Find Cheap Flights from Chicago to Pensacola (CHI - PNS)

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Sat 12/16
Sat 12/23
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Good to Know

Low Season:
October
Best time to beat the crowds
2%
expected price decrease
High Season:
March
Most popular time to fly
2%
expected price increase
Average Price:
$390
(avg. price over the last 2 weeks)
Good Deal:
$316
or less (round trip)

When to Book Flights from Chicago to Pensacola

Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $316 or less.
The cheapest flight from Chicago to Pensacola was found 63 days before departure, on average.
Book at least 2 weeks before departure in order to get a below-average price.
High season is considered to be February, March and April. The cheapest month to fly is October.
Morning departure is around 4% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Chicago to Pensacola Flights

How long does a flight from Chicago to Pensacola take?
An average nonstop flight takes 2h 20m, covering a distance of 789 miles.
How many flights are there between Chicago and Pensacola?
There are 7 (nonstop) flights between Chicago and Pensacola per week, averaging 1 per day.
Which airlines provide the cheapest flights from Chicago to Pensacola?
In the past 3 days, the cheapest round-trip tickets were found on Frontier ($161), Multiple Airlines ($299) and American Airlines ($327).
Do I need a passport to fly between Chicago and Pensacola?
No.
Which airlines fly most frequently between Chicago and Pensacola?
United (1 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Chicago to Pensacola?
For Chicago to Pensacola, Saturday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Pensacola back to Chicago, the best deals are generally found on Saturday, with Wednesday being the most expensive.

Book cheap flights from Chicago to Pensacola (round-trip)

Airports
Origin
Chicago
$161
only
$161
$346
only
$346
Destination
Pensacola
$161
only
$161
Sat, May 12
ORD
PNS
2h 25m
Sat, May 19
PNS
ORD
2h 38m
Trip: 8 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 33270 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
MSY
MCO
Excellent 10.0

Great crew great flight

Nothing, everything was awesome. Crazy to believe this was a 19 dollar flight

MKE
TPA
Good 6.6

2nd row had plenty of leg room, nice new jet, Nice flight attendants, smooth flight, on time, made it to my destination safe. Successful flight! TSA Pre-chek was nice.

Idiot in front of me reclined his seat. Plane didn't get catered overnight. Water only.

DEN
MKE
Good 6.6

Direct flight from Denver to Milwaukee. Didn't have to wait on tarmac so that was a plus.

Have to pay for every little thring down to the peanuts

TYS
MCO
Okay 5.0

Great people

The plane wasn’t very clean

SJU
ATL
Excellent 10.0

Fast luggage checking

No cash accepted for overweight baggage

Fri, May 11
ORD
PNS
2h 20m
Tue, May 15
PNS
ORD
14h 48m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Feb 7
ORD
PNS
6h 37m
Tue, Feb 13
PNS
ORD
6h 39m
Trip: 7 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 26055 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
LAX
LHR
Excellent 9.2

Easy and efficient boarding for a busy flight. Efficient, attentive and intuitive cabin crew. Good in-flight entertainment and facilities.

The aircraft was extremely cold throughout the duration of the flight. Of all of the long haul airlines I've flown with, I find that American Airlines offers the least leg room.

DFW
SCL
Excellent 9.6

The food is very tasty, but AA has not changed the menu in at least one year.

BNA
DFW
Good 7.3

Everything else

LAX
AKL
Okay 5.6

Smooth operation, on time

Seat pitch on the plane unbelievably cramped. When seats are so close that if you drop something on the floor you have to be a contortionist to get it, you know it's a problem NEVER fly the 787-900 economy.

SFO
DFW
Excellent 10.0

On time. Comfortable seat. Courteous crew. Easy transfer.

Sat, Feb 17
ORD
PNS
2h 24m
Thu, Feb 22
PNS
ORD
2h 38m
Trip: 6 days
6.9GoodShow reviews
Overall 6.9 Good
Based on 4 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
RSW
EWR
Okay 5.3

Waiting

IAD
MUC
Good 6.3

Crew and food.

The old bait and switch. United is not and will never be Lufthansa. Cattle call seating.

IAD
CDG
Good 7.6

The food was particularly poor this flight.

ATL
ORD
Excellent 8.0

The United pilot we flew that day. did great job. we arrive safe to the distination despite of the climate condition. im happy for the service.so far im satified..

the delayed flight this time almost cause us to lost our next flight in chicago. thats what i dont like. wish this wont happen next time..

ORD
PNS
Mediocre 3.3

Delays

Wed, Jun 6
ORD
PNS
2h 25m
Sat, Jun 16
PNS
ORD
2h 38m
Trip: 11 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 33270 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
PHL
MCO
Mediocre 2.3

Its a scam! They act like they are giving you a break by having you buy cheap flights but in reality it costs more than a bit more expensive flight. I had to pay $45.00 each bag no matter if it was checked or carry-on. In total round trip I paid $180.00 extra just for my husbands carry-on as well as mine. Must add that our flights together cost 286.00. We should of went with American Airlines. On top of that we couldn't select our own seat if so, we had to pay extra, so we had to sit separated from each other. It was ridiculous! Never Again with this company!!!!!

IAD
LAS
Good 6.3

They gave me and someone else the same seat luckily it wasn’t a packed flight and was able to move to a row that was empty

DEN
SFO
Mediocre 2.0

Website would not let me check in the day before or the morning or my flight. There was an error every time and I almost got to the end once. I could not change the time of my transportation and arrived 10 minutes past the check in deadline (an hour prior to the flight taking off). I was refused access to the flight and offered a flight 5 hours later. The staff was rude and not helpful. I had heard negative things about Frontier and now I know why.

DEN
MKE
Good 6.6

Direct flight from Denver to Milwaukee. Didn't have to wait on tarmac so that was a plus.

Have to pay for every little thring down to the peanuts

ATL
DEN
Mediocre 3.6

The price was good, and it was a non stop flight.

The crew was rude and the seats didn't recline.

Sat, Feb 17
MDW
PNS
5h 38m
Wed, Feb 21
PNS
MDW
4h 55m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

ATL
DFW
Excellent 10.0

My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime.

ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

Sat, Jun 9
ORD
PNS
2h 25m
Sat, Jun 16
PNS
ORD
2h 38m
Trip: 8 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 33270 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
SJU
ATL
Excellent 10.0

Fast luggage checking

No cash accepted for overweight baggage

PHL
MCO
Mediocre 2.3

Its a scam! They act like they are giving you a break by having you buy cheap flights but in reality it costs more than a bit more expensive flight. I had to pay $45.00 each bag no matter if it was checked or carry-on. In total round trip I paid $180.00 extra just for my husbands carry-on as well as mine. Must add that our flights together cost 286.00. We should of went with American Airlines. On top of that we couldn't select our own seat if so, we had to pay extra, so we had to sit separated from each other. It was ridiculous! Never Again with this company!!!!!

AUS
LAS
Excellent 8.0

Efficient

N/a

MKE
TPA
Good 6.6

2nd row had plenty of leg room, nice new jet, Nice flight attendants, smooth flight, on time, made it to my destination safe. Successful flight! TSA Pre-chek was nice.

Idiot in front of me reclined his seat. Plane didn't get catered overnight. Water only.

MSY
MCO
Excellent 10.0

Great crew great flight

Nothing, everything was awesome. Crazy to believe this was a 19 dollar flight

Tue, May 8
ORD
PNS
9h 55m
Wed, May 16
PNS
ORD
2h 38m
Trip: 9 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 33270 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
ATL
DEN
Mediocre 3.6

The price was good, and it was a non stop flight.

The crew was rude and the seats didn't recline.

IAD
LAS
Good 6.3

They gave me and someone else the same seat luckily it wasn’t a packed flight and was able to move to a row that was empty

DEN
MKE
Good 6.6

Direct flight from Denver to Milwaukee. Didn't have to wait on tarmac so that was a plus.

Have to pay for every little thring down to the peanuts

SJU
ATL
Excellent 10.0

Fast luggage checking

No cash accepted for overweight baggage

TYS
MCO
Okay 5.0

Great people

The plane wasn’t very clean

Sat, May 12
ORD
PNS
2h 25m
Tue, May 15
PNS
ORD
14h 48m
Trip: 4 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 33270 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
DEN
SFO
Mediocre 2.0

Website would not let me check in the day before or the morning or my flight. There was an error every time and I almost got to the end once. I could not change the time of my transportation and arrived 10 minutes past the check in deadline (an hour prior to the flight taking off). I was refused access to the flight and offered a flight 5 hours later. The staff was rude and not helpful. I had heard negative things about Frontier and now I know why.

ATL
DEN
Mediocre 3.6

The price was good, and it was a non stop flight.

The crew was rude and the seats didn't recline.

TYS
MCO
Okay 5.0

Great people

The plane wasn’t very clean

MSY
MCO
Excellent 10.0

Great crew great flight

Nothing, everything was awesome. Crazy to believe this was a 19 dollar flight

MKE
TPA
Good 6.6

2nd row had plenty of leg room, nice new jet, Nice flight attendants, smooth flight, on time, made it to my destination safe. Successful flight! TSA Pre-chek was nice.

Idiot in front of me reclined his seat. Plane didn't get catered overnight. Water only.

Wed, May 16
ORD
PNS
2h 25m
Tue, May 22
PNS
ORD
14h 48m
Trip: 7 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 33270 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
MKE
TPA
Good 6.6

2nd row had plenty of leg room, nice new jet, Nice flight attendants, smooth flight, on time, made it to my destination safe. Successful flight! TSA Pre-chek was nice.

Idiot in front of me reclined his seat. Plane didn't get catered overnight. Water only.

LAS
IAD
Good 6.3

The staff on the flight was awesome, very helpful and kind to my friend who is terrified to fly. We were even ahead of schedule.

To pay for a carry on item is just crazy to me... not to mention you have to pay for beverages and snacks. All you are given is water.

DEN
MKE
Good 6.6

Direct flight from Denver to Milwaukee. Didn't have to wait on tarmac so that was a plus.

Have to pay for every little thring down to the peanuts

AUS
LAS
Excellent 8.0

Efficient

N/a

MSY
PVD
Excellent 8.0

The price!

Tue, May 8
ORD
PNS
2h 20m
Tue, May 15
PNS
ORD
14h 48m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Mar 8
ORD
PNS
2h 24m
Thu, Mar 15
PNS
ORD
2h 37m
Trip: 7 days
6.9GoodShow reviews
Overall 6.9 Good
Based on 4 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
IAD
MUC
Good 6.3

Crew and food.

The old bait and switch. United is not and will never be Lufthansa. Cattle call seating.

ORD
PNS
Mediocre 3.3

Delays

ATL
ORD
Excellent 8.0

The United pilot we flew that day. did great job. we arrive safe to the distination despite of the climate condition. im happy for the service.so far im satified..

the delayed flight this time almost cause us to lost our next flight in chicago. thats what i dont like. wish this wont happen next time..

RSW
EWR
Okay 5.3

Waiting

IAD
CDG
Good 7.6

The food was particularly poor this flight.

Thu, May 10
ORD
PNS
2h 20m
Tue, May 15
PNS
ORD
14h 48m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Jan 17
ORD
PNS
4h 52m
Sun, Jan 21
PNS
ORD
4h 56m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 26055 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
CLE
JFK
Mediocre 3.3

Plane was dirty and crew inattentive.

JFK
CDG
Mediocre 2.0

Nothing. From the plane to the awful delay and poor service.

Lack of communication. Old plane, no comfort and 6 HOURS DELAYED. Truly disappointed by the airline

DFW
SCL
Excellent 9.6

The food is very tasty, but AA has not changed the menu in at least one year.

ATL
CLT
Excellent 9.6

The flight was late

JFK
MXP
Mediocre 2.6

Plane was old and dirty, seat pocket had junk in it. Seat was broken and couldn’t stay up. In flight movies were from few years back with a center tv and no head rest screen. Crew on overseas flights tend to be older in age and less tolerant..much better on continental on the same route.

Fri, Mar 9
MDW
PNS
5h 44m
Wed, Mar 14
PNS
MDW
5h 58m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ATL
DFW
Excellent 10.0

My entire flight experience was delightful. Was dry impressed with the staff both at Hartsfield-Jackson and DFW...and our flight crew was positively sublime.

JFK
ATL
Excellent 8.3

We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!

window seat in back didn't have window

BWI
JFK
Mediocre 3.6

There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked.

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

Fri, Mar 9
ORD
PNS
2h 24m
Thu, Mar 15
PNS
ORD
2h 37m
Trip: 6 days
6.9GoodShow reviews
Overall 6.9 Good
Based on 4 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
RSW
EWR
Okay 5.3

Waiting

ORD
MUC
Mediocre 2.0

Our plane was defective so had to be replaced. This is fine, I certainly am willing to wait for a new plane if it means not blowing up over the ocean. The problem was how little the attendants at the gate communicated the situation to us. What should have been a brief layover became a 12 hour nightmare. The gate attendants did finally issue meal vouchers but they waited until 10 minutes before all the restaurants closed and only issued $10 a person. This is enough to buy a hot dog at an airport... We were told there wouldn't be any rescheduling of missed connections until we were "airborne". This resulted in mass panic and confusion upon reaching our destination. We were told to go to the service desk, half an airport away, but once the entire passenger contents of the plane arrived at that far flung service desk, we were mostly turned away to seek help at individual gates. This lack of communication meant I missed the next next available connecting flight and now have a further six hour layover. I understand accidents happen and planes can break down but the nearly complete lack of care and customer attention is, frankly, disappointing. I've now had nearly an entire day added to my travel time. If I'd been willing to loose that time I would have paid $600 less for my ticket. United finally offered a token of their appreciation : a $100 e-voucher. I have spent more than that on food and coffee in airports for the past two days while trying to survive until my next connections.

IAD
CDG
Good 7.6

The food was particularly poor this flight.

ORD
PNS
Good 7.0

Time

FLL
ORD
Excellent 8.0

no aisle seat

Sun, May 13
ORD
PNS
2h 20m
Tue, May 15
PNS
ORD
14h 48m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Jan 18
ORD
PNS
5h 25m
Tue, Jan 23
PNS
ORD
6h 16m
Trip: 6 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 26055 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
LAX
LHR
Excellent 9.2

Easy and efficient boarding for a busy flight. Efficient, attentive and intuitive cabin crew. Good in-flight entertainment and facilities.

The aircraft was extremely cold throughout the duration of the flight. Of all of the long haul airlines I've flown with, I find that American Airlines offers the least leg room.

ORD
LAX
Excellent 9.5

Easy, smooth.

ATL
CLT
Excellent 9.6

The flight was late

JFK
MXP
Mediocre 2.6

Plane was old and dirty, seat pocket had junk in it. Seat was broken and couldn’t stay up. In flight movies were from few years back with a center tv and no head rest screen. Crew on overseas flights tend to be older in age and less tolerant..much better on continental on the same route.

DFW
SCL
Excellent 9.6

The food is very tasty, but AA has not changed the menu in at least one year.

Wed, Jan 17
MDW
PNS
6h 11m
Sun, Jan 21
PNS
MDW
4h 40m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14257 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LGA
ORD
Excellent 10.0

Flight was on time. Boarded quickly with no fuss.

GSO
ATL
Excellent 10.0

Plane nice and comfortable

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

AMS
DTW
Mediocre 2.0

The most horrible experience. Pathetic to say the least. No water in the flight lavotries. Such a pathetic service from so called top airline.

ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

Sun, May 6
ORD
PNS
9h 55m
Wed, May 16
PNS
ORD
2h 38m
Trip: 11 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 33270 reviews
Overall
5.9
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.5
Food
4.7
SJU
ATL
Excellent 10.0

Fast luggage checking

No cash accepted for overweight baggage

AUS
LAS
Excellent 8.0

Efficient

N/a

PHL
MCO
Mediocre 2.3

Its a scam! They act like they are giving you a break by having you buy cheap flights but in reality it costs more than a bit more expensive flight. I had to pay $45.00 each bag no matter if it was checked or carry-on. In total round trip I paid $180.00 extra just for my husbands carry-on as well as mine. Must add that our flights together cost 286.00. We should of went with American Airlines. On top of that we couldn't select our own seat if so, we had to pay extra, so we had to sit separated from each other. It was ridiculous! Never Again with this company!!!!!

DEN
SFO
Mediocre 2.0

Website would not let me check in the day before or the morning or my flight. There was an error every time and I almost got to the end once. I could not change the time of my transportation and arrived 10 minutes past the check in deadline (an hour prior to the flight taking off). I was refused access to the flight and offered a flight 5 hours later. The staff was rude and not helpful. I had heard negative things about Frontier and now I know why.

LAS
IAD
Good 6.3

The staff on the flight was awesome, very helpful and kind to my friend who is terrified to fly. We were even ahead of schedule.

To pay for a carry on item is just crazy to me... not to mention you have to pay for beverages and snacks. All you are given is water.

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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.