Popular in | July |
---|---|
Cheapest in | April |
Round-trip from | $223 |
One-way from | $179 |
Wednesday is generally a great day to depart. Flying on this day could help you save up to 52%.
Travelers have found it’s best to book a flight 32 days in advance to save up to 71% 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 32 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 $262, or $365 for flights within the next 24 hours.
Flights from Pensacola to Chicago lean towards being more expensive in July. Prices are generally better when you fly from Pensacola to Chicago in April, with the cheapest ticket starting at $155.
Unlike in the morning, when flights are generally more expensive, you can save up to 21% on flights from Pensacola to Chicago by exploring options for tickets in the afternoon.
Fly from
Fly to
Budget
$87 - $309
Route
Depart
Return
Price
PensacolaChicago O'Hare Intl
PNS - ORD
PNSORD
Pensacola
Wed 5/22
1 stop11h 28m
Chicago O'Hare Intl
Wed 5/29
1 stop6h 33m
PensacolaChicago O'Hare Intl
PNS - ORD
PNSORD
Pensacola
Wed 5/22
2 stops27h 17m
Chicago O'Hare Intl
Wed 5/29
1 stop6h 33m
PensacolaChicago O'Hare Intl
PNS - ORD
PNSORD
Pensacola
Fri 5/31
1 stop9h 05m
Chicago O'Hare Intl
Tue 6/4
1 stop6h 33m
PensacolaChicago O'Hare Intl
PNS - ORD
PNSORD
Pensacola
Wed 5/22
3 stops32h 44m
Chicago O'Hare Intl
Wed 5/29
1 stop6h 33m
PensacolaChicago Midway
PNS - MDW
PNSMDW
Pensacola
Fri 5/31
1 stop13h 29m
Chicago Midway
Tue 6/4
1 stop10h 55m
PensacolaChicago Midway
PNS - MDW
PNSMDW
Pensacola
Thu 5/30
1 stop19h 01m
Chicago Midway
Mon 6/3
1 stop15h 41m
PensacolaChicago O'Hare Intl
PNS - ORD
PNSORD
Pensacola
Wed 8/28
1 stop6h 21m
Chicago O'Hare Intl
Sun 9/1
1 stop11h 13m
PensacolaChicago Midway
PNS - MDW
PNSMDW
Pensacola
Sat 8/24
1 stop4h 02m
Chicago Midway
Wed 8/28
1 stop4h 15m
PensacolaChicago O'Hare Intl
PNS - ORD
PNSORD
Pensacola
Wed 7/17
1 stop6h 16m
Chicago O'Hare Intl
Sat 7/20
Nonstop2h 29m
Currently, February is the cheapest month in which you can book a flight from Pensacola to Chicago (average of $244). Flying from Pensacola to Chicago in June is currently the most expensive (average of $348). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
January
$248
February
$244
March
$280
April
$258
May
$278
June
$348
July
$330
August
$274
September
$258
October
$248
November
$270
December
$248
CHI Temperature | 23 - 73.4 °F |
---|
Food
Overall
Boarding
Entertainment
Comfort
Crew
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Food
Overall
Boarding
Entertainment
Comfort
Crew
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Food
Overall
Boarding
Entertainment
Comfort
Crew
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Food
Overall
Boarding
Entertainment
Comfort
Crew
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Food
Overall
Boarding
Entertainment
Comfort
Crew
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Food
Overall
Boarding
Entertainment
Comfort
Crew
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
0%of flight departures | Early morningMidnight to 6 am |
---|---|
0%of flight departures | Morning6 am to noon |
100%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |
Sunday | 2daily flights |
---|---|
Monday | 1daily flight |
Tuesday | 1daily flight |
Wednesday | 1daily flight |
Thursday | 0daily flights |
Friday | 1daily flight |
Saturday | 2daily flights |
900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chicago from Pensacola today with Cheapflights!
It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Pensacola to Chicago.
Cheapflights does show flights with no change fees to all users. To see these options for flights from Pensacola to Chicago, users can toggle the no change fees filter when performing a flight search.
Not ready to book yet? You can track prices for flights from Pensacola to Chicago on Cheapflights with our Price Alert feature and get notified when better prices are available.