Find Cheap Flights from Connecticut to Chicago

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Wed 2/21
Wed 2/28
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Book cheap flights from Connecticut to Chicago (round-trip)

Airports
Origin
New Haven
$148
only
$148
Hartford
$222
only
$222
Destination
Chicago
$148
only
$148
$424
only
$424
Wed, Mar 7
HVN
ORD
4h 33m
Thu, Mar 8
ORD
HVN
3h 51m
Trip: 2 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 28339 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
BCN
JFK
Okay 5.6

We booked american because it was a direct flight. No explanation was given for the switch. Then we almost missed our connection because we sat on the tarmak in Barcelona for an hour. Again no explanation . Very stressful and irritating.

Having the flight switched from a direct to transferring in Madrid.

TUS
CLT
Excellent 10.0

No free wifi

DTW
MIA
Excellent 8.0

Easy check in.

Service staff was friendly enough; maybe I’m used to southwest. As someone who is anxious to fly smiling faces are always appreciate.

PHL
MAD
Okay 5.0

When our flight was delayed in Denver the agent at the check in gate worked very hard to get our flight plans changed with as little impact as possible.

We understand that delays happen but due to a delay on American Airlines we have lost our luggage and it doesn't seem likely it will be returned. We had five pieces of luggage lost during our flight from the U.S. to Spain. When we arrived in Madrid we were told that all five pieces had been located. When we went to pick them up the next day there were only four pieces at the airport. We were told the fifth suitcase would be delivered when it was located. It's ten days later and there's no sign of the luggage. It has taken multiple phone calls to get the information about the luggage correct. They assure me that they have everything correctly documented and then when I call back they haven't changed a thing. It has been a very frustrating process overall.

ORD
CLE
Excellent 10.0

It was a very good fight

I didn't like the fact that the gate kept on changed 3-4 times and that it was delayed for an hour

Wed, Feb 28
BDL
ORD
12h 54m
Wed, Mar 7
ORD
BDL
12h 55m
Trip: 8 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 52841 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
TPA
BDL
Excellent 10.0

Flights arrived early

MCO
MSP
Okay 5.3

decent size plane with wide walking aisle, friendly staff

I will not fly the airline again due to the cheap quality seats, discomfort and lack of any entertainment. not to mention all the additional costs/fees they have separated from the cost of the flight.

MSY
MCO
Mediocre 3.6

We landed.

No free drinks available, not even water. Carry-on size limit is smaller than other airlines, which is deceptive. We sat on the tarmac waiting for another plane to move for 30 minutes after we landed.

MSP
MCO
Mediocre 2.3

NOTHING

VERY small aisle, seats were small and very uncomfortable. there was no entertainment and the extra fees for bags and even to have a drink of water or soda on the plane is ridiculous. I will not be flying spirit airlines again.

EWR
MYR
Excellent 10.0

With a receipt and they went above and beyond to locate me

Tue, Mar 20
HVN
ORD
5h 19m
Wed, Mar 28
ORD
HVN
3h 51m
Trip: 9 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 28339 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
BUF
PHL
Mediocre 2.0

None of the experience was pleasant

First flight was delayed causing us to miss the 2nd flight and we ended sleeping on a chair at the airport waiting for a morning flight. AMERICAN AIRLINES didn't even have the decency to put us in a hotel for the night due to their delay. Then they added a 2nd lay over which was delayed for hours also. Traveling was to visit my mother who had cancer and I was sick so this made the trip even more distasteful.

PHL
MAD
Okay 5.0

When our flight was delayed in Denver the agent at the check in gate worked very hard to get our flight plans changed with as little impact as possible.

We understand that delays happen but due to a delay on American Airlines we have lost our luggage and it doesn't seem likely it will be returned. We had five pieces of luggage lost during our flight from the U.S. to Spain. When we arrived in Madrid we were told that all five pieces had been located. When we went to pick them up the next day there were only four pieces at the airport. We were told the fifth suitcase would be delivered when it was located. It's ten days later and there's no sign of the luggage. It has taken multiple phone calls to get the information about the luggage correct. They assure me that they have everything correctly documented and then when I call back they haven't changed a thing. It has been a very frustrating process overall.

TUS
CLT
Excellent 10.0

No free wifi

DTW
MIA
Excellent 8.0

Easy check in.

Service staff was friendly enough; maybe I’m used to southwest. As someone who is anxious to fly smiling faces are always appreciate.

LHR
DFW
Excellent 8.0

Helpful and friendly ground crew in London.

The Muslim meal was a bit too spicy for me.

Tue, Apr 17
HVN
ORD
5h 02m
Tue, Apr 24
ORD
HVN
5h 23m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 28339 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
PHL
SFO
Good 7.6

Tight connection! The airlines need to Realize that a 2 hour layover is NOT enough when you have to go through immigration, customs, and security before making your next flight!

ORD
CLE
Excellent 10.0

It was a very good fight

I didn't like the fact that the gate kept on changed 3-4 times and that it was delayed for an hour

LHR
DFW
Excellent 8.0

Helpful and friendly ground crew in London.

The Muslim meal was a bit too spicy for me.

DFW
CMH
Excellent 8.0

Smooth takeoff and landing. The seats were comfortable for a 3 hour flight.

Stuffy on the plane. This might not be the airline’s problem but it was hot and the air vent didn’t cool me down.

BCN
JFK
Okay 5.6

We booked american because it was a direct flight. No explanation was given for the switch. Then we almost missed our connection because we sat on the tarmak in Barcelona for an hour. Again no explanation . Very stressful and irritating.

Having the flight switched from a direct to transferring in Madrid.

Tue, May 1
HVN
ORD
5h 02m
Tue, May 8
ORD
HVN
4h 27m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 28339 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
BCN
JFK
Okay 5.6

We booked american because it was a direct flight. No explanation was given for the switch. Then we almost missed our connection because we sat on the tarmak in Barcelona for an hour. Again no explanation . Very stressful and irritating.

Having the flight switched from a direct to transferring in Madrid.

SAT
MIA
Excellent 10.0

All

Nothing

CLT
RSW
Excellent 10.0

No free wifi

SAT
DFW
Excellent 8.0

Smooth takeoff and landing. The seats were comfortable for a 3 hour flight.

Nothing to complain about. I was satisfied with this flight.

BUF
PHL
Mediocre 2.0

None of the experience was pleasant

First flight was delayed causing us to miss the 2nd flight and we ended sleeping on a chair at the airport waiting for a morning flight. AMERICAN AIRLINES didn't even have the decency to put us in a hotel for the night due to their delay. Then they added a 2nd lay over which was delayed for hours also. Traveling was to visit my mother who had cancer and I was sick so this made the trip even more distasteful.

Fri, Mar 23
BDL
ORD
11h 17m
Mon, Mar 26
ORD
BDL
2h 03m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Feb 27
HVN
ORD
5h 14m
Mon, Mar 5
ORD
HVN
5h 54m
Trip: 7 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 28339 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
SAT
DFW
Excellent 8.0

Smooth takeoff and landing. The seats were comfortable for a 3 hour flight.

Nothing to complain about. I was satisfied with this flight.

DTW
MIA
Excellent 8.0

Easy check in.

Service staff was friendly enough; maybe I’m used to southwest. As someone who is anxious to fly smiling faces are always appreciate.

CLT
RSW
Excellent 10.0

No free wifi

PHL
MAD
Okay 5.0

When our flight was delayed in Denver the agent at the check in gate worked very hard to get our flight plans changed with as little impact as possible.

We understand that delays happen but due to a delay on American Airlines we have lost our luggage and it doesn't seem likely it will be returned. We had five pieces of luggage lost during our flight from the U.S. to Spain. When we arrived in Madrid we were told that all five pieces had been located. When we went to pick them up the next day there were only four pieces at the airport. We were told the fifth suitcase would be delivered when it was located. It's ten days later and there's no sign of the luggage. It has taken multiple phone calls to get the information about the luggage correct. They assure me that they have everything correctly documented and then when I call back they haven't changed a thing. It has been a very frustrating process overall.

DFW
CMH
Excellent 8.0

Smooth takeoff and landing. The seats were comfortable for a 3 hour flight.

Stuffy on the plane. This might not be the airline’s problem but it was hot and the air vent didn’t cool me down.

Mon, Mar 12
BDL
MDW
5h 59m
Thu, Mar 15
MDW
BDL
4h 50m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DTW
SLC
Okay 5.3

Its a 3.5 hr flight. No charging outlets available. Food options very limited by the time they got to me, row 26. No in -seat entertainment screen. Hard seats.

SLC
RAP
Excellent 8.6

Crowded boarding area, but no standing around for long. Quick boarding. Entertainment not available so can't rate that. Good crew

ATL
DCA
Good 6.6

The movie availability was very much appreciated.

Although my TSA Pre check number was on my flight coming into Atlanta, it wss not on my fight leaving Atlanta. That caused me to arrive at my gate 5 mins before boarding time and prevented me from having time to eat breakfast before my flight.

MEX
LAX
Excellent 10.0

The Delta flight was such a pleasant contrast to the funky Interjet flight that I took from L.A. to Mexico that my Economy Class felt like First Class.

ATL
SLC
Excellent 10.0

Quick boarding for a big plane. Lots of room for overhead luggage. Two beverage services. Nice crew!

Wed, Feb 28
HVN
ORD
4h 33m
Thu, Mar 1
ORD
HVN
3h 51m
Trip: 2 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 28339 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
SAT
DFW
Excellent 8.0

Smooth takeoff and landing. The seats were comfortable for a 3 hour flight.

Nothing to complain about. I was satisfied with this flight.

BUF
PHL
Mediocre 2.0

None of the experience was pleasant

First flight was delayed causing us to miss the 2nd flight and we ended sleeping on a chair at the airport waiting for a morning flight. AMERICAN AIRLINES didn't even have the decency to put us in a hotel for the night due to their delay. Then they added a 2nd lay over which was delayed for hours also. Traveling was to visit my mother who had cancer and I was sick so this made the trip even more distasteful.

TUS
CLT
Excellent 10.0

No free wifi

PHL
MAD
Okay 5.0

When our flight was delayed in Denver the agent at the check in gate worked very hard to get our flight plans changed with as little impact as possible.

We understand that delays happen but due to a delay on American Airlines we have lost our luggage and it doesn't seem likely it will be returned. We had five pieces of luggage lost during our flight from the U.S. to Spain. When we arrived in Madrid we were told that all five pieces had been located. When we went to pick them up the next day there were only four pieces at the airport. We were told the fifth suitcase would be delivered when it was located. It's ten days later and there's no sign of the luggage. It has taken multiple phone calls to get the information about the luggage correct. They assure me that they have everything correctly documented and then when I call back they haven't changed a thing. It has been a very frustrating process overall.

DFW
CMH
Excellent 8.0

Smooth takeoff and landing. The seats were comfortable for a 3 hour flight.

Stuffy on the plane. This might not be the airline’s problem but it was hot and the air vent didn’t cool me down.

Tue, Apr 10
BDL
ORD
13h 11m
Wed, Apr 11
ORD
BDL
12h 44m
Trip: 2 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 52841 reviews
Overall
5.7
Boarding
6.0
Comfort
5.3
Crew
6.4
Entertainment
4.5
Food
4.6
MCO
BDL
Good 6.3

Easy boarding, printing boarding passes,nice flight attendants, early arrival times, clean

The chairs don’t recline and very little leg room. Couldn’t go on a flight over 3 hours on spirit

MSP
MCO
Mediocre 2.3

NOTHING

VERY small aisle, seats were small and very uncomfortable. there was no entertainment and the extra fees for bags and even to have a drink of water or soda on the plane is ridiculous. I will not be flying spirit airlines again.

MSY
MCO
Mediocre 3.6

We landed.

No free drinks available, not even water. Carry-on size limit is smaller than other airlines, which is deceptive. We sat on the tarmac waiting for another plane to move for 30 minutes after we landed.

EWR
MYR
Excellent 10.0

With a receipt and they went above and beyond to locate me

DTW
MSY
Okay 4.6

Please at least give free cups of water. Every time I fly, someone needs a cup if water.

Wed, Mar 14
HVN
ORD
4h 33m
Fri, Mar 16
ORD
HVN
3h 51m
Trip: 3 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 28339 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
DFW
CMH
Excellent 8.0

Smooth takeoff and landing. The seats were comfortable for a 3 hour flight.

Stuffy on the plane. This might not be the airline’s problem but it was hot and the air vent didn’t cool me down.

SAT
MIA
Excellent 10.0

All

Nothing

SAT
DFW
Excellent 8.0

Smooth takeoff and landing. The seats were comfortable for a 3 hour flight.

Nothing to complain about. I was satisfied with this flight.

PHL
SFO
Good 7.6

Tight connection! The airlines need to Realize that a 2 hour layover is NOT enough when you have to go through immigration, customs, and security before making your next flight!

TUS
CLT
Excellent 10.0

No free wifi

Tue, May 29
HVN
ORD
5h 02m
Tue, Jun 12
ORD
HVN
6h 21m
Trip: 15 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 28339 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
BCN
JFK
Okay 5.6

We booked american because it was a direct flight. No explanation was given for the switch. Then we almost missed our connection because we sat on the tarmak in Barcelona for an hour. Again no explanation . Very stressful and irritating.

Having the flight switched from a direct to transferring in Madrid.

PHL
MAD
Okay 5.0

When our flight was delayed in Denver the agent at the check in gate worked very hard to get our flight plans changed with as little impact as possible.

We understand that delays happen but due to a delay on American Airlines we have lost our luggage and it doesn't seem likely it will be returned. We had five pieces of luggage lost during our flight from the U.S. to Spain. When we arrived in Madrid we were told that all five pieces had been located. When we went to pick them up the next day there were only four pieces at the airport. We were told the fifth suitcase would be delivered when it was located. It's ten days later and there's no sign of the luggage. It has taken multiple phone calls to get the information about the luggage correct. They assure me that they have everything correctly documented and then when I call back they haven't changed a thing. It has been a very frustrating process overall.

TUS
CLT
Excellent 10.0

No free wifi

DFW
CMH
Excellent 8.0

Smooth takeoff and landing. The seats were comfortable for a 3 hour flight.

Stuffy on the plane. This might not be the airline’s problem but it was hot and the air vent didn’t cool me down.

LHR
DFW
Excellent 8.0

Helpful and friendly ground crew in London.

The Muslim meal was a bit too spicy for me.

Fri, May 25
BDL
ORD
2h 39m
Mon, May 28
ORD
BDL
2h 03m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Apr 27
BDL
ORD
2h 39m
Sun, Apr 29
ORD
BDL
8h 19m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Mar 13
BDL
MDW
6h 02m
Wed, Mar 14
MDW
BDL
3h 47m
Trip: 2 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
DCA
Good 6.6

The movie availability was very much appreciated.

Although my TSA Pre check number was on my flight coming into Atlanta, it wss not on my fight leaving Atlanta. That caused me to arrive at my gate 5 mins before boarding time and prevented me from having time to eat breakfast before my flight.

DTW
RSW
Excellent 9.6

Free movies. Clean and modern look to airplane.

Could not get wifi to work.

ORD
LGA
Good 6.0

The crew and pilot were absolutely amazing.

This is my 3rd delta flight in a row that has been delayed. I understand these things happen, just extremely frustrating.

LAX
IND
Excellent 10.0

The comfort, space, quiet, snacks

DTW
SLC
Okay 5.3

Its a 3.5 hr flight. No charging outlets available. Food options very limited by the time they got to me, row 26. No in -seat entertainment screen. Hard seats.

Wed, Jun 6
HVN
ORD
5h 02m
Sat, Jun 9
ORD
HVN
6h 21m
Trip: 4 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 28339 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
LHR
DFW
Excellent 8.0

Helpful and friendly ground crew in London.

The Muslim meal was a bit too spicy for me.

CLT
RSW
Excellent 10.0

No free wifi

BCN
JFK
Okay 5.6

We booked american because it was a direct flight. No explanation was given for the switch. Then we almost missed our connection because we sat on the tarmak in Barcelona for an hour. Again no explanation . Very stressful and irritating.

Having the flight switched from a direct to transferring in Madrid.

BUF
PHL
Mediocre 2.0

None of the experience was pleasant

First flight was delayed causing us to miss the 2nd flight and we ended sleeping on a chair at the airport waiting for a morning flight. AMERICAN AIRLINES didn't even have the decency to put us in a hotel for the night due to their delay. Then they added a 2nd lay over which was delayed for hours also. Traveling was to visit my mother who had cancer and I was sick so this made the trip even more distasteful.

SAT
DFW
Excellent 8.0

Smooth takeoff and landing. The seats were comfortable for a 3 hour flight.

Nothing to complain about. I was satisfied with this flight.

Thu, Mar 15
BDL
MDW
4h 11m
Sat, Mar 17
MDW
BDL
4h 14m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
DCA
ATL
Excellent 10.0

The in-flight movie was very much appreciated.

ATL
DCA
Good 6.6

The movie availability was very much appreciated.

Although my TSA Pre check number was on my flight coming into Atlanta, it wss not on my fight leaving Atlanta. That caused me to arrive at my gate 5 mins before boarding time and prevented me from having time to eat breakfast before my flight.

DTW
RSW
Excellent 9.6

Free movies. Clean and modern look to airplane.

Could not get wifi to work.

LAX
SFO
Good 7.6

Crew was wonderful, fine flight, very prompt

Was unable to board an earlier flight without paying $75. If there are seats it shouldn't be so difficult to be moved.

MEX
LAX
Excellent 10.0

The Delta flight was such a pleasant contrast to the funky Interjet flight that I took from L.A. to Mexico that my Economy Class felt like First Class.

Tue, Jul 24
BDL
ORD
9h 25m
Fri, Jul 27
ORD
BDL
5h 20m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Apr 30
BDL
MDW
3h 59m
Tue, May 8
MDW
BDL
5h 26m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16124 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
SLC
Excellent 10.0

Quick boarding for a big plane. Lots of room for overhead luggage. Two beverage services. Nice crew!

LAX
SFO
Good 7.6

Crew was wonderful, fine flight, very prompt

Was unable to board an earlier flight without paying $75. If there are seats it shouldn't be so difficult to be moved.

ATL
DCA
Good 6.6

The movie availability was very much appreciated.

Although my TSA Pre check number was on my flight coming into Atlanta, it wss not on my fight leaving Atlanta. That caused me to arrive at my gate 5 mins before boarding time and prevented me from having time to eat breakfast before my flight.

LAX
IND
Excellent 10.0

The comfort, space, quiet, snacks

SLC
RAP
Excellent 8.6

Crowded boarding area, but no standing around for long. Quick boarding. Entertainment not available so can't rate that. Good crew

Sat, May 19
BDL
ORD
2h 33m
Sun, May 20
ORD
BDL
2h 03m
Trip: 2 days
Overall 0.0 Poor
Based on 0 reviews

Connecticut to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Connecticut
Flight Price $148
Airlines American Airlines, Spirit Airlines, Delta
*
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