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 20 days early can save you up to 10% on average compared to booking a flight this week. If booking 20 days before your flight isn’t an option for you, users have found flights from Alaska to Chicago for as little as $137 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 $157 for flights departing within the next 3 days.

What is the cheapest month to fly from Alaska to Chicago?

April can be a great time to fly to Chicago from Alaska with a flight ticket averaging about $135. Cheapflights users have found deals in the month of April for as cheap as $33. The most expensive prices can be found in the month of December.

Cheap flights from Alaska to Chicago in March, April 2021

25 Mar - 28 Mar
$241pp
ANC
Anchorage
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
ANC
Anchorage
25 Mar - 28 Mar
$245pp
ANC
Anchorage
Delta
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
ANC
Anchorage
25 Mar - 29 Mar
$249pp
ANC
Anchorage
Delta
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
ANC
Anchorage

Alaska to Chicago 2021 flight deals

25 Mar - 29 Mar
$241pp
ANC
Anchorage
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
ANC
Anchorage
25 Mar - 29 Mar
$245pp
ANC
Anchorage
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
ANC
Anchorage
25 Mar - 29 Mar
$249pp
ANC
Anchorage
Delta
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
ANC
Anchorage

Non-stop flights to Chicago from Alaska

6 May - 11 May
$279pp
ANC
Anchorage
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
ANC
Anchorage
2 Jun - 14 Jun
$299pp
ANC
Anchorage
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
Non-Stop
ANC
Anchorage
1 Jun - 15 Jun
$306pp
ANC
Anchorage
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
Non-Stop
ANC
Anchorage

Last minute flights from Alaska to Chicago

12 Mar - 20 Mar
$541pp
ANC
Anchorage
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
 
1 STOP
ANC
Anchorage
12 Mar - 20 Mar
$547pp
ANC
Anchorage
United Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
   
2 STOPS
ANC
Anchorage
11 Mar - 20 Mar
$548pp
ANC
Anchorage
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
ANC
Anchorage

One-way flights to Chicago from Alaska

6:00 pm - 2:44 am
American Airlines
Nonstop
5h 44m
ANC - ORD
American Airlines
11:45 pm - 7:59 pm
Alaska Airlines
2 Stops
17h 14m
ANC - ORD
Alaska Airlines
$208
CheapFlights
8:05 pm - 10:40 am
Delta
2 Stops
11h 35m
ANC - MDW
Delta
$213
Delta

Related info for your journey

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.

What safety measures are being taken by airlines flying from Alaska to Chicago to control the spread of COVID-19?

Airlines globally have implemented additional safety measures to accommodate you. Alaska Airlines and Delta are some airlines that have done so. Some of the new policies that have been implemented to accommodate travelers flying from Alaska to Chicago are improved sanitation, HEPA filters, mask requirements, social distance seating (for a limited time), and pre-flight testing for antibodies and symptoms. Policies will vary by airline.

Which airlines flying from Alaska to Chicago have flexible cancellations due to COVID-19?

Alaska Airlines, Delta, and United Airlines are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

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 $241, but on average you can expect to pay $285.

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

Cheapflights has at least 15 direct flights from Alaska to Chicago under $300. A good price for a nonstop flight from Alaska to Chicago is less than $544.

Are there last-minute flights available from Alaska to Chicago for under $600?

There are currently 17+ open flights from Alaska to Chicago within the next 7 days for less than $600.

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 Fairbanks - Chicago O'Hare Intl, Anchorage - Chicago O'Hare Intl and Anchorage - Chicago Midway.

What are the cheapest Flights from Alaska to Chicago?

While on average a flight from Alaska to Chicago is generally $721, our data shows the cheapest flight currently is $178. When looking at the most popular route, (Fairbanks - Chicago O'Hare Intl), you can expect to pay $329 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 Cathay Pacific (77%), Asiana Airlines (31%) or Korean Air (29%) 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 $279, American Airlines can have you in Chicago from Alaska in 5h 44m. This flight may include one or multiple stops.

What are the cheapest airlines flying from Alaska to Chicago round-trip?

Currently priced at $241, Delta will fly you from Alaska to Chicago and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Alaska Airlines and American Airlines - these airlines can fly you to your destination from $274 and $279, respectively.

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

For one-way options, check prices for Alaska Airlines. According to our data, you can fly for as low as $137. Users have also found prices from $139 and $160 on Alaska Airlines and American Airlines, respectively.

Departure points for flights from Alaska to Chicago

Destination information for Chicago

Flight duration
6h 14m
Average temperature for March in Chicago
50.0 °F
Avg rainfall for March in Chicago
1.6 ″

Airports servicing

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

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 4 airlines flying from Alaska to Chicago

Airline Cheapest Average Flexibility On-time COVID-19 safety
United Airlines
$198 $439 No cancel fee 69%
American Airlines
$287 $498 No cancel fee 71%
Alaska Airlines
$197 $500 No cancel fee 75%
Delta
$206 $564 No cancel fee N/A
Home North America USA Illinois Chicago Cheap flights from Alaska to Chicago