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Maine to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Maine
Flight Price $273
Airlines JetBlue, Delta, American Airlines, United Airlines

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

Airports
Origin
Augusta
$378
only
$378
Bangor
$294
only
$294
Portland
$273
only
$273
Rockland
$504
only
$504
Destination
Chicago
$273
only
$273
$333
only
$333
Wed, Sep 4
PWM
Portland
ORD
Chicago O'Hare Intl
7h 45m
Wed, Sep 11
ORD
Chicago O'Hare Intl
PWM
Portland
5h 59m
Trip: 8 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 17,387 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
7.9
Food
7.8
JFK
ORD
Good 7.6

Pros: The seats are comfortable with enough leg room.

Cons: My husband's display controls didn't work. We didn't ask for help as he planned to read anyway.

MEX
JFK
Okay 5.3

Cons: Why do the seats no longer recline. Try flying 6 hours sitting uncomfortably. If they changed it si seats no longer recline I’m changing airlines

JFK
FLL
Mediocre 2.0

Cons: Everything

BWI
BOS
Excellent 10.0

Pros: Yes, crew were amazing.

PBI
BOS
Excellent 9.0

Pros: Crew very understanding, service very efficient.

Cons: The boarding process stalled.

Tue, Oct 22
BGR
Bangor
ORD
Chicago O'Hare Intl
5h 30m
Sat, Oct 26
ORD
Chicago O'Hare Intl
BGR
Bangor
4h 59m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,835 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
MSP
BOS
Excellent 10.0

Pros: Delta, as always, comes through! Although my original flight was delayed, Delta provided the option to rebook on another DL flight at no additional cost. They made it super easy! As always, the crew was friendly, helpful and professional! Thanks!

MSP
PDX
Excellent 9.0

Cons: Seat assignment with Economy ticket.

ATL
SAT
Excellent 10.0

Pros: I liked the entertainment

ATL
MSN
Excellent 8.4

Cons: Wider seats, more leg room

MSP
AMS
Excellent 8.0

Pros: Crew very good

Cons: Breakfast sandwich was close to tasteless; all bread, very very little filling.

Fri, Jun 14
PWM
Portland
ORD
Chicago O'Hare Intl
16h 01m
Mon, Jun 17
ORD
Chicago O'Hare Intl
PWM
Portland
7h 25m
Trip: 4 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,148 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
ORD
EWR
Mediocre 2.0

Cons: American Airlines cancelled this flight and then sent one of my two checked luggages to another flight to Newark from Chicago O'Hare and didn't even think to put me and the luggage I left behind on said flight? Either they should have left both and let me deal with it OR send me on a flight.

PDX
LAX
Excellent 9.3

Pros: Arrived early with great service which is most important when flying.

Cons: Entertainment was not on par with competitors like Delta, especially on a long flight. Movies depended on downloading the gogo app before you boarded which most were not aware of until we were airborne.

CLT
DCA
Good 6.6

Pros: No entertainment system only for those who are vested with AA and using their app

Cons: A modern plane not old A320 without entertainment system

ORD
LHR
Excellent 10.0

Pros: Crew did a great job!

Cons: Not much everything was smooth.

IAD
LAX
Mediocre 3.2

Cons: I'm expecting more from AA. We were delayed for 2.5 hr since we didn't have a pilot !!!!!

Sun, Oct 13
BGR
Bangor
ORD
Chicago O'Hare Intl
2h 56m
Tue, Oct 15
ORD
Chicago O'Hare Intl
BGR
Bangor
14h 06m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 8 reviews
Overall
7.3
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
EWR
ARN
Good 7.0

Pros: I find airline seats to be getting smaller, even though I have lost 5% of my mass. Perhaps it is my age. My chair at home is a prototype airline seat, designed by a Scandinavian.

Cons: Entertainment on airlines is "meh" at best, but I prefer old movies. So I bring a book. Then the airline comes up with novel locations for the light switch. Airlines should remember that travelers have just had the "TSA experience."

BOS
SFO
Good 6.5

Pros: I found it appalling that on a 6 hour flight there were not only no complimentary alcoholic beverages, but that the price of a mini bottle of wine was $9!!!! Ridiculous.

Cons: One complimentary alcoholic beverage.

RDU
EWR
Good 6.3

Pros: Flight delayed for over an hour Only served water Sodas on demand

Cons: Staying on time

EWR
RDU
Excellent 10.0

Pros: Yes

Cons: Nothing

IAH
SFO
Mediocre 2.0

Pros: Crew was accommodating.

Thu, Aug 22
PWM
Portland
ORD
Chicago O'Hare Intl
6h 25m
Sun, Aug 25
ORD
Chicago O'Hare Intl
PWM
Portland
9h 23m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,850 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
OMA
MSP
Excellent 10.0

Cons: It was great

SLC
DTW
Okay 5.3

Pros: the entertainment choices were adequate

Cons: More efficient deplanning. It took us 40 minutes to get off the plane after it landed

ATL
CLT
Excellent 10.0

Cons: The girls were sweet as usual!

LFT
ATL
Good 7.0

Pros: United Airlines culturally has a very big issue. The crews are not friendly and the seating is awful.

MSP
AMS
Excellent 8.0

Pros: Crew very good

Cons: Breakfast sandwich was close to tasteless; all bread, very very little filling.

Thu, Aug 8
PWM
Portland
ORD
Chicago O'Hare Intl
5h 04m
Mon, Aug 12
ORD
Chicago O'Hare Intl
PWM
Portland
4h 23m
Trip: 5 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 17,387 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
7.9
Food
7.8
TPA
BDL
Good 6.0

Pros: The crew was very nice.

Cons: I was going home for a funeral, so my thoughts were just in another world and not occupied with the travel.

BOS
SEA
Excellent 10.0

Pros: Crew was great, seat very comfy with good legroom.

SAN
JFK
Excellent 9.6

Pros: We landed an hour early

DEN
BOS
Excellent 8.0

Pros: The crew was really professional and I liked a lot of leg space.

PBI
BOS
Excellent 9.0

Pros: Crew very understanding, service very efficient.

Cons: The boarding process stalled.

Tue, Oct 22
BGR
Bangor
MDW
Chicago Midway
9h 45m
Sat, Oct 26
MDW
Chicago Midway
BGR
Bangor
9h 39m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,835 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
MEX
DTW
Excellent 10.0

Cons: Todo excelente!!!gracias!!!

DTW
MSP
Excellent 10.0

Pros: It was quick

Cons: The head sets cost $2 There wasn’t food served It was very cramped.

DTW
FLL
Excellent 9.6

Pros: While biased since I was in First class, everything was enjoyable and as expected of a first class experience. The free Wi-Fi on this flight made it extra special- can’t wait until its standard on all flights!!

Cons: Only real complaint is that Delta doesn’t seem to restrict size of bags taken as carry on and the time wasted but some trying to squeeze their obviously oversized bags into overhead compartments is painful.

LAS
LAX
Mediocre 3.0

Pros: 5 hours delay

Cons: 5 hours delay

VCE
ATL
Excellent 10.0

Pros: I was originally booked through jfk with an 80 minute layover. When I told a delta.help desk employee i feared it was too tight (I flew out through jf k and that was enough to convince me...) he booked me through Atlanta with a.comfortable schedule. Thank you!

Tue, Jul 23
AUG
Augusta
ORD
Chicago O'Hare Intl
7h 54m
Wed, Jul 24
ORD
Chicago O'Hare Intl
AUG
Augusta
6h 50m
Trip: 2 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 17,387 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
7.9
Food
7.8
LGA
FLL
Okay 5.6

Cons: TV wasn’t working

JFK
FLL
Mediocre 2.0

Cons: Everything

BOS
LAS
Good 7.0

Cons: Flight two hours late

MSY
JFK
Okay 4.3

Pros: Boarding was fast

Cons: Outlets on the plane Flight attendant seemed to have an attitude

CHS
JFK
Good 7.0

Cons: Plane arrived too late

Mon, Jun 17
BGR
Bangor
ORD
Chicago O'Hare Intl
3h 02m
Thu, Jun 27
ORD
Chicago O'Hare Intl
BGR
Bangor
2h 24m
Trip: 11 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 39,148 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
ECP
CLT
Excellent 8.0

Pros: Very convenient

Cons: The check in process was like a goat rodeo. Very very very slow.

KIN
MIA
Excellent 9.6

Cons: Have coach passengers prepay for meals

BHM
PHL
Mediocre 3.0

Cons: The female staff at the desk where the luggage is dropped and boarding passes are issued was very rude. A little smile makes a difference vs being rude to customers. Apparently she needed to know that she is getting paid because customers like us choose to fly AA or BA

EWR
CLT
Okay 4.6

Pros: Regular delays. This one by 2 hours. Easier to fly a different airline.

Cons: Just the chronic delays. It’s a good airline, great crew. Tired of damaging delays without compensation.

CLT
EWR
Good 6.0

Pros: Everything was generally fine. The flight left about 1 hour late, but the pilot made up the time on the flight and we landed about the same time as originally expected.

Cons: The crew, particularly the flight attendants were rude and impatient. Have they forgotten their manners?

Thu, Aug 22
PWM
Portland
MDW
Chicago Midway
5h 48m
Sun, Aug 25
MDW
Chicago Midway
PWM
Portland
4h 54m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,850 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
AMS
ATL
Excellent 8.0

Pros: The flight was delayed several times due to bad weather in Tampa. The gate agent was good at explaining the problem and said it was the FAA that had put a ground stop in place. It was nice to be informed about what was going on.

Cons: The cabin was very noisy -- don't know if the AC fans were cranked up or what, but the constant roar made it difficult to converse with the crew about snack and drink choices.

BWI
JFK
Mediocre 3.6

Pros: It wasn’t delayed 3 hours like the first flight

Cons: Departing on time

MDT
ATL
Mediocre 3.6

Cons: Worst first class service. Only came by twice in two hour flight

CDG
ATL
Excellent 10.0

Pros: Food and movies

LGA
ATL
Excellent 8.6

Pros: The crew was fantastic. The seats were very comfortable and the entertainment screen functioned perfectly with a great selection of things to watch.

Cons: The boarding process seems slightly longer for delta than other airlines. I figure you’re aware of this and are working on streamlining this. Further while the safety animation yo have made is cute is a little confusing at times.

Thu, Jul 4
PWM
Portland
MDW
Chicago Midway
4h 05m
Mon, Jul 8
MDW
Chicago Midway
PWM
Portland
4h 32m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,850 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
DTW
FLL
Excellent 9.6

Pros: While biased since I was in First class, everything was enjoyable and as expected of a first class experience. The free Wi-Fi on this flight made it extra special- can’t wait until its standard on all flights!!

Cons: Only real complaint is that Delta doesn’t seem to restrict size of bags taken as carry on and the time wasted but some trying to squeeze their obviously oversized bags into overhead compartments is painful.

SJU
ATL
Good 6.4

Cons: They have to improve the boarding process a bit.

KIN
ATL
Excellent 8.0

Pros: For me the boarding was of fast

Cons: The food

TVC
DTW
Excellent 9.0

Pros: Quick flight

Cons: Coffee or beverage service would have been a nice touch.

VCE
ATL
Excellent 10.0

Pros: I was originally booked through jfk with an 80 minute layover. When I told a delta.help desk employee i feared it was too tight (I flew out through jf k and that was enough to convince me...) he booked me through Atlanta with a.comfortable schedule. Thank you!

Tue, Jul 23
RKD
Rockland Knox County Regional
ORD
Chicago O'Hare Intl
8h 24m
Wed, Jul 24
ORD
Chicago O'Hare Intl
RKD
Rockland Knox County Regional
5h 31m
Trip: 2 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 17,387 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
7.9
Food
7.8
CHS
JFK
Good 7.0

Cons: Plane arrived too late

BOS
PBI
Excellent 8.4

Pros: Very comfortable. Crew was good. An easy, pleasant flight.

Cons: The entertainment unit on the back of my seat didn’t work for the entire flight.

JFK
POS
Good 7.0

Pros: The friendly crew members

Cons: The snack items. After paying so much money for a flight to only be fed with a snack for a 4 and 1/2 hour flight is poor

JFK
CHS
Mediocre 2.0

Pros: Our flight was delayed a grand total of 5 hours

Cons: They could’ve had a backup plane more readily available

LGB
LAS
Good 7.6

Pros: good snacks and good drink options for free

Cons: rough landing, could have been better

Thu, Aug 1
BGR
Bangor
ORD
Chicago O'Hare Intl
7h 59m
Tue, Aug 6
ORD
Chicago O'Hare Intl
BGR
Bangor
7h 32m
Trip: 6 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,835 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
DCA
ATL
Excellent 10.0

Pros: The crew rocked!!!! Professional and fun. We enjoyed the music.

Cons: WiFi didn’t work well. Still great flight.

CUN
MCI
Mediocre 3.6

Pros: We had the worst flight ever on Delta flight worst Attitude of the flight attendant she was very Rude i even told her she was

Cons: We didn't get served nothing to drink until 45 min to kc then by then i was so dehydrated i asked for a can of pop she said NO I SAID REALLY SHE SAID DELTAS NOT IN CHARGE OF STOCKING DRINKS & SNACKS SHE HAD MORE PEOPLE' TO SERVE REALLY EVERBODY IN FRONT OF US GOT WHAT THEY WANTED SO I HAD NOTHIN AT

STL
ATL
Good 6.4

Pros: Nothing special

Cons: That was the most uncomfortable and cramped seat I had ever had on a plane flight. Even sitting on the pillow did not help.

PHL
ATL
Excellent 10.0

Cons: Safe and happy travel!

CDG
ATL
Excellent 10.0

Pros: Food and movies

Wed, Jun 19
PWM
Portland
ORD
Chicago O'Hare Intl
5h 25m
Sun, Jun 23
ORD
Chicago O'Hare Intl
PWM
Portland
4h 36m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,850 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
ATL
ILM
Excellent 8.6

Cons: No wifi

MSP
OMA
Excellent 10.0

Cons: Couldn't have been better

JFK
AMS
Good 6.3

Pros: This was a Delta codeshare on KLM metal. We left on time and arrived early. The crew was very professional. The bathrooms were very clean.

Cons: The seat in Economy Comfort was awful. Not enough padding and no place to put my feet because of a very large entertainment control box on the floor.

ATL
AUS
Good 6.4

Cons: They could improve the boarding process.

CUN
MCI
Mediocre 3.6

Pros: We had the worst flight ever on Delta flight worst Attitude of the flight attendant she was very Rude i even told her she was

Cons: We didn't get served nothing to drink until 45 min to kc then by then i was so dehydrated i asked for a can of pop she said NO I SAID REALLY SHE SAID DELTAS NOT IN CHARGE OF STOCKING DRINKS & SNACKS SHE HAD MORE PEOPLE' TO SERVE REALLY EVERBODY IN FRONT OF US GOT WHAT THEY WANTED SO I HAD NOTHIN AT

Thu, May 30
PWM
Portland
ORD
Chicago O'Hare Intl
5h 03m
Sat, Jun 1
ORD
Chicago O'Hare Intl
PWM
Portland
5h 31m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,850 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
TVC
DTW
Excellent 9.0

Pros: Quick flight

Cons: Coffee or beverage service would have been a nice touch.

SYD
LAX
Excellent 8.6

Cons: I really like more legs room and comfort and crew member were very good and helpful. Regarding food I say it’s just ok.

DTW
MSP
Excellent 10.0

Pros: It was quick

Cons: The head sets cost $2 There wasn’t food served It was very cramped.

OMA
MSP
Excellent 10.0

Cons: It was great

DTW
FRA
Okay 4.0

Cons: Notes were in the computer that our flight was delayed in someone at Delta told us we had to re book because we were not 2 hours prior to our flight after arriving in a cab. Delta error. Other lady told us to run to a security and get to the gate which we did and there were notes in the system and t

Thu, May 30
PWM
Portland
MDW
Chicago Midway
3h 51m
Sat, Jun 1
MDW
Chicago Midway
PWM
Portland
5h 52m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,850 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
MSP
BOS
Good 7.3

Pros: individual TVs

Cons: it would be great if you could not use all those one-use plastic cups. waste is a real issue in the US and the solution is using re-usable items like washable cups. Unboarding was a nightmare and it started to get really hot waiting to get off.

STL
ATL
Good 6.4

Pros: Nothing special

Cons: That was the most uncomfortable and cramped seat I had ever had on a plane flight. Even sitting on the pillow did not help.

PBI
ATL
Okay 4.6

Cons: Plane was FREEZING!!!

MDT
ATL
Mediocre 3.6

Cons: Worst first class service. Only came by twice in two hour flight

DTW
MSP
Excellent 10.0

Pros: It was quick

Cons: The head sets cost $2 There wasn’t food served It was very cramped.

Wed, Sep 4
PWM
Portland
MDW
Chicago Midway
4h 12m
Wed, Sep 11
MDW
Chicago Midway
PWM
Portland
5h 43m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,850 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
ATL
PDX
Excellent 9.0

Pros: The best

Cons: Again the boarding process took forever

DTW
MSP
Excellent 10.0

Pros: It was quick

Cons: The head sets cost $2 There wasn’t food served It was very cramped.

MDT
ATL
Mediocre 3.6

Cons: Worst first class service. Only came by twice in two hour flight

ATL
AUS
Good 6.4

Cons: They could improve the boarding process.

MSP
BOS
Good 7.3

Pros: individual TVs

Cons: it would be great if you could not use all those one-use plastic cups. waste is a real issue in the US and the solution is using re-usable items like washable cups. Unboarding was a nightmare and it started to get really hot waiting to get off.

Tue, Jun 25
BGR
Bangor
MDW
Chicago Midway
9h 31m
Thu, Jun 27
MDW
Chicago Midway
BGR
Bangor
8h 22m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,835 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
ATL
AUS
Good 6.4

Cons: They could improve the boarding process.

MDT
ATL
Mediocre 3.6

Cons: Worst first class service. Only came by twice in two hour flight

DTW
MCO
Okay 4.0

Cons: It could have left on time or they could have told us they weren’t leaving and let us get some sleep.

DTW
FRA
Okay 4.0

Cons: Notes were in the computer that our flight was delayed in someone at Delta told us we had to re book because we were not 2 hours prior to our flight after arriving in a cab. Delta error. Other lady told us to run to a security and get to the gate which we did and there were notes in the system and t

YYZ
MSP
Excellent 10.0

Pros: The flight attendants were amazing. 12 people had a connecting flight and they brought a shuttle bus. You dont see that kind of service any more 10 stars for that

Cons: Super small plane.

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