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

As of July 2025, there are 11 flights per day flying from Alaska to Chicago. The most common time of day flights depart is 9:00PM, with 100% of flights taking off in the evening.

What airlines fly to Chicago?

Alaska Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago from Alaska according to our data. Alaska Airlines is the first choice among our users, with 40% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

As of July 2025, 81 flights take off from Alaska and land in Chicago each week. The most common flight departure day for this route is Thu, with 16% of weekly flights taking off on this day.

What is the cheapest airline that flies from Alaska to Chicago?

Hawaiian Airlines, Delta, and United Airlines are the most popular carriers operating from Alaska to Chicago

How long does it take to fly to Chicago?

Average flight duration from Alaska to Chicago depends on which airport you fly into and out of. Flying from Anchorage to Chicago O'Hare Intl Airport is 6h 02m on average, while flying from Fairbanks to Chicago O'Hare Intl Airport is 6h 04m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

When did momondo last update prices for flights from Alaska to Chicago?

Prices for flights from Alaska to Chicago were last updated today.

How many operators does momondo search for flights from Alaska to Chicago?

There are 5 operators available for flights from Alaska to Chicago as of July 2025.

How old do you have to be to fly from Alaska to Chicago?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Alaska to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$159 Cheap Flights from Alaska to Chicago in 2025

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Alaska to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

11:25 pm - 8:40 amANC-ORD

6h 15mnonstop

8:10 am - 12:08 pmORD-ANC

6h 58mnonstop

$318Alaska Airlines

Find Deal

Thu, Oct 2 - Sat, Oct 11

9:53 pm - 7:17 amANC-ORD

6h 24mnonstop

5:01 pm - 8:48 pmORD-ANC

6h 47mnonstop

$319American Airlines

Find Deal

Thu, Sep 18 - Sun, Sep 21

11:25 pm - 8:40 amANC-ORD

6h 15mnonstop

7:00 am - 1:22 pmORD-ANC

9h 22m1 stop

$328Alaska Airlines

Find Deal

Thu, Oct 2 - Sat, Oct 11

10:30 pm - 12:28 pmANC-MDW

10h 58m1 stop

1:08 pm - 8:55 pmMDW-ANC

10h 47m1 stop

$338Delta

Find Deal

Fri, Sep 5 - Sun, Sep 7

5:20 pm - 9:03 amANC-ORD

12h 43m2 stops

7:37 am - 3:19 pmORD-ANC

10h 42m1 stop

$343Delta

Find Deal

Fri, Oct 10 - Sat, Oct 18

5:19 pm - 8:51 amANC-MDW

12h 32m2 stops

1:08 pm - 8:55 pmMDW-ANC

10h 47m1 stop

$343Delta

Find Deal

Fri, Sep 5 - Sun, Sep 7

11:25 pm - 8:40 amANC-ORD

6h 15mnonstop

8:00 am - 3:04 pmORD-ANC

10h 04m1 stop

$358Hawaiian Airlines

Find Deal

Thu, Sep 18 - Sun, Sep 21

9:04 pm - 6:13 amANC-ORD

6h 09mnonstop

4:05 pm - 7:59 pmORD-ANC

6h 54mnonstop

$361United Airlines

Find Deal

Thu, Oct 23 - Mon, Oct 27

11:11 pm - 8:40 amANC-ORD

6h 29mnonstop

8:10 am - 12:08 pmORD-ANC

6h 58mnonstop

$377Hawaiian Airlines

Find Deal

Sat, Oct 11 - Sat, Oct 18

9:04 pm - 6:13 amANC-ORD

6h 09mnonstop

4:05 pm - 7:59 pmORD-ANC

6h 54mnonstop

$398United Airlines

Find Deal

Wed, Oct 22 - Mon, Oct 27

Alaska Airlines flights from Alaska to Chicago

Our best Alaska Airlines deals on Alaska to Chicago flight tickets

Alaska Airlines

Oct 2

ANC11:25 pmAnchorage

6h 15m

ORD8:40 amChicago O'Hare Intl

Oct 11

ORD8:10 amChicago O'Hare Intl

6h 58m

ANC12:08 pmAnchorage

$318

Find similar

Alaska Airlines

Oct 2

ANC11:25 pmAnchorage

6h 15m

ORD8:40 amChicago O'Hare Intl

Oct 11

ORD7:00 amChicago O'Hare Intl

9h 22m

1 stop

ANC1:22 pmAnchorage

$328

Find similar

Alaska Airlines

Oct 23

ANC11:11 pmAnchorage

6h 29m

ORD8:40 amChicago O'Hare Intl

Oct 28

ORD8:00 amChicago O'Hare Intl

11h 35m

1 stop

ANC4:35 pmAnchorage

$338

Find similar

American Airlines flights from Alaska to Chicago

Our best American Airlines deals on Alaska to Chicago flight tickets

American Airlines

Sep 18

ANC9:53 pmAnchorage

6h 24m

ORD7:17 amChicago O'Hare Intl

Sep 21

ORD5:01 pmChicago O'Hare Intl

6h 47m

ANC8:48 pmAnchorage

$319

Find similar

American Airlines

Oct 1

ANC9:53 pmAnchorage

6h 24m

ORD7:17 amChicago O'Hare Intl

Oct 7

ORD10:32 amChicago O'Hare Intl

11h 12m

1 stop

ANC6:44 pmAnchorage

$347

Find similar

American Airlines

Sep 11

ANC9:53 pmAnchorage

6h 24m

ORD7:17 amChicago O'Hare Intl

Sep 16

ORD5:01 pmChicago O'Hare Intl

6h 47m

ANC8:48 pmAnchorage

$369

Find similar

Fly from

Fly to

Route

Depart

Return

Price

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 10/2

11:25 pm-8:40 am

Nonstop6h 15m

Chicago O'Hare Intl

Sat 10/11

8:10 am-12:08 pm

Nonstop6h 58m

$318

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 9/18

9:53 pm-7:17 am

Nonstop6h 24m

Chicago O'Hare Intl

Sun 9/21

5:01 pm-8:48 pm

Nonstop6h 47m

$319

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 10/2

11:25 pm-8:40 am

Nonstop6h 15m

Chicago O'Hare Intl

Sat 10/11

7:00 am-1:22 pm

1 stop9h 22m

$328

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 9/5

10:30 pm-12:28 pm

1 stop10h 58m

Chicago Midway

Sun 9/7

1:08 pm-8:55 pm

1 stop10h 47m

$338

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Fri 10/10

5:20 pm-9:03 am

2 stops12h 43m

Chicago O'Hare Intl

Sat 10/18

7:37 am-3:19 pm

1 stop10h 42m

$343

AnchorageChicago

ANC - MDW

ANCMDW

Anchorage

Fri 9/5

5:19 pm-8:51 am

2 stops12h 32m

Chicago Midway

Sun 9/7

1:08 pm-8:55 pm

1 stop10h 47m

$343

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 9/18

11:25 pm-8:40 am

Nonstop6h 15m

Chicago O'Hare Intl

Sun 9/21

8:00 am-3:04 pm

1 stop10h 04m

$358

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Thu 10/23

9:04 pm-6:13 am

Nonstop6h 09m

Chicago O'Hare Intl

Mon 10/27

4:05 pm-7:59 pm

Nonstop6h 54m

$361

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Sat 10/11

11:11 pm-8:40 am

Nonstop6h 29m

Chicago O'Hare Intl

Sat 10/18

8:10 am-12:08 pm

Nonstop6h 58m

$377

AnchorageChicago

ANC - ORD

ANCORD

Anchorage

Wed 10/22

9:04 pm-6:13 am

Nonstop6h 09m

Chicago O'Hare Intl

Mon 10/27

4:05 pm-7:59 pm

Nonstop6h 54m

$398

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Alaska to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Alaska, with most prices found around $395. If you’re not able to fly to Chicago in November, then October is your next best option. Flight prices from Alaska to Chicago during October average around $399.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $707. This is often the case because there is less demand to fly during this day of the week. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Alaska to Chicago for around $889.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Alaska to Chicago during this time can be as low as $331. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $755.

What is the cheapest Alaska to Chicago flight route?

Fly from Fairbanks to Chicago O'Hare Intl for the best Alaska - Chicago flight prices

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

You are more likely to see cheaper flights to Chicago from Alaska when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $488 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Alaska for as low as $377 on momondo.

What cabin class options are available on Alaska to Chicago flights?

There are 4 cabin classes available to choose from on Alaska to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Alaska to Chicago flights?

No. A direct flight is the cheapest option for a flight between Alaska to Chicago.

Cheap Alaska to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Alaska to Chicago

Best Price Found	$159
Fastest flight time	5h 59m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Alaska in the past 72 hours is $159. The best round-trip flight deal from Alaska to Chicago found on momondo in the last 72 hours is $318.

The fastest flight from Alaska to Chicago takes 5h 59m

Direct flights go from Alaska to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

When did momondo last update prices for flights from Alaska to Chicago?
Prices for flights from Alaska to Chicago were last updated today.
How many operators does momondo search for flights from Alaska to Chicago?
There are 5 operators available for flights from Alaska to Chicago as of July 2025.
How old do you have to be to fly from Alaska to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Alaska to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Alaska to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Alaska to Chicago is Boeing 737 MAX 9, representing 26.50% of all bookings. The subsequent popular models are Boeing 737-900 Passenger/BBJ3 (winglets) at 19.43%, Boeing 737 MAX 8 at 19.08%, and Boeing 737 at 12.37%.

Best airlines flying from Alaska to Chicago

Compare and see reviews for airlines that fly from Alaska to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Hawaiian Airlines	PriceFrom $197	Free Cancellation	Rating 7.8 2,611 reviews	Search Hawaiian Airlines flights
American Airlines	PriceFrom $338	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Delta	PriceFrom $338	Free Cancellation	Rating 8.0 7,981 reviews	Search Delta flights
United Airlines	PriceFrom $345	Free Cancellation	Rating 7.4 8,900 reviews	Search United Airlines flights
Alaska Airlines	PriceFrom $354	Free Cancellation	Rating 8.0 10,000 reviews	Search Alaska Airlines flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Alaska to Chicago?

Finding the right flight to Chicago from Alaska is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Alaska to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Alaska to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Alaska to Chicago?

Once all potential Alaska to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Alaska to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Alaska are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Tue 8/5

Tue 8/12

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Popular cities in the United States

Flights to New Yorkfrom $39

Flights to Los Angelesfrom $37

Flights to Miamifrom $58

Flights to Orlandofrom $54

Flights to Las Vegasfrom $35

Flights to San Franciscofrom $49

Flights to Washington, D.C.from $49

Flights to Bostonfrom $77

Flights to Atlantafrom $29

Flights to Dallasfrom $55

Flights to Seattlefrom $93

Flights to Denverfrom $49

Cheap flights from Alaska to Chicago from $159

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Alaska to Chicago departing on 8/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Alaska to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Alaska Airlines flights from Alaska to Chicago

Our best Alaska Airlines deals on Alaska to Chicago flight tickets

American Airlines flights from Alaska to Chicago

Our best American Airlines deals on Alaska to Chicago flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Alaska to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Alaska to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Alaska, with most prices found around $395. If you’re not able to fly to Chicago in November, then October is your next best option. Flight prices from Alaska to Chicago during October average around $399.

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Alaska to Chicago during this time can be as low as $331. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $755.

What is the cheapest Alaska to Chicago flight route?

Fly from Fairbanks to Chicago O'Hare Intl for the best Alaska - Chicago flight prices

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

What cabin class options are available on Alaska to Chicago flights?

There are 4 cabin classes available to choose from on Alaska to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Alaska to Chicago flights?

No. A direct flight is the cheapest option for a flight between Alaska to Chicago.

What is the cheapest airline that flies from Alaska to Chicago?

Hawaiian Airlines, Delta, and United Airlines are the most popular carriers operating from Alaska to Chicago

What airlines fly to Chicago?

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

As of July 2025, there are 11 flights per day flying from Alaska to Chicago. The most common time of day flights depart is 9:00PM, with 100% of flights taking off in the evening.

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

As of July 2025, 81 flights take off from Alaska and land in Chicago each week. The most common flight departure day for this route is Thu, with 16% of weekly flights taking off on this day.

How long does it take to fly to Chicago?

Cheap Alaska to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Alaska to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

When did momondo last update prices for flights from Alaska to Chicago?

How many operators does momondo search for flights from Alaska to Chicago?

How old do you have to be to fly from Alaska to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from Alaska to Chicago?

Best airlines flying from Alaska to Chicago

Compare and see reviews for airlines that fly from Alaska to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Alaska to Chicago?

Can I find flights from Alaska to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Alaska to Chicago?

I’m not ready to book a flight from Alaska to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago