Cheap flights from Chicago (CHI) to Alaska

CHI — ANC
Dec 5 — Dec 121

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

Travelers have found it’s best to book a flight 40 days in advance to save up to 43% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 40 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago to Alaska 1-2 weeks in advance for as low as $633, or $733 for flights within the next 24 hours.

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

Our data shows that February tends to be the cheapest month to fly to Alaska from Chicago. Users have commonly found prices around $420 for the month, but tickets can be as low as $280. Due to multiple factors, prepare for potentially higher prices in July.

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

When flying from Chicago to Alaska, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap flights from Chicago to Alaska in November, December 2022

The best prices found for CHI to Alaska flights for November, December
Dec 20 - Dec 25
ORD

Chicago O'Hare Intl

ANC

Anchorage

Nonstop

6h 58m
ANC

Anchorage

ORD

Chicago O'Hare Intl

Nonstop

6h 00m
$314

Alaska Airlines

Pick Dates

Deal found 11/29

Dec 20 - Dec 25
ORD

Chicago O'Hare Intl

ANC

Anchorage

Nonstop

6h 58m
ANC

Anchorage

ORD

Chicago O'Hare Intl

1 stop

9h 47m
$315

Alaska Airlines

Pick Dates

Deal found 11/29

Dec 23 - Dec 25
ORD

Chicago O'Hare Intl

ANC

Anchorage

Nonstop

6h 58m
ANC

Anchorage

ORD

Chicago O'Hare Intl

1 stop

9h 47m
$316

Alaska Airlines

Pick Dates

Deal found 11/29

Chicago to Alaska 2022 flight deals

Cheap flights to Alaska from Chicago found for this year
Dec 20 - Dec 25
ORD

Chicago O'Hare Intl

ANC

Anchorage

Nonstop

6h 58m
ANC

Anchorage

ORD

Chicago O'Hare Intl

Nonstop

6h 00m
$314

Alaska Airlines

Pick Dates

Deal found 11/29

Dec 20 - Dec 25
ORD

Chicago O'Hare Intl

ANC

Anchorage

Nonstop

6h 58m
ANC

Anchorage

ORD

Chicago O'Hare Intl

1 stop

9h 47m
$315

Alaska Airlines

Pick Dates

Deal found 11/29

Dec 23 - Dec 25
ORD

Chicago O'Hare Intl

ANC

Anchorage

Nonstop

6h 58m
ANC

Anchorage

ORD

Chicago O'Hare Intl

1 stop

9h 47m
$316

Alaska Airlines

Pick Dates

Deal found 11/29

Cheap Delta flights from Chicago to Alaska

Jan 18 - Jan 24
ORD

Chicago O'Hare Intl

ANC

Anchorage

1 stop

9h 46m
ANC

Anchorage

ORD

Chicago O'Hare Intl

1 stop

14h 56m
$322

Delta

Pick Dates

Deal found 11/29

Jan 18 - Jan 25
ORD

Chicago O'Hare Intl

ANC

Anchorage

2 stops

11h 36m
ANC

Anchorage

ORD

Chicago O'Hare Intl

1 stop

14h 56m
$326

Delta

Pick Dates

Deal found 11/28

Jan 13 - Jan 21
ORD

Chicago O'Hare Intl

ANC

Anchorage

1 stop

9h 54m
ANC

Anchorage

ORD

Chicago O'Hare Intl

1 stop

14h 56m
$330

Delta

Pick Dates

Deal found 11/30

Cheap Alaska Airlines flights from Chicago to Alaska

Jan 27 - Jan 31
ORD

Chicago O'Hare Intl

JNU

Juneau Intl

1 stop

17h 22m
JNU

Juneau Intl

ORD

Chicago O'Hare Intl

1 stop

18h 15m
$300

Alaska Airlines

Pick Dates

Deal found 11/29

Jan 27 - Feb 1
ORD

Chicago O'Hare Intl

JNU

Juneau Intl

1 stop

17h 22m
JNU

Juneau Intl

ORD

Chicago O'Hare Intl

1 stop

12h 24m
$301

Alaska Airlines

Pick Dates

Deal found 11/29

Jan 19 - Jan 22
ORD

Chicago O'Hare Intl

ANC

Anchorage

1 stop

10h 42m
ANC

Anchorage

ORD

Chicago O'Hare Intl

1 stop

11h 57m
$310

Alaska Airlines

Pick Dates

Deal found 11/28

Non-stop flights to Alaska from Chicago

Save time with Chicago to Alaska direct flight deals
Dec 20 - Dec 25
ORD

Chicago O'Hare Intl

ANC

Anchorage

Nonstop

6h 58m
ANC

Anchorage

ORD

Chicago O'Hare Intl

Nonstop

6h 00m
$314

Alaska Airlines

Pick Dates

Deal found 11/29

Apr 13 - Apr 16
ORD

Chicago O'Hare Intl

ANC

Anchorage

Nonstop

6h 44m
ANC

Anchorage

ORD

Chicago O'Hare Intl

Nonstop

6h 05m
$318

Multiple Airlines

Pick Dates

Deal found 11/27

Apr 15 - Apr 21
ORD

Chicago O'Hare Intl

ANC

Anchorage

Nonstop

6h 44m
ANC

Anchorage

ORD

Chicago O'Hare Intl

Nonstop

6h 01m
$320

United Airlines

Pick Dates

Deal found 11/27

Last minute flights from Chicago to Alaska

Late deals on return flights to Alaska from Chicago, departing today and this week
Dec 6 - Dec 28
ORD

Chicago O'Hare Intl

ANC

Anchorage

1 stop

8h 20m
ANC

Anchorage

ORD

Chicago O'Hare Intl

1 stop

9h 08m
$427

Delta

Pick Dates

Deal found 11/29

Dec 6 - Dec 28
ORD

Chicago O'Hare Intl

ANC

Anchorage

2 stops

11h 30m
ANC

Anchorage

ORD

Chicago O'Hare Intl

1 stop

9h 08m
$431

Delta

Pick Dates

Deal found 11/29

Dec 6 - Dec 29
ORD

Chicago O'Hare Intl

ANC

Anchorage

1 stop

16h 17m
ANC

Anchorage

ORD

Chicago O'Hare Intl

Nonstop

6h 00m
$453

Alaska Airlines

Pick Dates

Deal found 11/29

One-way flights to Alaska from Chicago

The cheapest one-way flights from Chicago to Alaska
Dec 20
ORD

Chicago O'Hare Intl

ANC

Anchorage

Nonstop

6h 58m
$159

Alaska Airlines

Pick Dates

Deal found 11/29

Jan 12
ORD

Chicago O'Hare Intl

ANC

Anchorage

2 stops

24h 19m
$160

Alaska Airlines

Pick Dates

Deal found 11/29

Dec 20
ORD

Chicago O'Hare Intl

ANC

Anchorage

Nonstop

6h 58m
$161

Alaska Airlines

Pick Dates

Deal found 11/27

Related info for your journey

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

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

Due to the rapidly changing circumstances due to COVID-19, airlines like Alaska Airlines, United Airlines, and Delta flying from Chicago to Alaska have implemented new flexible cancellation policies.

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

Yes, there are multiple flights from Chicago to Alaska for under $300. The cheapest flight booked recently is on Multiple Airlines for just $295, but on average you can expect to pay $312.

Are there nonstop flights from Chicago to Alaska for under $400 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Alaska under $400. A good price for a nonstop flight from Chicago to Alaska is less than $373.

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

There are currently 20+ open flights from Chicago to Alaska within the next 7 days for less than $500.

What are the most popular routes from Chicago to Alaska?

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

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

American Airlines, Alaska Airlines and Delta are the most popular airlines when flying from Chicago to Alaska.

What are the most reliable airlines from Chicago to Alaska?

Before booking your flight to Alaska from Chicago, check out the most reliable airlines to get you to your destination on time: United Airlines (90%), Air Canada (81%), Lufthansa( 81%).

What are the cheapest flights from Chicago to Alaska?

Looking at all options, your cheapest flight can be booked for $165. While the most popular route (Chicago O'Hare Intl - Anchorage) can be booked for $318 on average our data indicates $948 when flying from Chicago to Alaska.

Destination points for flights from Chicago to Alaska

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

Top 5 airlines flying from Chicago to Alaska

The chart below displays the airlines Cheapflights users traveling from Chicago to Alaska choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$11Average$20FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
Alaska AirlinesCheapest$159Average$505FlexibilityNo cancel feeOn-time75%COVID-19 safety
Search Alaska Airlines flights
DeltaCheapest$169Average$503FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
United AirlinesCheapest$210Average$688FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
American AirlinesCheapest$241Average$690FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights