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Alaska to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Alaska
Flight Price $376
Airlines United Airlines, Alaska Airlines, Delta, Sun Country Air

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

Airports
Origin
Fairbanks
$531
only
$531
Sitka
$466
only
$466
Anchorage
$376
only
$376
Nome
$712
only
$712
Destination
Chicago
$376
only
$376
$406
only
$406
Thu, May 2
ANC
Anchorage
ORD
Chicago O'Hare Intl
5h 58m
Thu, May 9
ORD
Chicago O'Hare Intl
ANC
Anchorage
6h 35m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 26 reviews
Overall
7.3
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
IAH
SJO
Poor 0.0

Cons: Flight was canceled due to United's mismanagement of crews.

IAD
LIS
Good 7.3

Pros: Fast boarding and helpful crew.

Cons: Food was cold and soggy.

EWR
SLC
Excellent 9.6

Pros: We landed 45 minutes early!

ORD
SFO
Excellent 8.6

Cons: If they had veggie options or any options for food when they arrived to my seat

SEA
IAH
Good 6.4

Pros: The flight attendants were great.

Cons: Cabin was very very stuffy and hot. Very uncomfortable. Paying for WiFi? When other airlines offer it for free????

Tue, Apr 9
ANC
Anchorage
ORD
Chicago O'Hare Intl
14h 00m
Thu, Apr 11
ORD
Chicago O'Hare Intl
ANC
Anchorage
6h 40m
Trip: 3 days
7.7GoodShow reviews
Overall 7.7 Good
Based on 42 reviews
Overall
8.5
Boarding
8.6
Comfort
8.3
Crew
8.8
Entertainment
7.9
Food
7.9
ANC
ORD
Excellent 8.0

Pros: Was in time. Leg space was good

ANC
ORD
Excellent 8.6

Pros: Efficient boarding and on time flight-crew was friendly and helpful.

Cons: Being between two big men, I felt squished in the middle, so I don't know if the seats are smaller than other airlines, or just my situation, but sleeping was pretty much out of the question, as I could barely move.

JFK
LAX
Mediocre 2.0

Pros: I missed my flight.

Cons: Help me get my money back for a miss understanding

LIH
SEA
Okay 4.3

Cons: Politely asked boarding agent Michelle if my wife could be put in the isle because she's pregnant and needs to get up a lot. She rudely told me to sit down and she would call me up when she was ready. She serviced everybody else first, made us wait until last, and gave us two window seats instead.

ANC
ORD
Mediocre 2.0

Pros: The flight was fine. Typical of any other airline company.

Cons: They managed to lose my box of fish on a Direct flight from Anchorage to Chicago. I might be more understanding if I had connecting flights. Unacceptable...

Tue, Apr 23
ANC
Anchorage
MDW
Chicago Midway
10h 20m
Wed, May 1
MDW
Chicago Midway
ANC
Anchorage
11h 27m
Trip: 9 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,552 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
PBI
ATL
Excellent 10.0

Pros: Crew was great.

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.

BRU
JFK
Mediocre 2.6

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

ORD
SEA
Excellent 8.6

Pros: Jeff was our flight attendant in first class. He is an excellent flight attendant. He has an amazing attitude and his manner made us feel as if we had been friends with him for years.

Cons: Passengers who pay retail for first class on domestic flights should get access to the Delta lounges even without the AE card. Other airlines do this, and we have come to expect it.

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.

Wed, Jun 5
ANC
Anchorage
ORD
Chicago O'Hare Intl
16h 40m
Sat, Jun 8
ORD
Chicago O'Hare Intl
ANC
Anchorage
6h 40m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 8,606 reviews
Overall
8.1
Boarding
8.2
Comfort
7.7
Crew
8.5
Entertainment
6.8
Food
7.1
MSP
MZT
Okay 4.0

Cons: Leave on time

PDX
PHX
Excellent 10.0

Pros: The price was perfect and suited my needs. Very friendly staff. Thank you

Cons: I cant think of anything to complain about. My trip went very smoothly

PSP
PDX
Excellent 9.0

Pros: Amazingly polite and attentive flight crew...great attitudes!

MSP
LAX
Mediocre 2.0

Pros: Nothing

Cons: Everything ! Internet wasn’t working and the charging port didn’t work

TPA
MSP
Excellent 10.0

Cons: Please bring back your higher seats. Please.

Tue, Jun 4
ANC
Anchorage
MDW
Chicago Midway
15h 15m
Sun, Jun 9
MDW
Chicago Midway
ANC
Anchorage
19h 19m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Apr 13
ANC
Anchorage
ORD
Chicago O'Hare Intl
9h 40m
Sun, Apr 28
ORD
Chicago O'Hare Intl
ANC
Anchorage
9h 34m
Trip: 16 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,552 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
CDG
MSP
Excellent 8.3

Pros: Excellent cabin crew!

Cons: Boarding on time and announcing changes to the bowrding schedule instead of leaving customers guessing.

DTW
PVR
Excellent 10.0

Cons: It was perfect.

ATL
TPA
Okay 4.0

Pros: Boarded on time.

Cons: After boarding the door was closed and the jet way was moved back. 5 minutes later they said they were going to bring the jet way back and open door to let more people on board. They broke 2 FAA regulations by doing this and we were delayed an hour because Deltas computer would not allow this.

LGA
SRQ
Excellent 8.0

Pros: Didn’t like security. They were rude

Cons: Security

BIL
MSP
Excellent 9.6

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

Thu, Jul 11
ANC
Anchorage
ORD
Chicago O'Hare Intl
6h 20m
Sun, Jul 14
ORD
Chicago O'Hare Intl
ANC
Anchorage
13h 58m
Trip: 4 days
7.7GoodShow reviews
Overall 7.7 Good
Based on 42 reviews
Overall
8.5
Boarding
8.6
Comfort
8.3
Crew
8.8
Entertainment
7.9
Food
7.9
EUG
SEA
Good 7.3

Pros: Good entertainment

Cons: My issue was about Kayak... I booked 2 airline tickets and yet I was not seated next to my husband. Who books more than 1 airline ticket and DOESNT want to sit together? Airlines couldn’t do anything about it at the gate. Not sure where the issue took place, but not happy about that.

SEA
SMF
Excellent 8.0

Pros: Great crew.

PHL
LAX
Okay 5.6

Pros: Entertainment system.

Cons: Cabin crew.

SJC
PDX
Mediocre 3.5

Pros: there was nothing to like. A few hours before the early morning flight Alaska cancelled the flight and rebooked us fir a flight 12 hours later. Their phone is off during the night and we had to go to the airport in the middle of the night to get a flight that would get us to our cruise on time. A

Cons: use something other than Alaska and it will be better

IND
SEA
Okay 5.6

Cons: Alaska Airlines is great to fly with, THE SEATTLE AIRPORT IS A NIGHTMARE TO TRAVEL THROUGH!!!Last week SEATTLE AIRPORT WAS UNPREPARED TO HANDLE the traffic,16 AIRCRAFT IN LINE WAITING FOR A GATE. Countless passengers Missed flights. Last night our pilot was instructed to Slow Down and still no gate!

Fri, May 10
ANC
Anchorage
ORD
Chicago O'Hare Intl
5h 58m
Mon, May 13
ORD
Chicago O'Hare Intl
ANC
Anchorage
6h 35m
Trip: 4 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 26 reviews
Overall
7.3
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
ORD
MSP
Good 6.5

Cons: Transfer from international (T5) to T1 at O'Hare is very unpleasant..Generally O'Hare is a terrible airport.

ANC
ORD
Mediocre 2.3

Pros: The one crew member that talked the whole flight was nice

Cons: Entertainment was not given freely, as if you didn't just pay 300 per ticket to fly on United. It would cut in and out just to tell you it wanted your credit card. The seats were so full the middle person doesn't even have room to sit up straight without touching shoulders

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!

ANC
ORD
Good 7.3

Pros: The crew was very attentive and responsive to the needs of the flyers. They did numerous beverage calls for the long flight.

Cons: Nothing

SEA
IAH
Okay 5.6

Cons: The fact that United forces basic economy customers to check carry-on luggage is nothing but a cash grab. Some of the overhead compartments were completely empty yet they force you to pay ?30/ bag. They also gouge you an extra $25 per bag if you bring your carry on to the gate.

Sat, Aug 17
SIT
Sitka
ORD
Chicago O'Hare Intl
13h 57m
Sat, Aug 31
ORD
Chicago O'Hare Intl
SIT
Sitka
8h 56m
Trip: 15 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,575 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
LGA
MIA
Excellent 8.3

Pros: Crew was very attentive and friendly

Cons: Boarding could be better.

JFK
AMS
Excellent 8.0

Pros: Crew was courteous.

SEA
SAN
Excellent 10.0

Pros: It was a nice flight. No troubles

Cons: Nothing

BGR
LGA
Okay 4.0

Cons: If it had left on time Waited 3 hours at the airport

CVG
ATL
Excellent 9.0

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

Cons: Comfort

Wed, Apr 17
FAI
Fairbanks
ORD
Chicago O'Hare Intl
15h 51m
Tue, Apr 23
ORD
Chicago O'Hare Intl
FAI
Fairbanks
9h 51m
Trip: 7 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,575 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

DTW
PVR
Excellent 10.0

Cons: It was perfect.

MCO
IND
Good 7.6

Pros: The flight timings and the arrival time

LIM
ATL
Excellent 9.2

Pros: Delta did a great job getting our checked bags from an overseas arrival to this flight. Boarding smooth.

Cons: Seats are cramped in coach. Fact of life for all carriers.

YYZ
ATL
Excellent 9.6

Pros: I liked the touch screen displays in each headrest. Seats and leg room comfortable

Cons: Boarding was somewhat unorganized

Wed, Apr 17
FAI
Fairbanks
MDW
Chicago Midway
15h 29m
Thu, May 2
MDW
Chicago Midway
FAI
Fairbanks
10h 59m
Trip: 16 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,575 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
MEM
MSP
Good 7.3

Cons: I booked a business class ticket through klm, but it was a delta code share flight. Delta was unable to locate me in their system, and I had to contact klm myself to straighten it out.

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

RDU
LGA
Good 6.0

Cons: Too much delay - departure was planned on March 15 @ 7 pm and take off happened on March 16 @ 12pm - a complete failure!!!!

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?

RDU
ATL
Good 6.0

Pros: The seats were awful .how many can squeeze in. .horrible

Cons: Room to breathe, move a little

Tue, Apr 30
OME
Nome
ORD
Chicago O'Hare Intl
36h 15m
Thu, May 2
ORD
Chicago O'Hare Intl
OME
Nome
43h 20m
Trip: 3 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 26,165 reviews
Overall
8.5
Boarding
8.6
Comfort
8.3
Crew
8.8
Entertainment
7.9
Food
7.9
JFK
LAX
Good 7.0

Pros: Crew was amazing.

Cons: Better informed check-in process.

SFO
SAN
Excellent 9.0

Cons: Extra leg space

JFK
LAX
Excellent 8.0

Pros: I liked the free biscuits, the free drinks, the leg room, the overhead room, and the three bathrooms.

Cons: I would have liked free WiFi.

BOS
SFO
Excellent 10.0

Pros: Crew was great

Cons: It was tight at the gert

EUG
SEA
Good 7.3

Pros: Good entertainment

Cons: My issue was about Kayak... I booked 2 airline tickets and yet I was not seated next to my husband. Who books more than 1 airline ticket and DOESNT want to sit together? Airlines couldn’t do anything about it at the gate. Not sure where the issue took place, but not happy about that.

Sat, Apr 13
ANC
Anchorage
MDW
Chicago Midway
10h 52m
Sun, Apr 28
MDW
Chicago Midway
ANC
Anchorage
12h 40m
Trip: 16 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,552 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
RDU
LGA
Good 6.0

Cons: Too much delay - departure was planned on March 15 @ 7 pm and take off happened on March 16 @ 12pm - a complete failure!!!!

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?

LAX
SYD
Good 7.6

Pros: The staff was friendly and helpful

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

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

JFK
MSY
Excellent 9.0

Cons: Snacks

Wed, May 1
OME
Nome
ORD
Chicago O'Hare Intl
15h 05m
Sat, May 4
ORD
Chicago O'Hare Intl
OME
Nome
30h 50m
Trip: 4 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 26,165 reviews
Overall
8.5
Boarding
8.6
Comfort
8.3
Crew
8.8
Entertainment
7.9
Food
7.9
SMF
SAN
Excellent 9.0

Pros: The crew was good, on top of refills and trash. We were able to board and take off on time and landed early.

Cons: Even for first class, the seats aren’t really much roomier or comfy than coach. More leg room, but that’s it.

SEA
MSP
Okay 4.0

Cons: There was a lavatory directly across the aisle from me

LAS
SEA
Excellent 10.0

Pros: Crew was good

Cons: Again, board plane back to front after boarding special needs passenger and your priority passengers. Why have us climb over everyone when we have to get to the back. Also verify size of 2 carry ons. This is what is a hassle.

SFO
JFK
Excellent 10.0

Pros: Crew was ‘amazing’!!!

OAK
KOA
Excellent 8.8

Pros: Excellent crew. Seats pretty comfortable and fair leg room for economy

Cons: Good choices of movies and shows, but was tricky getting access.

Thu, Mar 28
FAI
Fairbanks
ORD
Chicago O'Hare Intl
16h 05m
Sun, Mar 31
ORD
Chicago O'Hare Intl
FAI
Fairbanks
23h 20m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Mar 28
ANC
Anchorage
ORD
Chicago O'Hare Intl
8h 35m
Tue, Apr 9
ORD
Chicago O'Hare Intl
ANC
Anchorage
6h 40m
Trip: 13 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,552 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
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
SAN
Good 6.0

Pros: Crew was nice, despite multiple hoardings and time delays.

Cons: Plane was originally set to leave at 11:30 am, but was delayed until 3:00 pm for equipment. We boarded the plane at 3:00, the door was closed, and 30 minutes of waiting at the gate, where told to deplane, and the flight would leave at 5:06. There was another flight to San Diego, also delayed for hou

SJD
ATL
Excellent 8.3

Pros: The crew very nice and helpful

SAN
LAS
Excellent 10.0

Pros: Great flight

BGR
LGA
Okay 4.0

Cons: If it had left on time Waited 3 hours at the airport

Fri, May 10
ANC
Anchorage
ORD
Chicago O'Hare Intl
7h 37m
Mon, May 13
ORD
Chicago O'Hare Intl
ANC
Anchorage
10h 19m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,552 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
DTW
PVR
Excellent 10.0

Cons: It was perfect.

JFK
MEX
Excellent 10.0

Pros: The flight was on time at departure and 30 minutes on arrival.

Cons: Since I got a good deal on the ticket, my boarding zone was “Basic”. That kind of sucked, but I still could fit bag in the airplane so it all worked out

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.

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

SAN
LAS
Excellent 10.0

Pros: Great flight

Fri, May 10
ANC
Anchorage
MDW
Chicago Midway
9h 43m
Mon, May 13
MDW
Chicago Midway
ANC
Anchorage
14h 31m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,552 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
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?

SEA
SAN
Excellent 10.0

Pros: It was a nice flight. No troubles

Cons: Nothing

MSP
ATL
Excellent 8.0

Pros: Attendant was friendly and efficient.

Cons: No beverages or snacks.

DUB
JFK
Excellent 8.0

Cons: The seats are not very comfortable for such a long flight

LGA
DTW
Excellent 9.6

Pros: We landed 45 minutes ahead of schedule.

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

Thu, Mar 28
ANC
Anchorage
MDW
Chicago Midway
14h 26m
Mon, Apr 8
MDW
Chicago Midway
ANC
Anchorage
11h 19m
Trip: 12 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,552 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
ATL
BOS
Good 6.6

Pros: Delta in flight entertainment is great.

Cons: Always delayed.

LGA
SRQ
Excellent 8.0

Pros: Didn’t like security. They were rude

Cons: Security

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

YEG
MSP
Excellent 9.0

Pros: WiFi and Entertainment

SEA
SAN
Excellent 10.0

Pros: It was a nice flight. No troubles

Cons: Nothing

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