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Alaska to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Alaska
Flight Price $404
Airlines Alaska Airlines, Delta, United Airlines

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

Airports
Origin
Fairbanks
$433
only
$433
Anchorage
$404
only
$404
Destination
Chicago
$404
only
$404
$457
only
$457
Sun, Jan 6
ANC
Anchorage
ORD
Chicago O'Hare International
18h 55m
Sat, Jan 26
ORD
Chicago O'Hare International
ANC
Anchorage
9h 40m
Trip: 21 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 41 reviews
Overall
8.6
Boarding
8.6
Comfort
8.3
Crew
8.9
Entertainment
7.9
Food
7.9
ANC
ORD
Good 6.0

No leg room

ANC
ORD
Good 7.6

Everything other than the seats

Seats. Especially when I paid more for Exit seats and found out the first row of exit seats did not recline.

ANC
ORD
Excellent 8.3

20 minute luggage delivery policy. Great entertainment system based on app and wifi. Free texting and messaging on flight to keep you connected. Usb and full charger available in every seat.

Limited reclining. Small pocket below table to hold your stuff. No food included in such a long flight (5.5 hours)

ANC
ORD
Okay 4.3

A straight flight

The fact that I watched the crew throw my luggage 5 feet and broke things in my suitcase. The won't do anything about it

ANC
ORD
Excellent 8.3

The crew and the flight was awesome. Came in 50 minutes early!!!-

The screaming children I was surrounded by. No fault of the airline tho... The food smelled a lot better than it tasted tho... All three bites...

Mon, Dec 3
FAI
Fairbanks
ORD
Chicago O'Hare International
19h 40m
Tue, Dec 25
ORD
Chicago O'Hare International
FAI
Fairbanks
8h 56m
Trip: 23 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,906 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
PDX
SEA
Okay 4.0

I was placed on an earlier flight as soon as I arrived at the Portland airport. The flight was full, there was no room for my bag in the overhead bins. The bag was checked, not to just Seattle but all the way to Venice. Well, surprise, surprise, the bag was lost on the way to Venice. KLM does not allow enough time in Amsterdam for luggage to make a connecting flight.

MSP
EWR
Good 6.3

The staff are great very nice pleasant

Wifi doesn't work for long time and have wait long periods to watch something. TV on head reat is nice

MSP
BZN
Excellent 10.0

Everything! Flight-Flight Attendants-Peanuts-Coffee-Pilot

I’d love to have a free fruit or veggie snack. Just a small bag

DTW
MTY
Excellent 9.3

I did not like that they would not assign me a seat because the flight appeared to be oversold. Finally I was allowed to board (and it was a good seat location but the seat back was locked in the upright position and I wanted to knap)

IND
JFK
Excellent 10.0

Quick and smooth boarding. Crew was very pleasant and welcoming. Temperature was for the most part comfortable. Quick disembarkment

Very tight carry on space requiring gate check. Delay leaving aircraft. Seating at gate assigned. No options. This was a short flight and I was in an exit row, making this flight comfortable

Mon, Oct 29
ANC
Anchorage
ORD
Chicago O'Hare International
25h 33m
Wed, Oct 31
ORD
Chicago O'Hare International
ANC
Anchorage
18h 33m
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Dec 24
ANC
Anchorage
ORD
Chicago O'Hare International
6h 00m
Mon, Dec 31
ORD
Chicago O'Hare International
ANC
Anchorage
6h 48m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 26 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
ANC
ORD
Good 7.3

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

Nothing

ANC
ORD
Okay 4.3

Weight restriction on the plane, almost didn't make it out

Late to leave anchorage because of a weight restriction. Flight was only 3/4 full.

ANC
ORD
Okay 5.6

Crew were friendly and helpful.

I don't think it's possible to construct a plane more cramped than that, but I'm sure someone will rise to the challenge.

ANC
ORD
Mediocre 2.3

The one crew member that talked the whole flight was nice

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

ANC
ORD
Good 6.0

The attendents were helpful and nice except in the situation I've listed in dislike. The plane left on time and arrived early and we didn't have to wait 20 minutes for a gate to open up.

I chose the back window seat right in front of the restrooms. Crewmember even said it was the worst seat in the house. Although I didn't pay to upgrade, thee were available seats up there. The attendant even said she would ttry to move things around once people were seate without anyone asking. She just knew our row was going to be uncomfortable.. I am tall with big shoulders, the gentleman next to me was large. All that I ask is the attendant come back after all is settled and explain that it wasn't possible to move things around. Although, if there were seats available I should have been offered a different seat. I have flown a lot on different airlines. I've flown on a 15 hour flight overseas. This is BY FAR the most uncomfortable I have EVER been.

Mon, Dec 3
ANC
Anchorage
ORD
Chicago O'Hare International
14h 10m
Thu, Dec 6
ORD
Chicago O'Hare International
ANC
Anchorage
10h 46m
Trip: 4 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 41 reviews
Overall
8.6
Boarding
8.6
Comfort
8.3
Crew
8.9
Entertainment
7.9
Food
7.9
ANC
ORD
Okay 4.3

A straight flight

The fact that I watched the crew throw my luggage 5 feet and broke things in my suitcase. The won't do anything about it

ANC
ORD
Good 6.3

Boarding process was smooth and efficient.

Flight was super warm!!

ANC
ORD
Excellent 10.0

Very professional staff yet personable, helpful with questions r/t the flight. Great flight and great landing! I love that you do not have to pay for every single thing and that the weight limit on luggage is still at 50 lbs! Definitely will use this airline again!

ANC
ORD
Good 7.0

Cabin crew

Even in Premium seats, there is no room for comfort. I am a skinny guy, and still those seats are killers. Time for a re-do! I suggest making Premium seats 5 to a row instead of 6.

ANC
ORD
Okay 5.3

i liked that the flight attendants were attentaive.

the wifi which i paid for didnt work the entire tome and it was frustrating

Mon, Nov 19
ANC
Anchorage
ORD
Chicago O'Hare International
12h 51m
Thu, Nov 29
ORD
Chicago O'Hare International
ANC
Anchorage
15h 20m
Trip: 11 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,906 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
DTW
MTY
Excellent 9.3

I did not like that they would not assign me a seat because the flight appeared to be oversold. Finally I was allowed to board (and it was a good seat location but the seat back was locked in the upright position and I wanted to knap)

PDX
SEA
Okay 4.0

I was placed on an earlier flight as soon as I arrived at the Portland airport. The flight was full, there was no room for my bag in the overhead bins. The bag was checked, not to just Seattle but all the way to Venice. Well, surprise, surprise, the bag was lost on the way to Venice. KLM does not allow enough time in Amsterdam for luggage to make a connecting flight.

MSP
ATL
Excellent 9.6

The crew was very nice. Quite helpful and pleasant.

The only small item is the gate size in MSP. Always a bit crowded but still departed on time so it’s not a large issue.

LAX
SFO
Mediocre 2.0

That it got me home

VPS
ATL
Good 7.3

Food and entertainment were non-existent since the flights were so short and on smaller jets.....so I guess 1star isn't really fair, but there was no option for N/A Flight attendants were friendly. VPS-ATL lead attendant was very sweet to a passenger in front of us who was on her first flight alone with her child to go to her fathers funeral in the Philippines. She also thanked a soldier for her service. Love these little touches.

I'm so used to the nice screens with free tv games and flight tracker and really missed that on this trip. I'm glad I decided not to pay to upgrade to comfort + this trip for the first time in a long time.

Sat, Feb 16
ANC
Anchorage
ORD
Chicago O'Hare International
12h 03m
Sat, Feb 23
ORD
Chicago O'Hare International
ANC
Anchorage
10h 16m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,906 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
LAX
SFO
Mediocre 2.0

That it got me home

MSP
ATL
Excellent 9.6

The crew was very nice. Quite helpful and pleasant.

The only small item is the gate size in MSP. Always a bit crowded but still departed on time so it’s not a large issue.

IND
JFK
Excellent 10.0

Quick and smooth boarding. Crew was very pleasant and welcoming. Temperature was for the most part comfortable. Quick disembarkment

Very tight carry on space requiring gate check. Delay leaving aircraft. Seating at gate assigned. No options. This was a short flight and I was in an exit row, making this flight comfortable

MSP
BZN
Excellent 10.0

Everything! Flight-Flight Attendants-Peanuts-Coffee-Pilot

I’d love to have a free fruit or veggie snack. Just a small bag

ATL
MCI
Excellent 10.0

The movies kept my daughter busy.

Mon, Dec 3
ANC
Anchorage
MDW
Chicago Midway
13h 29m
Thu, Dec 6
MDW
Chicago Midway
ANC
Anchorage
14h 05m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,906 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
MSP
ATL
Excellent 9.6

The crew was very nice. Quite helpful and pleasant.

The only small item is the gate size in MSP. Always a bit crowded but still departed on time so it’s not a large issue.

MSP
BZN
Excellent 10.0

Everything! Flight-Flight Attendants-Peanuts-Coffee-Pilot

I’d love to have a free fruit or veggie snack. Just a small bag

IND
JFK
Excellent 10.0

Quick and smooth boarding. Crew was very pleasant and welcoming. Temperature was for the most part comfortable. Quick disembarkment

Very tight carry on space requiring gate check. Delay leaving aircraft. Seating at gate assigned. No options. This was a short flight and I was in an exit row, making this flight comfortable

ATL
PHF
Excellent 8.6

Gate agent inATL helped an elderly man get on board early at my suggestion.Proud of our female pilot from ATL-PHF

I'm so used to the nice screens with free tv games and flight tracker and really missed that on this trip. I'm glad I decided not to pay to upgrade to comfort + this trip for the first time in a long time. I was able to use my tablet for flight tracker but could only see the map and not the stats

ATL
MCI
Excellent 10.0

The movies kept my daughter busy.

Tue, Jan 15
ANC
Anchorage
MDW
Chicago Midway
10h 28m
Fri, Feb 1
MDW
Chicago Midway
ANC
Anchorage
11h 39m
Trip: 18 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,906 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
MSP
ATL
Excellent 9.6

The crew was very nice. Quite helpful and pleasant.

The only small item is the gate size in MSP. Always a bit crowded but still departed on time so it’s not a large issue.

IND
JFK
Excellent 10.0

Quick and smooth boarding. Crew was very pleasant and welcoming. Temperature was for the most part comfortable. Quick disembarkment

Very tight carry on space requiring gate check. Delay leaving aircraft. Seating at gate assigned. No options. This was a short flight and I was in an exit row, making this flight comfortable

MSP
BZN
Excellent 10.0

Everything! Flight-Flight Attendants-Peanuts-Coffee-Pilot

I’d love to have a free fruit or veggie snack. Just a small bag

LAX
SFO
Mediocre 2.0

That it got me home

PDX
SEA
Okay 4.0

I was placed on an earlier flight as soon as I arrived at the Portland airport. The flight was full, there was no room for my bag in the overhead bins. The bag was checked, not to just Seattle but all the way to Venice. Well, surprise, surprise, the bag was lost on the way to Venice. KLM does not allow enough time in Amsterdam for luggage to make a connecting flight.

Wed, Nov 7
ANC
Anchorage
MDW
Chicago Midway
14h 01m
Sat, Nov 10
MDW
Chicago Midway
ANC
Anchorage
15h 25m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,906 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
MSP
BZN
Excellent 10.0

Everything! Flight-Flight Attendants-Peanuts-Coffee-Pilot

I’d love to have a free fruit or veggie snack. Just a small bag

VPS
ATL
Good 7.3

Food and entertainment were non-existent since the flights were so short and on smaller jets.....so I guess 1star isn't really fair, but there was no option for N/A Flight attendants were friendly. VPS-ATL lead attendant was very sweet to a passenger in front of us who was on her first flight alone with her child to go to her fathers funeral in the Philippines. She also thanked a soldier for her service. Love these little touches.

I'm so used to the nice screens with free tv games and flight tracker and really missed that on this trip. I'm glad I decided not to pay to upgrade to comfort + this trip for the first time in a long time.

PDX
SEA
Okay 4.0

I was placed on an earlier flight as soon as I arrived at the Portland airport. The flight was full, there was no room for my bag in the overhead bins. The bag was checked, not to just Seattle but all the way to Venice. Well, surprise, surprise, the bag was lost on the way to Venice. KLM does not allow enough time in Amsterdam for luggage to make a connecting flight.

DTW
MTY
Excellent 9.3

I did not like that they would not assign me a seat because the flight appeared to be oversold. Finally I was allowed to board (and it was a good seat location but the seat back was locked in the upright position and I wanted to knap)

ATL
PHF
Excellent 8.6

Gate agent inATL helped an elderly man get on board early at my suggestion.Proud of our female pilot from ATL-PHF

I'm so used to the nice screens with free tv games and flight tracker and really missed that on this trip. I'm glad I decided not to pay to upgrade to comfort + this trip for the first time in a long time. I was able to use my tablet for flight tracker but could only see the map and not the stats

Mon, Nov 19
ANC
Anchorage
ORD
Chicago O'Hare International
7h 33m
Fri, Nov 23
ORD
Chicago O'Hare International
ANC
Anchorage
11h 30m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,906 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
PDX
SEA
Okay 4.0

I was placed on an earlier flight as soon as I arrived at the Portland airport. The flight was full, there was no room for my bag in the overhead bins. The bag was checked, not to just Seattle but all the way to Venice. Well, surprise, surprise, the bag was lost on the way to Venice. KLM does not allow enough time in Amsterdam for luggage to make a connecting flight.

DTW
MTY
Excellent 9.3

I did not like that they would not assign me a seat because the flight appeared to be oversold. Finally I was allowed to board (and it was a good seat location but the seat back was locked in the upright position and I wanted to knap)

LAX
SFO
Mediocre 2.0

That it got me home

ATL
PHF
Excellent 8.6

Gate agent inATL helped an elderly man get on board early at my suggestion.Proud of our female pilot from ATL-PHF

I'm so used to the nice screens with free tv games and flight tracker and really missed that on this trip. I'm glad I decided not to pay to upgrade to comfort + this trip for the first time in a long time. I was able to use my tablet for flight tracker but could only see the map and not the stats

VPS
ATL
Good 7.3

Food and entertainment were non-existent since the flights were so short and on smaller jets.....so I guess 1star isn't really fair, but there was no option for N/A Flight attendants were friendly. VPS-ATL lead attendant was very sweet to a passenger in front of us who was on her first flight alone with her child to go to her fathers funeral in the Philippines. She also thanked a soldier for her service. Love these little touches.

I'm so used to the nice screens with free tv games and flight tracker and really missed that on this trip. I'm glad I decided not to pay to upgrade to comfort + this trip for the first time in a long time.

Mon, Nov 19
ANC
Anchorage
MDW
Chicago Midway
11h 00m
Fri, Nov 23
MDW
Chicago Midway
ANC
Anchorage
11h 20m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,906 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
ATL
PHF
Excellent 8.6

Gate agent inATL helped an elderly man get on board early at my suggestion.Proud of our female pilot from ATL-PHF

I'm so used to the nice screens with free tv games and flight tracker and really missed that on this trip. I'm glad I decided not to pay to upgrade to comfort + this trip for the first time in a long time. I was able to use my tablet for flight tracker but could only see the map and not the stats

MSP
EWR
Good 6.3

The staff are great very nice pleasant

Wifi doesn't work for long time and have wait long periods to watch something. TV on head reat is nice

IND
JFK
Excellent 10.0

Quick and smooth boarding. Crew was very pleasant and welcoming. Temperature was for the most part comfortable. Quick disembarkment

Very tight carry on space requiring gate check. Delay leaving aircraft. Seating at gate assigned. No options. This was a short flight and I was in an exit row, making this flight comfortable

ATL
MCI
Excellent 10.0

The movies kept my daughter busy.

PDX
SEA
Okay 4.0

I was placed on an earlier flight as soon as I arrived at the Portland airport. The flight was full, there was no room for my bag in the overhead bins. The bag was checked, not to just Seattle but all the way to Venice. Well, surprise, surprise, the bag was lost on the way to Venice. KLM does not allow enough time in Amsterdam for luggage to make a connecting flight.

Sat, Oct 27
ANC
Anchorage
ORD
Chicago O'Hare International
17h 40m
Sat, Dec 1
ORD
Chicago O'Hare International
ANC
Anchorage
17h 12m
Trip: 36 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,906 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
YYJ
SEA
Mediocre 2.0

Was not allowed to check in even tho flight was delayed. Horrible!

IND
JFK
Excellent 10.0

Quick and smooth boarding. Crew was very pleasant and welcoming. Temperature was for the most part comfortable. Quick disembarkment

Very tight carry on space requiring gate check. Delay leaving aircraft. Seating at gate assigned. No options. This was a short flight and I was in an exit row, making this flight comfortable

MSP
ATL
Excellent 9.6

The crew was very nice. Quite helpful and pleasant.

The only small item is the gate size in MSP. Always a bit crowded but still departed on time so it’s not a large issue.

ATL
MCI
Excellent 10.0

The movies kept my daughter busy.

VPS
ATL
Good 7.3

Food and entertainment were non-existent since the flights were so short and on smaller jets.....so I guess 1star isn't really fair, but there was no option for N/A Flight attendants were friendly. VPS-ATL lead attendant was very sweet to a passenger in front of us who was on her first flight alone with her child to go to her fathers funeral in the Philippines. She also thanked a soldier for her service. Love these little touches.

I'm so used to the nice screens with free tv games and flight tracker and really missed that on this trip. I'm glad I decided not to pay to upgrade to comfort + this trip for the first time in a long time.

Mon, Oct 29
ANC
Anchorage
MDW
Chicago Midway
13h 05m
Wed, Oct 31
MDW
Chicago Midway
ANC
Anchorage
12h 03m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 20,906 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
ATL
MCI
Excellent 10.0

The movies kept my daughter busy.

IND
JFK
Excellent 10.0

Quick and smooth boarding. Crew was very pleasant and welcoming. Temperature was for the most part comfortable. Quick disembarkment

Very tight carry on space requiring gate check. Delay leaving aircraft. Seating at gate assigned. No options. This was a short flight and I was in an exit row, making this flight comfortable

PDX
SEA
Okay 4.0

I was placed on an earlier flight as soon as I arrived at the Portland airport. The flight was full, there was no room for my bag in the overhead bins. The bag was checked, not to just Seattle but all the way to Venice. Well, surprise, surprise, the bag was lost on the way to Venice. KLM does not allow enough time in Amsterdam for luggage to make a connecting flight.

ATL
PHF
Excellent 8.6

Gate agent inATL helped an elderly man get on board early at my suggestion.Proud of our female pilot from ATL-PHF

I'm so used to the nice screens with free tv games and flight tracker and really missed that on this trip. I'm glad I decided not to pay to upgrade to comfort + this trip for the first time in a long time. I was able to use my tablet for flight tracker but could only see the map and not the stats

DTW
MTY
Excellent 9.3

I did not like that they would not assign me a seat because the flight appeared to be oversold. Finally I was allowed to board (and it was a good seat location but the seat back was locked in the upright position and I wanted to knap)

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