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Connecticut to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Connecticut
Flight Price $237
Airlines American Airlines, Spirit Airlines, Delta, United Airlines

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

Airports
Origin
New Haven
$237
only
$237
Hartford
$281
only
$281
Destination
Chicago
$237
only
$237
$409
only
$409
Mon, Jul 1
HVN
Tweed-New Haven
ORD
Chicago O'Hare Intl
7h 22m
Sat, Jul 6
ORD
Chicago O'Hare Intl
HVN
Tweed-New Haven
4h 10m
Trip: 6 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,077 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
ORD
BCN
Okay 4.0

Pros: The entertainment and crew in flight(not the ticket crew)

Cons: First of all, We were delayed 5 hours, I did not know finnair was operated by American Airlines(I wouldn’t never bought this thickets) we so many issues with AA in the past that we refused to fly with them, on top of all this they were trying to split us up(2 times) I bought 2 ticket for a reason...

CLT
CLE
Mediocre 3.6

Cons: Economy cabin is not meant for anyone over 6' tall. Worst seats I have experienced on any airline. My knees were jammed against the seat on front of me the entire flight. The seats lacked cushion. My legs became numb 20 minutes into the flight. The most uncomfortable flight I have ever experienced.

DEN
ORD
Mediocre 2.3

Cons: We are delayed 7.5 hours dues to mechanical issues with our plane and told we would have to wait or book another flight the following day. American Airlines sucks!!!!

YYZ
ORD
Excellent 10.0

Pros: Fast boarding, flight relatively smooth, got to my destination pretty quickly as well.

ORD
PHX
Okay 5.0

Pros: Quick turnaround from incoming flight. Crew was friendly and efficient

Cons: Flight was delayed over 3 hours.

Fri, Sep 13
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare Intl
25h 18m
Sun, Sep 15
ORD
Chicago O'Hare Intl
BDL
Windsor Locks Bradley Intl
23h 11m
Trip: 3 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 59,057 reviews
Overall
5.8
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
OAK
LAS
Good 7.0

Pros: It was quick and easy

Cons: The seats are not comfortable for long trips they sit too straight up

MCO
GSO
Mediocre 2.0

Cons: Everything

FLL
PHL
Excellent 8.5

Pros: Easy travel

Cons: Easy travel. Until you get in a seat. Really uncomfortable. Even though this time I spent extra for a window seat. I thought it would be nice to lean on something since the seats don't recline at all. Still not good comfort wise.

SJU
FLL
Okay 4.0

Pros: friendly crew

Cons: flight was 3 hours behind schedule

DFW
LAX
Okay 4.6

Cons: The Flight was delayed 1hour 40 Min . My schedule is confused. But you and Spirit gave the delay information Andthen Healed

Fri, Oct 11
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare Intl
5h 30m
Mon, Oct 14
ORD
Chicago O'Hare Intl
BDL
Windsor Locks Bradley Intl
5h 55m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,835 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
ATL
ECP
Excellent 9.0

Pros: Quick flight

Cons: I wish there was a way to access the delta movies in small planes that don’t have seat back entertainment

SLC
MSO
Okay 5.2

Cons: There was huge issues with our original plane and the lady at the desk was horrible with communication to all the passengers waiting for the flight updates. The one time I finally asked her if there was any updates, after almost 1.5 hours of delay and waiting, she took a very rude and snappy tone.

ATL
MSN
Excellent 8.4

Cons: Wider seats, more leg room

MEX
JFK
Okay 4.3

Pros: The crew was extremely rude. They did not come to collect trash and so all passengers were left holding their coffee/ tea: beverages during bumpy landing.

Cons: Attendants were rude. I didnt understand why. Also, I purchased a window seat but there was no window in my row. I spent the majority of the flight feeling ill.

LGA
ATL
Good 7.6

Pros: Crew was good. As always not enough leg room if you are taller. Resent having to pay extra for more leg room.

Mon, Aug 12
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare Intl
2h 33m
Tue, Aug 20
ORD
Chicago O'Hare Intl
BDL
Windsor Locks Bradley Intl
2h 10m
Trip: 9 days
6.7GoodShow reviews
Overall 6.7 Good
Based on 42 reviews
Overall
7.3
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
DEN
DDC
Good 7.6

Cons: More turbulence, too much.

BDL
ORD
Mediocre 2.0

Cons: Flight was cancelled. Stayed on hold for over 2 hours to rebook.

BDL
ORD
Good 7.6

Pros: The roominess of the sets on this plane were excellent and the stewardesses were very friendly and accommodating .

BDL
ORD
Mediocre 2.0

Pros: Nothing

Cons: Canceled, delayed....delayed again and again! Spent over 7 hours at O'hare and had my IPad stolen in the process!! I will avoid flying United whenever possible! Had a MUCH better experience flying home on Delta!!!

GJT
DEN
Okay 5.5

Pros: Plane was delayed then we were switched to later flight.

Cons: Send another plane to get the three flights that were bumped.

Wed, Nov 6
HVN
Tweed-New Haven
ORD
Chicago O'Hare Intl
5h 33m
Sun, Nov 10
ORD
Chicago O'Hare Intl
HVN
Tweed-New Haven
5h 34m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,077 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
ORF
CLT
Excellent 8.0

Cons: Cramped seating and illogical boarding process

YYZ
ORD
Excellent 10.0

Pros: Fast boarding, flight relatively smooth, got to my destination pretty quickly as well.

PHX
JFK
Good 6.0

Pros: crew made me feel guilty to change my paid for seat so a married couple could sit together and I was solo

Cons: choice of snacks or food

PHX
JFK
Okay 4.8

Cons: Flight was delayed, flight was overbooked, and WiFi wasn't working on the plane, so no entertainment at all, as the plane had no screens and we were supposed to use our own devices.

GRU
DFW
Good 7.0

Pros: Used system wide upgrade to first class. Seat is spacious and comfortable. Mattress pad is a good addition.

Cons: Crew member serving 1st class was bad, average business was class crew is much nicer and more helpful

Thu, Oct 17
HVN
Tweed-New Haven
ORD
Chicago O'Hare Intl
7h 38m
Wed, Oct 23
ORD
Chicago O'Hare Intl
HVN
Tweed-New Haven
5h 34m
Trip: 7 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,077 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
CLT
DCA
Good 6.6

Pros: No entertainment system only for those who are vested with AA and using their app

Cons: A modern plane not old A320 without entertainment system

JFK
CLT
Mediocre 2.0

Pros: Nothing.

Cons: All. Crew did not arrive on time. Boarding was a mess. Many arguments with customers.

DFW
FCO
Excellent 9.3

Cons: Excelentt , Only delayed flight

DFW
BNA
Excellent 8.5

Pros: Pleasant and attentive crew

ANC
DFW
Mediocre 3.0

Pros: Nothing

Cons: Everything comfort communication

Wed, Jun 26
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare Intl
8h 54m
Thu, Jul 4
ORD
Chicago O'Hare Intl
BDL
Windsor Locks Bradley Intl
7h 37m
Trip: 9 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 59,057 reviews
Overall
5.8
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
MSY
BWI
Mediocre 2.0

Pros: Absolutely nothing was positive about this experience. The flight was delayed over 5 hours. The communication was atrocious and inconsistent. Absolutely no attempt was made to remedy what is the worst customer service experience that I’ve had in a very long time.

Cons: Everything. I ended up rebooking myself on a significantly more expensive flight on a different airline. The experience was terrible at every level- the gate, the airport, and the customer service line.

PHX
DFW
Okay 4.0

Cons: The flight was diverted and I missed my connecting flight. Spirit’s seats are uncomfortable.

LGA
DFW
Good 6.8

Pros: Price

Cons: More Comfortable seats

ORD
DEN
Good 7.0

Cons: Flight was delayed over an hour.

CUN
FLL
Excellent 8.0

Pros: Very friendly crew.

Sat, Aug 17
HVN
Tweed-New Haven
ORD
Chicago O'Hare Intl
5h 01m
Tue, Aug 20
ORD
Chicago O'Hare Intl
HVN
Tweed-New Haven
3h 46m
Trip: 4 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,077 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
MAF
DFW
Mediocre 3.3

Cons: Yo actually take off on time

LIR
MIA
Mediocre 2.0

Pros: Nothing

Cons: Flight was delayed 3 hours

CLT
RDU
Excellent 10.0

Cons: Landing

LAS
CLT
Mediocre 2.0

Cons: Organization on when the flight would be leaving. BETTER food vouchers. And prudence goes a long way

IAH
PHX
Mediocre 2.0

Cons: Smoke in cabin, has to return to Houston. Then they never transferred our luggage as promised.

Wed, Jul 24
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare Intl
19h 20m
Mon, Jul 29
ORD
Chicago O'Hare Intl
BDL
Windsor Locks Bradley Intl
8h 17m
Trip: 6 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 59,057 reviews
Overall
5.8
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
LAS
OAK
Okay 4.8

Pros: It was fast to get in the plane but stuff wise kind of lost when ask questions

Cons: Better communication with the customer

DEN
AUS
Excellent 9.3

Cons: Boarding not clear over overhead. 2 flights boarding at same time, both through spirit made things confusing for passengers. Speaker not loud and clear.

RDU
MCO
Mediocre 2.3

Cons: It was the most uncomfortable plane ever, had to pay $50 to bring a carry on, and the first flight was so late I almost missed my connection.

LAS
OAK
Okay 5.2

Pros: Crew was nice

Cons: Seat comfort.

DFW
BOS
Excellent 8.5

Pros: No frills

Cons: Everything was great

Tue, Jun 25
HVN
Tweed-New Haven
ORD
Chicago O'Hare Intl
6h 00m
Sat, Jun 29
ORD
Chicago O'Hare Intl
HVN
Tweed-New Haven
6h 10m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,077 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
DFW
PHL
Mediocre 2.0

Cons: The crew could not have been any less accommodating for a nursing mother flying without my baby and needing to pump. I will be writing and submitting an official complaint to American Airlines .

DFW
MIA
Excellent 10.0

Pros: Great crew, very attentive.

FLL
ORD
Excellent 10.0

Cons: Chicago to Venice flight was amazing. We were in premium economy, although the seats were larger it was hard to sleep in them, we all felt it needed some back support in order to sleep better. Crew was fantastic, would fly AA again internationally

DFW
ORD
Excellent 8.0

Pros: We were delayed due to inbound flight being late. Then weather set in, which delayed all flights outbound in ORD. The flight crew went above and beyond to make up for your delay.

CLT
CLE
Mediocre 3.6

Cons: Economy cabin is not meant for anyone over 6' tall. Worst seats I have experienced on any airline. My knees were jammed against the seat on front of me the entire flight. The seats lacked cushion. My legs became numb 20 minutes into the flight. The most uncomfortable flight I have ever experienced.

Fri, Oct 4
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare Intl
4h 55m
Sun, Oct 6
ORD
Chicago O'Hare Intl
BDL
Windsor Locks Bradley Intl
23h 11m
Trip: 3 days
5.6OkayShow reviews
Overall 5.6 Okay
Based on 59,057 reviews
Overall
5.8
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
PIT
LAX
Good 6.0

Pros: Simplicity

Cons: Nothing remotely close to comfort

LGA
DFW
Good 6.8

Pros: Price

Cons: More Comfortable seats

SAN
LAS
Okay 5.5

Pros: Nothing stands out...

Cons: Prices after added baggage fee.

PHL
MCO
Excellent 10.0

Pros: The crew was nice and the boarding process was simple.

Cons: Offering complimentary snack and a drink would have made it the best.

DEN
MSP
Excellent 9.0

Pros: Friendly flight attendants, on-time flight, simple boarding process.

Cons: Seat didn't recline which makes sleeping tough.

Fri, Sep 20
BDL
Windsor Locks Bradley Intl
MDW
Chicago Midway
5h 50m
Tue, Sep 24
MDW
Chicago Midway
BDL
Windsor Locks Bradley Intl
7h 03m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,813 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
ATL
ECP
Excellent 9.0

Pros: Quick flight

Cons: I wish there was a way to access the delta movies in small planes that don’t have seat back entertainment

MEX
DTW
Excellent 10.0

Cons: Todo excelente!!!gracias!!!

MSP
YUL
Good 6.6

Cons: Slow WiFi

JFK
BWI
Mediocre 2.0

Pros: Crew was nice

Cons: It would have been better if the flight wasn’t 3 hours late.

MDT
ATL
Mediocre 3.6

Cons: Worst first class service. Only came by twice in two hour flight

Tue, Jul 2
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare Intl
2h 29m
Mon, Jul 8
ORD
Chicago O'Hare Intl
BDL
Windsor Locks Bradley Intl
2h 09m
Trip: 7 days
6.7GoodShow reviews
Overall 6.7 Good
Based on 42 reviews
Overall
7.3
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
IAH
LHR
Excellent 10.0

Pros: Very nice leg room. This is one best flights I have been on. It was United Airlines 5. Definitely fly again.

BDL
ORD
Excellent 10.0

Pros: All of our flights left on time & arrived early. We had wonderful flight attendants as well.

Cons: Arriving in Chicago we had to wait to dock the plane and were not able to get up and use the restroom.

BDL
ORD
Excellent 10.0

Pros: Very nice flying out of Bradley. Flight was ahead of schedule (weather, of course, helped) Pilot was helpfully informative and friendly. Crew very pleasant.

BDL
ORD
Excellent 9.6

Pros: Everything went excellent for a snowey day! Flight was good!!!

GJT
DEN
Okay 5.5

Pros: Plane was delayed then we were switched to later flight.

Cons: Send another plane to get the three flights that were bumped.

Thu, Jun 13
BDL
Windsor Locks Bradley Intl
MDW
Chicago Midway
3h 35m
Sat, Jun 15
MDW
Chicago Midway
BDL
Windsor Locks Bradley Intl
3h 49m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,813 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
LGA
ATL
Good 7.6

Pros: Crew was good. As always not enough leg room if you are taller. Resent having to pay extra for more leg room.

JFK
AMS
Good 6.3

Pros: This was a Delta codeshare on KLM metal. We left on time and arrived early. The crew was very professional. The bathrooms were very clean.

Cons: The seat in Economy Comfort was awful. Not enough padding and no place to put my feet because of a very large entertainment control box on the floor.

SYD
LAX
Excellent 8.6

Cons: I really like more legs room and comfort and crew member were very good and helpful. Regarding food I say it’s just ok.

CDG
ATL
Excellent 10.0

Pros: Food and movies

ATL
ILM
Excellent 8.6

Cons: No wifi

Sat, May 25
HVN
Tweed-New Haven
ORD
Chicago O'Hare Intl
6h 53m
Sat, Jun 1
ORD
Chicago O'Hare Intl
HVN
Tweed-New Haven
4h 44m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,077 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
DFW
ORD
Excellent 8.0

Pros: We were delayed due to inbound flight being late. Then weather set in, which delayed all flights outbound in ORD. The flight crew went above and beyond to make up for your delay.

GCM
MIA
Excellent 10.0

Pros: We got to our destination safely and sooner than expected!

LAX
CLT
Excellent 9.3

Cons: New AA internet is NOT good. Much prefer GoGo. Otherwise a great flight.

ORF
CLT
Excellent 8.0

Cons: Cramped seating and illogical boarding process

DFW
CHA
Excellent 10.0

Pros: Right on time

Cons: Wife on board

Thu, Jun 20
BDL
Windsor Locks Bradley Intl
MDW
Chicago Midway
3h 35m
Tue, Jun 25
MDW
Chicago Midway
BDL
Windsor Locks Bradley Intl
4h 19m
Trip: 6 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,813 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
MSP
BOS
Good 7.3

Pros: individual TVs

Cons: it would be great if you could not use all those one-use plastic cups. waste is a real issue in the US and the solution is using re-usable items like washable cups. Unboarding was a nightmare and it started to get really hot waiting to get off.

MEX
LAX
Good 6.6

Pros: The entertainment system was good and they had free text messaging through the plane’s wifi network.

Cons: The plane stank. I was 3/4 in the back of the plane and there was a strong pee odor.

DTW
ATL
Excellent 8.6

Pros: The male in the crew was fantastic!!! As always love the entertainment options.

Cons: Uncomfortable. Stuffed between two large men.

ATL
AUS
Good 6.4

Cons: They could improve the boarding process.

AMS
JFK
Mediocre 3.6

Pros: Seat was uncomfortable and hard as a rock, confined and tight.

Cons: a new plane with more space and bigger seats, better service at T4 at arrivals, that place is a zoo

Wed, Jul 3
HVN
Tweed-New Haven
ORD
Chicago O'Hare Intl
6h 00m
Sat, Jul 6
ORD
Chicago O'Hare Intl
HVN
Tweed-New Haven
4h 07m
Trip: 4 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,077 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
DEN
ORD
Mediocre 2.3

Cons: We are delayed 7.5 hours dues to mechanical issues with our plane and told we would have to wait or book another flight the following day. American Airlines sucks!!!!

DFW
YUL
Mediocre 2.0

Cons: We stay stuck in PVR

CLT
RDU
Excellent 10.0

Cons: Landing

ORD
LAX
Excellent 9.2

Cons: Flight delayed one hour

DFW
PHL
Mediocre 2.0

Cons: The crew could not have been any less accommodating for a nursing mother flying without my baby and needing to pump. I will be writing and submitting an official complaint to American Airlines .

Wed, Jul 3
BDL
Windsor Locks Bradley Intl
MDW
Chicago Midway
3h 35m
Mon, Jul 8
MDW
Chicago Midway
BDL
Windsor Locks Bradley Intl
5h 56m
Trip: 6 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,813 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
BOS
ATL
Excellent 8.3

Cons: The flight attendants were quick with the pick up of drinks. I had only been served my drink for five minutes and they were already coming around to pick up trash.

MEX
JFK
Okay 4.3

Pros: The crew was extremely rude. They did not come to collect trash and so all passengers were left holding their coffee/ tea: beverages during bumpy landing.

Cons: Attendants were rude. I didnt understand why. Also, I purchased a window seat but there was no window in my row. I spent the majority of the flight feeling ill.

CUN
MCI
Mediocre 3.6

Pros: We had the worst flight ever on Delta flight worst Attitude of the flight attendant she was very Rude i even told her she was

Cons: We didn't get served nothing to drink until 45 min to kc then by then i was so dehydrated i asked for a can of pop she said NO I SAID REALLY SHE SAID DELTAS NOT IN CHARGE OF STOCKING DRINKS & SNACKS SHE HAD MORE PEOPLE' TO SERVE REALLY EVERBODY IN FRONT OF US GOT WHAT THEY WANTED SO I HAD NOTHIN AT

JFK
JAX
Okay 4.5

Cons: Late taking off. Let's leave on time

JFK
FLL
Good 7.6

Cons: Passengers should have the option to ask for additional snacks.

Sat, Jul 20
BDL
Windsor Locks Bradley Intl
MDW
Chicago Midway
3h 34m
Sat, Jul 27
MDW
Chicago Midway
BDL
Windsor Locks Bradley Intl
6h 20m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,813 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
FLL
ATL
Okay 4.3

Pros: The crew was polite and attentive the entertainment was good. Every thing else was pretty disappointing. The bathrooms onboard were pretty Dirty. The flight was delayed and no overhead baggage space. For such a long and delayed flight they gave me one pack of cheez it. Terrible value for money :(

Cons: More snacks considering the delay. Maybe even a some sort of credit for my time wasted.

BOS
ATL
Excellent 8.3

Cons: The flight attendants were quick with the pick up of drinks. I had only been served my drink for five minutes and they were already coming around to pick up trash.

PHL
ATL
Excellent 10.0

Cons: Safe and happy travel!

ATL
CLT
Excellent 10.0

Cons: The girls were sweet as usual!

GRR
ATL
Excellent 10.0

Pros: Crew was awesome. Movie was awesome. Delta always comes through.

Fri, Aug 9
BDL
Windsor Locks Bradley Intl
MDW
Chicago Midway
3h 35m
Wed, Aug 14
MDW
Chicago Midway
BDL
Windsor Locks Bradley Intl
4h 09m
Trip: 6 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,813 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
KIN
ATL
Excellent 8.0

Pros: For me the boarding was of fast

Cons: The food

ATL
CLT
Excellent 10.0

Cons: The girls were sweet as usual!

LGA
ATL
Good 7.6

Pros: Crew was good. As always not enough leg room if you are taller. Resent having to pay extra for more leg room.

LGA
ATL
Excellent 10.0

Pros: Yes

Cons: It was well executed flight

MSP
OMA
Excellent 10.0

Cons: Couldn't have been better

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