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Alaska to Chicago Flight Information

Flights Arrive in Chicago
Flights Depart from Alaska
Flight Price $388
Airlines Delta, Alaska Airlines, Sun Country Air

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

Airports
Origin
Fairbanks
$427
only
$427
Anchorage
$388
only
$388
Destination
Chicago
$388
only
$388
$481
only
$481
Wed, Jul 24
ANC
Anchorage
ORD
Chicago O'Hare Intl
10h 00m
Tue, Aug 20
ORD
Chicago O'Hare Intl
ANC
Anchorage
18h 20m
Trip: 28 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,835 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
SYD
LAX
Excellent 8.6

Cons: I really like more legs room and comfort and crew member were very good and helpful. Regarding food I say it’s just ok.

SLC
DTW
Okay 5.3

Pros: the entertainment choices were adequate

Cons: More efficient deplanning. It took us 40 minutes to get off the plane after it landed

LAN
DTW
Mediocre 2.0

Cons: The flight was delayed and it ended up being delayed for 4 hours and we had to take a cab to Detroit to catch our flight to Europe

STL
ATL
Good 6.4

Pros: Nothing special

Cons: That was the most uncomfortable and cramped seat I had ever had on a plane flight. Even sitting on the pillow did not help.

ATL
ECP
Excellent 9.0

Pros: Quick flight

Cons: I wish there was a way to access the delta movies in small planes that don’t have seat back entertainment

Mon, Aug 5
ANC
Anchorage
ORD
Chicago O'Hare Intl
14h 10m
Sun, Aug 11
ORD
Chicago O'Hare Intl
ANC
Anchorage
6h 45m
Trip: 7 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
SEA
BNA
Excellent 9.3

Pros: Flight was great. Crew was great. Alaska Air delivers great service!

Cons: WiFi was poor

ANC
ORD
Good 7.0

Pros: Cabin crew

Cons: 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.

PDX
STS
Excellent 10.0

Pros: Great crew, easy boarding

Cons: More luggage space in the overhead bin

SNA
SFO
Excellent 10.0

Pros: Fllight landed early and departed a few minutes early too - YAY!

LAX
JFK
Excellent 9.6

Pros: I love the legroom. Alaska seems to have more of it and I will fly when I can on Alaska just for that! Crew was very nice too.

Cons: Nothing to eat! By the time I ordered at the back of the plane there wasn’t any food left except one cheese plate. Very disappointed as I wanted the Asian salad and there were none. Need more selections and more food onboard. Some free peanuts would be nice.

Wed, Jun 26
ANC
Anchorage
ORD
Chicago O'Hare Intl
16h 40m
Thu, Jul 11
ORD
Chicago O'Hare Intl
ANC
Anchorage
20h 01m
Trip: 16 days
7.7GoodShow reviews
Overall 7.7 Good
Based on 8,709 reviews
Overall
8.1
Boarding
8.2
Comfort
7.7
Crew
8.4
Entertainment
6.8
Food
7.1
MSP
SAN
Excellent 10.0

Pros: Everything went amazing and smooth! Very well done Sun Country

PHX
PDX
Excellent 10.0

Pros: Crew was amazing, and the boarding was VERY quick!

MSP
SAN
Good 7.6

Pros: Crew was great.

Cons: Video capability or included would be great

HUX
MSP
Okay 5.2

Pros: Crew was awesome. Our flight was delayed 6 hours but they were so kind about it and we got vouchers.

Cons: My glasses were stolen from my bag. I assume the airport staff before they were put on plane.

LAS
MSP
Okay 5.5

Pros: The plane was sort of clean.

Cons: Cleaner plane, more comfortable seating, smoother landings, climate controlled interior (so hot).

Thu, Aug 15
ANC
Anchorage
ORD
Chicago O'Hare Intl
8h 35m
Sun, Aug 18
ORD
Chicago O'Hare Intl
ANC
Anchorage
9h 40m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,835 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
MSP
BOS
Good 7.3

Pros: individual TVs

Cons: it would be great if you could not use all those one-use plastic cups. waste is a real issue in the US and the solution is using re-usable items like washable cups. Unboarding was a nightmare and it started to get really hot waiting to get off.

CUN
MCI
Mediocre 3.6

Pros: We had the worst flight ever on Delta flight worst Attitude of the flight attendant she was very Rude i even told her she was

Cons: We didn't get served nothing to drink until 45 min to kc then by then i was so dehydrated i asked for a can of pop she said NO I SAID REALLY SHE SAID DELTAS NOT IN CHARGE OF STOCKING DRINKS & SNACKS SHE HAD MORE PEOPLE' TO SERVE REALLY EVERBODY IN FRONT OF US GOT WHAT THEY WANTED SO I HAD NOTHIN AT

DTW
MCO
Okay 4.0

Cons: It could have left on time or they could have told us they weren’t leaving and let us get some sleep.

EWR
MSP
Mediocre 3.3

Cons: Issues with connecting flights so had to sit in different place, seat was broken

PHL
ATL
Excellent 10.0

Cons: Safe and happy travel!

Tue, Sep 17
ANC
Anchorage
ORD
Chicago O'Hare Intl
9h 07m
Wed, Sep 18
ORD
Chicago O'Hare Intl
ANC
Anchorage
9h 26m
Trip: 2 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,835 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
PBI
ATL
Okay 4.6

Cons: Plane was FREEZING!!!

MEX
LAX
Good 6.6

Pros: The entertainment system was good and they had free text messaging through the plane’s wifi network.

Cons: The plane stank. I was 3/4 in the back of the plane and there was a strong pee odor.

MSP
AMS
Excellent 8.0

Pros: Crew very good

Cons: Breakfast sandwich was close to tasteless; all bread, very very little filling.

ATL
PDX
Excellent 9.0

Pros: The best

Cons: Again the boarding process took forever

MCO
LAX
Excellent 8.0

Pros: The booking in staff person was positive and friendly. I was disappointed that the system would not allow me to be placed on the upgrade list as a silver Velosity me mm ber partner to Delta.

Tue, Jul 2
FAI
Fairbanks
ORD
Chicago O'Hare Intl
9h 14m
Sun, Jul 7
ORD
Chicago O'Hare Intl
FAI
Fairbanks
6h 35m
Trip: 6 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,850 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
DTW
LAX
Excellent 10.0

Pros: Bags were waiting on Carousel

Cons: Slightly delayed due to incoming flight delayed

JFK
AMS
Good 6.3

Pros: This was a Delta codeshare on KLM metal. We left on time and arrived early. The crew was very professional. The bathrooms were very clean.

Cons: The seat in Economy Comfort was awful. Not enough padding and no place to put my feet because of a very large entertainment control box on the floor.

PBI
ATL
Okay 4.6

Cons: Plane was FREEZING!!!

TVC
DTW
Excellent 9.0

Pros: Quick flight

Cons: Coffee or beverage service would have been a nice touch.

LGA
ATL
Good 7.6

Pros: Crew was good. As always not enough leg room if you are taller. Resent having to pay extra for more leg room.

Tue, Sep 17
ANC
Anchorage
MDW
Chicago Midway
12h 52m
Mon, Sep 30
MDW
Chicago Midway
ANC
Anchorage
8h 10m
Trip: 14 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,850 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
ATL
SAT
Excellent 10.0

Pros: I liked the entertainment

EWR
MSP
Mediocre 3.3

Cons: Issues with connecting flights so had to sit in different place, seat was broken

MDT
ATL
Mediocre 3.6

Cons: Worst first class service. Only came by twice in two hour flight

MSP
AMS
Excellent 8.0

Pros: Crew very good

Cons: Breakfast sandwich was close to tasteless; all bread, very very little filling.

DTW
ATL
Excellent 8.6

Pros: The male in the crew was fantastic!!! As always love the entertainment options.

Cons: Uncomfortable. Stuffed between two large men.

Thu, Aug 15
FAI
Fairbanks
ORD
Chicago O'Hare Intl
9h 16m
Mon, Aug 19
ORD
Chicago O'Hare Intl
FAI
Fairbanks
13h 49m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,850 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
CLT
ATL
Good 7.6

Cons: We were late getting into ATL.

BWI
JFK
Mediocre 3.6

Pros: It wasn’t delayed 3 hours like the first flight

Cons: Departing on time

MSP
AMS
Excellent 8.0

Pros: Crew very good

Cons: Breakfast sandwich was close to tasteless; all bread, very very little filling.

TVC
DTW
Excellent 9.0

Pros: Quick flight

Cons: Coffee or beverage service would have been a nice touch.

CDG
ATL
Excellent 10.0

Pros: Food and movies

Fri, May 31
ANC
Anchorage
ORD
Chicago O'Hare Intl
16h 40m
Sun, Jun 2
ORD
Chicago O'Hare Intl
ANC
Anchorage
6h 35m
Trip: 3 days
7.7GoodShow reviews
Overall 7.7 Good
Based on 8,709 reviews
Overall
8.1
Boarding
8.2
Comfort
7.7
Crew
8.4
Entertainment
6.8
Food
7.1
SFO
MSP
Good 7.0

Cons: As we landed in MSP my young son got sick. There was not a vomit bag available in our row. We cleaned it up the best we could. I told the gals as we exited and they were sympathetic. As my husband exited he heard them say. Well that’s lovely...I sure wasn’t impressed to hear that.

PDX
SFO
Good 7.2

Pros: Exceptional price on a direct PDX-SFO flight at $66 roundtrip. USB outlets at all seats I could see. Looked to have a good selection of in-flight entertainment available to stream to personal devices (phones, tablets, etc) Staff were low-key.

Cons: Basic fare: no reserved seats, only personal item. Like United (but not Alaska/Delta) require desk check-in at airport!! No online check-in/mobile boarding pass, and *limited agent hours* Lame. Buy-up reserved seat (fee) Stupid policy for passengers, extra work for staff.

MSP
SAN
Good 7.6

Pros: Crew was great.

Cons: Video capability or included would be great

MSP
PHL
Excellent 9.0

Cons: More leg room

MSP
PHX
Good 6.6

Pros: The crew were super nice!

Cons: Weather delays! Seemed like all of the other airlines cancelled flight and/or were flying and my flight got pushed back our after hour after from leaving at 8:05 til 1:30. Would have been since to just come to the airport later vs having to wait there

Thu, Jul 18
FAI
Fairbanks
MDW
Chicago Midway
12h 15m
Tue, Jul 23
MDW
Chicago Midway
FAI
Fairbanks
14h 06m
Trip: 6 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,850 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
LGA
ATL
Good 7.6

Pros: Crew was good. As always not enough leg room if you are taller. Resent having to pay extra for more leg room.

MSP
OMA
Excellent 10.0

Cons: Couldn't have been better

DTW
FRA
Okay 4.0

Cons: Notes were in the computer that our flight was delayed in someone at Delta told us we had to re book because we were not 2 hours prior to our flight after arriving in a cab. Delta error. Other lady told us to run to a security and get to the gate which we did and there were notes in the system and t

DTW
FLL
Excellent 9.6

Pros: While biased since I was in First class, everything was enjoyable and as expected of a first class experience. The free Wi-Fi on this flight made it extra special- can’t wait until its standard on all flights!!

Cons: Only real complaint is that Delta doesn’t seem to restrict size of bags taken as carry on and the time wasted but some trying to squeeze their obviously oversized bags into overhead compartments is painful.

KIN
ATL
Excellent 8.0

Pros: For me the boarding was of fast

Cons: The food

Sat, Aug 31
ANC
Anchorage
MDW
Chicago Midway
11h 44m
Fri, Sep 6
MDW
Chicago Midway
ANC
Anchorage
10h 11m
Trip: 7 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,850 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
JFK
JAX
Okay 4.5

Cons: Late taking off. Let's leave on time

MSP
AMS
Excellent 8.0

Pros: Crew very good

Cons: Breakfast sandwich was close to tasteless; all bread, very very little filling.

ATL
MSN
Excellent 8.4

Cons: Wider seats, more leg room

MEX
JFK
Okay 4.3

Pros: The crew was extremely rude. They did not come to collect trash and so all passengers were left holding their coffee/ tea: beverages during bumpy landing.

Cons: Attendants were rude. I didnt understand why. Also, I purchased a window seat but there was no window in my row. I spent the majority of the flight feeling ill.

MCO
DTW
Excellent 9.0

Pros: Crew were great, on time, helpful, friendly.

Tue, Jul 9
ANC
Anchorage
MDW
Chicago Midway
12h 36m
Sat, Jul 13
MDW
Chicago Midway
ANC
Anchorage
12h 38m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,850 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
SJU
ATL
Good 6.4

Cons: They have to improve the boarding process a bit.

AMS
PDX
Excellent 10.0

Pros: The flight wasn’t overbooked so there was plenty of room. So important on such a long flight.

MDT
ATL
Mediocre 3.6

Cons: Worst first class service. Only came by twice in two hour flight

DTW
MCO
Okay 4.0

Cons: It could have left on time or they could have told us they weren’t leaving and let us get some sleep.

ICN
DTW
Good 7.0

Pros: Nice to have more room in the premium economy section.

Cons: Not even a smile from the crew and no help when asked. I don't expect Asian-style grace and class from an American airline, but I do expect good old-fashioned American friendliness, and there wasn't even that. Also hate the all-darkened cabin in the daytime.

Mon, Jun 10
ANC
Anchorage
MDW
Chicago Midway
12h 37m
Tue, Jun 18
MDW
Chicago Midway
ANC
Anchorage
8h 53m
Trip: 9 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,850 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
EWR
MSP
Mediocre 3.3

Cons: Issues with connecting flights so had to sit in different place, seat was broken

MDT
ATL
Mediocre 3.6

Cons: Worst first class service. Only came by twice in two hour flight

DTW
MCO
Okay 4.0

Cons: It could have left on time or they could have told us they weren’t leaving and let us get some sleep.

CDG
ATL
Excellent 10.0

Pros: Food and movies

VCE
ATL
Excellent 10.0

Pros: I was originally booked through jfk with an 80 minute layover. When I told a delta.help desk employee i feared it was too tight (I flew out through jf k and that was enough to convince me...) he booked me through Atlanta with a.comfortable schedule. Thank you!

Thu, May 30
ANC
Anchorage
MDW
Chicago Midway
13h 13m
Sun, Jun 2
MDW
Chicago Midway
ANC
Anchorage
10h 49m
$1084
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 24,850 reviews
Overall
8.1
Boarding
8.2
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
DTW
LAX
Excellent 10.0

Pros: Bags were waiting on Carousel

Cons: Slightly delayed due to incoming flight delayed

MSP
BOS
Good 7.3

Pros: individual TVs

Cons: it would be great if you could not use all those one-use plastic cups. waste is a real issue in the US and the solution is using re-usable items like washable cups. Unboarding was a nightmare and it started to get really hot waiting to get off.

MSP
AMS
Excellent 8.0

Pros: Crew very good

Cons: Breakfast sandwich was close to tasteless; all bread, very very little filling.

ATL
CLT
Excellent 10.0

Cons: The girls were sweet as usual!

MSP
BOS
Excellent 10.0

Pros: Delta, as always, comes through! Although my original flight was delayed, Delta provided the option to rebook on another DL flight at no additional cost. They made it super easy! As always, the crew was friendly, helpful and professional! Thanks!

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