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Maine to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Maine
Flight Price $220
Airlines JetBlue, American Airlines, Delta, United

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

Airports
Origin
Augusta
$220
only
$220
Portland
$233
only
$233
Bar Harbor
$336
only
$336
Rockland
$434
only
$434
Destination
Chicago
$220
only
$220
$288
only
$288
Thu, Sep 6
AUG
Augusta
ORD
Chicago O'Hare International
7h 21m
Sun, Sep 9
ORD
Chicago O'Hare International
AUG
Augusta
7h 05m
Trip: 4 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 12,603 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
7.9
Food
7.8
BOS
DTW
Excellent 10.0

Jet Blue is our airline by choice. We have always had very good service from their staff and the only time there was a change because of weather, we were notified in order to make a change to our flight. We will continue to choose Jet Blue whenever possible.

My only complaint with all of the airlines is allowing people to check their bags free at the gate when others have done the required thing of paying for checked bags. It is obvious that people are taking advantage if this. It would be great to see something more fair take place.

BOS
DCA
Excellent 9.6

Flight delayed. Other than that everything was good, friendly crew, TV program on board, drinks and snacks, plus a carry-on item allowed, will use JetBlue more in the future .

PWM
JFK
Good 6.0

Crew attitude was totally professional

2 1/2 hour delay. Old fleet’s falling apart.

JFK
BUR
Okay 5.0

Too much talking on the loud speaker. Cabin lights on with over an hour left in flight

DEN
BOS
Excellent 8.0

Extra room seat was great. Crew was nice. Boarding was easy. Lots of leg room. Appreciate mask and overnight kit for sure.

Flight was very cold.

Tue, Oct 16
PWM
Portland
ORD
Chicago O'Hare International
5h 08m
Wed, Oct 17
ORD
Chicago O'Hare International
PWM
Portland
6h 27m
Trip: 2 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 32,952 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
SEA
DFW
Mediocre 3.6

We landed safely; Beautiful infotainment screen that did NOT work

Extreme delays; Beautiful infotainment screen that did NOT work; Sitting on the runway/tarmac for hours

STL
ORD
Excellent 8.6

A cheap option to upgrade to 1st was offered that ended up being a net 0 cost upgrade for me so I took it. Comfortable on an old (but oh so nice) aircraft.

Arrived 30 minutes early to the airport but then had to sit at a remote pad so that we ended up being 5 minutes late to the gate. A short transfer was made even more difficult, and a massive waste if time and fuel sitting and waiting. Figure out your gates early and better, and move around if needed. At the very least, bring up some stairs and buses to get passengers to the terminal and then tow the aircraft in when you have a gate available.

FCO
DFW
Excellent 10.0

much improved food quality and entertainment quality then previous international flights on AA.

DFW
GRR
Okay 4.3

The flight attendant for the back of the plane was lovely.

The plane was unbearably hot and stuffy. My row wasn’t offered any snacks (some other rows were). A giant moth flew into my forehead, which was extremely startling. There was no entertainment offered and no power outlets for my phone, which was dead.

CDG
MIA
Excellent 8.0

The flight attendants, the service,, the movies, the food, the flight were great, the pilot was very smooth, the plane was very clean

The boarding took forever, including because my wife was picked for extra security search... for an american citizen who lives in miami ?... Inside the plane during the whole flight was freezing Paying for suitcases and changing or selecting seats??? .. really?

Sat, Oct 20
PWM
Portland
ORD
Chicago O'Hare International
6h 55m
Mon, Oct 22
ORD
Chicago O'Hare International
PWM
Portland
5h 40m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,603 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
LGA
BOS
Excellent 8.6

No delay and friendly crew!

Not much leg room and the coffee was horrific.

ITH
DTW
Excellent 10.0

Quick and easy

LGA
YUL
Excellent 10.0

On time

LGA
MSP
Excellent 8.0

The last time we flew Delta, we were underwhelmed. Our flight was delayed several hours and there was nothing exceptional about it when it did finally leave. That was 5 years ago, and there's been a lot of changes. There I'd now in-flight entertainment, reasonably comfortable seats, and everything was on time.

Virtually no food options.

JFK
SJC
Excellent 8.0

Everything ran smoothly on this flight. No delays before, pleasant staff, great entertainment selection, okay food options, working equipment (e.g., tv in the headrest worked, seatbelts worked, lavatories were operational, etc.). This flight met all my expectations

The only hiccup was the wait time on the runway before take off. Not sure if that was the airport’s fault or the airline’s fault. We must have waited 45 minutes.

Thu, Sep 6
PWM
Portland
ORD
Chicago O'Hare International
2h 38m
Sat, Sep 8
ORD
Chicago O'Hare International
PWM
Portland
2h 23m
Trip: 3 days
6.1GoodShow reviews
Overall 6.1 Good
Based on 32 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
PWM
ORD
Okay 5.0

It use to be, I could put up with the lack of comfort and services because the cost savings made it bearable. But thes days, the basic ticket costs are high and increasing despite ala Carter pricing. The flights are always full and the number of flights are down. Airline profits are at a peak yet very little is flowing back to improve the flying experience.

PWM
ORD
Okay 5.3

Seating next to the bathroom is gross

PWM
ORD
Excellent 8.3

Couldn't really figure out your Wi-Fi system so I just read a book

It's not really easy to set up your Wi-Fi system through the United app

PWM
ORD
Mediocre 3.0

I only made it as far as Chicago, and my bag was fairly comprehensively lost as I did so

PWM
ORD
Mediocre 2.0

Not a single thing!

Arrived late

Tue, Oct 30
BHB
Bar Harbor
ORD
Chicago O'Hare International
17h 43m
Wed, Oct 31
ORD
Chicago O'Hare International
BHB
Bar Harbor
17h 23m
Trip: 2 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Nov 10
PWM
Portland
ORD
Chicago O'Hare International
5h 20m
Mon, Nov 12
ORD
Chicago O'Hare International
PWM
Portland
5h 45m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,603 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
CUN
ATL
Mediocre 2.0

The schedule was not good and I was needed to take later flight than I ordered.

HNL
LAX
Good 6.3

The crew are very nice on both flights and they were very courteous the seats.T

The seats were not that comfortable.

ATL
LGA
Excellent 10.0

On time

LGA
YUL
Excellent 10.0

On time

ITH
DTW
Excellent 10.0

Quick and easy

Tue, Dec 4
PWM
Portland
ORD
Chicago O'Hare International
5h 49m
Thu, Jan 3
ORD
Chicago O'Hare International
PWM
Portland
4h 46m
Trip: 31 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,603 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
LAX
TUS
Okay 5.6

The bag service

The flight delays

LGA
MSP
Excellent 8.0

The last time we flew Delta, we were underwhelmed. Our flight was delayed several hours and there was nothing exceptional about it when it did finally leave. That was 5 years ago, and there's been a lot of changes. There I'd now in-flight entertainment, reasonably comfortable seats, and everything was on time.

Virtually no food options.

HNL
LAX
Good 6.3

The crew are very nice on both flights and they were very courteous the seats.T

The seats were not that comfortable.

JFK
TPA
Okay 4.0

They ran out of blankets, earphones on the flight

JFK
SJC
Excellent 8.0

Everything ran smoothly on this flight. No delays before, pleasant staff, great entertainment selection, okay food options, working equipment (e.g., tv in the headrest worked, seatbelts worked, lavatories were operational, etc.). This flight met all my expectations

The only hiccup was the wait time on the runway before take off. Not sure if that was the airport’s fault or the airline’s fault. We must have waited 45 minutes.

Thu, Aug 30
PWM
Portland
ORD
Chicago O'Hare International
5h 37m
Sun, Sep 2
ORD
Chicago O'Hare International
PWM
Portland
2h 18m
Trip: 4 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 12,603 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
7.9
Food
7.8
JFK
BUR
Okay 5.0

Too much talking on the loud speaker. Cabin lights on with over an hour left in flight

BOS
DTW
Excellent 10.0

Jet Blue is our airline by choice. We have always had very good service from their staff and the only time there was a change because of weather, we were notified in order to make a change to our flight. We will continue to choose Jet Blue whenever possible.

My only complaint with all of the airlines is allowing people to check their bags free at the gate when others have done the required thing of paying for checked bags. It is obvious that people are taking advantage if this. It would be great to see something more fair take place.

BOS
RDU
Excellent 10.0

On time. Courteous staff.

BOS
DCA
Okay 5.0

Delayed by an hour

I was an hour late to my meeting.

DCA
BDL
Excellent 10.0

lots of leg room. I'm 6'2" and that is rare.

Thu, Sep 27
PWM
Portland
ORD
Chicago O'Hare International
6h 45m
Mon, Oct 1
ORD
Chicago O'Hare International
PWM
Portland
5h 40m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,603 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
JFK
SJC
Excellent 8.0

Everything ran smoothly on this flight. No delays before, pleasant staff, great entertainment selection, okay food options, working equipment (e.g., tv in the headrest worked, seatbelts worked, lavatories were operational, etc.). This flight met all my expectations

The only hiccup was the wait time on the runway before take off. Not sure if that was the airport’s fault or the airline’s fault. We must have waited 45 minutes.

SFO
DTW
Okay 4.6

The flight attendants were very kind and hoped to make up for the pilot’s negligence.

Boarding was weird with a lack of overhead bins and then the pilot was inconsistent with updates to safety issues. We were delayed by an hour and twenty mins and then had to wait on the tarmac for another plane to leave the gate. Feels like I wasted two hours in limbo.

HNL
LAX
Good 6.3

The crew are very nice on both flights and they were very courteous the seats.T

The seats were not that comfortable.

JFK
TPA
Okay 4.0

They ran out of blankets, earphones on the flight

DTW
DSM
Excellent 10.0

Quick and easy.

Fri, Sep 21
PWM
Portland
ORD
Chicago O'Hare International
6h 03m
Sun, Sep 23
ORD
Chicago O'Hare International
PWM
Portland
2h 18m
Trip: 3 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 32,952 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.7
CLT
BWI
Excellent 9.3

Amazing and comfortable

We left a little late.

STL
ORD
Excellent 8.6

A cheap option to upgrade to 1st was offered that ended up being a net 0 cost upgrade for me so I took it. Comfortable on an old (but oh so nice) aircraft.

Arrived 30 minutes early to the airport but then had to sit at a remote pad so that we ended up being 5 minutes late to the gate. A short transfer was made even more difficult, and a massive waste if time and fuel sitting and waiting. Figure out your gates early and better, and move around if needed. At the very least, bring up some stairs and buses to get passengers to the terminal and then tow the aircraft in when you have a gate available.

BUR
PHX
Excellent 10.0

Fast all to boarding and everything

No comment

MSP
ORD
Excellent 8.0

Short flight

Delayed for some unknown reason

DFW
GRR
Okay 4.3

The flight attendant for the back of the plane was lovely.

The plane was unbearably hot and stuffy. My row wasn’t offered any snacks (some other rows were). A giant moth flew into my forehead, which was extremely startling. There was no entertainment offered and no power outlets for my phone, which was dead.

Thu, Jan 17
PWM
Portland
ORD
Chicago O'Hare International
7h 58m
Sun, Jan 20
ORD
Chicago O'Hare International
PWM
Portland
7h 11m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,603 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
LGA
MSP
Excellent 8.0

The last time we flew Delta, we were underwhelmed. Our flight was delayed several hours and there was nothing exceptional about it when it did finally leave. That was 5 years ago, and there's been a lot of changes. There I'd now in-flight entertainment, reasonably comfortable seats, and everything was on time.

Virtually no food options.

CUN
ATL
Mediocre 2.0

The schedule was not good and I was needed to take later flight than I ordered.

HNL
LAX
Good 6.3

The crew are very nice on both flights and they were very courteous the seats.T

The seats were not that comfortable.

LGA
BOS
Excellent 8.6

No delay and friendly crew!

Not much leg room and the coffee was horrific.

DTW
DSM
Excellent 10.0

Quick and easy.

Tue, Oct 16
AUG
Augusta
ORD
Chicago O'Hare International
8h 41m
Wed, Oct 17
ORD
Chicago O'Hare International
AUG
Augusta
5h 47m
Trip: 2 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 12,603 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
7.9
Food
7.8
PWM
JFK
Good 6.0

Crew attitude was totally professional

2 1/2 hour delay. Old fleet’s falling apart.

BOS
DCA
Okay 5.0

Delayed by an hour

I was an hour late to my meeting.

BOS
RDU
Excellent 10.0

On time. Courteous staff.

EWR
BOS
Excellent 10.0

Everything was on time

BOS
DTW
Excellent 10.0

Jet Blue is our airline by choice. We have always had very good service from their staff and the only time there was a change because of weather, we were notified in order to make a change to our flight. We will continue to choose Jet Blue whenever possible.

My only complaint with all of the airlines is allowing people to check their bags free at the gate when others have done the required thing of paying for checked bags. It is obvious that people are taking advantage if this. It would be great to see something more fair take place.

Wed, Sep 19
PWM
Portland
MDW
Chicago Midway
7h 12m
Mon, Sep 24
MDW
Chicago Midway
PWM
Portland
6h 52m
Trip: 6 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,603 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
DTW
DSM
Excellent 10.0

Quick and easy.

LGA
BOS
Excellent 8.6

No delay and friendly crew!

Not much leg room and the coffee was horrific.

JFK
SJC
Excellent 8.0

Everything ran smoothly on this flight. No delays before, pleasant staff, great entertainment selection, okay food options, working equipment (e.g., tv in the headrest worked, seatbelts worked, lavatories were operational, etc.). This flight met all my expectations

The only hiccup was the wait time on the runway before take off. Not sure if that was the airport’s fault or the airline’s fault. We must have waited 45 minutes.

LGA
YUL
Excellent 10.0

On time

CUN
ATL
Mediocre 2.0

The schedule was not good and I was needed to take later flight than I ordered.

Fri, Oct 5
PWM
Portland
ORD
Chicago O'Hare International
27h 33m
Mon, Oct 8
ORD
Chicago O'Hare International
PWM
Portland
40h 43m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Sep 27
PWM
Portland
MDW
Chicago Midway
4h 04m
Mon, Oct 1
MDW
Chicago Midway
PWM
Portland
7h 01m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,603 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
LGA
MSP
Excellent 8.0

The last time we flew Delta, we were underwhelmed. Our flight was delayed several hours and there was nothing exceptional about it when it did finally leave. That was 5 years ago, and there's been a lot of changes. There I'd now in-flight entertainment, reasonably comfortable seats, and everything was on time.

Virtually no food options.

ITH
DTW
Excellent 10.0

Quick and easy

JFK
TPA
Okay 4.0

They ran out of blankets, earphones on the flight

JFK
SJC
Excellent 8.0

Everything ran smoothly on this flight. No delays before, pleasant staff, great entertainment selection, okay food options, working equipment (e.g., tv in the headrest worked, seatbelts worked, lavatories were operational, etc.). This flight met all my expectations

The only hiccup was the wait time on the runway before take off. Not sure if that was the airport’s fault or the airline’s fault. We must have waited 45 minutes.

DTW
DSM
Excellent 10.0

Quick and easy.

Wed, Oct 24
PWM
Portland
MDW
Chicago Midway
7h 09m
Tue, Oct 30
MDW
Chicago Midway
PWM
Portland
6h 59m
Trip: 7 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,603 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
SFO
DTW
Okay 4.6

The flight attendants were very kind and hoped to make up for the pilot’s negligence.

Boarding was weird with a lack of overhead bins and then the pilot was inconsistent with updates to safety issues. We were delayed by an hour and twenty mins and then had to wait on the tarmac for another plane to leave the gate. Feels like I wasted two hours in limbo.

LAX
TUS
Okay 5.6

The bag service

The flight delays

JFK
TPA
Okay 4.0

They ran out of blankets, earphones on the flight

LGA
YUL
Excellent 10.0

On time

DTW
DSM
Excellent 10.0

Quick and easy.

Tue, Oct 16
RKD
Rockland Knox County Regional
ORD
Chicago O'Hare International
6h 01m
Wed, Oct 17
ORD
Chicago O'Hare International
RKD
Rockland Knox County Regional
5h 20m
Trip: 2 days
8.1ExcellentShow reviews
Overall 8.1 Excellent
Based on 12,603 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
7.9
Food
7.8
BOS
RDU
Excellent 10.0

On time. Courteous staff.

BOS
DCA
Excellent 9.6

Flight delayed. Other than that everything was good, friendly crew, TV program on board, drinks and snacks, plus a carry-on item allowed, will use JetBlue more in the future .

DCA
BDL
Excellent 10.0

lots of leg room. I'm 6'2" and that is rare.

BOS
LGA
Mediocre 3.3

Flight attendants seemed inexperienced: did not convey confidence about 1) the flight, 2) the experience, 3) their ability to manage the flight.

BOS
DTW
Excellent 10.0

Jet Blue is our airline by choice. We have always had very good service from their staff and the only time there was a change because of weather, we were notified in order to make a change to our flight. We will continue to choose Jet Blue whenever possible.

My only complaint with all of the airlines is allowing people to check their bags free at the gate when others have done the required thing of paying for checked bags. It is obvious that people are taking advantage if this. It would be great to see something more fair take place.

Thu, Sep 6
BHB
Bar Harbor
ORD
Chicago O'Hare International
12h 46m
Fri, Sep 7
ORD
Chicago O'Hare International
BHB
Bar Harbor
26h 30m
Trip: 2 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Oct 25
PWM
Portland
MDW
Chicago Midway
7h 15m
Mon, Oct 29
MDW
Chicago Midway
PWM
Portland
5h 09m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,603 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
SFO
DTW
Okay 4.6

The flight attendants were very kind and hoped to make up for the pilot’s negligence.

Boarding was weird with a lack of overhead bins and then the pilot was inconsistent with updates to safety issues. We were delayed by an hour and twenty mins and then had to wait on the tarmac for another plane to leave the gate. Feels like I wasted two hours in limbo.

JFK
SJC
Excellent 8.0

Everything ran smoothly on this flight. No delays before, pleasant staff, great entertainment selection, okay food options, working equipment (e.g., tv in the headrest worked, seatbelts worked, lavatories were operational, etc.). This flight met all my expectations

The only hiccup was the wait time on the runway before take off. Not sure if that was the airport’s fault or the airline’s fault. We must have waited 45 minutes.

ATL
LGA
Excellent 10.0

On time

DTW
DSM
Excellent 10.0

Quick and easy.

ITH
DTW
Excellent 10.0

Quick and easy

Thu, Jan 17
PWM
Portland
MDW
Chicago Midway
6h 09m
Sun, Jan 20
MDW
Chicago Midway
PWM
Portland
5h 50m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,603 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
HNL
LAX
Good 6.3

The crew are very nice on both flights and they were very courteous the seats.T

The seats were not that comfortable.

LGA
YUL
Excellent 10.0

On time

ITH
DTW
Excellent 10.0

Quick and easy

CUN
ATL
Mediocre 2.0

The schedule was not good and I was needed to take later flight than I ordered.

LGA
BOS
Excellent 8.6

No delay and friendly crew!

Not much leg room and the coffee was horrific.

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