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Find Cheap Flights from Anchorage to Chicago (ANC - CHI)

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Anchorage to Chicago Flight Information

Avg. Flight Duration 6h 24m
Flights Arrive in Chicago
Flights Depart from Anchorage
Flight Price $452
Distance 2,852 miles
Airlines Alaska Airlines, United, American Airlines, Delta

Good to Know

Average Price:
$280
(avg. price over the last 2 weeks)
Good Deal:
$250
or less (round trip)

When to Book Flights from Anchorage to Chicago

Flight prices as travel date approaches
-1 day
-2 days

Top Tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $250 or less.
The cheapest flight from Anchorage to Chicago was found 59 days before departure, on average.
Book at least 3 weeks before departure in order to get a below-average price.
Morning departure is around 39% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Anchorage to Chicago Flights

How long does a flight from Anchorage to Chicago take?
An average nonstop flight takes 6h 00m, covering a distance of 2852 miles.
How many flights are there between Anchorage and Chicago?
There are 32 (nonstop) flights between Anchorage and Chicago per week, averaging 4 per day.
Which airlines provide the cheapest flights from Anchorage to Chicago?
In the past 3 days, the cheapest round-trip tickets were found on Alaska Airlines ($452), United ($500) and American Airlines ($508).
Do I need a passport to fly between Anchorage and Chicago?
No.
Which airlines fly most frequently between Anchorage and Chicago?
Alaska Airlines (3 times daily), United (1 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Anchorage to Chicago?
For Anchorage to Chicago, Tuesday is the cheapest day to fly on average and Friday is the most expensive. Flying from Chicago back to Anchorage, the best deals are generally found on Tuesday, with Friday being the most expensive.

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

Airports
Origin
Anchorage
$452
only
$452
Destination
Chicago
$452
only
$452
$517
only
$517
Tue, Oct 16
ANC
Anchorage
ORD
Chicago O'Hare International
6h 10m
Tue, Oct 23
ORD
Chicago O'Hare International
ANC
Anchorage
24h 30m
Trip: 8 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 38 reviews
Overall
8.6
Boarding
8.6
Comfort
8.3
Crew
8.9
Entertainment
7.9
Food
7.9
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
Good 6.0

No leg room

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 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
Excellent 8.0

Was in time. Leg space was good

Fri, Sep 21
ANC
Anchorage
ORD
Chicago O'Hare International
6h 03m
Sun, Sep 23
ORD
Chicago O'Hare International
ANC
Anchorage
6h 54m
Trip: 3 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
OKC
IAH
Mediocre 2.0

You had us leaving from Dallas...we were on flight from Houston to Amsterdam

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 4.0

The base price is better than Alaska Air. The travel time is acceptable.

The base price is for a cramped seat with no checked bag included. Food and entertainment are also extras The human element has been eliminated from the check in process.

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
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

Fri, Oct 5
ANC
Anchorage
ORD
Chicago O'Hare International
11h 15m
Sun, Oct 7
ORD
Chicago O'Hare International
ANC
Anchorage
6h 52m
Trip: 3 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 32,923 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
CLT
DAB
Excellent 10.0

The flight was on time and I was upgraded to First Class!

AMS
DFW
Excellent 9.0

Great movies and food

Being delayed

MSP
MIA
Mediocre 3.3

Let's see - I was in first class. The flight itself was fine - and only one hour + late!

Food - Served the "breakfast" (when it was called a protein plate) I had coming (into MSP). for "lunch" on the way back (called it a meat plate for lunch. One slice turkey, one slice jamon, one egg, cinnamon roll and fruit. Just because they don't want to serve bread - they call it a protein plate? I'm not on a protein diet. Food was pretty sick for the amount I paid for the fight. Stewardess said it was against Republic's rules to give a customer a can of tonic water (so I could add to the small amount of vodka) - she also told me that it was against Delta's, American's and United's rules to give a can - strange? First Class seat did not recline. First Class was freezing per every flight on this segment (the stewardesses sit in the back and don't want to be uncomfortable - if they make the front warm - the back is too hot for them (not joking on this one). So many things to list - that I will finish on the AA site.

ORD
MCO
Excellent 8.0

Great crew, on-time arrival, quick boarding

Crowded seats in the back of the plane, Low quality and bland snack options

JAX
CLT
Good 6.0

Bumpy

Sat, Sep 29
ANC
Anchorage
MDW
Chicago Midway
10h 15m
Wed, Oct 31
MDW
Chicago Midway
ANC
Anchorage
10h 44m
Trip: 33 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,595 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.

EWR
ATL
Mediocre 2.0

Boarding issues cause delay after plane had to be replaced People were double booked Then land awaited on tarmac because of no ground crew Caused me to miss my next flight

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.

LGA
TYS
Good 6.8

Although we ended up being stuck on the plane for 2 hours prior to take off due to high volume, weather and as the pilot put it, "possible military activity" the crew kept us informed every step of the way. There was one flight attendant in particular who was so full of energy and made the unfortunate circumstances not so bad. She entertained us and kept us in the loop the entire time as did the pilots. It made the 2 hours not feel so bad which was appreciated.

That we were delayed on the plane for two hours on a small plane but I know it was out of their control.

LAX
TUS
Okay 5.6

The bag service

The flight delays

Wed, Oct 31
ANC
Anchorage
ORD
Chicago O'Hare International
14h 35m
Tue, Nov 6
ORD
Chicago O'Hare International
ANC
Anchorage
9h 49m
Trip: 7 days
7.6GoodShow reviews
Overall 7.6 Good
Based on 38 reviews
Overall
8.6
Boarding
8.6
Comfort
8.3
Crew
8.9
Entertainment
7.9
Food
7.9
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
Excellent 10.0

I had an unforeseen challenge as I prepped to move my life from AK to WI. Where upon this arose, I called, and after extensive efforts, she managed to resolve my departure problems. Without going into too much detail, I will attempt to fly with Alaska Airlines whenever I can.

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
Excellent 10.0

Pre-check, loaded and landed on time. Great pilot on the way home back to O'Hare. All flight attendants were super to work with...no hassles/problems.

No pillows for 6.25 hour flight:(

ANC
ORD
Excellent 8.0

Was in time. Leg space was good

Wed, Oct 3
ANC
Anchorage
MDW
Chicago Midway
7h 44m
Tue, Oct 9
MDW
Chicago Midway
ANC
Anchorage
8h 28m
Trip: 7 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,595 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
JFK
CUN
Okay 5.6

Flight was delayed.

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.

JFK
MXP
Excellent 8.0

The flight was very smooth and the landing also was very good. The selection of movie are plenty.

EWR
ATL
Mediocre 2.0

Boarding issues cause delay after plane had to be replaced People were double booked Then land awaited on tarmac because of no ground crew Caused me to miss my next flight

Fri, Dec 21
ANC
Anchorage
ORD
Chicago O'Hare International
6h 00m
Sat, Dec 29
ORD
Chicago O'Hare International
ANC
Anchorage
6h 36m
Trip: 9 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
OKC
IAH
Mediocre 2.0

You had us leaving from Dallas...we were on flight from Houston to Amsterdam

LHR
IAD
Excellent 10.0

Service

Nothing

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
Okay 4.0

The base price is better than Alaska Air. The travel time is acceptable.

The base price is for a cramped seat with no checked bag included. Food and entertainment are also extras The human element has been eliminated from the check in process.

ANC
ORD
Good 7.6

Good in flight entertainment

seats were a little less shitty but still shitty

Wed, Dec 5
ANC
Anchorage
MDW
Chicago Midway
7h 42m
Mon, Dec 10
MDW
Chicago Midway
ANC
Anchorage
8h 45m
Trip: 6 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,595 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
LGA
TYS
Good 6.8

Although we ended up being stuck on the plane for 2 hours prior to take off due to high volume, weather and as the pilot put it, "possible military activity" the crew kept us informed every step of the way. There was one flight attendant in particular who was so full of energy and made the unfortunate circumstances not so bad. She entertained us and kept us in the loop the entire time as did the pilots. It made the 2 hours not feel so bad which was appreciated.

That we were delayed on the plane for two hours on a small plane but I know it was out of their control.

EWR
ATL
Mediocre 2.0

Boarding issues cause delay after plane had to be replaced People were double booked Then land awaited on tarmac because of no ground crew Caused me to miss my next 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.

JFK
TPA
Okay 4.0

They ran out of blankets, earphones on the flight

CUN
ATL
Mediocre 2.0

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

Sat, Nov 3
ANC
Anchorage
MDW
Chicago Midway
10h 13m
Tue, Nov 6
MDW
Chicago Midway
ANC
Anchorage
14h 23m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,595 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.

LAX
TUS
Okay 5.6

The bag service

The flight delays

JFK
MXP
Excellent 8.0

The flight was very smooth and the landing also was very good. The selection of movie are plenty.

LGA
TYS
Good 6.8

Although we ended up being stuck on the plane for 2 hours prior to take off due to high volume, weather and as the pilot put it, "possible military activity" the crew kept us informed every step of the way. There was one flight attendant in particular who was so full of energy and made the unfortunate circumstances not so bad. She entertained us and kept us in the loop the entire time as did the pilots. It made the 2 hours not feel so bad which was appreciated.

That we were delayed on the plane for two hours on a small plane but I know it was out of their control.

PBI
LGA
Excellent 10.0

Boarding was on time; flight departures on time and arrived earlier than expected! Pilot told us exactly what was the status and gave us updates; cabin was well air conditioned; flight attendants were friendly; bags came out very quick! Very nice flight

Thu, Aug 30
ANC
Anchorage
ORD
Chicago O'Hare International
8h 10m
Thu, Sep 6
ORD
Chicago O'Hare International
ANC
Anchorage
10h 10m
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 19,595 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
EWR
ATL
Mediocre 2.0

Boarding issues cause delay after plane had to be replaced People were double booked Then land awaited on tarmac because of no ground crew Caused me to miss my next flight

JFK
CUN
Okay 5.6

Flight was delayed.

LGA
PBI
Excellent 10.0

There were many delays and cancellations due to bad thunderstorms at LGA. Despite a few hours delayed (because the airport was closed due to the storm), the flight was still schedule to leave! I was very happy about that. They did issue waivers for those who could not make the later time. Once delta got the ok to fly.. The flight left the gate very fast and we arrived and exited the plane super fast too. The process was so efficient and quick, I did not feel the waiting period. The flight attendance were so happy and positive, they made he flight very enjoyable. Great job delta!

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
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.

Fri, Dec 21
ANC
Anchorage
ORD
Chicago O'Hare International
6h 00m
Wed, Dec 26
ORD
Chicago O'Hare International
ANC
Anchorage
6h 56m
Trip: 6 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
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
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 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 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 3.6

Lost my luggage and made us late

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