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Maine to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Maine
Flight Price $248
Airlines American Airlines, Delta, United Airlines, JetBlue

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

Airports
Origin
Augusta
$268
only
$268
Bangor
$328
only
$328
Portland
$248
only
$248
Rockland
$643
only
$643
Destination
Chicago
$248
only
$248
$292
only
$292
Tue, Jul 9
PWM
Portland
ORD
Chicago O'Hare Intl
7h 13m
Tue, Jul 16
ORD
Chicago O'Hare Intl
PWM
Portland
6h 11m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 37,839 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
DFW
OAK
Excellent 10.0

Pros: Comfortable seat

Cons: Umm, maybe a tv in the headrest

DEN
MIA
Good 6.0

Pros: Good, cheap flight that gets the job done. No issues boarding, seats were fine. Cannot comment on most things as I fell asleep almost immediately.

Cons: Would've been nice to have had an eye mask / blankets on a red eye flight...

BOS
DFW
Excellent 10.0

Pros: Everything worked out well and plane arrived 20 minutes early.

Cons: Seemed like it took longer than average to get bags from baggage claim.

SEA
PHX
Okay 5.6

Pros: Crew was very friendly

Cons: Seats were extremely uncomfortable, and hurt my back very much.

MIA
SFO
Okay 4.0

Cons: Plane was changed, lost all upgrades and assigned a random seat. One of the flight attendant had poor customer skills, was just rude overall.

Fri, Jun 14
PWM
Portland
ORD
Chicago O'Hare Intl
6h 16m
Tue, Jun 18
ORD
Chicago O'Hare Intl
PWM
Portland
6h 20m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,619 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
DTW
BWI
Excellent 8.0

Cons: If there could have been some sort of services to take travelers to their connecting flight, for cases of really short time window of course, it’d be extremely helpful.

SLC
SFO
Okay 5.6

Pros: Nice new seats

Cons: Was too warm inside the plane. Boarding address was mobbed and not very well managed

DTW
BWI
Excellent 10.0

Cons: Excellent

ORD
SLC
Good 7.6

Pros: Crew was great.

Cons: Couldn’t hear/understand the pilot

YEG
MSP
Excellent 9.0

Pros: WiFi and Entertainment

Sat, Aug 10
PWM
Portland
ORD
Chicago O'Hare Intl
2h 45m
Tue, Aug 13
ORD
Chicago O'Hare Intl
PWM
Portland
7h 09m
Trip: 4 days
6.1GoodShow reviews
Overall 6.1 Good
Based on 33 reviews
Overall
7.3
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
IAH
DCA
Excellent 8.0

Cons: There was a very strong smell of urine in the back of the plane. Unfortunately, I was in the last row (38F). They (IAH) should offer TSA precheck after customs in the "connecting flights" area.

PWM
ORD
Mediocre 3.0

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

NRT
DEN
Excellent 8.0

Pros: The UA crew from NRT to DEN met my (lowered) expectations. The best thing is the exceptional comfort afforded by the 787--it is hard to book any other aircraft if I have a choice! Going through immigration and customs at DEN is very efficient as well, and DEN makes a great connecting point.

Cons: I wish the NRT-DEN service were offered by NH instead of UA!

PWM
ORD
Okay 5.3

Cons: Seating next to the bathroom is gross

PWM
ORD
Good 7.0

Cons: Kayak did not provide me with confirming email for flight in either direction and I missed my first flight to LA from Portland This is the second time I was not contacted via email from Kayak on flight reservations

Wed, May 1
AUG
Augusta
ORD
Chicago O'Hare Intl
9h 28m
Tue, May 7
ORD
Chicago O'Hare Intl
AUG
Augusta
5h 12m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Fri, May 31
PWM
Portland
ORD
Chicago O'Hare Intl
15h 06m
Tue, Jun 4
ORD
Chicago O'Hare Intl
PWM
Portland
4h 37m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 37,839 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
DCA
ORD
Okay 5.6

Pros: Nice seating

Cons: They asked who would give there seat up for 600$ future flight credit and The first two people could be eligible. They ignored me (who was first) for a white couple who Came after me, and they got chosen and got the flight credit, but I was as clearly first. So I think it was more of a racist matter

MIA
CMH
Okay 5.2

Cons: Plane was too warm during flight. Aisle is narrow, seats are semi-hard. Lav needed attention (ran out of towels).

BOS
DFW
Excellent 10.0

Pros: Everything worked out well and plane arrived 20 minutes early.

Cons: Seemed like it took longer than average to get bags from baggage claim.

STL
CLT
Mediocre 3.6

Cons: 2 hour delays on both flights of a round trip

CRW
CLT
Mediocre 3.6

Pros: I liked that we arrived on time. Besides that. Not much.

Cons: Having to us use our cell phones to watch a few channels was terrible. No movie. No help. You were just left on your own. Total of waste of time. Give us a monitor. Give us options. You are American Airlines, not Allegiant Air

Thu, Sep 19
PWM
Portland
ORD
Chicago O'Hare Intl
5h 31m
Mon, Sep 23
ORD
Chicago O'Hare Intl
PWM
Portland
7h 50m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,619 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
MCO
IND
Good 7.6

Pros: The flight timings and the arrival time

ATL
BOS
Good 6.6

Pros: Delta in flight entertainment is great.

Cons: Always delayed.

MSP
BIL
Okay 4.8

Cons: I was assigned a seat on the last row of the plane--these not only don't recline, but it feels as though they push you forward. Also, the engine sound was so deafening with such intense vibration that I was unable to hear the flight attendant speaking to me from 2 feet away, much less anything overh

ATL
IAD
Excellent 9.2

Pros: The crew was dealing with NOVA/DC residents

BDL
ATL
Excellent 8.0

Pros: I liked the wide variety of movies and snacks available.

Cons: The kid behind me wouldn't stop kicking my seat.

Fri, Apr 26
PWM
Portland
ORD
Chicago O'Hare Intl
5h 25m
Mon, Apr 29
ORD
Chicago O'Hare Intl
PWM
Portland
5h 36m
Trip: 4 days
6.1GoodShow reviews
Overall 6.1 Good
Based on 33 reviews
Overall
7.3
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
BOI
SFO
Excellent 10.0

Pros: Good crew, good and safe flight. Thank you!

Cons: Nothing.

SJC
ORD
Good 6.3

Cons: The seats are getting smaller and the leg space is nonexistent.

PWM
ORD
Okay 5.3

Cons: Seating next to the bathroom is gross

LAX
SBP
Excellent 10.0

Pros: This plane has more space than larger plane, was more comfortable.

ORD
LAX
Excellent 9.5

Cons: Longer seat belts

Fri, May 10
PWM
Portland
MDW
Chicago Midway
6h 11m
Tue, May 14
MDW
Chicago Midway
PWM
Portland
7h 11m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,631 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
ANC
SEA
Excellent 9.3

Pros: Good service

Cons: Video system locked up at my seat

DEN
SEA
Good 7.0

Pros: On time flight, bag made it, great price, can’t complain.

Cons: Seat pretty tight for an average size adult man. No inflight phone charger.

LAX
MSY
Good 6.6

Pros: Great service

Cons: Stuck at landing. For over 20+ minutes

SLC
SFO
Okay 5.6

Pros: Nice new seats

Cons: Was too warm inside the plane. Boarding address was mobbed and not very well managed

JFK
AMS
Excellent 8.0

Pros: Crew was courteous.

Fri, May 10
RKD
Rockland Knox County Regional
ORD
Chicago O'Hare Intl
7h 26m
Tue, May 14
ORD
Chicago O'Hare Intl
RKD
Rockland Knox County Regional
7h 09m
Trip: 5 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 16,833 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
7.9
Food
7.8
JFK
SJU
Excellent 9.0

Pros: Very good experience with Jetblue’s Crew, comfortable.

Cons: Food is not something to crave for, 4 hours trip I had to buy a sandwich because the only included is chips and basic beverages. Definitely need to improve.

PSP
JFK
Okay 4.0

Cons: If the flight leaves at the scheduled time.

LGA
MCO
Good 7.0

Cons: The wifi didn't work, and this wasn't the first time thier wifi was out. I've been flying on jetblue frequently lately and that's my only issue. Everything else was good.

JFK
SAV
Good 6.3

Pros: Old but clean plane

Cons: Crew had no personality

RSW
BOS
Excellent 9.3

Pros: Free Wi-Fi

Cons: Outlets on plane for charging phone

Thu, Apr 4
PWM
Portland
ORD
Chicago O'Hare Intl
2h 58m
Sun, Apr 7
ORD
Chicago O'Hare Intl
PWM
Portland
5h 31m
Trip: 4 days
6.1GoodShow reviews
Overall 6.1 Good
Based on 33 reviews
Overall
7.3
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
OGG
LAX
Mediocre 3.0

Pros: Haven't flown United, now we remember why. Paid extra for comfort and the seats we had were actually more cramped than those around our seating. A long trip with no food, unless you want to pay more than a high end restaurant in Maui. No entertainment made a long, uncomfortable flight unbearable.

NRT
DEN
Excellent 8.0

Pros: The UA crew from NRT to DEN met my (lowered) expectations. The best thing is the exceptional comfort afforded by the 787--it is hard to book any other aircraft if I have a choice! Going through immigration and customs at DEN is very efficient as well, and DEN makes a great connecting point.

Cons: I wish the NRT-DEN service were offered by NH instead of UA!

DEN
LAX
Mediocre 3.6

Pros: Customer Service was kind and helpful.

Cons: When there was a ground delay, Desk checkin people should not have said go get something to eat when the flight was delayed an hour. Apparently the captain sped up the departure and me and a whole row of people missed the flight despite sitting in front of them with the plane still at gate.

SEA
LAX
Okay 5.2

Pros: Was your standard airlplane.

Cons: Plane was delayed due to a mechanical, then again because the cleaning crew didn’t do a good enough job the first time, then a seat mechanical, and then the truck used to back out onto the tarmac broke down

ORD
SFO
Good 6.3

Cons: Boarding/unloading

Sat, Jun 1
PWM
Portland
MDW
Chicago Midway
4h 38m
Sat, Jun 8
MDW
Chicago Midway
PWM
Portland
3h 41m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,631 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
SAN
LAS
Excellent 10.0

Pros: Great flight

JAX
JFK
Good 7.3

Cons: No in flight entertainment

DEN
ATL
Good 7.0

Pros: Nothing spectacular.

Cons: The headrests won’t stay up. And it’s hot.

ANC
SEA
Excellent 9.3

Pros: Good service

Cons: Video system locked up at my seat

LGA
DTW
Excellent 9.6

Pros: We landed 45 minutes ahead of schedule.

Cons: Boarding was rushed and we left the gate late.

Fri, Jul 5
PWM
Portland
MDW
Chicago Midway
3h 55m
Mon, Jul 15
MDW
Chicago Midway
PWM
Portland
4h 45m
Trip: 11 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,631 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
AMS
BOS
Excellent 10.0

Pros: Good seating, great food, good service.

CHS
ATL
Okay 5.0

Cons: I had window seats on all flights and was boarded after those in middle/aisle seats 3 out of 4 times. Less legroom in the cheap seats. High whining pitch on speaker during announcements on last leg.

DTW
PHX
Excellent 10.0

Pros: All was good

Cons: All was good

SYD
LAX
Excellent 10.0

Pros: Delta always does a superior job - domestically and internationally!

BIL
MSP
Excellent 9.6

Pros: The crew was helpful and seemed genuinely nice. The seats felt a little narrow

Thu, Jun 6
BGR
Bangor
ORD
Chicago O'Hare Intl
5h 32m
Mon, Jun 10
ORD
Chicago O'Hare Intl
BGR
Bangor
5h 50m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,631 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
PDX
MSP
Excellent 10.0

Pros: Fantastic crew!

AMS
BOS
Excellent 10.0

Pros: Good seating, great food, good service.

ATL
BOS
Good 6.6

Pros: Delta in flight entertainment is great.

Cons: Always delayed.

BRU
JFK
Mediocre 2.6

Cons: Healthier snacks instead of just candy and cookies... an apple for example would be great.

SJD
ATL
Excellent 8.3

Pros: The crew very nice and helpful

Wed, Mar 27
PWM
Portland
ORD
Chicago O'Hare Intl
3h 00m
Sat, Mar 30
ORD
Chicago O'Hare Intl
PWM
Portland
5h 30m
Trip: 4 days
6.1GoodShow reviews
Overall 6.1 Good
Based on 33 reviews
Overall
7.3
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
BOI
SFO
Good 6.4

Pros: Yes, crew were great, seat was okay

Cons: Have life vests on board for the crew, was delayed over 2 1/2 hours on run way!

LGA
DEN
Good 6.0

Cons: I was in coach. I am 6’2” and my legs were pressed against the seat in front of me for the full 4 hours. Uncomfortable.

YAP
GUM
Good 6.0

Pros: ANA was excellent in getting us on an earlier flight-

Cons: Unfortunately, they sent us to the "wrong" security checkpoint- at the opposite side of the airport. From the checkin desk, we were told to go to the NORTH security checkpoint. Walking the terminal again from where we came, we passed the SOUTH security checkpoint and made it another 5mins to gate.

PWM
ORD
Okay 4.0

Cons: 3 hour mechanical delay

PWM
ORD
Excellent 9.3

Pros: AT THE TERMINAL IN PORTLAND THE ATTENDANTS WERE SUPER HELPFUL AS I WAS CONFUSED ABOUT GETTING MY TICKETS.

Cons: JUST BEFORE BOARDING THOSE OF US PASSENGERS NOT ALREADY BOARDED WERE TOLD WE COULD NOT BRING OUR CARRY ONS WITH US AS THERE WAS NOT ENOUGH SPACE TO STOW THEM OVERHEAD. SO WE WERE TOLD TO SEND THEM DIRECTLY TO OUR FINAL DESTINATION. WHEN I BOARDED THE PLANE I COUNTED 7 OVERHEAD STORAGE BINS ON THE OPPOSITE SIDE TO MY AISLE WHERE I WAS SEATED WERE NOT FILLED AND THERE WERE SEVERAL SUCH BINS ON MY SIDE OF THE AISLE (I DID NOT HAVE TIME TO COUNT THEM BEFORE I SAT DOWN). I ASKED AN ATTENDANT WHY THIS WAS SO GIVEN WE WERE TOLD THE BINS WERE FILLED JUST AS WE BOARDING FROM THE DEPARTURE AREA. SHE WAS POLITE AND SAID SHE WASN'T SURE ABOUT WHO MADE THE ANNOUNCEMENT IN THE TERMINAL BUT THAT IN ANY EVENT MY CARRY ON WOULD ARRIVE SAFE AND SOUND IN VANCOUVER - IT DID BUT WITH MY BOOK FOOD SNACK WHICH i HAD INTENDED TO USE WHILE ON MY WAY TO CHI. AND VAN.

Fri, May 24
PWM
Portland
ORD
Chicago O'Hare Intl
6h 43m
Mon, May 27
ORD
Chicago O'Hare Intl
PWM
Portland
6h 20m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,619 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
SAN
LAS
Excellent 10.0

Pros: Great flight

BTV
DTW
Excellent 9.3

Cons: The gate was changed but it was not updated to the app. Many of us were waiting in the wrong gate until 10 mins before departure.

DTW
PHX
Excellent 10.0

Pros: All was good

Cons: All was good

MCI
DTW
Excellent 8.0

Cons: If there could have been some sort of service at DTW to take customers to the gate of their connecting flight, for cases of really short time window of course, it’d be extremely helpful.

ATL
SJO
Excellent 10.0

Cons: Let was a typical flight. About all you can hope for is that it is on time. That makes it excellent.

Sat, Aug 10
PWM
Portland
MDW
Chicago Midway
3h 55m
Tue, Aug 13
MDW
Chicago Midway
PWM
Portland
4h 40m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,631 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
CVG
ATL
Excellent 9.0

Pros: Crew was very professional. Seat uncomfortable. No entertainment. did get water or coffee.

Cons: Comfort

LAX
MSY
Good 6.6

Pros: Great service

Cons: Stuck at landing. For over 20+ minutes

ATL
MSY
Okay 5.2

Cons: CheezIts were too salty. We had to sit on NO tarmac for over 10 minutes because a plane was stuck at our gate...several other gates empty - what's up?

BKK
ICN
Excellent 9.6

Cons: More comfortable seats!!!

AMS
BOS
Excellent 10.0

Pros: Good seating, great food, good service.

Fri, Mar 29
PWM
Portland
ORD
Chicago O'Hare Intl
3h 00m
Sat, Mar 30
ORD
Chicago O'Hare Intl
PWM
Portland
7h 29m
Trip: 2 days
6.1GoodShow reviews
Overall 6.1 Good
Based on 33 reviews
Overall
7.3
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
PWM
ORD
Okay 5.3

Cons: Seating next to the bathroom is gross

SFO
HNL
Good 6.0

Pros: crew good, seats good

Cons: The delay was over 2- 1/2 hours on the run way to honolulu..

DEN
MSY
Excellent 8.6

Pros: Ok.

Cons: Less time with seatbelt sign on.

PHL
DEN
Excellent 10.0

Pros: The attendants were amazing, fun, attentive and provided for a very quick four-hour trip!

Cons: Not one thing.

LAX
SBP
Excellent 10.0

Pros: This plane has more space than larger plane, was more comfortable.

Wed, Apr 17
PWM
Portland
MDW
Chicago Midway
4h 15m
Tue, Apr 30
MDW
Chicago Midway
PWM
Portland
5h 33m
Trip: 14 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,631 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
SFO
SEA
Excellent 8.3

Pros: free movies on the flight

Cons: The check-in process at SFO airport was poorly managed.

DEN
SEA
Good 7.0

Pros: On time flight, bag made it, great price, can’t complain.

Cons: Seat pretty tight for an average size adult man. No inflight phone charger.

LAS
YYC
Mediocre 3.0

Pros: Seats were horrible, we all booked together and a bunch of my group got bumped to a different flight.

LAX
SYD
Good 7.6

Pros: The staff was friendly and helpful

Cons: Outlets to charge my electronic devices for the long flight

ATL
SFO
Excellent 10.0

Pros: Yes

Cons: Took off late. Other than that very comfortable and great experience

Wed, May 22
BGR
Bangor
ORD
Chicago O'Hare Intl
8h 16m
Sun, May 26
ORD
Chicago O'Hare Intl
BGR
Bangor
7h 49m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,631 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
SEA
SAN
Excellent 10.0

Pros: It was a nice flight. No troubles

Cons: Nothing

LGA
SRQ
Excellent 8.0

Pros: Didn’t like security. They were rude

Cons: Security

BOS
SEA
Excellent 10.0

Pros: The crew was so lovely and accommodating, flight was smooth, and I was impressed with the meal service. I travel a lot and this was one of my best experiences. I will definitely favor Delta in the future.

ATL
SJO
Excellent 10.0

Cons: Let was a typical flight. About all you can hope for is that it is on time. That makes it excellent.

BTV
DTW
Excellent 9.3

Cons: The gate was changed but it was not updated to the app. Many of us were waiting in the wrong gate until 10 mins before departure.

Sat, Jun 15
PWM
Portland
MDW
Chicago Midway
3h 55m
Fri, Jun 21
MDW
Chicago Midway
PWM
Portland
4h 45m
Trip: 7 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,631 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
DTW
PHX
Excellent 10.0

Pros: All was good

Cons: All was good

HNL
FUK
Good 7.3

Cons: Ran out of hot water on flight

BDL
ATL
Excellent 8.0

Pros: I liked the wide variety of movies and snacks available.

Cons: The kid behind me wouldn't stop kicking my seat.

ATL
CRW
Excellent 9.0

Pros: The ctew was awesome, super sweet and very acomodating

Cons: Its a flight to WV (my birth place).... it is what it is... smll planes, tight quarters and people who don’t get any of that and are not happy anout any of it

BOS
SEA
Excellent 10.0

Pros: The crew was so lovely and accommodating, flight was smooth, and I was impressed with the meal service. I travel a lot and this was one of my best experiences. I will definitely favor Delta in the future.

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