Find Cheap Flights from Alaska to Chicago

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

Airports
Origin
Anchorage
$462
only
$462
Destination
Chicago
$462
only
$462
$502
only
$502
Sun, Apr 1
ANC
ORD
8h 35m
Mon, Apr 2
ORD
ANC
9h 28m
Trip: 2 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 28416 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
HKG
BKK
Good 6.0

Flight delayed by 35 minutes

DEN
ORD
Good 6.4

I'm not sure where the problem was - whether with AA or Royal Jordanian, but my luggage did not make it to Amman with me. In fact, there was a whole group of passengers traveling on American from different US cities, switching to RJ in Chicago, whose luggage did not come on the flight to Amman. My advice: be sure to pack enough for a couple of days in your carryon - and don't accept an offer to check your carryon to its final destination!

LAX
CLT
Mediocre 2.6

I got there safely.

I will never fly American Airlines again. From the moment I checked in with the ticket agent to getting off the plane it was a disaster. The ticket agent was rude, hostile, and dismissive. Employees walked through the line at security forcing everyone to consolidate their belongings to one bag. I had a large wallet in my hand and was told I had to step out of line to put it in my backpack. They only allow you one bag to carry on without paying extra. At the time of boarding they announced that the overhead storage was full so even those that paid extra were still forced to check their bags. The plane was dirty, the service was slow, overall just gross. They don’t have WiFi or in flight entertainment so I paid the $20 to purchase the WiFi. It was worthless. I couldn’t stream anything, even music kept stopping to buffer. I understand it will be slower then on ground WiFi, but it was impossible to watch anything and a complete waste of money.

DFW
DEN
Excellent 10.0

Easy and quick boarding. Excellwnt service in first class. Comfortable ride.

Nothing. Excellent travel experience.

LAX
MIA
Mediocre 2.0

Couldn’t sleep because the AC wasnt working. Most miserable flight my life

The AC wasn’t working it was the most miserable flight ever

Thu, Jul 12
ANC
ORD
6h 05m
Mon, Aug 13
ORD
ANC
6h 43m
Trip: 33 days
7.7GoodShow reviews
Overall 7.7 Good
Based on 36 reviews
Overall
8.6
Boarding
8.7
Comfort
8.4
Crew
8.9
Entertainment
7.9
Food
8.0
ANC
ORD
Excellent 8.0

Was in time. Leg space was good

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

ANC
ORD
Good 6.0

No leg room

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 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.

Thu, May 3
ANC
ORD
9h 35m
Mon, May 7
ORD
ANC
8h 49m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Jun 14
ANC
ORD
6h 02m
Mon, Jun 18
ORD
ANC
10h 01m
Trip: 5 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 25 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.4
ANC
ORD
Excellent 8.3

Everything you are..

ANC
ORD
Mediocre 3.6

Lost my luggage and made us late

IAD
NRT
Excellent 10.0

For a little over $2000 you get an economy seat non-stop from DC to Tokyo and back. Meals were good. As economy seats go, it's comfortable. Midweek the flight is about half to two thirds full. So you might be able to stretch out even!

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.

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

Fri, Mar 23
ANC
MDW
12h 56m
Tue, Mar 27
MDW
ANC
11h 01m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
BJX
LAX
Excellent 8.0

I liked the check-in kiosk, but only because I had no bags to check. I liked being able to choose my own seat. I liked that the flight was uneventful. I liked the staff at all stages, they were friendly and helpful.

They made me shove my purse into my knapsack to fit within their two bag policy. That's a first for me. My Delta flight did not do that.

GDL
ATL
Excellent 9.6

Expensive food

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

PVR
MSP
Good 7.3

They have few movies selection that was good

I like being in a big space faster. And clean good service I

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

Thu, Mar 29
ANC
ORD
10h 37m
Mon, Apr 2
ORD
ANC
9h 28m
Trip: 5 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 28416 reviews
Overall
7.4
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
PHL
AMS
Okay 4.6

Fo

DEN
ORD
Good 6.4

I'm not sure where the problem was - whether with AA or Royal Jordanian, but my luggage did not make it to Amman with me. In fact, there was a whole group of passengers traveling on American from different US cities, switching to RJ in Chicago, whose luggage did not come on the flight to Amman. My advice: be sure to pack enough for a couple of days in your carryon - and don't accept an offer to check your carryon to its final destination!

LAX
MIA
Mediocre 2.0

Couldn’t sleep because the AC wasnt working. Most miserable flight my life

The AC wasn’t working it was the most miserable flight ever

JFK
MAD
Okay 4.0

Very old plane. No personal entertainment. Very basic service.

BWI
CLT
Mediocre 3.0

One of the flight attendants was nice.

AA is now trying to save money (presumably) by doing like Delta: forcing half of us to connect in Charlotte. Unfortunately, the Charlotte airport is not ready to accommodate so many people. The airport looks like it is being renovated, which is fine, but there is no tape/cones to mark off the renovated areas from the walkways. You literally walk through dirt and construction sites. I didn't even think that was legal in the US?! Anyway, maybe it will be worth it once the renovations are complete, especially if AA is going to use it as a hub.

Sun, Jul 1
ANC
MDW
14h 10m
Wed, Jul 4
MDW
ANC
11h 44m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
GDL
ATL
Excellent 9.6

Expensive food

SLC
YYZ
Excellent 9.6

Z

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

JFK
CDG
Excellent 10.0

The food and the service

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

Thu, Jul 5
ANC
ORD
6h 05m
Fri, Jul 13
ORD
ANC
10h 44m
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Jun 30
ANC
MDW
12h 59m
Wed, Jul 4
MDW
ANC
11h 44m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
BJX
LAX
Excellent 8.0

I liked the check-in kiosk, but only because I had no bags to check. I liked being able to choose my own seat. I liked that the flight was uneventful. I liked the staff at all stages, they were friendly and helpful.

They made me shove my purse into my knapsack to fit within their two bag policy. That's a first for me. My Delta flight did not do that.

SLC
YYZ
Excellent 9.6

Z

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

Fri, May 11
ANC
MDW
13h 15m
Thu, May 17
MDW
ANC
13h 54m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

SLC
YYZ
Excellent 9.6

Z

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

JFK
CDG
Excellent 10.0

The food and the service

Thu, Jul 5
ANC
MDW
11h 21m
Fri, Jul 13
MDW
ANC
8h 16m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

ATL
EWR
Excellent 8.6

No LCD screen for entertainment.

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

BJX
LAX
Excellent 8.0

I liked the check-in kiosk, but only because I had no bags to check. I liked being able to choose my own seat. I liked that the flight was uneventful. I liked the staff at all stages, they were friendly and helpful.

They made me shove my purse into my knapsack to fit within their two bag policy. That's a first for me. My Delta flight did not do that.

Sat, Feb 24
ANC
MDW
10h 51m
Fri, Mar 2
MDW
ANC
11h 01m
$1252
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
SLC
YYZ
Excellent 9.6

Z

JFK
CDG
Excellent 10.0

The food and the service

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

GDL
ATL
Excellent 9.6

Expensive food

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

Alaska to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Alaska
Flight Price $462
Airlines American Airlines, Alaska Airlines, United, Delta
*
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