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

Airports
Origin
Newport News
$205
only
$205
Staunton
$210
only
$210
Lynchburg
$211
only
$211
Norfolk
$191
only
$191
Richmond
$199
only
$199
Destination
Chicago
$191
only
$191
$208
only
$208
Wed, Apr 11
ORF
ORD
2h 14m
Wed, Apr 18
ORD
ORF
2h 12m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Apr 24
ORF
ORD
2h 24m
Sat, Apr 28
ORD
ORF
2h 11m
Trip: 5 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 49 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
ORF
ORD
Excellent 10.0

Early arrival. Smooth flight

Check in was confusing.

ORF
ORD
Mediocre 3.0

The staff that is it

The plane broke down I was put on standby offered a middle seat and I'm a bigger guy I was stuck in between 2 other bigger guys and wasn't offered any compensation I'm anyway!!!! The next review will be on yelp

ORF
ORD
Okay 4.6

The crew was pleasant.

Delayed for an excessive amount of time before the flight was finally Cancelled. Got stuck waiting for over 7hrs before the flight was eventually cancelled. Barley made it home in time for my grandfather's funeral as a result.

ORF
ORD
Good 6.0

The flight was delayed 2 hours

ORF
ORD
Excellent 9.3

I think your agents on up did well handling rebooking and upset people. I was told I would miss my flight first thing this morning but the agent was able to get me on and I arrived in CR only 1. Hour late. Thank you for the great service. It has to be hard picking up the pieces after the hurricane.

Tue, Mar 20
RIC
ORD
6h 23m
Tue, Mar 27
ORD
RIC
4h 34m
Trip: 8 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 8432 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
JFK
PHX
Excellent 9.6

Leg space, free carry on, nice staff, good snacks

15 minute delay

BDL
FLL
Excellent 10.0

The flight wa on time, fast and safe.

Everthing was fine

BOS
PHX
Okay 4.6

Flight attendants were very friendly

Paid $70 for a ticket that provides a seat that had a broken TV. No power outlets as well is annoying.

BOS
PHL
Excellent 9.2

Jetblue is very reliable, very friendly and professional crew, and the make the flight very smooth.

Food choices are limited, but I understand it is a short flight.

SJU
JFK
Good 6.6

The bathroom was filthy and the toilet did not flush properly. Overall cleanliness lacking.

Tue, May 8
PHF
ORD
6h 36m
Sat, May 12
ORD
PHF
6h 45m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 28211 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
DFW
SAN
Okay 5.3

Direct flight from desired origin to destination Boarding by zones

Uncomfortable, small, seat space with inadequate legroom. Lack of personal entertainment options. Paid extra for earlier boarding group which only benefited me by about 5 people. (NOT WORTH IT!) Lack of complimentary food options. (Pay for everything)

SJU
MIA
Excellent 9.3

New onboard entertainment

JAX
DFW
Excellent 8.6

Polite. Clean. Nice business class.

Would like more Western food.

CLT
LGA
Excellent 10.0

Ability to upgrade to first class

Security taking forever

LAS
DFW
Excellent 8.0

Flight was punctual and service was good.

Gate change

Sat, Mar 10
PHF
ORD
5h 29m
Tue, Mar 13
ORD
PHF
4h 24m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DTW
MEX
Excellent 8.3

Even though I was disappointed by not being able to get the boarding passes from Delta for Aeromexico’s connecting flight to Bogota, I had an agent greet me after customs in Mexico to issue the boarding pass so I could use the transfer flight line. Excellent service throughout the entire trip.

Confusion over my boarding pass at the Delta terminal in Detroit.

BOS
ATL
Okay 4.0

Comfort Plus allowed us to board early, useful USB ports.

BOS
BNA
Excellent 8.0

Service vey Good. Nice choices. Comfort seating very nice

WiFi awful. Useless.

GDL
ATL
Excellent 9.0

Staff was great!

No TV for movies.

SJC
SLC
Excellent 8.8

Good clean aircraft. Fairly comfortable seats. Even had a power outlet in my row. Not too bad for an aircraft from the late 70s.

for some reason, i had to pay to gate check a bag. It didnt seem like anyone else did while boarding my flight.

Tue, Apr 10
RIC
ORD
7h 21m
Wed, Apr 11
ORD
RIC
5h 40m
Trip: 2 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Mar 10
PHF
MDW
6h 22m
Tue, Mar 13
MDW
PHF
4h 24m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
MEX
Excellent 10.0

Flight was on time, crew was friendly, plane was clean, and boarding was painless and efficient. Food was served which was a huge plus. I appreciate having a choice of almonds for a snack.

ECP
ATL
Excellent 9.6

We have been on 6 flights over the last 8 days, all with Delta and we have already started telling people how wonderful the service was. Sherry on this last flight was amazing, working so hard all by herself as our flight attendant. We were very impressed. And the pilots all came out to say goodbye and thank you. All very nice...esp for me who needed some wheelchair assistance. We will certainly fly with you again in the future.

Smaller plane but ok for short flight

ATL
DTW
Excellent 10.0

Pls see above

BOS
JFK
Excellent 9.3

The volume controls on the tv we’re pretty poor. Was either too loud or too soft with only 5-6 volume settings.

SJC
SLC
Excellent 8.8

Good clean aircraft. Fairly comfortable seats. Even had a power outlet in my row. Not too bad for an aircraft from the late 70s.

for some reason, i had to pay to gate check a bag. It didnt seem like anyone else did while boarding my flight.

Fri, May 18
ORF
ORD
2h 14m
Mon, May 21
ORD
ORF
2h 10m
Trip: 4 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 49 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
ORF
ORD
Excellent 8.8

The plane was not very full...that made the experience so nice. All passengers were there early and boarded quickly allowing us to leave the ground ahead of schedule. They offer entertainment using their app on your phone or notepad.

ORF
ORD
Good 6.0

The flight was delayed 2 hours

ORF
ORD
Excellent 9.0

Clean newer plane. Nice staff. Smooth flight. Flight was on time

Tsa frisk

ORF
ORD
Excellent 10.0

Everything went well.

Just wish the planes had more leg room for the taller people.

ORF
ORD
Okay 4.6

The crew was pleasant.

Delayed for an excessive amount of time before the flight was finally Cancelled. Got stuck waiting for over 7hrs before the flight was eventually cancelled. Barley made it home in time for my grandfather's funeral as a result.

Tue, Jul 31
ORF
ORD
2h 27m
Mon, Aug 6
ORD
ORF
2h 03m
Trip: 7 days
7.4GoodShow reviews
Overall 7.4 Good
Based on 6 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
PHX
GEG
Good 7.3

The crew was friendly and informative. They were very helpful. The

The seats were uncomfortable. They were hard and so narrow I had to sit crooked in the seat to keep from getting banged into by the service carts and every person going by to the bathrooms. I'm not tiny, but I'm not huge either, it was just overcrowded. It was also very hot in the airplane the entire way from Phoenix to Spokane. My husband, who is always cold, was even hot.

ORF
ORD
Mediocre 3.6

Attitude of flight attendants.

CLT
ILM
Mediocre 3.0

Three hours delay. I paid for a upgrade to first class. But because of the flight change i didn't get to keep my upgrade and I had to beg for a refund. I have had two trips in the past 5 days and all flights have been anywhere from 1 to 3 hours late. Worst experience with AA I have had in a long time.

SJU
MIA
Excellent 9.3

New onboard entertainment

ORD
CLT
Mediocre 3.0

Three hours delay. I paid for a upgrade to first class. But because of the flight change i didn't get to keep my upgrade and I had to beg for a refund. I have had two trips in the past 5 days and all flights have been anywhere from 1 to 3 hours late. Worst experience with AA I have had in a long time.

Wed, Jun 13
ORF
ORD
2h 37m
Sat, Jun 16
ORD
ORF
2h 00m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Mar 10
ORF
MDW
6h 31m
Tue, Mar 13
MDW
ORF
3h 59m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ECP
ATL
Excellent 9.6

We have been on 6 flights over the last 8 days, all with Delta and we have already started telling people how wonderful the service was. Sherry on this last flight was amazing, working so hard all by herself as our flight attendant. We were very impressed. And the pilots all came out to say goodbye and thank you. All very nice...esp for me who needed some wheelchair assistance. We will certainly fly with you again in the future.

Smaller plane but ok for short flight

BOS
ATL
Okay 4.0

Comfort Plus allowed us to board early, useful USB ports.

ATL
JNB
Okay 4.0

Aircraft seemed shabby despite refresh of Comfort Plus, food was really mediocre. Steer clear of the Asian Veg option.

DTW
MEX
Excellent 8.3

Even though I was disappointed by not being able to get the boarding passes from Delta for Aeromexico’s connecting flight to Bogota, I had an agent greet me after customs in Mexico to issue the boarding pass so I could use the transfer flight line. Excellent service throughout the entire trip.

Confusion over my boarding pass at the Delta terminal in Detroit.

BOS
BNA
Excellent 8.0

Service vey Good. Nice choices. Comfort seating very nice

WiFi awful. Useless.

Fri, Aug 17
ORF
ORD
2h 37m
Sun, Aug 19
ORD
ORF
2h 03m
Trip: 3 days
7.4GoodShow reviews
Overall 7.4 Good
Based on 6 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
ORD
CLT
Mediocre 3.0

Three hours delay. I paid for a upgrade to first class. But because of the flight change i didn't get to keep my upgrade and I had to beg for a refund. I have had two trips in the past 5 days and all flights have been anywhere from 1 to 3 hours late. Worst experience with AA I have had in a long time.

ORF
ORD
Mediocre 3.6

Attitude of flight attendants.

JAX
DFW
Excellent 8.6

Polite. Clean. Nice business class.

Would like more Western food.

SJU
MIA
Excellent 9.3

New onboard entertainment

LAS
DFW
Excellent 8.0

Flight was punctual and service was good.

Gate change

Thu, Apr 5
SHD
ORD
2h 56m
Mon, Apr 9
ORD
SHD
2h 35m
Trip: 5 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 54591 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
DEN
PSP
Okay 4.3

Paid for Econoplus seat but was assigned a seat in the row before the emergency exit. Seat uncomfortable didn’t recline had to go through refund process

GRR
IAH
Good 6.0

Pay for food, cold on plane entire time, everyone bundled up in blankets, jackets but staff friendly

DFW
ORD
Excellent 10.0

I LIKE THE SERVICE ON BORD OF THE PLANE

NOTHING

IAD
GVA
Excellent 10.0

Best flight I have ever experienced!

Nothing

DEN
LAX
Okay 5.0

Great crew and process

For the fare, the leg room is not enough for average 6'0 person to be comfortable for longer than an hour.

Sat, Apr 21
PHF
MDW
7h 06m
Wed, Apr 25
MDW
PHF
5h 50m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DTW
YOW
Excellent 9.3

Please see above. Sherry was amazing

Plane was small and older but it was a short flight

ECP
ATL
Excellent 9.6

We have been on 6 flights over the last 8 days, all with Delta and we have already started telling people how wonderful the service was. Sherry on this last flight was amazing, working so hard all by herself as our flight attendant. We were very impressed. And the pilots all came out to say goodbye and thank you. All very nice...esp for me who needed some wheelchair assistance. We will certainly fly with you again in the future.

Smaller plane but ok for short flight

ATL
DTW
Excellent 10.0

Pls see above

BOS
JFK
Excellent 9.3

The volume controls on the tv we’re pretty poor. Was either too loud or too soft with only 5-6 volume settings.

SJC
SLC
Excellent 8.8

Good clean aircraft. Fairly comfortable seats. Even had a power outlet in my row. Not too bad for an aircraft from the late 70s.

for some reason, i had to pay to gate check a bag. It didnt seem like anyone else did while boarding my flight.

Tue, Apr 17
SHD
ORD
2h 55m
Tue, Apr 24
ORD
SHD
2h 35m
Trip: 8 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 54591 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
DEN
PSP
Okay 4.3

Paid for Econoplus seat but was assigned a seat in the row before the emergency exit. Seat uncomfortable didn’t recline had to go through refund process

DEN
IAH
Mediocre 2.0

Nothing

Never made it. Stuck in Denver.

SFO
SNA
Okay 5.0

Cold, not enough space for carry on

IAH
CUN
Mediocre 2.0

poor service, rude flight attendants, no leg room, dirty plane...

poor service, rude flight attendants, no leg room, dirty plane...

GRR
IAH
Good 6.0

Pay for food, cold on plane entire time, everyone bundled up in blankets, jackets but staff friendly

Tue, Apr 10
LYH
ORD
6h 47m
Wed, Apr 11
ORD
LYH
4h 24m
Trip: 2 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 28211 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
PHX
GEG
Good 7.3

The crew was friendly and informative. They were very helpful. The

The seats were uncomfortable. They were hard and so narrow I had to sit crooked in the seat to keep from getting banged into by the service carts and every person going by to the bathrooms. I'm not tiny, but I'm not huge either, it was just overcrowded. It was also very hot in the airplane the entire way from Phoenix to Spokane. My husband, who is always cold, was even hot.

DFW
FLL
Excellent 8.0

No issues at all

N/A

SAT
PHL
Excellent 8.0

I took American's first direct flight between Philadelphia and San Antonio. It was a nice plane, good service, and amenities for a cost. Love that the plane had plugs!

LAS
DFW
Excellent 8.0

Flight was punctual and service was good.

Gate change

ORD
CLT
Mediocre 3.0

Three hours delay. I paid for a upgrade to first class. But because of the flight change i didn't get to keep my upgrade and I had to beg for a refund. I have had two trips in the past 5 days and all flights have been anywhere from 1 to 3 hours late. Worst experience with AA I have had in a long time.

Thu, May 3
RIC
ORD
4h 32m
Sat, May 5
ORD
RIC
8h 21m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Apr 24
ORF
MDW
5h 23m
Tue, May 1
MDW
ORF
4h 36m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16027 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
BOS
BNA
Excellent 8.0

Service vey Good. Nice choices. Comfort seating very nice

WiFi awful. Useless.

GDL
ATL
Excellent 9.0

Staff was great!

No TV for movies.

ATL
JNB
Okay 4.0

Aircraft seemed shabby despite refresh of Comfort Plus, food was really mediocre. Steer clear of the Asian Veg option.

ATL
MEX
Excellent 10.0

Flight was on time, crew was friendly, plane was clean, and boarding was painless and efficient. Food was served which was a huge plus. I appreciate having a choice of almonds for a snack.

MSP
CUN
Mediocre 2.0

nothing

They lost my luggage.

Sat, Apr 14
PHF
ORD
4h 49m
Mon, Apr 16
ORD
PHF
5h 16m
Trip: 3 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 28211 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
LHR
ORD
Mediocre 2.0

Nothing really. I will never book from Kayak ever

Everything

ORD
CLT
Mediocre 3.0

Three hours delay. I paid for a upgrade to first class. But because of the flight change i didn't get to keep my upgrade and I had to beg for a refund. I have had two trips in the past 5 days and all flights have been anywhere from 1 to 3 hours late. Worst experience with AA I have had in a long time.

DFW
FLL
Excellent 8.0

No issues at all

N/A

CLT
ILM
Mediocre 3.0

Three hours delay. I paid for a upgrade to first class. But because of the flight change i didn't get to keep my upgrade and I had to beg for a refund. I have had two trips in the past 5 days and all flights have been anywhere from 1 to 3 hours late. Worst experience with AA I have had in a long time.

JAX
DFW
Excellent 8.6

Polite. Clean. Nice business class.

Would like more Western food.

Tue, May 8
RIC
ORD
9h 01m
Wed, May 9
ORD
RIC
6h 30m
Trip: 2 days
Overall 0.0 Poor
Based on 0 reviews

Virginia to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Virginia
Flight Price $191
Airlines United, JetBlue, American Airlines, Delta
*
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