Cheap flights from Alaska to Chicago (CHI)

ANC — CHI
Oct 4 — Oct 111

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

To save on the cost of your flight from Alaska to Chicago, book at least 61 days before your planned departure. Booking around this time can save you about 30% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $512 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $607.

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

Due to multiple factors, expect to potentially pay more when booking in July. For low rates, October can be a great choice for travel to Chicago. Flights to Chicago from Alaska in October are about $503 on average during October, but can be found for as low as $193.

When is the cheapest time to fly from Alaska to Chicago (AK - CHI)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Alaska to Chicago as you normally would.

Cheap flights from Alaska to Chicago in September, October 2022

The best prices found for Alaska to CHI flights for September, October
Oct 25 - Oct 27
ANC

Anchorage

ORD

Chicago O'Hare Intl

2 stops

12h 27m
ORD

Chicago O'Hare Intl

ANC

Anchorage

Nonstop

6h 50m
$313

Multiple Airlines

Pick Dates

Deal found 9/28/22

Oct 29 - Oct 31
ANC

Anchorage

ORD

Chicago O'Hare Intl

1 stop

11h 28m
ORD

Chicago O'Hare Intl

ANC

Anchorage

1 stop

10h 00m
$318

Multiple Airlines

Pick Dates

Deal found 9/29/22

Oct 29 - Oct 31
ANC

Anchorage

ORD

Chicago O'Hare Intl

2 stops

13h 54m
ORD

Chicago O'Hare Intl

ANC

Anchorage

1 stop

10h 00m
$322

Delta

Pick Dates

Deal found 9/29/22

Alaska to Chicago 2022 flight deals

Cheap flights to Chicago from Alaska found for this year
Nov 7 - Nov 11
ANC

Anchorage

ORD

Chicago O'Hare Intl

1 stop

17h 38m
ORD

Chicago O'Hare Intl

ANC

Anchorage

Nonstop

6h 50m
$309

Alaska Airlines

Pick Dates

Deal found 9/27/22

Oct 25 - Oct 27
ANC

Anchorage

ORD

Chicago O'Hare Intl

2 stops

12h 27m
ORD

Chicago O'Hare Intl

ANC

Anchorage

Nonstop

6h 50m
$313

Multiple Airlines

Pick Dates

Deal found 9/28/22

Dec 9 - Jan 30
ANC

Anchorage

ORD

Chicago O'Hare Intl

1 stop

7h 30m
ORD

Chicago O'Hare Intl

ANC

Anchorage

1 stop

12h 31m
$316

Multiple Airlines

Pick Dates

Deal found 9/28/22

Cheap Alaska Airlines flights from Alaska to Chicago

Nov 7 - Nov 11
ANC

Anchorage

ORD

Chicago O'Hare Intl

1 stop

17h 38m
ORD

Chicago O'Hare Intl

ANC

Anchorage

Nonstop

6h 50m
$309

Alaska Airlines

Pick Dates

Deal found 9/27/22

Dec 10 - Feb 2
ANC

Anchorage

ORD

Chicago O'Hare Intl

2 stops

22h 04m
ORD

Chicago O'Hare Intl

ANC

Anchorage

1 stop

14h 33m
$319

Alaska Airlines

Pick Dates

Deal found 9/28/22

Feb 26 - Mar 1
ANC

Anchorage

ORD

Chicago O'Hare Intl

1 stop

13h 59m
ORD

Chicago O'Hare Intl

ANC

Anchorage

2 stops

22h 41m
$328

Alaska Airlines

Pick Dates

Deal found 9/27/22

Cheap Delta flights from Alaska to Chicago

Dec 3 - Dec 11
ANC

Anchorage

ORD

Chicago O'Hare Intl

1 stop

9h 11m
ORD

Chicago O'Hare Intl

ANC

Anchorage

1 stop

11h 48m
$318

Delta

Pick Dates

Deal found 9/28/22

Dec 11 - Feb 1
ANC

Anchorage

ORD

Chicago O'Hare Intl

2 stops

14h 34m
ORD

Chicago O'Hare Intl

ANC

Anchorage

1 stop

9h 46m
$322

Delta

Pick Dates

Deal found 9/28/22

Oct 24 - Oct 27
ANC

Anchorage

ORD

Chicago O'Hare Intl

2 stops

12h 53m
ORD

Chicago O'Hare Intl

ANC

Anchorage

1 stop

11h 50m
$341

Delta

Pick Dates

Deal found 9/28/22

Non-stop flights to Chicago from Alaska

Save time with Alaska to Chicago direct flight deals
Oct 25 - Oct 27
ANC

Anchorage

ORD

Chicago O'Hare Intl

Nonstop

6h 15m
ORD

Chicago O'Hare Intl

ANC

Anchorage

Nonstop

6h 50m
$429

Alaska Airlines

Pick Dates

Deal found 9/28/22

Oct 27 - Oct 30
ANC

Anchorage

ORD

Chicago O'Hare Intl

Nonstop

6h 15m
ORD

Chicago O'Hare Intl

ANC

Anchorage

Nonstop

6h 50m
$478

Alaska Airlines

Pick Dates

Deal found 9/28/22

Jan 2 - Jan 7
ANC

Anchorage

ORD

Chicago O'Hare Intl

Nonstop

6h 02m
ORD

Chicago O'Hare Intl

ANC

Anchorage

Nonstop

6h 58m
$485

Alaska Airlines

Pick Dates

Deal found 9/28/22

Last minute flights from Alaska to Chicago

Late deals on return flights to Chicago from Alaska, departing today and this week
Oct 7 - Oct 14
ANC

Anchorage

ORD

Chicago O'Hare Intl

2 stops

22h 13m
ORD

Chicago O'Hare Intl

ANC

Anchorage

Nonstop

6h 50m
$518

Alaska Airlines

Pick Dates

Deal found 9/27/22

Oct 6 - Oct 9
ANC

Anchorage

ORD

Chicago O'Hare Intl

2 stops

16h 48m
ORD

Chicago O'Hare Intl

ANC

Anchorage

1 stop

18h 30m
$526

Multiple Airlines

Pick Dates

Deal found 9/26/22

Oct 7 - Oct 14
ANC

Anchorage

ORD

Chicago O'Hare Intl

2 stops

25h 23m
ORD

Chicago O'Hare Intl

ANC

Anchorage

1 stop

9h 26m
$534

Multiple Airlines

Pick Dates

Deal found 9/27/22

One-way flights to Chicago from Alaska

The cheapest one-way flights from Alaska to Chicago
Dec 3
ANC

Anchorage

ORD

Chicago O'Hare Intl

1 stop

13h 54m
$138

Alaska Airlines

Pick Dates

Deal found 9/27/22

Dec 3
ANC

Anchorage

ORD

Chicago O'Hare Intl

2 stops

22h 04m
$140

Alaska Airlines

Pick Dates

Deal found 9/27/22

Jan 2
ANC

Anchorage

ORD

Chicago O'Hare Intl

Nonstop

6h 02m
$155

Alaska Airlines

Pick Dates

Deal found 9/27/22

Related info for your journey

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

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

United Airlines, Alaska Airlines, and Delta 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 $400 on Cheapflights?

Yes, there are multiple flights from Alaska to Chicago for under $400. The cheapest flight booked recently is on Alaska Airlines for just $309, but on average you can expect to pay $323.

Are there nonstop flights from Alaska to Chicago for under $500 on Cheapflights?

Cheapflights has at least 20 direct flights from Alaska to Chicago under $500. A good price for a nonstop flight from Alaska to Chicago is less than $585.

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

There are currently 20+ open flights from Alaska to Chicago within the next 7 days for less than $600.

What days are nonstop flights available from Alaska to Chicago?

Days when nonstop flights are available for this flight are: Thursday.

How many flights depart from Alaska to Chicago on average per day?

2 flight departures from Alaska to Chicago per day on average.
Evening (6pm - Midnight) - 100% of flight departures

How long is the flight from Alaska to Chicago?

There are many flights that can get you from Alaska to Chicago in 9h 11m. Fly via Alaska Airlines or Delta to get the fastest option. Alaska and Chicago are separated by a distance of 2854 mi. This flight may include one or multiple stops.

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

The cheapest airline one-way is Alaska Airlines, with whom users have recently found tickets for as low as $138. However, be on the lookout for offers from Delta and American Airlines, as they are both options that can get you from Alaska to Chicago for a low price.

What are the most popular routes from Alaska to Chicago?

When deciding which route to take from Alaska to Chicago consider Anchorage - Chicago O'Hare Intl, Anchorage - Chicago Midway or Fairbanks - Chicago O'Hare Intl as they are the most popular.

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

The most popular airlines flying from Alaska to Chicago are American Airlines, Alaska Airlines and Delta. Something to consider prior to booking your flight.

What are the most reliable airlines from Alaska to Chicago?

Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Alaska to Chicago on time: EVA Air (100%), Alaska Airlines (86%), American Airlines (86%).

What are the cheapest flights from Alaska to Chicago?

Looking for the cheapest flight from Alaska to Chicago? While on average our users pay $1,164, our data indicates the cheapest price to be $160. The most popular route (Anchorage - Chicago O'Hare Intl), is priced around $308.

Departure points for flights from Alaska to Chicago

Select to see more specific information for flights to Chicago from all departure points in Alaska

Top 4 airlines flying from Alaska to Chicago

The chart below displays the airlines Cheapflights users traveling from Alaska to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Alaska AirlinesCheapest$154Average$431FlexibilityNo cancel feeOn-time75%COVID-19 safety
Search Alaska Airlines flights
American AirlinesCheapest$159Average$666FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
United AirlinesCheapest$160Average$631FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
DeltaCheapest$172Average$475FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights

Hourly flight availability from Alaska to Chicago

See what time of day planes typically take off from Alaska to Chicago
0%of flight departuresEarly morningMidnight to 6 am
0%of flight departuresMorning6 am to noon
0%of flight departuresAfternoonNoon to 6 pm
100%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM