Menu

Cheap flights from Alaska (AK) to Chicago (CHI)

Know your dates, get live prices in seconds:

From
To
Depart
Return
Any month
Compare vs. Cheapflights |
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime

We work with more than 300 partners to bring you better travel deals

How to find the cheapest flight from
Alaska to Chicago (CHI)

How far in advance should I book a flight from Alaska to Chicago?

Users have found that booking a flight from Alaska to Chicago at least 37 days early can save you up to 10% on average compared to booking a flight this week. If booking 37 days before your flight isn’t an option for you, users have found flights from Alaska to Chicago for as little as $177 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $177 for flights departing within the next 3 days.

Cheap flights from Alaska to Chicago in September, October 2020

The best prices found for Alaska to CHI flights for September, October
27 Oct - 3 Nov
$296pp
ANC
Anchorage
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
ANC
Anchorage
30 Oct - 12 Nov
$305pp
ANC
Anchorage
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
ANC
Anchorage
27 Oct - 3 Nov
$326pp
ANC
Anchorage
Delta
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
ANC
Anchorage

Alaska to Chicago 2020 flight deals

Cheap flights to Chicago from Alaska found for this year
2 Dec - 6 Dec
$295pp
FAI
Fairbanks
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
FAI
Fairbanks
27 Oct - 3 Nov
$296pp
ANC
Anchorage
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
ANC
Anchorage
11 Nov - 14 Nov
$298pp
FAI
Fairbanks
Delta
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
FAI
Fairbanks

Last minute flights from Alaska to Chicago

Late deals on round-trip flights to Chicago from Alaska, departing today and this week
5 Oct - 3 Nov
$409pp
FAI
Fairbanks
Delta
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
FAI
Fairbanks
7 Oct - 21 Oct
$443pp
ANC
Anchorage
Delta
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
ANC
Anchorage
6 Oct - 4 Nov
$459pp
FAI
Fairbanks
Delta
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
FAI
Fairbanks

One-way flights to Chicago from Alaska

The cheapest one-way flights from Alaska to Chicago
2:00 am - 7:25 pm
Delta
1 Stop
14h 25m
ANC - ORD
Delta
$166
Delta
2:00 am - 7:25 pm
Delta
1 Stop
14h 25m
ANC - ORD
Delta
$170
Delta
2:00 am - 7:25 pm
Delta
1 Stop
14h 25m
ANC - ORD
Delta
$175
Delta

Related info for your journey

Useful info, stats and facts about Alaska to Chicago flights.

Flight FAQs

From Alaska to Chicago

Are flight prices decreasing from Alaska to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Alaska and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

Can I find flights from Alaska to Chicago for under $300 on Cheapflights?

Yes, there are multiple flights from Alaska to Chicago for under $300. The cheapest flight booked recently is on Delta for just $295, but on average you can expect to pay $333.

Are there nonstop flights from Alaska to Chicago for under $300 on Cheapflights?

There are no nonstop flights from Alaska to Chicago, but Cheapflights can provide you with all the information you need to find the fastest route with the fewest stops.

Are there last-minute flights available from Alaska to Chicago for under $500?

There are currently 14+ open flights from Alaska to Chicago within the next 7 days for less than $500.

What are the most popular airlines that fly from Alaska to Chicago?

Consider American Airlines, Alaska Airlines or Delta when booking your flight. These represent the most popular airlines when flying from Alaska to Chicago.

What are the most popular routes from Alaska to Chicago?

The most popular flight routes from Alaska to Chicago are Anchorage - Chicago O'Hare Intl, Anchorage - Chicago Midway and Fairbanks - Chicago O'Hare Intl.

What are the cheapest Flights from Alaska to Chicago?

While on average a flight from Alaska to Chicago is generally $351, our data shows the cheapest flight currently is $178. When looking at the most popular route, (Anchorage - Chicago O'Hare Intl), you can expect to pay $296 for that flight.

What are the most reliable airlines from Alaska to Chicago?

No one likes to see their flight delayed. When booking a flight from Alaska to Chicago consider choosing Alaska Airlines (92%), American Airlines (91%) or British Airways (91%) as they are the most reliable in getting you off to your destination on time.

How long is the flight from Alaska to Chicago?

For as low as $460, Delta can have you in Chicago from Alaska in 8h 08m.

What is the cheapest airline to fly from Alaska to Chicago round-trip?

Currently priced at $295, Delta will fly you from Alaska to Chicago and back. In addition to Delta, many other airlines offer competitively priced options for your trip.

What are the cheapest airlines to fly from Alaska to Chicago one-way?

For one-way options, check prices for Delta. According to our data, you can fly for as low as $127.

Arrival points for flights from Alaska to Chicago

Destination information for Chicago

Things to know before you go. Useful info for your trip from Alaska to Chicago
Average temperature for September in Chicago
77.0 °F
Avg rainfall for September in Chicago
2.4 ″

Airports servicing

Buckland (BKC)
Barrow (BRW)
Barter Island (BTI)
Bettles (BTT)
Cold Bay (CDB)

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)
Home North America USA Illinois Chicago Cheap flights from Alaska to Chicago