What percentage of Anchorage to Chicago flights are direct?

In the trailing 90 days, approximately 37.5% of flights from Anchorage to Chicago were direct. For flights that included a stopover, the median number of stopovers was 1. This means that while direct options are available, a significant portion of flights on this route involve at least one connection.

How long is the flight from Anchorage to Chicago?

A direct flight from Anchorage to Chicago typically takes about 6 hours and 18 minutes, covering a distance of 4593 kilometers. Flights with one stopover, on average, have a median duration of 9 hours and 14 minutes. This difference in flight time highlights the convenience of direct routes when available.

How often do cheap flights from Anchorage to Chicago come up?

Historically, cheap flights from Anchorage to Chicago are a frequent occurrence. This route is regularly observed to have competitive pricing. Travelers can often find good deals when planning their trips between these two cities.

Flights From Anchorage

To Chicago

Cheap Flights from Anchorage to Chicago

Browse current best options from Anchorage. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Anchorage

RatePunk searches hundreds of travel sites at once for deals on flights to Chicago

Prices updated 6 days ago

454 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Aug 25, 2026.)

Today’s best flight deals from Anchorage to Chicago

Explore current cheapest deals departing from Anchorage to Chicago

2026-10-12 – 2026-10-26
ANC - Chicago
74% AI deal score
$358
$424
Round trip
2026-09-24 – 2026-09-30
ANC - Chicago
74% AI deal score
$367
$438
Round trip
2026-10-13 – 2026-10-20
ANC - Chicago
73% AI deal score
$342
$439
Round trip
2026-10-13 – 2026-10-27
ANC - Chicago
73% AI deal score
$310
$439
Round trip
2026-10-14 – 2026-10-21
ANC - Chicago
73% AI deal score
$342
$439
Round trip
2026-10-14 – 2026-10-28
ANC - Chicago
73% AI deal score
$310
$439
Round trip
2026-10-12 – 2026-10-19
ANC - Chicago
73% AI deal score
$342
$439
Round trip
2026-10-19 – 2026-10-26
ANC - Chicago
73% AI deal score
$342
$440
Round trip
2026-10-20 – 2026-10-27
ANC - Chicago
73% AI deal score
$343
$440
Round trip
2026-10-21 – 2026-10-28
ANC - Chicago
73% AI deal score
$344
$440
Round trip

Anchorage to Chicago: Overview

Insights for flights from Anchorage to Chicago

Most itineraries for cheap flights from Anchorage to Chicago connect at least once, with only 37.5% of recent fares being non-stop. For connecting flights, the typical number of stopovers is 1. This means that while direct options exist, you will frequently encounter itineraries that include a layover.

Right now, fares from Anchorage to Chicago are typically $399–$839, with a median of $594. Current fares are significantly below the typical level, with 31% of recent fares classified as a good price. New deals appear almost daily, offering frequent opportunities to find competitive prices.

When looking for the cheapest time to fly from Anchorage to Chicago, November stands out as the most affordable month, with a median fare of $290. Following closely, August offers a median fare of $402, and September presents a median of $404. These months typically provide better value compared to other times of the year.

A typical journey from Anchorage to Chicago takes approximately 6h 18m, including connections. For non-stop flights, the median duration is also 6h 18m. However, if your itinerary includes connections, the median journey time extends to about 9h 28m, so it is important to factor in the additional travel time for connecting routes.

The flight distance between Anchorage and Chicago is approximately 4593 kilometers. This route is classified as a long-haul journey, indicating a significant distance that typically involves several hours of flight time.

How much is a round trip from Anchorage to Chicago

Regular price: $318 - $611

Prices for flights from Anchorage to Chicago are currently within the regular range.

The regular price range for flights from Anchorage to Chicago is between $318 and $611. The current lowest deal is $424 with Alaska Airlines, Inc. for travel from Oct 12-Oct 26.

now $424

Low $318

High $611

The cheapest time to fly from Anchorage to Chicago

The cheapest month to fly from Anchorage to Chicago is November, with a median price of $290. The most expensive month is April, with a median price of $868. Prices are generally lower from March to November.

November

Cheapest

Flights from $290

April

Most Expensive

Flights from $868

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Anchorage to Chicago

Alaska Airlines, Inc.

Last-minute flights going from Anchorage to Chicago

Tue, Aug 25

⌛ Last-Minute

ANC - Chicago

Anchorage (ANC) - Chicago (ORD)

Alaska Airlines, Inc.

$523

$490

One-way

Tue, Aug 25

⌛ Last-Minute

ANC - Chicago

Anchorage (ANC) - Chicago (ORD)

Alaska Airlines, Inc.

$523

$490

One-way

Tue, Aug 25

⌛ Last-Minute

ANC - Chicago

Anchorage (ANC) - Chicago (ORD)

Alaska Airlines, Inc.

$551

$518

One-way

Tue, Aug 25

⌛ Last-Minute

ANC - Chicago

Anchorage (ANC) - Chicago (ORD)

Alaska Airlines, Inc.

$783

$518

One-way

Tue, Aug 25

⌛ Last-Minute

ANC - Chicago

Anchorage (ANC) - Chicago (ORD)

Alaska Airlines, Inc.

$540

$518

One-way

Tue, Aug 25

⌛ Last-Minute

ANC - Chicago

Anchorage (ANC) - Chicago (ORD)

Alaska Airlines, Inc.

$598

$518

One-way

Biggest price drops on these dates for flights from Anchorage to Chicago

2 nights

Aug 31 - Sep 2

$783 → $528

33%

3 nights

Aug 31 - Sep 3

$763 → $519

32%

3 nights

Sep 1 - Sep 4

$700 → $538

23%

2 nights

Sep 2 - Sep 4

$691 → $539

22%

Popular Airports to fly from Anchorage to Chicago

Anchorage - Chicago route insights

💸 Price insights

Recent fares are below the typical level.

Recent fares for Anchorage to Chicago are below the typical level at $424.

📅 Best time to fly

Fly in November for the lowest prices.

Historically, November offers the lowest median prices at $290 for this route.

⏱️ Flight duration

Direct flights take 6h 18m.

The median flight duration for a direct flight from Anchorage to Chicago is 6h 18m.

✈️ Airlines & availability

Connecting flights are more common.

Connecting flights make up 62.5% of recent routes, typically with 1 stopover.

🏆 Airline highlight

Alaska Airlines, Inc. offers direct flights.

Alaska Airlines, Inc. has offered direct flights on the Anchorage to Chicago route.

🎯 Booking tip

Deals appear frequently.

Deals for flights from Anchorage to Chicago appear frequently, typically within 30 days.

Anchorage main airports to depart from

Ted Stevens Anchorage International (ANC)

Cheapest

Ted Stevens Anchorage International is a convenient option for flights from Anchorage to Chicago.

📍 ~7 km from Anchorage city center (reachable by car).

💸 Flights from ~$353

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O Hare International Airport is a major hub, offering many flight options for travelers to Chicago.

📍 ~25 km from Chicago (reachable by car)

💸 Flights from ~$353

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International Airport (MKE) is a major international airport with significant carrier presence and direct flight options.

📍 ~135 km from Chicago (reachable by train or car)

💸 Flights from ~$425

Business & First Class Flight Deals to Chicago

$1,469

Save $1,290

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the best deals for flights from Anchorage to Chicago are found when booking between 7 and 13 days in advance. During this period, the average price for a flight was approximately $603. Booking within 6 days of departure typically sees prices rise to around $634. For travelers planning further ahead, booking 60 or more days out showed an average price of $610, indicating that last-minute bookings can sometimes offer better value than very early bookings on this route.

Across the trailing quarter, a good price for a flight from Anchorage to Chicago was considered to be $399 or less. The median price observed for this route was $594. Prices can vary, with 75% of fares being $839 or less. This $399 threshold represents the lower end of the pricing spectrum for this route.

Historically, November has been the cheapest month to fly from Anchorage to Chicago, with a median price of $290. Other relatively inexpensive months include August and September, which had median prices of $402 and $404 respectively. The annual median price for this route was $594, indicating that these months offer significant savings compared to the yearly average.

Related routes

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Anchorage to Chicago: Overview

Insights for flights from Anchorage to Chicago

How much is a round trip from Anchorage to Chicago

Regular price: $318 - $611

Prices for flights from Anchorage to Chicago are currently within the regular range.

The regular price range for flights from Anchorage to Chicago is between $318 and $611. The current lowest deal is $424 with Alaska Airlines, Inc. for travel from Oct 12-Oct 26.

now $424

Low $318

High $611

The cheapest time to fly from Anchorage to Chicago

November

Cheapest

Flights from $290

April

Most Expensive

Flights from $868

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec