Cheap flights from Pensacola (PNS) to Chicago (CHI)

PNS — CHI
Aug 21 — Aug 281

The best prices from Pensacola to Chicago are usually found in August or September, booked 60 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

How to find the cheapest flight from Pensacola (PNS) to Chicago (CHI)

All the information you need to plan the best PNS to CHI flight in 2022: compare Pensacola to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.

PNS - CHI

Price

$236 - $566

CHI

Temperature

23 - 73.4 °F

CHI

Rainfall

1.7 - 4.9 inches

Popular inJuneHigh demand for flights, 32% potential price rise
Cheapest inAugustBest time to find cheap flights, 39% potential price drop
Round-trip from$236From Pensacola to Chicago (CHI)
One-way from$156One-way flight from Pensacola to Chicago (CHI)

What is the cheapest day to fly round-trip from Pensacola to Chicago?

Monday is generally a great day to depart. Flying on this day could help you save up to 36%.

How far in advance should I book a flight from Pensacola to Chicago?

Travelers have found it’s best to book a flight 61 days in advance to save up to 44% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 61 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Pensacola to Chicago 1-2 weeks in advance for as low as $436, or $472 for flights within the next 24 hours.

What is the cheapest month to fly from Pensacola to Chicago?

Flights from Pensacola to Chicago lean towards being more expensive in June. Prices are generally better when you fly from Pensacola to Chicago in August, with the cheapest ticket starting at $128.

When is the cheapest time to fly from Pensacola to Chicago (PNS - CHI)?

Unlike at noon, when flights are generally more expensive, you can save up to 94% on flights from Pensacola to Chicago by exploring options for tickets in the evening.

Cheap flights from Pensacola to Chicago in August, September 2022

The best prices found for PNS to CHI flights for August, September
Aug 28 - Sep 3
PNS

Pensacola

MDW

Chicago Midway

1 stop

23h 57m
MDW

Chicago Midway

PNS

Pensacola

1 stop

18h 56m
$164

Frontier

Pick Dates

Deal found 8/15/22

Aug 21 - Aug 27
PNS

Pensacola

MDW

Chicago Midway

1 stop

23h 57m
MDW

Chicago Midway

PNS

Pensacola

2 stops

15h 23m
$169

Frontier

Pick Dates

Deal found 8/13/22

Aug 28 - Sep 3
PNS

Pensacola

MDW

Chicago Midway

1 stop

23h 57m
MDW

Chicago Midway

PNS

Pensacola

1 stop

18h 56m
$171

Frontier

Pick Dates

Deal found 8/14/22

Pensacola to Chicago 2022 flight deals

Cheap flights to Chicago from Pensacola found for this year
Aug 28 - Sep 3
PNS

Pensacola

MDW

Chicago Midway

1 stop

23h 57m
MDW

Chicago Midway

PNS

Pensacola

1 stop

18h 56m
$164

Frontier

Pick Dates

Deal found 8/15/22

Aug 21 - Aug 27
PNS

Pensacola

MDW

Chicago Midway

1 stop

23h 57m
MDW

Chicago Midway

PNS

Pensacola

2 stops

15h 23m
$169

Frontier

Pick Dates

Deal found 8/13/22

Aug 28 - Sep 3
PNS

Pensacola

MDW

Chicago Midway

1 stop

23h 57m
MDW

Chicago Midway

PNS

Pensacola

1 stop

18h 56m
$171

Frontier

Pick Dates

Deal found 8/14/22

Cheap American Airlines flights from Pensacola to Chicago

Aug 29 - Sep 5
PNS

Pensacola

ORD

Chicago O'Hare Intl

1 stop

4h 52m
ORD

Chicago O'Hare Intl

PNS

Pensacola

1 stop

5h 14m
$258

American Airlines

Pick Dates

Deal found 8/15/22

Sep 21 - Sep 23
PNS

Pensacola

ORD

Chicago O'Hare Intl

1 stop

5h 08m
ORD

Chicago O'Hare Intl

PNS

Pensacola

1 stop

8h 04m
$260

American Airlines

Pick Dates

Deal found 8/15/22

Sep 24 - Sep 26
PNS

Pensacola

ORD

Chicago O'Hare Intl

1 stop

6h 32m
ORD

Chicago O'Hare Intl

PNS

Pensacola

2 stops

8h 53m
$263

American Airlines

Pick Dates

Deal found 8/15/22

Cheap United Airlines flights from Pensacola to Chicago

Aug 29 - Sep 4
PNS

Pensacola

ORD

Chicago O'Hare Intl

Nonstop

2h 41m
ORD

Chicago O'Hare Intl

PNS

Pensacola

Nonstop

2h 29m
$294

United Airlines

Pick Dates

Deal found 8/15/22

Sep 8 - Sep 13
PNS

Pensacola

ORD

Chicago O'Hare Intl

Nonstop

2h 34m
ORD

Chicago O'Hare Intl

PNS

Pensacola

Nonstop

2h 30m
$326

United Airlines

Pick Dates

Deal found 8/14/22

Sep 1 - Sep 4
PNS

Pensacola

ORD

Chicago O'Hare Intl

Nonstop

2h 41m
ORD

Chicago O'Hare Intl

PNS

Pensacola

Nonstop

2h 21m
$330

United Airlines

Pick Dates

Deal found 8/15/22

Non-stop flights to Chicago from Pensacola

Save time with Pensacola to Chicago direct flight deals
Aug 29 - Sep 4
PNS

Pensacola

ORD

Chicago O'Hare Intl

Nonstop

2h 41m
ORD

Chicago O'Hare Intl

PNS

Pensacola

Nonstop

2h 29m
$294

United Airlines

Pick Dates

Deal found 8/15/22

Sep 8 - Sep 13
PNS

Pensacola

ORD

Chicago O'Hare Intl

Nonstop

2h 34m
ORD

Chicago O'Hare Intl

PNS

Pensacola

Nonstop

2h 30m
$326

United Airlines

Pick Dates

Deal found 8/14/22

Sep 1 - Sep 4
PNS

Pensacola

ORD

Chicago O'Hare Intl

Nonstop

2h 41m
ORD

Chicago O'Hare Intl

PNS

Pensacola

Nonstop

2h 21m
$330

United Airlines

Pick Dates

Deal found 8/15/22

Last minute flights from Pensacola to Chicago

Late deals on return flights to Chicago from Pensacola, departing today and this week
Aug 21 - Aug 27
PNS

Pensacola

MDW

Chicago Midway

1 stop

23h 57m
MDW

Chicago Midway

PNS

Pensacola

1 stop

18h 56m
$164

Frontier

Pick Dates

Deal found 8/13/22

Aug 21 - Aug 27
PNS

Pensacola

MDW

Chicago Midway

1 stop

23h 57m
MDW

Chicago Midway

PNS

Pensacola

2 stops

15h 23m
$169

Frontier

Pick Dates

Deal found 8/13/22

Aug 21 - Aug 22
PNS

Pensacola

MDW

Chicago Midway

1 stop

23h 57m
MDW

Chicago Midway

PNS

Pensacola

1 stop

15h 54m
$204

Frontier

Pick Dates

Deal found 8/14/22

One-way flights to Chicago from Pensacola

The cheapest one-way flights from Pensacola to Chicago
Nov 10
PNS

Pensacola

MDW

Chicago Midway

1 stop

7h 10m
$80

Frontier

Pick Dates

Deal found 8/14/22

Aug 28
PNS

Pensacola

MDW

Chicago Midway

1 stop

23h 57m
$86

Frontier

Pick Dates

Deal found 8/14/22

Sep 3
PNS

Pensacola

MDW

Chicago Midway

1 stop

23h 40m
$90

Frontier

Pick Dates

Deal found 8/13/22

Related info for your journey

Useful info, stats and facts about Pensacola to Chicago flights.

What airport do you fly from for flights from Pensacola to Chicago?

Located just 4.0 mi from the city center, Pensacola is the airport most travelers will use when flying to Chicago from Pensacola. Booking flights from Pensacola (PNS) to Chicago should be relatively easy as there are 2 daily outbound flights to Chicago from 5 different airlines.

Which airlines flying from Pensacola to Chicago have flexible cancellations due to COVID-19?

United Airlines, American Airlines, and Delta are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

Can I find flights from Pensacola to Chicago for under $200 on Cheapflights?

Yes, there are multiple flights from Pensacola to Chicago for under $200. The cheapest flight booked recently is on Frontier for just $164, but on average you can expect to pay $246.

Are there nonstop flights from Pensacola to Chicago for under $300 on Cheapflights?

Cheapflights has at least 20 direct flights from Pensacola to Chicago under $300. A good price for a nonstop flight from Pensacola to Chicago is less than $424.

Are there last-minute flights available from Pensacola to Chicago for under $200?

There are currently 20+ open flights from Pensacola to Chicago within the next 7 days for less than $200.

What are the cheapest airlines flying from Pensacola to Chicago round-trip?

Our cheapest airline available from Pensacola to Chicago is Frontier. Our recent data shows that you can find tickets from as low as $164 on this airline. Additional options worth looking into are American Airlines and Spirit Airlines, starting at $258 and $270 round-trip. Frontier is 57% cheaper than the average price of flights available within the next 90 days to this destination.

What are the cheapest airlines to fly from Pensacola to Chicago one-way?

The cheapest airlines for a one-way flight from Pensacola to Chicago are Frontier ($80), Spirit Airlines ($116), and United Airlines ($121).

What are the most popular routes from Pensacola to Chicago?

Most travelers choose Pensacola - Chicago O'Hare Intl, Pensacola - Chicago Midway or Pensacola - Chicago Greater Rockford when deciding on the best route from Pensacola to Chicago.

What are the most popular airlines that fly from Pensacola to Chicago?

Before booking your flight from Pensacola to Chicago check out the most popular airlines for this route: American Airlines, Delta or Juneyao Airlines.

What are the most reliable airlines from Pensacola to Chicago?

The top 3 most reliable airlines when flying from Pensacola to Chicago are SkyWest Airlines (97%), United Airlines (95%) and Lufthansa (92%).

What are the cheapest flights from Pensacola to Chicago?

On average you can expect to pay $337 for a flight from Pensacola to Chicago. The cheapest flight overall is $139 while the most popular route, (Pensacola - Chicago O'Hare Intl) is currently priced at $266.

Alternative routes for Pensacola to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top 5 airlines flying from Pensacola to Chicago

The chart below displays the airlines Cheapflights users traveling from Pensacola to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$16Average$21FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
DeltaCheapest$129Average$454FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
American AirlinesCheapest$173Average$359FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
Spirit AirlinesCheapest$175Average$281FlexibilityNo cancel feeOn-time65%COVID-19 safety
Search Spirit Airlines flights
United AirlinesCheapest$210Average$478FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights

Hourly flight availability from Pensacola to Chicago

See what time of day planes typically take off from Pensacola to Chicago
0%of flight departuresEarly morningMidnight to 6 am
20%of flight departuresMorning6 am to noon
80%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Pensacola to Chicago

See how many times per day planes take to the skies headed from Pensacola to Chicago
Sunday2daily flights
Monday2daily flights
Tuesday2daily flights
Wednesday2daily flights
Thursday2daily flights
Friday2daily flights
Saturday3daily flights