ANC - CHI

$261 Find Cheap Flights from Anchorage to Chicago - Compare and Save

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Everything you should know

Cheapest round-trip
$495
Typical prices: $417-$641
Alaska Airlines
Sun 12/9Mon 12/17
ANC - ORD • 2 stops
Cheapest non-stop
$583
Typical prices: $428-$621
United Airlines
Sat 12/1Sat 12/8
ANC - ORD • Non-stop
Nonstop flights
Every day
You can fly direct with United Airlines. Average duration is 6h 21m
Direct flights
+1
Direct flights
+1
Top routes
ANC - MDW
Cheapest • 10% average savings
ANC - ORD
Most popular
Insights
Insights
When to book
22 weeks
in advance
Our data shows that travelers who book at least 22 weeks in advance save around 43% compared to booking last minute.
Insights
Insights
When to travel
February
Cheapest • 33% price drop
June
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Dallas/Fort Worth (DFW)
Cheapest • Avg $498 (round-trip)
Minneapolis St Paul (MSP)
Shortest trip • 9h 33m (one-way)
Insights
Insights
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Expert advice
Flight Deals

Cheap Flights from Anchorage to Chicago (ANC-CHI)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Anchorage to Chicago

Wed, Dec 9 - Thu, Dec 17
Alaska Airlines Logo
2:26 am - 7:00 pmANC  Anchorage-ORD Chicago O'Hare Intl
13h 34m2 stops Seattle/Tacoma Intl San Diego
Alaska Airlines Logo
6:00 am - 2:14 pmORD  Chicago O'Hare Intl-ANC Anchorage
11h 14m1 stop Seattle/Tacoma Intl
$495Alaska Airlines
Thu, Apr 15 - Mon, Apr 19
Alaska Airlines Logo
3:20 pm - 6:35 amANC  Anchorage-ORD Chicago O'Hare Intl
12h 15m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
7:59 pm - 2:11 amORD  Chicago O'Hare Intl-ANC Anchorage
9h 12m1 stop Seattle/Tacoma Intl
$507Alaska Airlines
Thu, Dec 10 - Thu, Dec 17
Alaska Airlines Logo
12:24 pm - 11:59 pmANC  Anchorage-ORD Chicago O'Hare Intl
8h 35m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
6:00 am - 1:13 pmORD  Chicago O'Hare Intl-ANC Anchorage
10h 13m1 stop Seattle/Tacoma Intl
$522Alaska Airlines
Sun, Nov 29 - Mon, Dec 7
Delta Logo
1:15 am - 1:37 pmANC  Anchorage-ORD Chicago O'Hare Intl
9h 22m1 stop Seattle/Tacoma Intl
Delta Logo
12:34 pm - 8:53 pmORD  Chicago O'Hare Intl-ANC Anchorage
11h 19m1 stop Minneapolis St Paul
$523Delta
Mon, Feb 22 - Tue, Mar 9
Delta Logo
6:00 am - 11:46 pmANC  Anchorage-ORD Chicago O'Hare Intl
14h 46m1 stop Seattle/Tacoma Intl
Delta Logo
12:50 pm - 10:36 pmORD  Chicago O'Hare Intl-ANC Anchorage
12h 46m1 stop Seattle/Tacoma Intl
$523Delta
Tue, Dec 1 - Tue, Dec 8
Delta Logo
6:05 am - 11:57 pmANC  Anchorage-ORD Chicago O'Hare Intl
14h 52m1 stop Seattle/Tacoma Intl
Delta Logo
12:58 pm - 11:28 pmORD  Chicago O'Hare Intl-ANC Anchorage
13h 30m1 stop Seattle/Tacoma Intl
$523Delta
Thu, Dec 3 - Mon, Dec 7
United Airlines Logo
8:45 pm - 5:59 amANC  Anchorage-ORD Chicago O'Hare Intl
6h 14mnonstop
United Airlines Logo
3:35 pm - 7:39 pmORD  Chicago O'Hare Intl-ANC Anchorage
7h 04mnonstop
$583United Airlines
Tue, Dec 1 - Tue, Dec 8
United Airlines Logo
8:45 pm - 5:59 amANC  Anchorage-ORD Chicago O'Hare Intl
6h 14mnonstop
United Airlines Logo
3:35 pm - 7:39 pmORD  Chicago O'Hare Intl-ANC Anchorage
7h 04mnonstop
$583United Airlines
Thu, Dec 3 - Tue, Dec 8
United Airlines Logo
8:45 pm - 5:59 amANC  Anchorage-ORD Chicago O'Hare Intl
6h 14mnonstop
United Airlines Logo
4:20 pm - 10:59 pmORD  Chicago O'Hare Intl-ANC Anchorage
9h 39m1 stop Denver Intl
$593United Airlines
Thu, Apr 15 - Mon, Apr 19
American Airlines Logo
8:30 pm - 11:11 amANC  Anchorage-ORD Chicago O'Hare Intl
11h 41m1 stop Dallas/Fort Worth
American Airlines Logo
8:09 am - 6:50 pmORD  Chicago O'Hare Intl-ANC Anchorage
13h 41m1 stop Dallas/Fort Worth
$733American Airlines
Booking Insights

Price, demand and travel trends for Anchorage to Chicago flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Anchorage to Chicago?

Round-trip flights from Anchorage to Chicago typically range from $417 to $641. The lowest price found in the past 5 days was $495, on Alaska Airlines.

What is the cheapest Anchorage to Chicago flight route?

Anchorage (ANC) to Chicago Midway Airport (MDW) is the cheapest Anchorage to Chicago route, averaging $437 round-trip. Other Anchorage to Chicago routes average $534, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Anchorage to Chicago?

Based on deals KAYAK users found in the last 12 months, Monday is the cheapest day of the week to fly from Anchorage to Chicago. It’s 20% cheaper than the average day, while Friday is the most expensive, with prices 10% higher.

What’s the cheapest month to fly from Anchorage to Chicago?

•February is the cheapest month to fly from Anchorage to Chicago at $358 round-trip.
•January ($734) and December ($701) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 105% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Anchorage to Chicago the cheapest?

Flights from Anchorage to Chicago are cheapest 22 weeks before departure. Booking in this window typically costs about 43% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

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Expert advice

Expert advice for your flight from Anchorage to Chicago

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on Alaska Airlines and American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ANC

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

Key details for Anchorage to Chicago flights

Low season

February

Cheapest flight

$261
Beat the crowds with an average 62% drop in travelers.
The most popular month to fly with an average 72% increase in travelers.
One-way flight from Anchorage to Chicago O'Hare Intl Airport

When to book flights from Anchorage to Chicago

Are your dates flexible? Find out the best times to travel from Anchorage to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Anchorage to Chicago flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Anchorage to Chicago?

    These are the earliest and latest flight times available from Anchorage to Chicago:

    • Earliest: departs at 8:30 pm and lands at 2:51 am
    • Latest: departs at 8:54 pm and lands at 3:15 am.

    The flight takes about 6h 21m.

  • What cabin classes can I book on flights from Anchorage to Chicago?

    Three cabin classes are available on flights from Anchorage to Chicago:

    • Economy Class
    • Business Class
    • First Class

  • How long is a flight from Anchorage to Chicago?

    A nonstop flight from Anchorage to Chicago takes 6h 21m, covering 2,851 miles.

  • Do I need a passport to fly from Anchorage to Chicago?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Anchorage to Chicago flight?

    Round-trip flights from Anchorage to Chicago range from $417 to $641, with an average of $534 over the past 12 months. Anything below $417 counts as a good deal.

  • How expensive are last-minute Anchorage to Chicago flights?

    Last-minute fares on this route (booked within two weeks of departure) run 30% above the $534 route average. Book 22 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Anchorage to Chicago?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $498 round-trip via Dallas/Fort Worth (DFW), compared to $535 for nonstop.

  • What is the standard checked-bag allowance on flights from Anchorage to Chicago?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • How are flight departures from Anchorage to Chicago spread across the day?

    Evening is the busiest departure period on Anchorage to Chicago flights, with 100% of flights leaving in that window. Morning departures account for 0%, afternoon flights for 0%, and night flights for 0%.

  • Have flight prices from Anchorage to Chicago changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $495 to $3,542. That means the highest observed fare was about 7x higher than the lowest one.

  • Which airlines offer Wi-Fi on Anchorage to Chicago flights?

    Alaska Airlines is the only airline on the Anchorage to Chicago route offering in-flight Wi-Fi. Pricing depends on fare class.

  • How are flight prices from Anchorage to Chicago looking right now?

    One-way fares from Anchorage to Chicago are currently higher than usual. Average one-way flight prices are about $335, which is 16% above the typical average for this route.

  • What car rental options are available in Chicago?

    Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) — daily rates averaging $64:

    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Ace
    • Dollar

    Near Chicago Midway Airport (MDW) — daily rates averaging $84:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

    Near Chicago Greater Rockford Airport (RFD) — daily rates averaging $81:

    • Alamo
    • Enterprise Rent-A-Car
    • Budget
    • Avis
    • National

  • Which airports can I use when flying from Anchorage to Chicago?

    Flights from Anchorage to Chicago usually depart from Anchorage (ANC) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • Which airports do connecting flights from Anchorage to Chicago pass through?

    One-stop flights from Anchorage to Chicago most commonly connect through:

    • Seattle/Tacoma Intl (SEA) - 63% of one-stop connections
    • Minneapolis St Paul (MSP) - 31% of one-stop connections
    • Dallas/Fort Worth (DFW) - 2% of one-stop connections
    • Chicago O'Hare Intl (ORD) - 2% of one-stop connections

  • Can I save money by using flexible dates for flights from Anchorage to Chicago?

    Yes. Flexible dates can save you up to 28% on flights from Anchorage to Chicago. Monday is the cheapest departure day at $428 round-trip on average, while Friday is the most expensive at $588, a difference of $160.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Anchorage to Chicago?

    Only United Airlines operates flights between Anchorage and Chicago.

  • How much time can I save by choosing a different layover airport from Anchorage to Chicago?

    Flying via Minneapolis St Paul (MSP) gives the shortest average 1-stop total travel time at 9h 33m, compared with 9h 37m via Portland (PDX) and 10h 16m via Seattle/Tacoma Intl (SEA).

  • What is the time difference between Anchorage and Chicago?

    Chicago is 3 hours ahead of Anchorage (Central Time vs Alaska Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Chicago?

    Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Anchorage to Chicago flights?

    Among airlines operating Anchorage to Chicago flights:

    • United Airlines: offers extra legroom; offers free seat selection
    • American Airlines: offers extra legroom; offers free seat selection
    • Alaska Airlines: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Anchorage to Chicago flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • United Airlines: a cabin bag and a checked bag in Economy Class
    • American Airlines: a cabin bag and a checked bag in Economy Class
    • Alaska Airlines: a cabin bag and a checked bag in Business Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Anchorage to Chicago flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Monday departure and avoid flying on Friday. On this route, Monday flights average $428, about $160 less than Friday fares (27% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 22 weeks before you fly. On this route, that window historically saves about 43% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Anchorage to Chicago trip for February. Fares historically average $358 round-trip in that month - typically $376 less than the most expensive month, which is January (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Dallas/Fort Worth Airport (DFW) can be cheaper than flying direct. The cheapest layover option averages $498 round-trip on this route - about $36 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel Chicago Midway Airport

Prefer to fly direct from Anchorage to Chicago?

 
Find which airlines fly direct from Anchorage Airport to Chicago, which days they fly and book direct flights.

Direct departures

Anchorage to Chicago

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

Chicago to Anchorage

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

More options for your flight from Anchorage to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Car rentals in Chicago
Hotels in Chicago
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