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Latest Flight Deals from Pensacola to Chicago

Book one-way or return flights from Pensacola to Chicago from as little as SGD 88. Choose from the popular airlines below and book your flight today!

  • One way
  • Round-trip
      • PNS11:22
        6h 24m
        1 stop
        ORD17:46
        Wed, Aug 7|Pensacola - Chicago|Spirit Airlines
        SGD 88SGD 154
        43% OFF
        43% OFF
        SGD 154SGD 88
      • PNS08:03
        5h 31m
        1 stop
        MDW13:34
        Wed, Aug 7|Pensacola - Chicago|Frontier Airlines
        SGD 95SGD 154
        38% OFF
        38% OFF
        SGD 154SGD 95
      • PNS21:27
        27h 8m
        1 stop
        ORD00:35
        Wed, Jul 31|Pensacola - Chicago|Frontier Airlines
        SGD 105SGD 154
        32% OFF
        32% OFF
        SGD 154SGD 105
      • PNS21:14
        23h 7m
        1 stop
        ORD20:21
        Mon, Aug 12|Pensacola - Chicago|Frontier Airlines
        SGD 111
        SGD 111
      • PNS08:48
        11h
        1 stop
        ORD19:48
        Thu, Aug 8|Pensacola - Chicago|Spirit Airlines
        SGD 112
        SGD 112
      • PNS11:15
        6h 47m
        1 stop
        ORD18:02
        Fri, Aug 9|Pensacola - Chicago|Spirit Airlines
        SGD 118
        SGD 118
      • PNS11:57
        11h 41m
        1 stop
        MDW23:38
        Mon, Aug 12|Pensacola - Chicago|Breeze Airways
        SGD 124
        SGD 124
      • PNS12:02
        11h 34m
        1 stop
        MDW23:36
        Fri, Jul 19|Pensacola - Chicago|Breeze Airways
        SGD 133
        SGD 133
      • PNS15:35
        9h 24m
        1 stop
        ORD00:59
        Wed, Aug 7|Pensacola - Chicago|Silver Airways
        SGD 134
        SGD 134
      • PNS15:20
        5h 47m
        1 stop
        ORD21:07
        Tue, Jul 23|Pensacola - Chicago|Delta Air Lines
        SGD 135
        SGD 135
      • PNS13:00
        3h 5m
        Direct
        CHI14:00
        Mon, Jul 8|Pensacola - Chicago|Spirit Airlines
        Find More Flights
        Find More Flights

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

Searching for the best last minute flight from Pensacola to Chicago? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Pensacola to Chicago. Stay updated on price trends and snag the best deals for your upcoming trip.

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

View airlines operating flights from Pensacola to Chicago. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Spirit Airlines
From SGD 88
Frontier Airlines
From SGD 95
Breeze Airways
From SGD 124
Silver Airways
From SGD 134
Delta Air Lines
From SGD 135
United Airlines
From SGD 158
American Airlines
From SGD 188
Southwest Airlines
From SGD 195
ANA airlines

Find more flights and airlines

Alternative Routes from Pensacola to Chicago

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Pensacola to Chicago.

  • Cheapest
    Spirit Airlines
    PNS
    11:22
    6h 24m
    1 transfer
    ORD
    17:46
    Pensacola International Airport - O'Hare International Airport
    Wed, Aug 7Spirit Airlines
    SGD 88
  • Frontier Airlines
    PNS
    08:03
    5h 31m
    1 transfer
    MDW
    13:34
    Pensacola International Airport - Midway International Airport
    Wed, Aug 7Frontier Airlines
    SGD 95
  • United Airlines
    PNS
    07:45
    11h 34m
    1 transfer
    RFD
    19:19
    Pensacola International Airport - Chicago Rockford International Airport
    Fri, Jul 5United Airlines
    SGD 328
  • United Airlines
    PNS
    07:45
    11h 34m
    1 transfer
    RFD
    19:19
    Pensacola International Airport - Chicago Rockford International Airport
    Fri, Jul 5United Airlines
    SGD 328
    Find More Flights

How do I find the cheapest flights?

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

    Airlines adjust prices for flights from Pensacola to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Pensacola (PNS) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around SGD 474.

  • How long does it take to fly from Pensacola (PNS) to Chicago (CHI) and what is the distance?

    It takes around 2 hours 24 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. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14km. It takes about 30 minutes by taxi.

  • What are the most popular airlines that fly from Pensacola (PNS) to Chicago (CHI)?

    Airlines with flights from Pensacola (PNS) to Chicago (CHI): American Airlines, Lufthansa, Air New Zealand, Qatar Airways, United Airlines, Southwest Airlines and Emirates.

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
Flight Information from Pensacola to Chicago

Cheapest nonstop flight price

SGD 88

Cheapest round-trip ticket price

SGD 232

Off-season for travel

April

Peak season for travel

September

Flight distance

1,269.14km

Average flight time

2 hours 24 minutes

Popular airline

American Airlines

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