlines, American Airlines and Emirates.
  • What's the most popular airline for direct flights from Pensacola (PNS) to Chicago (CHI)?

    United Airlines operates 1 direct flights from Pensacola (PNS) to Chicago (CHI).
  • How many airports in Chicago?

How to find a cheap flight from Pensacola to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Pensacola to Chicago. Book your flights at the right time and save more.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Find cheapest flight ticket from Pensacola to Chicago

Cheapest direct flight price

S$ 77

Cheapest return ticket price

S$ 310

Cheapest month

April

Peak season for travel

July

Flight distance

1,269.14km

Average flight time

2 hours 56 minutes

Popular airline

United Airlines