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

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Sat 12/16
Sat 12/23
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Good to Know

Average Price:
$373
(avg. price over the last 2 weeks)
Good Deal:
$297
or less (round trip)

When to Book Flights from Pensacola to Chicago

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 $297 or less.
The cheapest flight from Pensacola to Chicago was found 90 days before departure, on average.
Book at least 2 weeks before departure in order to get a below-average price.
Morning departure is around 7% cheaper 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 Pensacola to Chicago Flights

How long does a flight from Pensacola to Chicago take?
An average nonstop flight takes 2h 35m, covering a distance of 789 miles.
How many flights are there between Pensacola and Chicago?
There are 28 (nonstop) flights between Pensacola and Chicago per week, averaging 4 per day.
Which airlines provide the cheapest flights from Pensacola to Chicago?
In the past 3 days, the cheapest round-trip tickets were found on Frontier ($231), United ($313) and American Airlines ($327).
Do I need a passport to fly between Pensacola and Chicago?
No.
Which airlines fly most frequently between Pensacola and Chicago?
United (2 times daily), Lufthansa (1 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Pensacola to Chicago?
For Pensacola to Chicago, Saturday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Chicago back to Pensacola, the best deals are generally found on Saturday, with Tuesday being the most expensive.

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

Airports
Origin
Pensacola
$231
only
$231
Destination
Chicago
$231
only
$231
$330
only
$330
Sat, Jun 23
PNS
ORD
2h 38m
Sat, Jun 30
ORD
PNS
2h 25m
Trip: 8 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 33263 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

MSY
MCO
Excellent 10.0

Great crew great flight

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

AUS
LAS
Excellent 8.0

Efficient

N/a

TYS
MCO
Okay 5.0

Great people

The plane wasn’t very clean

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

Thu, Mar 1
PNS
ORD
2h 38m
Mon, Mar 5
ORD
PNS
2h 24m
Trip: 5 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 6 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
RSW
EWR
Okay 5.3

Boarding quickly

No PED was available didn’t have anything for entertainment if you weren’t buying it seems every thing available for 3 hour flight and flight was scheduled for 2 hours and 55 minutes No snacks made available came thru once had a small bag of pretzels cup of coffee and never came back

PNS
ORD
Okay 5.6

Seats were uncomfortable, very firm, back of seat was like leaning against a piece of wood. OK for this short flight, longer flight would have been extremely uncomfortable.

RSW
EWR
Okay 5.3

Waiting

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..

FLL
ORD
Excellent 8.0

no aisle seat

Fri, Jan 5
PNS
ORD
4h 45m
Sun, Jan 7
ORD
PNS
6h 50m
Trip: 3 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 26019 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
ABQ
ORD
Excellent 8.0

everything fine

having to gate-check our hand luggage

HPN
DCA
Mediocre 2.0

Nothing

Comfort, timeliness.

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.

CLT
SJU
Mediocre 3.3

Direct flight

Horrible customer service, excessive baggage fees, rude counter staff, no leg room, narrow seats

DFW
LAX
Excellent 8.3

I liked the expediency of being rescheduled for another flight and the kindness of the American Airlines staff. When I first received my boarding pass, the pass listed gate A24 as the one where my flight was scheduled to depart. The plane destined to depart from Dallas to LAX did not show up. However, a few of us were kindly offered a cot and blankets to sleep on. The next morning I folded the cot and the blankets and found an American Airline staff member who swiftly rescheduled me for another flight to LAX. She did state that the original flight had departed at 11:15 p.m.

From around 6 P.M., December 11, 2017, I was at gate A24 - the gate listed as the Departure gate for my return flight to Los Angeles. The last flight that left went to Saint Louis, I believe. There was never a flight to depart from Gate 24 to Los Angeles. I believe the gate may have been changed and for some reason, those who were at Gate 24 were not informed. Also, the travel instructions on the advertisement for scheduling the flight mentioned the ability to carry on luggage for no additional charge. When I received my boarding pass, it stated I was only allowed to carry on baggage that would fit underneath the seat and not in the overhead bin. I had to pay to check my baggage that I thought was free. In spite of the changes, the flight was a good flight. Thank you

Fri, Apr 13
PNS
MDW
6h 29m
Sun, Apr 15
MDW
PNS
4h 14m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 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.

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

MSP
YXE
Excellent 9.3

I was traveling for medical reasons and the Delta crew took great care of me, made sure I was at my connecting gate on time, and even put me in a better seat on the plane. Not sure if that was a coincidental upgrade, or intentional, but it was perfect.

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

Thu, Dec 21
PNS
ORD
2h 37m
Sun, Dec 24
ORD
PNS
5h 34m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Mar 2
PNS
ORD
2h 38m
Mon, Mar 5
ORD
PNS
2h 24m
Trip: 4 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 6 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
PNS
ORD
Excellent 8.6

Good Speedy trip very awesome Pleasant helpful people

when I suggested window seat I thought I would have it throughout the entire flight that was pretty much the only disappointing thing about the whole trip

RSW
EWR
Okay 5.3

Boarding quickly

No PED was available didn’t have anything for entertainment if you weren’t buying it seems every thing available for 3 hour flight and flight was scheduled for 2 hours and 55 minutes No snacks made available came thru once had a small bag of pretzels cup of coffee and never came back

PNS
ORD
Okay 4.0

my daughter and I didn't even have seats together...and the plane was not full. We spent $69 and $77 to get seats together and the seat backs didn't work, no TV screens, and my expensive purse was soaking wet when I retrieved it from under the seat. So gross. And of course the food was gross...but that's to be expected, I guess.

FLL
ORD
Excellent 8.0

no aisle seat

RSW
EWR
Okay 5.3

Waiting

Tue, Jan 9
PNS
ORD
4h 47m
Tue, Jan 16
ORD
PNS
5h 25m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 26019 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.

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.

HPN
DCA
Mediocre 2.0

Nothing

Comfort, timeliness.

AUS
CLT
Excellent 10.0

My Mom was very grateful for the friendly assistance as she is wheelchair bound and was flying aline. Excellent service!!

Nothing.

ATL
CLT
Excellent 9.6

The flight was late

Tue, Apr 17
PNS
MDW
4h 19m
Tue, Apr 24
MDW
PNS
4h 25m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSP
YXE
Excellent 9.3

I was traveling for medical reasons and the Delta crew took great care of me, made sure I was at my connecting gate on time, and even put me in a better seat on the plane. Not sure if that was a coincidental upgrade, or intentional, but it was perfect.

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.

GSO
ATL
Excellent 10.0

Plane nice and comfortable

JFK
YYZ
Excellent 10.0

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

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

Fri, Apr 13
PNS
ORD
2h 35m
Sun, Apr 15
ORD
PNS
2h 20m
Trip: 3 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 6 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
PNS
ORD
Mediocre 3.0

Flight was delayed not enough information. Missed connection.

RSW
EWR
Okay 5.3

Boarding quickly

No PED was available didn’t have anything for entertainment if you weren’t buying it seems every thing available for 3 hour flight and flight was scheduled for 2 hours and 55 minutes No snacks made available came thru once had a small bag of pretzels cup of coffee and never came back

RSW
EWR
Okay 5.3

Waiting

PNS
ORD
Okay 5.6

Seats were uncomfortable, very firm, back of seat was like leaning against a piece of wood. OK for this short flight, longer flight would have been extremely uncomfortable.

IAD
CDG
Good 7.6

The food was particularly poor this flight.

Thu, Jan 11
PNS
ORD
4h 56m
Tue, Jan 16
ORD
PNS
4h 50m
Trip: 6 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 26019 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
ORD
LAX
Excellent 9.5

Easy, smooth.

DFW
LAX
Excellent 8.3

I liked the expediency of being rescheduled for another flight and the kindness of the American Airlines staff. When I first received my boarding pass, the pass listed gate A24 as the one where my flight was scheduled to depart. The plane destined to depart from Dallas to LAX did not show up. However, a few of us were kindly offered a cot and blankets to sleep on. The next morning I folded the cot and the blankets and found an American Airline staff member who swiftly rescheduled me for another flight to LAX. She did state that the original flight had departed at 11:15 p.m.

From around 6 P.M., December 11, 2017, I was at gate A24 - the gate listed as the Departure gate for my return flight to Los Angeles. The last flight that left went to Saint Louis, I believe. There was never a flight to depart from Gate 24 to Los Angeles. I believe the gate may have been changed and for some reason, those who were at Gate 24 were not informed. Also, the travel instructions on the advertisement for scheduling the flight mentioned the ability to carry on luggage for no additional charge. When I received my boarding pass, it stated I was only allowed to carry on baggage that would fit underneath the seat and not in the overhead bin. I had to pay to check my baggage that I thought was free. In spite of the changes, the flight was a good flight. Thank you

BNA
DFW
Good 7.3

Everything else

SFO
DFW
Excellent 10.0

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

CLT
SJU
Mediocre 3.3

Direct flight

Horrible customer service, excessive baggage fees, rude counter staff, no leg room, narrow seats

Tue, Apr 17
PNS
ORD
2h 37m
Wed, Apr 25
ORD
PNS
2h 20m
Trip: 9 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 6 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
PNS
ORD
Mediocre 3.0

Flight was delayed not enough information. Missed connection.

IAD
CDG
Good 7.6

The food was particularly poor this flight.

LAX
NRT
Good 7.3

Good price

Stink in the plane

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..

PNS
ORD
Okay 5.6

Seats were uncomfortable, very firm, back of seat was like leaning against a piece of wood. OK for this short flight, longer flight would have been extremely uncomfortable.

Fri, Jan 12
PNS
ORD
6h 32m
Tue, Jan 16
ORD
PNS
6h 37m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 26019 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
CLT
SJU
Mediocre 3.3

Direct flight

Horrible customer service, excessive baggage fees, rude counter staff, no leg room, narrow seats

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.

LHR
ORD
Excellent 8.0

The staff were nice and helpful.

Internet sucks

HPN
DCA
Mediocre 2.0

Nothing

Comfort, timeliness.

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.

Thu, Feb 15
PNS
MDW
4h 14m
Mon, Feb 19
MDW
PNS
4h 38m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSP
YXE
Excellent 9.3

I was traveling for medical reasons and the Delta crew took great care of me, made sure I was at my connecting gate on time, and even put me in a better seat on the plane. Not sure if that was a coincidental upgrade, or intentional, but it was perfect.

ZAG
CDG
Good 6.0

Old plane, bad food & old crew

SLC
SNA
Excellent 8.0

Comfortable seats in coach Good snacks Friendly crew

Nothing

GSO
ATL
Excellent 10.0

Plane nice and comfortable

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.

Wed, Apr 18
PNS
ORD
2h 37m
Wed, Apr 25
ORD
PNS
2h 20m
Trip: 8 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 6 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
IAD
CDG
Good 7.6

The food was particularly poor this flight.

RSW
EWR
Okay 5.3

Waiting

RSW
EWR
Okay 5.3

Boarding quickly

No PED was available didn’t have anything for entertainment if you weren’t buying it seems every thing available for 3 hour flight and flight was scheduled for 2 hours and 55 minutes No snacks made available came thru once had a small bag of pretzels cup of coffee and never came back

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..

MIA
ORD
Excellent 9.0

That it got me to Paris safe

No outlets to charge your phone, and the tv played the same movie over and over. The meals were also cheap. Didn't like any of them. Should have flown southwest or delta.

Thu, Jan 25
PNS
ORD
4h 56m
Sun, Jan 28
ORD
PNS
6h 35m
Trip: 4 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 26019 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
ORD
LAX
Excellent 9.5

Easy, smooth.

ABQ
ORD
Excellent 8.0

everything fine

having to gate-check our hand luggage

ATL
CLT
Excellent 9.6

The flight was late

LHR
ORD
Excellent 8.0

The staff were nice and helpful.

Internet sucks

SFO
DFW
Excellent 10.0

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

Fri, Apr 13
PNS
ORD
4h 52m
Sun, Apr 15
ORD
PNS
5h 57m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ZAG
CDG
Good 6.0

Old plane, bad food & old crew

SYR
MSP
Excellent 8.0

WiFi and free tv shows

My seat wouldn’t recline

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.

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.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

Thu, Apr 19
PNS
ORD
2h 35m
Wed, Apr 25
ORD
PNS
2h 20m
Trip: 7 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 6 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
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..

LAX
NRT
Good 7.3

Good price

Stink in the plane

PNS
ORD
Okay 5.6

Seats were uncomfortable, very firm, back of seat was like leaning against a piece of wood. OK for this short flight, longer flight would have been extremely uncomfortable.

FLL
ORD
Excellent 8.0

no aisle seat

IAD
CDG
Good 7.6

The food was particularly poor this flight.

Fri, Feb 2
PNS
ORD
4h 48m
Mon, Feb 5
ORD
PNS
6h 37m
Trip: 4 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 26019 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
CLT
SJU
Mediocre 3.3

Direct flight

Horrible customer service, excessive baggage fees, rude counter staff, no leg room, narrow seats

ATL
CLT
Excellent 9.6

The flight was late

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.

LHR
ORD
Excellent 8.0

The staff were nice and helpful.

Internet sucks

ORD
LAX
Excellent 9.5

Easy, smooth.

Tue, Jan 9
PNS
MDW
4h 14m
Thu, Jan 11
MDW
PNS
4h 00m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14235 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
YYZ
Excellent 10.0

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

IND
DTW
Okay 4.0

No wifi couldn’t do any work

Was looking forward to completing some work but the wifi never came on.

DEN
ATL
Excellent 8.6

On two of the legs of the trip they notice I was a tall person with long legs and upgraded me to seats with more leg room!! I didn't even ask. Thank you.

On the way back there were open seats with extra leg room and I asked the gate attendant if it was possible to switch my seat to one with more room and they said they only could if I paid extra.

GSO
ATL
Excellent 10.0

Plane nice and comfortable

SLC
SNA
Excellent 8.0

Comfortable seats in coach Good snacks Friendly crew

Nothing

Fri, Apr 20
PNS
ORD
2h 37m
Wed, Apr 25
ORD
PNS
2h 20m
Trip: 6 days
5.4OkayShow reviews
Overall 5.4 Okay
Based on 6 reviews
Overall
7.2
Boarding
7.4
Comfort
6.9
Crew
7.7
Entertainment
6.5
Food
6.4
RSW
EWR
Okay 5.3

Boarding quickly

No PED was available didn’t have anything for entertainment if you weren’t buying it seems every thing available for 3 hour flight and flight was scheduled for 2 hours and 55 minutes No snacks made available came thru once had a small bag of pretzels cup of coffee and never came back

IAD
CDG
Good 7.6

The food was particularly poor this flight.

PNS
ORD
Okay 5.6

Seats were uncomfortable, very firm, back of seat was like leaning against a piece of wood. OK for this short flight, longer flight would have been extremely uncomfortable.

PUJ
EWR
Good 7.3

The flight was very hot and uncomfortable

PNS
ORD
Excellent 8.6

Good Speedy trip very awesome Pleasant helpful people

when I suggested window seat I thought I would have it throughout the entire flight that was pretty much the only disappointing thing about the whole trip

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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.