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Connecticut to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Connecticut
Flight Price $150
Airlines American Airlines, Spirit Airlines, Delta, United Airlines

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

Airports
Origin
New Haven
$150
only
$150
Hartford
$260
only
$260
Destination
Chicago
$150
only
$150
$374
only
$374
Sat, Apr 20
HVN
Tweed-New Haven
ORD
Chicago O'Hare Intl
5h 24m
Tue, Apr 23
ORD
Chicago O'Hare Intl
HVN
Tweed-New Haven
4h 04m
Trip: 4 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 37,781 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
PHX
ONT
Excellent 9.5

Cons: No concerns What I expected for a quick flight

LGA
DFW
Okay 5.2

Cons: Entertainment system for myself and my wife failed after an hour.

CUN
ORD
Excellent 10.0

Pros: I liked the big 787 plane and the in flight entertainment with individual TVs!

Cons: Not a huge fan of the captive audience announcements for the credit card and the meal pre-orders

JFK
MIA
Excellent 10.0

Pros: Calm no crowd organized and perfect

Cons: Umm

CLE
CLT
Excellent 8.0

Cons: Departing on time...30 minutes late.

Tue, May 14
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare Intl
26h 01m
Mon, May 20
ORD
Chicago O'Hare Intl
BDL
Windsor Locks Bradley Intl
18h 02m
Trip: 7 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 58,568 reviews
Overall
5.8
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
IAH
BWI
Good 6.0

Pros: Very tight seating

ATL
BWI
Good 6.4

Cons: Please offer free water.

MSY
EWR
Okay 5.0

Pros: The lady crew members were well dressed, helpful and very nice.

ORD
MSY
Excellent 8.8

Pros: Very friendly crew

Cons: Head rests

BWI
MCO
Okay 5.3

Pros: Great prices

Cons: Seats are uncomfortable

Tue, Jun 18
HVN
Tweed-New Haven
ORD
Chicago O'Hare Intl
6h 00m
Sat, Jun 22
ORD
Chicago O'Hare Intl
HVN
Tweed-New Haven
6h 10m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 37,781 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
DFW
OAK
Excellent 10.0

Pros: Comfortable seat

Cons: Umm, maybe a tv in the headrest

AVL
CLT
Excellent 8.3

Cons: Be on time. Also we sat in first class and it would be nice if the center counsel was smaller giving the passengers more seat room.

DCA
ORD
Okay 5.6

Pros: Nice seating

Cons: They asked who would give there seat up for 600$ future flight credit and The first two people could be eligible. They ignored me (who was first) for a white couple who Came after me, and they got chosen and got the flight credit, but I was as clearly first. So I think it was more of a racist matter

LAX
LHR
Excellent 8.3

Cons: We had a good trip

LGA
DFW
Okay 5.2

Cons: Entertainment system for myself and my wife failed after an hour.

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 10m
Trip: 4 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 37,781 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
SMF
PHX
Mediocre 3.6

Pros: Seat uncomfortable. AA put me on a middle seat in my last 4 trips. I will never fly with AA.

Cons: Better seat options.

BOS
MIA
Good 7.3

Pros: Seat was not comfortable

Cons: Need more room

EGE
JFK
Excellent 8.0

Cons: Leg room

SNU
MIA
Excellent 8.0

Cons: Okey

MDT
PHL
Okay 5.3

Pros: Plane was late missed all connecting flights

Tue, Apr 16
BDL
Windsor Locks Bradley Intl
MDW
Chicago Midway
4h 39m
Tue, Apr 23
MDW
Chicago Midway
BDL
Windsor Locks Bradley Intl
4h 08m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,631 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
BOS
SEA
Excellent 10.0

Pros: The crew was so lovely and accommodating, flight was smooth, and I was impressed with the meal service. I travel a lot and this was one of my best experiences. I will definitely favor Delta in the future.

MCO
IND
Good 7.6

Pros: The flight timings and the arrival time

AMS
BOS
Excellent 10.0

Pros: Good seating, great food, good service.

DTW
BWI
Excellent 10.0

Cons: Excellent

SLC
SFO
Okay 5.6

Pros: Nice new seats

Cons: Was too warm inside the plane. Boarding address was mobbed and not very well managed

Sat, Apr 13
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare Intl
2h 46m
Mon, Apr 15
ORD
Chicago O'Hare Intl
BDL
Windsor Locks Bradley Intl
2h 02m
Trip: 3 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
OGG
LAX
Mediocre 3.0

Pros: Haven't flown United, now we remember why. Paid extra for comfort and the seats we had were actually more cramped than those around our seating. A long trip with no food, unless you want to pay more than a high end restaurant in Maui. No entertainment made a long, uncomfortable flight unbearable.

BDL
ORD
Excellent 10.0

Pros: The United Wi-Fi that I paid for with my frequent flyer miles and the free entertainment via the United App

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: absolutely nothing

Cons: both flights were delayed, both planes needed maintenance, no reimbursement for inconvenience and for upgrades that were not fulfilled, customer service not helpful whatsoever and the chairs would not recline and the window slider would not go down on the plane. Never ever flying United ever again!

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!!!

Tue, Jun 11
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare Intl
5h 14m
Mon, Jun 17
ORD
Chicago O'Hare Intl
BDL
Windsor Locks Bradley Intl
8h 12m
Trip: 7 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 58,568 reviews
Overall
5.8
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
MGA
FLL
Excellent 8.0

Cons: The seats are just uncomfortable for longer flights They are narrow ( thank god I’m thin) and hard May have to reconsider Spirit for another airline on longer flights

LAX
MSP
Good 7.5

Pros: This was our first trip flying on Spirit Airlines. I was surprised at how simple it was to check in, once I figured out their site is built for mobile used more than computer use, and how good the flight was. We had good non-stop flights and the crew was great!

EWR
MYR
Excellent 10.0

Pros: Unfortunately I wasn't able to make my flight due to death in the family

LAS
MSP
Excellent 9.0

Pros: The crew was one of the best I have had on spirit.

Cons: nothing really, the few small things are ones that can’t change.

PHL
FLL
Mediocre 2.0

Pros: Nothing.

Cons: The crew was extremely rude and aggressive. Even a snack you had to pay for.

Fri, Sep 20
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare Intl
4h 55m
Mon, Sep 23
ORD
Chicago O'Hare Intl
BDL
Windsor Locks Bradley Intl
23h 26m
Trip: 4 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 58,568 reviews
Overall
5.8
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
PHL
FLL
Mediocre 2.0

Pros: Nothing.

Cons: The crew was extremely rude and aggressive. Even a snack you had to pay for.

MSY
EWR
Okay 5.0

Pros: The lady crew members were well dressed, helpful and very nice.

ORD
FLL
Excellent 9.0

Pros: I wasn’t expecting much from a “discount” airline but was pleasantly surprised by the crew and over all experience

Cons: Roomier Seats

MCO
BDL
Okay 4.5

Cons: This airline looked cheaper than the others at first but then hit you with a lot of fees for like carry-on baggage which is usually free. The seats are super uncomfortable sort of a kin to bolted down lawn chairs. No entertainment and no free food.

BWI
MCO
Okay 5.3

Pros: Great prices

Cons: Seats are uncomfortable

Mon, Mar 25
HVN
Tweed-New Haven
ORD
Chicago O'Hare Intl
7h 18m
Mon, Apr 1
ORD
Chicago O'Hare Intl
HVN
Tweed-New Haven
3h 58m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 37,781 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
MCO
JFK
Excellent 9.5

Cons: The hardest thing about any air travel is cramp seats in coach. That being said, AA makes the best of your cramp quarters with free online movies and television, and a power outlet for your cell on the headrest in front of you, which is so convenient and makes up for the tight seating!

DFW
LAX
Okay 5.2

Pros: The 787 is a nice aircraft

Cons: It should not take 2 hours from touchdown to the terminal. The flight arrived early but by the time the last passenger made it to the terminal, they probably missed their connection.

JAX
CLT
Mediocre 3.6

Cons: The crew was great, but AA needs to step it up with comfort and amenities!

LAX
ATL
Excellent 9.6

Cons: Crew serving food passed me by by, seemed rushed and missed my row.

ORD
SJD
Okay 4.8

Pros: Crew was friendly.

Cons: 4.5 hour flight to international destination and no meal provided. As usual, if you want a snack pay more. Slow chaotic boarding.

Sat, Apr 27
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare Intl
11h 10m
Mon, Apr 29
ORD
Chicago O'Hare Intl
BDL
Windsor Locks Bradley Intl
14h 09m
Trip: 3 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 58,568 reviews
Overall
5.8
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
DEN
FLL
Mediocre 2.0

Pros: I had to change my flight and you charged me close to 500.00 from Denver to Fort Lauderdale! Rip off!!!!!

Cons: I had to change my flight and you charged me close to 500.00 from Denver to Fort Lauderdale! Rip off!!!!!

ORD
FLL
Excellent 9.0

Pros: I wasn’t expecting much from a “discount” airline but was pleasantly surprised by the crew and over all experience

Cons: Roomier Seats

LAX
DTW
Excellent 9.3

Pros: Seats were comfortable

KIN
FLL
Okay 4.5

Cons: Flight delayed 4h. No real communication about reason for delay.

DEN
ORD
Mediocre 3.6

Cons: the flight attendants could have acted in a professional manner not like they were ten years old

Wed, May 1
HVN
Tweed-New Haven
ORD
Chicago O'Hare Intl
7h 31m
Thu, May 2
ORD
Chicago O'Hare Intl
HVN
Tweed-New Haven
6h 11m
Trip: 2 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 37,781 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
DCA
ORD
Okay 5.6

Pros: Nice seating

Cons: They asked who would give there seat up for 600$ future flight credit and The first two people could be eligible. They ignored me (who was first) for a white couple who Came after me, and they got chosen and got the flight credit, but I was as clearly first. So I think it was more of a racist matter

BOS
PHX
Good 6.8

Cons: PHX airport baggage claim was a mess. I had to wait 40 min to pick up the luggages.

STL
CLT
Mediocre 3.6

Cons: 2 hour delays on both flights of a round trip

PHX
SJO
Okay 4.0

Pros: 4 flights and all of them in middle uncomfortable seats. I requested aisle seats many times and counter agents were unhelpful and rude.

Cons: Better seat options and more comfortable seats

DFW
OAK
Excellent 10.0

Pros: Comfortable seat

Cons: Umm, maybe a tv in the headrest

Tue, May 7
BDL
Windsor Locks Bradley Intl
MDW
Chicago Midway
3h 50m
Sat, May 11
MDW
Chicago Midway
BDL
Windsor Locks Bradley Intl
3h 52m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,631 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
SEA
SAN
Excellent 10.0

Pros: It was a nice flight. No troubles

Cons: Nothing

JAX
JFK
Good 7.3

Cons: No in flight entertainment

DTW
PHX
Excellent 10.0

Pros: All was good

Cons: All was good

DCA
JFK
Okay 4.0

Cons: Virgin Atlantic has had better days. Living off of a long gone reputation. Great staff but old and worn out planes. Code sharing has done them no favors!

CHS
ATL
Okay 5.0

Cons: I had window seats on all flights and was boarded after those in middle/aisle seats 3 out of 4 times. Less legroom in the cheap seats. High whining pitch on speaker during announcements on last leg.

Fri, May 10
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare Intl
26h 01m
Mon, May 13
ORD
Chicago O'Hare Intl
BDL
Windsor Locks Bradley Intl
18h 02m
Trip: 4 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 58,568 reviews
Overall
5.8
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
LAX
OAK
Okay 5.3

Pros: The flight was pretty empty, so I had a whole row to myself.

Cons: Seats were very small and uncomfortable, as is the Spirit standard. Flight attendants also insisted on me staying my assigned seat until after takeoff, despite there being only about 30 people on board the entire flight.

FLL
PAP
Excellent 10.0

Cons: All was great

LAS
MSP
Excellent 9.0

Pros: The crew was one of the best I have had on spirit.

Cons: nothing really, the few small things are ones that can’t change.

IAH
BWI
Good 6.0

Pros: Very tight seating

EWR
SDQ
Mediocre 2.0

Pros: The airline delayed for an hour and checked bags did. Or arrive with flight. Had to wait more than 10 hours for my lost luggage to arrive at airport

Cons: Checked in bag got lost and had to wait mor than 10 hours to pick it up from another flight. Flight was delayed for more than an hour

Tue, Jun 25
BDL
Windsor Locks Bradley Intl
MDW
Chicago Midway
5h 46m
Tue, Jul 2
MDW
Chicago Midway
BDL
Windsor Locks Bradley Intl
6h 25m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,631 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
LAS
YYC
Mediocre 3.0

Pros: Seats were horrible, we all booked together and a bunch of my group got bumped to a different flight.

AMS
BOS
Excellent 10.0

Pros: Good seating, great food, good service.

LAX
SYD
Good 7.6

Pros: The staff was friendly and helpful

Cons: Outlets to charge my electronic devices for the long flight

SJD
ATL
Excellent 8.3

Pros: The crew very nice and helpful

ATL
BOS
Good 6.6

Pros: Delta in flight entertainment is great.

Cons: Always delayed.

Thu, Aug 29
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare Intl
2h 35m
Sun, Sep 1
ORD
Chicago O'Hare Intl
BDL
Windsor Locks Bradley Intl
2h 05m
Trip: 4 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
BDL
ORD
Excellent 10.0

Pros: I liked the comfortable seat and the empty seat between myself and the other passenger in my row. Staff were lovely and very friendly.

Cons: N/A

DEN
LAX
Mediocre 3.6

Pros: Customer Service was kind and helpful.

Cons: When there was a ground delay, Desk checkin people should not have said go get something to eat when the flight was delayed an hour. Apparently the captain sped up the departure and me and a whole row of people missed the flight despite sitting in front of them with the plane still at gate.

SFO
ORD
Okay 4.5

Pros: Crew was fine. Comfort zero.

Cons: I had to get out of the seat in order to reposition myself

BDL
ORD
Good 6.6

Pros: Free drink

Cons: Hard seats

SFO
RDD
Excellent 10.0

Pros: Good crew, good and safe flight. Thank you!

Cons: Nothing.

Thu, Aug 15
HVN
Tweed-New Haven
ORD
Chicago O'Hare Intl
7h 38m
Mon, Aug 19
ORD
Chicago O'Hare Intl
HVN
Tweed-New Haven
5h 34m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 37,781 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
DFW
OAK
Excellent 10.0

Pros: Comfortable seat

Cons: Umm, maybe a tv in the headrest

ORD
SJC
Okay 4.3

Cons: A toilet had no water. The internet was not working for the whole flight

MIA
EYW
Excellent 10.0

Cons: Nothing the flight was great and very fast.

SNU
MIA
Excellent 8.0

Cons: Okey

YUL
ORD
Good 6.4

Pros: Seat upgrade.

Sat, Jun 8
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare Intl
7h 22m
Thu, Jun 13
ORD
Chicago O'Hare Intl
BDL
Windsor Locks Bradley Intl
8h 12m
Trip: 6 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 58,568 reviews
Overall
5.8
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
BWI
RSW
Good 7.6

Cons: Airfare price was great but a lot of other charges Luggage charge if you’re luggage was over fourty pound usually fifty pounds Beverage charge of three dollars-free on other airlines

PHX
ORD
Excellent 8.6

Cons: Luggage never came

LAS
MSP
Excellent 9.0

Pros: The crew was one of the best I have had on spirit.

Cons: nothing really, the few small things are ones that can’t change.

BWI
MCO
Okay 5.3

Pros: Great prices

Cons: Seats are uncomfortable

RSW
MSP
Excellent 8.0

Pros: Nice crew, big aisle, early arrival, no terrible passengers near me

Cons: Seats that recline, free water

Fri, Aug 30
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare Intl
2h 33m
Mon, Sep 2
ORD
Chicago O'Hare Intl
BDL
Windsor Locks Bradley Intl
2h 10m
Trip: 4 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
ORD
LAX
Excellent 9.5

Cons: Longer seat belts

BDL
ORD
Excellent 10.0

Pros: I like the television system

Cons: N/A

BOI
SFO
Good 6.4

Pros: Yes, crew were great, seat was okay

Cons: Have life vests on board for the crew, was delayed over 2 1/2 hours on run way!

BDL
ORD
Excellent 10.0

Pros: The United Wi-Fi that I paid for with my frequent flyer miles and the free entertainment via the United App

BOI
SFO
Excellent 10.0

Pros: Good crew, good and safe flight. Thank you!

Cons: Nothing.

Mon, Jul 8
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare Intl
5h 31m
Sat, Jul 20
ORD
Chicago O'Hare Intl
BDL
Windsor Locks Bradley Intl
4h 41m
Trip: 13 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,593 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
SLC
SFO
Okay 5.6

Pros: Nice new seats

Cons: Was too warm inside the plane. Boarding address was mobbed and not very well managed

LAX
SAN
Good 6.0

Pros: Crew was nice, despite multiple hoardings and time delays.

Cons: Plane was originally set to leave at 11:30 am, but was delayed until 3:00 pm for equipment. We boarded the plane at 3:00, the door was closed, and 30 minutes of waiting at the gate, where told to deplane, and the flight would leave at 5:06. There was another flight to San Diego, also delayed for hou

DTW
BWI
Excellent 10.0

Cons: Excellent

PWM
ATL
Excellent 9.2

Pros: Flight attendants were very friendly.

JFK
SAN
Good 6.0

Pros: Very professional crew.

Cons: The plane was delayed 1 and a half hours getting out of the gate because of a malfunctioning fuel gauge

Mon, Mar 25
HVN
Tweed-New Haven
ORD
Chicago O'Hare Intl
7h 36m
Wed, Mar 27
ORD
Chicago O'Hare Intl
HVN
Tweed-New Haven
3h 58m
Trip: 3 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 37,781 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
BOS
JFK
Excellent 9.2

Pros: The crew was really nice and helpful.

Cons: The flight was delayed for awhile and there was little information on an ETA of when we would be able to leave.

PHX
SJO
Okay 4.0

Pros: 4 flights and all of them in middle uncomfortable seats. I requested aisle seats many times and counter agents were unhelpful and rude.

Cons: Better seat options and more comfortable seats

LGA
DFW
Okay 5.2

Cons: Entertainment system for myself and my wife failed after an hour.

EGE
JFK
Excellent 8.0

Cons: Leg room

CRW
CLT
Mediocre 3.6

Pros: I liked that we arrived on time. Besides that. Not much.

Cons: Having to us use our cell phones to watch a few channels was terrible. No movie. No help. You were just left on your own. Total of waste of time. Give us a monitor. Give us options. You are American Airlines, not Allegiant Air

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