Find Cheap Flights from Bermuda to Chicago

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Wed 1/17
Wed 1/24
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Book cheap flights from Bermuda to Chicago (round-trip)

Airports
Origin
Hamilton
$279
only
$279
Destination
Chicago
$279
only
$279
$455
only
$455
Wed, Mar 14
BDA
ORD
17h 22m
Thu, Mar 15
ORD
BDA
21h 51m
Trip: 2 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27225 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
MAD
PHL
Good 7.0

We shopped price, this was the most affordable flight for us.

Getting seat reservations should be easier and sooner.

GDL
DFW
Good 6.3

Friendly staff

Food was terrible and the seats tight

PHL
LHR
Good 7.3

Range of entertainment options, one crew member was terrific

Comfort of bed, some crew members snarky, old aircraft

DFW
COS
Excellent 10.0

Great service

FCO
PHL
Okay 4.3

Not much.

The flight was late due to maintenance and caused us to miss our connecting flight to Chicago. American Airlines customer assistance at the airport was absolutely terrible. They were rude and inconsiderate as they kept suggesting to fly standby. We shouldn't have to fly standby when it wasn't our fault why were late. They told us our bags would be ok going to Chicago and they we would make the flight, but we did not. I do not know why didn't wait for us considering there were 8 others that also missed the connecting flight. We had to fly to Denver and stay overnight with no luggage and catch a 7:00am flight to Chicago. The last surprise I received was my damaged bag when I got back to Chicago. Thank you for making this trip memorable in a terrible way. I will never book or recommend Kayak or use American Airlines again.

Wed, May 16
BDA
ORD
11h 05m
Mon, May 21
ORD
BDA
12h 24m
Trip: 6 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 7661 reviews
Overall
8.2
Boarding
8.2
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
PBI
HPN
Excellent 10.0

Up to expectation; on time, smooth check in with kiosk, efficient and courteous TSA security line, clear navigational sign, bookstore, clean windows, clean seat, and clean air.

waiting area after security checkpoint is a little too tight at West Palm Beach International Airport.

FLL
HPN
Excellent 10.0

Seems to be a problem between airline and county. Differing info about gate location.

FLL
DTW
Okay 5.3

Delayed flights.

BNA
FLL
Good 7.0

Every single employee I interacted with was awesome.

Over 5 hours in delay due to a maintenance issue. Problem wasn't discovered overnight when it was parked. Wasn't discovered until the next day. Had to wait for the delivery of a specific part and install it. I'm all for planes not breaking upon reentry, but the fact that the two flights were both subsequently delayed 4-5 hours each instead of bringing in a sub plane was inconsiderate. Now I've got a long drive home and I'll only get an hour of sleep before a 14-hour work day. So thanks for that, JetBlue

SDQ
JFK
Okay 4.6

The one thing I liked was the expedited service I got because my brother needed a wheelchair. The comfort of the plane was really nice as well, one of the best flights I had in a while.

What I didn’t like was how my flight got cancelled and the only flight I was able to get was 4 days later. So I was stuck in the Dominican Republic for a total of two weeks!! I had to miss another weekend at work which made me lose a lot of money since I’m a barber and lost some one my clientele. On top of my flight being cancelled it also got delayed again but only by 30 minutes so I wasn’t so upset. When it came to the boarding, that had to be the slowest boarding I’ve went through. The gate seemed very behind on the technology and that caused the workers to work even slower. At times they had to step away and go on their monitor to fix something out so it took an extra 30 minutes before I even got into my seat, and I was sitting in row 6 of the plane. Then after everyone was seated the flight got held back an extra half hour because a lady wanted to file a complaint saying that she got pushed and ended up being the only person that got kicked off the flight so she did it all for nothing. So with everything happening, our flight got delayed an hour and a half. Very disappointed..

Wed, Mar 14
BDA
ORD
6h 51m
Wed, Mar 21
ORD
BDA
5h 25m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Sun, Feb 25
BDA
ORD
9h 49m
Thu, Mar 1
ORD
BDA
6h 40m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SYR
JFK
Good 7.0

Nothing Special

LAX
CUN
Mediocre 2.6

Terrible customer service both on the phone before the flight, but Especially from the gate agent. Wow she was really horrible.

The flight attendants on board were good! They helped get everything straight. Easily could have been handled by the incompetent gate agent. Wow.

DEN
SLC
Excellent 10.0

Delta is great

BOS
MKE
Excellent 10.0

Direct flight, on time, friendly crew, smooth flight

YUL
DTW
Mediocre 2.0

Not applied

Not applied

Thu, Mar 15
BDA
ORD
7h 55m
Fri, Mar 16
ORD
BDA
6h 44m
Trip: 2 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27225 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
MAD
PHL
Good 7.0

We shopped price, this was the most affordable flight for us.

Getting seat reservations should be easier and sooner.

FLL
DFW
Excellent 10.0

Great service

GDL
DFW
Good 6.3

Friendly staff

Food was terrible and the seats tight

CLT
LHR
Excellent 10.0

Departure and arrival time

Nothing

PHL
LHR
Good 7.3

Range of entertainment options, one crew member was terrific

Comfort of bed, some crew members snarky, old aircraft

Tue, Mar 13
BDA
ORD
23h 48m
Thu, Mar 15
ORD
BDA
13h 53m
Trip: 3 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27225 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
PHL
MAN
Excellent 8.0

Efficient crew

Very full no isle seat!

MAD
PHL
Good 7.0

We shopped price, this was the most affordable flight for us.

Getting seat reservations should be easier and sooner.

GDL
DFW
Good 6.3

Friendly staff

Food was terrible and the seats tight

BNA
LAX
Excellent 10.0

The service from the flight attendants on the flight was absolutely amazing

DFW
YYZ
Okay 4.6

Lucked out with extra legroom seat. Seat was broken though.

The whole customs process is a seemingly endless mess.

Wed, Mar 28
BDA
ORD
6h 51m
Tue, Apr 17
ORD
BDA
6h 38m
Trip: 21 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Mar 14
BDA
ORD
11h 56m
Thu, Mar 15
ORD
BDA
9h 47m
Trip: 2 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 7661 reviews
Overall
8.2
Boarding
8.2
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
FLL
JFK
Excellent 10.0

Friendly, dependable service from online check in (easy) , check in, to flight. Very enjoyable. I flew Miami Doha non stop

SDQ
JFK
Okay 4.6

The one thing I liked was the expedited service I got because my brother needed a wheelchair. The comfort of the plane was really nice as well, one of the best flights I had in a while.

What I didn’t like was how my flight got cancelled and the only flight I was able to get was 4 days later. So I was stuck in the Dominican Republic for a total of two weeks!! I had to miss another weekend at work which made me lose a lot of money since I’m a barber and lost some one my clientele. On top of my flight being cancelled it also got delayed again but only by 30 minutes so I wasn’t so upset. When it came to the boarding, that had to be the slowest boarding I’ve went through. The gate seemed very behind on the technology and that caused the workers to work even slower. At times they had to step away and go on their monitor to fix something out so it took an extra 30 minutes before I even got into my seat, and I was sitting in row 6 of the plane. Then after everyone was seated the flight got held back an extra half hour because a lady wanted to file a complaint saying that she got pushed and ended up being the only person that got kicked off the flight so she did it all for nothing. So with everything happening, our flight got delayed an hour and a half. Very disappointed..

JFK
TPA
Excellent 8.0

My child had a very good escorted flight the attendants were very attentive and knowledgeable of my child's needs I highly recommend and if anyone needs an escorted flight they definitely will not regret it

All was good

ORD
BOS
Good 6.0

Turbulence was terrible, understand that is not JetBlue issue - wanted to note.

BNA
FLL
Good 7.0

Every single employee I interacted with was awesome.

Over 5 hours in delay due to a maintenance issue. Problem wasn't discovered overnight when it was parked. Wasn't discovered until the next day. Had to wait for the delivery of a specific part and install it. I'm all for planes not breaking upon reentry, but the fact that the two flights were both subsequently delayed 4-5 hours each instead of bringing in a sub plane was inconsiderate. Now I've got a long drive home and I'll only get an hour of sleep before a 14-hour work day. So thanks for that, JetBlue

Tue, Apr 3
BDA
ORD
6h 22m
Tue, Apr 17
ORD
BDA
7h 23m
Trip: 15 days
Overall 0.0 Poor
Based on 0 reviews
Thu, May 3
BDA
ORD
17h 47m
Sun, May 6
ORD
BDA
16h 50m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SAN
LAX
Excellent 10.0

on time

MSY
JFK
Excellent 10.0

The overhead bin did not stay down low enough so that I could place my bag in. It would lower then before I could place my bag raise slightly by a few inches. For someone of my height (5’5”) that was problematic. Fortunately another passenger saw my dilemma and held the bin lower to its full opening capacity. This also momentarily slowed down the boarding process.

HOU
ATL
Excellent 10.0

Service

DEN
SLC
Excellent 10.0

Delta is great

SYR
JFK
Good 7.0

Nothing Special

Fri, Mar 9
BDA
ORD
11h 58m
Wed, Mar 14
ORD
BDA
7h 08m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27225 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
MXP
JFK
Okay 5.0

i had a really horrible experience with a flight attendent but the 2 in my cabin were great. Earphones didnt work and couldnt see screen

DFW
YYZ
Okay 4.6

Lucked out with extra legroom seat. Seat was broken though.

The whole customs process is a seemingly endless mess.

MAD
PHL
Good 7.0

We shopped price, this was the most affordable flight for us.

Getting seat reservations should be easier and sooner.

FCO
PHL
Okay 4.3

Not much.

The flight was late due to maintenance and caused us to miss our connecting flight to Chicago. American Airlines customer assistance at the airport was absolutely terrible. They were rude and inconsiderate as they kept suggesting to fly standby. We shouldn't have to fly standby when it wasn't our fault why were late. They told us our bags would be ok going to Chicago and they we would make the flight, but we did not. I do not know why didn't wait for us considering there were 8 others that also missed the connecting flight. We had to fly to Denver and stay overnight with no luggage and catch a 7:00am flight to Chicago. The last surprise I received was my damaged bag when I got back to Chicago. Thank you for making this trip memorable in a terrible way. I will never book or recommend Kayak or use American Airlines again.

PHL
MAN
Excellent 8.0

Efficient crew

Very full no isle seat!

Wed, May 16
BDA
MDW
9h 01m
Sun, May 20
MDW
BDA
6h 40m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
ANC
Excellent 10.0

Alaska Airlines is way overpriced and way less comfortable than Delta. I’m a Delta loyalist forever now!

Nothing.

DEN
SLC
Excellent 10.0

Delta is great

SAN
LAX
Excellent 10.0

on time

SYR
JFK
Good 7.0

Nothing Special

YUL
DTW
Mediocre 2.0

Not applied

Not applied

Thu, Mar 15
BDA
ORD
11h 56m
Fri, Mar 16
ORD
BDA
9h 47m
Trip: 2 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 7661 reviews
Overall
8.2
Boarding
8.2
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
FLL
DTW
Okay 5.3

Delayed flights.

SDQ
JFK
Okay 4.6

The one thing I liked was the expedited service I got because my brother needed a wheelchair. The comfort of the plane was really nice as well, one of the best flights I had in a while.

What I didn’t like was how my flight got cancelled and the only flight I was able to get was 4 days later. So I was stuck in the Dominican Republic for a total of two weeks!! I had to miss another weekend at work which made me lose a lot of money since I’m a barber and lost some one my clientele. On top of my flight being cancelled it also got delayed again but only by 30 minutes so I wasn’t so upset. When it came to the boarding, that had to be the slowest boarding I’ve went through. The gate seemed very behind on the technology and that caused the workers to work even slower. At times they had to step away and go on their monitor to fix something out so it took an extra 30 minutes before I even got into my seat, and I was sitting in row 6 of the plane. Then after everyone was seated the flight got held back an extra half hour because a lady wanted to file a complaint saying that she got pushed and ended up being the only person that got kicked off the flight so she did it all for nothing. So with everything happening, our flight got delayed an hour and a half. Very disappointed..

ORD
BOS
Good 6.0

Turbulence was terrible, understand that is not JetBlue issue - wanted to note.

BNA
FLL
Good 7.0

Every single employee I interacted with was awesome.

Over 5 hours in delay due to a maintenance issue. Problem wasn't discovered overnight when it was parked. Wasn't discovered until the next day. Had to wait for the delivery of a specific part and install it. I'm all for planes not breaking upon reentry, but the fact that the two flights were both subsequently delayed 4-5 hours each instead of bringing in a sub plane was inconsiderate. Now I've got a long drive home and I'll only get an hour of sleep before a 14-hour work day. So thanks for that, JetBlue

FLL
JFK
Excellent 10.0

Friendly, dependable service from online check in (easy) , check in, to flight. Very enjoyable. I flew Miami Doha non stop

Mon, Mar 12
BDA
ORD
11h 58m
Tue, Mar 20
ORD
BDA
6h 44m
Trip: 9 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27225 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
GDL
DFW
Good 6.3

Friendly staff

Food was terrible and the seats tight

PHL
ORD
Mediocre 2.0

The baggage customer service said the crew will wait for us, but they never did. THANKS for NOTHING!

CLT
LHR
Excellent 10.0

Departure and arrival time

Nothing

DFW
YYZ
Okay 4.6

Lucked out with extra legroom seat. Seat was broken though.

The whole customs process is a seemingly endless mess.

BNA
LAX
Excellent 10.0

The service from the flight attendants on the flight was absolutely amazing

Sat, Mar 17
BDA
ORD
11h 56m
Wed, Mar 21
ORD
BDA
9h 47m
Trip: 5 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 7661 reviews
Overall
8.2
Boarding
8.2
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
JFK
TPA
Excellent 8.0

My child had a very good escorted flight the attendants were very attentive and knowledgeable of my child's needs I highly recommend and if anyone needs an escorted flight they definitely will not regret it

All was good

SDQ
JFK
Okay 4.6

The one thing I liked was the expedited service I got because my brother needed a wheelchair. The comfort of the plane was really nice as well, one of the best flights I had in a while.

What I didn’t like was how my flight got cancelled and the only flight I was able to get was 4 days later. So I was stuck in the Dominican Republic for a total of two weeks!! I had to miss another weekend at work which made me lose a lot of money since I’m a barber and lost some one my clientele. On top of my flight being cancelled it also got delayed again but only by 30 minutes so I wasn’t so upset. When it came to the boarding, that had to be the slowest boarding I’ve went through. The gate seemed very behind on the technology and that caused the workers to work even slower. At times they had to step away and go on their monitor to fix something out so it took an extra 30 minutes before I even got into my seat, and I was sitting in row 6 of the plane. Then after everyone was seated the flight got held back an extra half hour because a lady wanted to file a complaint saying that she got pushed and ended up being the only person that got kicked off the flight so she did it all for nothing. So with everything happening, our flight got delayed an hour and a half. Very disappointed..

FLL
HPN
Excellent 10.0

Seems to be a problem between airline and county. Differing info about gate location.

ORD
BOS
Good 6.0

Turbulence was terrible, understand that is not JetBlue issue - wanted to note.

FLL
DTW
Okay 5.3

Delayed flights.

Mon, Mar 12
BDA
ORD
6h 19m
Mon, Mar 19
ORD
BDA
7h 08m
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Apr 3
BDA
ORD
8h 41m
Wed, Apr 11
ORD
BDA
5h 14m
Trip: 9 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27225 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
MAD
PHL
Good 7.0

We shopped price, this was the most affordable flight for us.

Getting seat reservations should be easier and sooner.

PHL
LHR
Good 7.3

Range of entertainment options, one crew member was terrific

Comfort of bed, some crew members snarky, old aircraft

GDL
DFW
Good 6.3

Friendly staff

Food was terrible and the seats tight

MXP
JFK
Okay 5.0

i had a really horrible experience with a flight attendent but the 2 in my cabin were great. Earphones didnt work and couldnt see screen

PHL
ORD
Mediocre 2.0

The baggage customer service said the crew will wait for us, but they never did. THANKS for NOTHING!

Thu, Mar 15
BDA
ORD
7h 55m
Sun, Mar 18
ORD
BDA
5h 25m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Apr 11
BDA
ORD
7h 57m
Sun, Apr 15
ORD
BDA
7h 17m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27225 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
DFW
YYZ
Okay 4.6

Lucked out with extra legroom seat. Seat was broken though.

The whole customs process is a seemingly endless mess.

PHL
LHR
Good 7.3

Range of entertainment options, one crew member was terrific

Comfort of bed, some crew members snarky, old aircraft

DFW
COS
Excellent 10.0

Great service

GDL
DFW
Good 6.3

Friendly staff

Food was terrible and the seats tight

MAD
PHL
Good 7.0

We shopped price, this was the most affordable flight for us.

Getting seat reservations should be easier and sooner.

Sat, Mar 17
BDA
ORD
11h 56m
Mon, Mar 19
ORD
BDA
9h 47m
Trip: 3 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 7661 reviews
Overall
8.2
Boarding
8.2
Comfort
8.3
Crew
8.6
Entertainment
8.0
Food
7.8
LGA
PBI
Excellent 8.0

The terminal

PBI
HPN
Excellent 10.0

Up to expectation; on time, smooth check in with kiosk, efficient and courteous TSA security line, clear navigational sign, bookstore, clean windows, clean seat, and clean air.

waiting area after security checkpoint is a little too tight at West Palm Beach International Airport.

FLL
DTW
Okay 5.3

Delayed flights.

MSY
BOS
Excellent 10.0

Being on time is important. Jet blue always makes it easy

FLL
HPN
Excellent 10.0

Seems to be a problem between airline and county. Differing info about gate location.

*
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Bermuda to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Bermuda
Flight Price $279
Airlines American Airlines, JetBlue, Delta