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Connecticut to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Connecticut
Flight Price $174
Airlines American Airlines, Spirit Airlines, Delta, United Airlines

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

Airports
Origin
New Haven
$174
only
$174
Hartford
$180
only
$180
Destination
Chicago
$174
only
$174
$344
only
$344
Sat, Feb 2
HVN
Tweed-New Haven
ORD
Chicago O'Hare International
5h 12m
Wed, Feb 6
ORD
Chicago O'Hare International
HVN
Tweed-New Haven
4h 10m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 36,421 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.8
Entertainment
6.8
Food
6.7
JFK
ORD
Mediocre 2.0

Cons: New York to Fresno Glight delayed 2 hours.

MXP
JFK
Excellent 9.3

Pros: punctual and crew was very nice

Cons: old aircraft so each seat didn't have individual screens for entertainment

DCA
MHT
Good 7.0

Cons: Commuter jet boarding at DCA is going to stink until the new terminal is completed. Just is.

MSP
DCA
Okay 5.0

Pros: Short flight. Connection was gate next door.

Cons: Seating was for waif midgets.

ORD
PHX
Mediocre 2.0

Cons: Flight Chicago to Phoenix didn’t arrived on time st gate and we missed flight to Fresno

Tue, Feb 5
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare International
8h 03m
Wed, Feb 6
ORD
Chicago O'Hare International
BDL
Windsor Locks Bradley Intl
6h 29m
Trip: 2 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 57,951 reviews
Overall
5.7
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
LAS
LAX
Excellent 8.0

Pros: Flight crew was very nice and flight was right on time.

Cons: Seats a little small but for the price I can take it.

FLL
LAX
Mediocre 2.0

Pros: Made it one piece

Cons: Delayed 45 min after boarding on hard seats and no a/c. It was a red eye flight and they wouldn’t turn off the main cabin lights so I couldn’t sleep. The other usual spirit shitty seats not padded, no full table, can’t recline and charge for everything including even water on a six hour flight.

BOS
MCO
Excellent 10.0

Pros: Spirit staff, clean plane Safe arrival

FLL
DEN
Good 6.3

Pros: Pretty good stuff (Guys From Nicaragüa Airport)

Cons: A boy sitting behind me, kicking my chair, hitting my head and pulling the backrest used to eat !. the whole trip I asked to be moved, but that did not happen! Also, no one from the staff asked their parents to behave and reassure their child. Soo terrible.

ORD
DFW
Mediocre 2.0

Pros: Nothing

Cons: Flight was delayed 5 hours.

Sat, Mar 2
BDL
Windsor Locks Bradley Intl
MDW
Chicago Midway
4h 17m
Tue, Mar 5
MDW
Chicago Midway
BDL
Windsor Locks Bradley Intl
4h 38m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,499 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
DEN
JFK
Excellent 9.3

Pros: Staff from Check in to aircraft very pleasant. Snack choice in Coach impressive.

JFK
DUB
Good 6.0

Pros: The flight crew was very competent and welcoming.

Cons: The gate agent at JFK was annoying. She forced us to check carry on bags for no apparent reason. Much larger carry on’s were allowed both before and after us. Her fellow agent seemed like she wanted to apologize for her capricious behavior, but was understandably hesitant to do so. The airplane seating was cramped and uncomfortable. The rntertainment choices were very limited unless you enjoy superhero movies or a very limited range of audio/musical selections. So it goes in coach class.

ICN
ATL
Excellent 10.0

Cons: All was good

JFK
BCN
Excellent 8.6

Pros: Good food, entertainment and Delta Comfort section worth the extra cost.

Cons: Boarding at JFK a nightmare.

ATL
JFK
Okay 4.6

Cons: Flying from New York to Atlanta on business class there was no access to the lounge because I was not flying to Lima on the same day. I bought the whole international business ticket to Peru together, I don't understand why Delta consider my first portion not part of my international ticket!

Wed, Apr 10
HVN
Tweed-New Haven
ORD
Chicago O'Hare International
7h 31m
Mon, Apr 15
ORD
Chicago O'Hare International
HVN
Tweed-New Haven
4h 04m
Trip: 6 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 36,421 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.8
Entertainment
6.8
Food
6.7
SAT
DFW
Okay 5.6

Pros: Both flights on time. Boarding slow but organized

CDG
PHL
Excellent 8.3

Pros: The inflight entertainment and WiFi was great.

Cons: The food could’ve been better

DCA
MHT
Good 7.0

Cons: Commuter jet boarding at DCA is going to stink until the new terminal is completed. Just is.

PHX
FAT
Mediocre 2.0

Cons: American Arline’s gave us a meal voucher and hotel stay. Left be t day. Not happy.

MXP
JFK
Excellent 9.3

Pros: punctual and crew was very nice

Cons: old aircraft so each seat didn't have individual screens for entertainment

Mon, Feb 4
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare International
17h 01m
Mon, Feb 11
ORD
Chicago O'Hare International
BDL
Windsor Locks Bradley Intl
21h 33m
Trip: 8 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 57,951 reviews
Overall
5.7
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
FLL
LAX
Mediocre 2.0

Pros: Made it one piece

Cons: Delayed 45 min after boarding on hard seats and no a/c. It was a red eye flight and they wouldn’t turn off the main cabin lights so I couldn’t sleep. The other usual spirit shitty seats not padded, no full table, can’t recline and charge for everything including even water on a six hour flight.

PBI
BOS
Excellent 10.0

Pros: smooth as ice

Cons: liked everything

FLL
DEN
Good 6.0

Cons: at least give water

FLL
DEN
Good 6.3

Pros: Pretty good stuff (Guys From Nicaragüa Airport)

Cons: A boy sitting behind me, kicking my chair, hitting my head and pulling the backrest used to eat !. the whole trip I asked to be moved, but that did not happen! Also, no one from the staff asked their parents to behave and reassure their child. Soo terrible.

LAS
LAX
Excellent 8.0

Pros: Flight crew was very nice and flight was right on time.

Cons: Seats a little small but for the price I can take it.

Mon, Jun 3
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare International
2h 33m
Tue, Jun 4
ORD
Chicago O'Hare International
BDL
Windsor Locks Bradley Intl
5h 39m
Trip: 2 days
6.7GoodShow reviews
Overall 6.7 Good
Based on 42 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
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 10.0

Pros: I like the television system

Cons: N/A

BDL
ORD
Excellent 8.0

Pros: Good price

Cons: No leg room even for a short person like me!

BDL
ORD
Good 7.3

Pros: Everyone was pleasant.

Cons: Delays due to staffing issues led to missed connection and 7 hour wait for next available flight.

BDL
ORD
Mediocre 2.0

Pros: I liked that I personally wasn't beaten in the face

Cons: I don't like United. They can suck a fat one.

Thu, Mar 28
HVN
Tweed-New Haven
ORD
Chicago O'Hare International
7h 25m
Sun, Mar 31
ORD
Chicago O'Hare International
HVN
Tweed-New Haven
3h 58m
Trip: 4 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 36,421 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.8
Entertainment
6.8
Food
6.7
JFK
ORD
Mediocre 2.0

Cons: New York to Fresno Glight delayed 2 hours.

ORD
PHX
Mediocre 2.0

Cons: Flight Chicago to Phoenix didn’t arrived on time st gate and we missed flight to Fresno

DCA
MHT
Good 7.0

Cons: Commuter jet boarding at DCA is going to stink until the new terminal is completed. Just is.

LAX
SLC
Good 6.0

Pros: Comfortable seating and attentive service

Cons: Remote terminal which required walking stairs with carry-on bags, and two bus rides to reach the plane. No food other than packaged snacks in first class. No seatback video screen.

PHX
FAT
Mediocre 2.0

Cons: American Arline’s gave us a meal voucher and hotel stay. Left be t day. Not happy.

Tue, Mar 5
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare International
16h 57m
Wed, Mar 6
ORD
Chicago O'Hare International
BDL
Windsor Locks Bradley Intl
6h 39m
Trip: 2 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 57,951 reviews
Overall
5.7
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
PBI
BOS
Excellent 10.0

Pros: smooth as ice

Cons: liked everything

LAS
LAX
Excellent 8.0

Pros: Flight crew was very nice and flight was right on time.

Cons: Seats a little small but for the price I can take it.

FLL
LAX
Mediocre 2.0

Pros: Made it one piece

Cons: Delayed 45 min after boarding on hard seats and no a/c. It was a red eye flight and they wouldn’t turn off the main cabin lights so I couldn’t sleep. The other usual spirit shitty seats not padded, no full table, can’t recline and charge for everything including even water on a six hour flight.

MGA
FLL
Okay 5.0

Cons: at least give water

ORD
DFW
Mediocre 2.0

Pros: Nothing

Cons: Flight was delayed 5 hours.

Wed, Jan 30
BDL
Windsor Locks Bradley Intl
MDW
Chicago Midway
12h 00m
Thu, Jan 31
MDW
Chicago Midway
BDL
Windsor Locks Bradley Intl
11h 45m
Trip: 2 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Jan 26
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare International
17h 01m
Tue, Jan 29
ORD
Chicago O'Hare International
BDL
Windsor Locks Bradley Intl
6h 29m
Trip: 4 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 57,951 reviews
Overall
5.7
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
CUN
BWI
Okay 5.0

Cons: The flight was delayed for almost 2 hours.

PBI
BOS
Excellent 10.0

Pros: smooth as ice

Cons: liked everything

MGA
FLL
Okay 5.0

Cons: at least give water

ATL
DTW
Good 6.0

Pros: The Pilot

Cons: I didn’t like the fact that the flight was delayed. Also, it's as if Spirit doesn’t have priority at the airports. After boarding we were delayed yet again due to some passengers standing around while the flight attendants scurry around to find them a seat. I don’t understand how this could happen since seats are assigned. The we pull into DTW and we taxi around like shoppers at the mall on Black Friday.

FLL
DEN
Good 6.0

Cons: at least give water

Fri, Feb 15
HVN
Tweed-New Haven
ORD
Chicago O'Hare International
4h 44m
Sun, Feb 17
ORD
Chicago O'Hare International
HVN
Tweed-New Haven
3h 57m
Trip: 3 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 36,421 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.8
Entertainment
6.8
Food
6.7
SAT
DFW
Okay 5.6

Pros: Both flights on time. Boarding slow but organized

JFK
ORD
Mediocre 2.0

Cons: New York to Fresno Glight delayed 2 hours.

ORD
PHX
Mediocre 2.0

Cons: Flight Chicago to Phoenix didn’t arrived on time st gate and we missed flight to Fresno

CDG
PHL
Excellent 8.3

Pros: The inflight entertainment and WiFi was great.

Cons: The food could’ve been better

LAX
SLC
Good 6.0

Pros: Comfortable seating and attentive service

Cons: Remote terminal which required walking stairs with carry-on bags, and two bus rides to reach the plane. No food other than packaged snacks in first class. No seatback video screen.

Wed, Mar 6
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare International
16h 57m
Fri, Mar 8
ORD
Chicago O'Hare International
BDL
Windsor Locks Bradley Intl
21h 39m
Trip: 3 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 57,951 reviews
Overall
5.7
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
MGA
FLL
Okay 5.0

Cons: at least give water

PHX
MSP
Good 7.0

Pros: The price the plane clean crew was very helpful personnel at check in helpful

Cons: Confusing instructions in kiosk on what is baggage

BOS
MCO
Excellent 10.0

Pros: Spirit staff, clean plane Safe arrival

FLL
DEN
Good 6.0

Cons: at least give water

ATL
DTW
Good 6.0

Pros: The Pilot

Cons: I didn’t like the fact that the flight was delayed. Also, it's as if Spirit doesn’t have priority at the airports. After boarding we were delayed yet again due to some passengers standing around while the flight attendants scurry around to find them a seat. I don’t understand how this could happen since seats are assigned. The we pull into DTW and we taxi around like shoppers at the mall on Black Friday.

Fri, May 31
HVN
Tweed-New Haven
ORD
Chicago O'Hare International
5h 33m
Sun, Jun 2
ORD
Chicago O'Hare International
HVN
Tweed-New Haven
5h 34m
Trip: 3 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 36,421 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.8
Entertainment
6.8
Food
6.7
RDU
LHR
Excellent 9.6

Pros: Crew was kind & friendly. They found my wife and I empty seats where we could stretch out. Food was great too. No complaints.

Cons: N/A

PHX
FAT
Mediocre 2.0

Cons: American Arline’s gave us a meal voucher and hotel stay. Left be t day. Not happy.

JFK
ORD
Mediocre 2.0

Cons: New York to Fresno Glight delayed 2 hours.

MSP
DCA
Okay 5.0

Pros: Short flight. Connection was gate next door.

Cons: Seating was for waif midgets.

PHL
BOS
Excellent 10.0

Pros: Great short flight

Wed, Apr 24
BDL
Windsor Locks Bradley Intl
MDW
Chicago Midway
4h 11m
Sat, Apr 27
MDW
Chicago Midway
BDL
Windsor Locks Bradley Intl
4h 34m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,499 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
LAX
AMS
Excellent 9.0

Cons: flight was delayed

JFK
DUB
Good 6.0

Pros: The flight crew was very competent and welcoming.

Cons: The gate agent at JFK was annoying. She forced us to check carry on bags for no apparent reason. Much larger carry on’s were allowed both before and after us. Her fellow agent seemed like she wanted to apologize for her capricious behavior, but was understandably hesitant to do so. The airplane seating was cramped and uncomfortable. The rntertainment choices were very limited unless you enjoy superhero movies or a very limited range of audio/musical selections. So it goes in coach class.

JFK
BCN
Excellent 8.6

Pros: Good food, entertainment and Delta Comfort section worth the extra cost.

Cons: Boarding at JFK a nightmare.

TPA
DTW
Excellent 9.6

Pros: The entire crew was hospitable & accommodating; I was very pleased with all of the flight crew!

Cons: My disappointment regarding my flight experience had nothing to do with the flight crew I met/seen/corresponded with; I was unhappy & displeased to pick up my new luggage with the top zippered broke off & missing.

ICN
ATL
Excellent 10.0

Cons: All was good

Thu, Mar 7
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare International
16h 11m
Fri, Mar 8
ORD
Chicago O'Hare International
BDL
Windsor Locks Bradley Intl
21h 39m
Trip: 2 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 57,951 reviews
Overall
5.7
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
FLL
LAX
Mediocre 2.0

Pros: Made it one piece

Cons: Delayed 45 min after boarding on hard seats and no a/c. It was a red eye flight and they wouldn’t turn off the main cabin lights so I couldn’t sleep. The other usual spirit shitty seats not padded, no full table, can’t recline and charge for everything including even water on a six hour flight.

ATL
DTW
Good 6.0

Pros: The Pilot

Cons: I didn’t like the fact that the flight was delayed. Also, it's as if Spirit doesn’t have priority at the airports. After boarding we were delayed yet again due to some passengers standing around while the flight attendants scurry around to find them a seat. I don’t understand how this could happen since seats are assigned. The we pull into DTW and we taxi around like shoppers at the mall on Black Friday.

MGA
FLL
Okay 5.0

Cons: at least give water

PBI
BOS
Excellent 10.0

Pros: smooth as ice

Cons: liked everything

FLL
DEN
Good 6.0

Cons: at least give water

Wed, May 15
BDL
Windsor Locks Bradley Intl
MDW
Chicago Midway
4h 02m
Sat, May 18
MDW
Chicago Midway
BDL
Windsor Locks Bradley Intl
4h 17m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,499 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
LAX
PDX
Mediocre 2.0

Pros: It was ok

Cons: They lost my suitcase. Now I have to wait a day or two and they won’t sent it to me.

LAX
AMS
Excellent 9.0

Cons: flight was delayed

ATL
FLL
Excellent 10.0

Cons: Everything was good!

PVR
ATL
Excellent 9.3

Pros: Great entertainment options!

Cons: The seats are still too small. I also wish there were hot options for food.

ATL
JFK
Okay 4.6

Cons: Flying from New York to Atlanta on business class there was no access to the lounge because I was not flying to Lima on the same day. I bought the whole international business ticket to Peru together, I don't understand why Delta consider my first portion not part of my international ticket!

Thu, Apr 18
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare International
2h 36m
Sun, Apr 21
ORD
Chicago O'Hare International
BDL
Windsor Locks Bradley Intl
2h 03m
Trip: 4 days
6.7GoodShow reviews
Overall 6.7 Good
Based on 42 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
BDL
ORD
Good 7.6

Pros: They checked my carry on at the gate in Hartford and said it would go through to me final destination and it wasn't in Cincinnati when I arrived. In fact that was yesterday and I still don't have my luggage.

BDL
ORD
Excellent 10.0

Pros: Short lines, rapid boarding, on time, & courteous agents!!!

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
Mediocre 2.0

Pros: I liked that I personally wasn't beaten in the face

Cons: I don't like United. They can suck a fat one.

BDL
ORD
Good 7.6

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

Sat, May 18
BDL
Windsor Locks Bradley Intl
MDW
Chicago Midway
4h 30m
Tue, May 21
MDW
Chicago Midway
BDL
Windsor Locks Bradley Intl
3h 56m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,499 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
JFK
DUB
Good 6.0

Pros: The flight crew was very competent and welcoming.

Cons: The gate agent at JFK was annoying. She forced us to check carry on bags for no apparent reason. Much larger carry on’s were allowed both before and after us. Her fellow agent seemed like she wanted to apologize for her capricious behavior, but was understandably hesitant to do so. The airplane seating was cramped and uncomfortable. The rntertainment choices were very limited unless you enjoy superhero movies or a very limited range of audio/musical selections. So it goes in coach class.

TPA
DTW
Excellent 9.6

Pros: The entire crew was hospitable & accommodating; I was very pleased with all of the flight crew!

Cons: My disappointment regarding my flight experience had nothing to do with the flight crew I met/seen/corresponded with; I was unhappy & displeased to pick up my new luggage with the top zippered broke off & missing.

ATL
FLL
Excellent 10.0

Cons: Everything was good!

DEN
JFK
Excellent 9.3

Pros: Staff from Check in to aircraft very pleasant. Snack choice in Coach impressive.

MIA
LGA
Excellent 8.3

Pros: Arrived on time and smooth flight though it was completely full

Wed, May 8
BDL
Windsor Locks Bradley Intl
ORD
Chicago O'Hare International
5h 05m
Thu, May 9
ORD
Chicago O'Hare International
BDL
Windsor Locks Bradley Intl
8h 14m
Trip: 2 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 57,951 reviews
Overall
5.7
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
PBI
BOS
Excellent 10.0

Pros: smooth as ice

Cons: liked everything

FLL
DEN
Good 6.0

Cons: at least give water

FLL
LAX
Mediocre 2.0

Pros: Made it one piece

Cons: Delayed 45 min after boarding on hard seats and no a/c. It was a red eye flight and they wouldn’t turn off the main cabin lights so I couldn’t sleep. The other usual spirit shitty seats not padded, no full table, can’t recline and charge for everything including even water on a six hour flight.

BOS
MCO
Excellent 10.0

Pros: Spirit staff, clean plane Safe arrival

MGA
FLL
Okay 5.0

Cons: at least give water

Thu, Jul 18
HVN
Tweed-New Haven
ORD
Chicago O'Hare International
5h 01m
Tue, Jul 23
ORD
Chicago O'Hare International
HVN
Tweed-New Haven
5h 19m
Trip: 6 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 36,421 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.8
Entertainment
6.8
Food
6.7
SAT
DFW
Okay 5.6

Pros: Both flights on time. Boarding slow but organized

RDU
LHR
Excellent 9.6

Pros: Crew was kind & friendly. They found my wife and I empty seats where we could stretch out. Food was great too. No complaints.

Cons: N/A

MSP
DCA
Okay 5.0

Pros: Short flight. Connection was gate next door.

Cons: Seating was for waif midgets.

PHL
BOS
Excellent 10.0

Pros: Great short flight

PHX
FAT
Mediocre 2.0

Cons: American Arline’s gave us a meal voucher and hotel stay. Left be t day. Not happy.

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