Cheap flights from Anchorage to Chicago

Ted Stevens
ANC
Chicago FSS
CHI

Flight deals from Anchorage to Chicago

Below you can see the best deals on flights Anchorage — Chicago for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 13 October, from $164.

Top 10 cheap flights from Anchorage to Chicago

DL
DL
F9
$ 218

Anchorage — Chicago

06:15—12:50
1 Sep 2026
27 h 35 m
2 stops
AS
$ 233

Anchorage — Chicago

22:28—07:40
5 Sep 2026
6 h 12 m
Direct flight
AS
$ 233

Anchorage — Chicago

22:28—07:40
4 Sep 2026
6 h 12 m
Direct flight
AS
$ 233

Anchorage — Chicago

22:28—07:40
3 Sep 2026
6 h 12 m
Direct flight
AS
AS
AS
$ 235

Anchorage — Chicago

01:29—19:21
5 Sep 2026
14 h 52 m
2 stops
AS
AS
AS
$ 235

Anchorage — Chicago

01:29—19:21
5 Sep 2026
14 h 52 m
2 stops
AS
AS
AS
$ 235

Anchorage — Chicago

00:29—19:21
5 Sep 2026
15 h 52 m
2 stops
AS
AS
AS
$ 235

Anchorage — Chicago

00:29—19:21
5 Sep 2026
15 h 52 m
2 stops
AS
AS
AS
$ 235

Anchorage — Chicago

01:29—19:21
6 Sep 2026
14 h 52 m
2 stops
AS
AS
AS
$ 235

Anchorage — Chicago

01:29—19:21
6 Sep 2026
14 h 52 m
2 stops

Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the Anchorage — Chicago flight

Looking for cheap flights from Anchorage to Chicago? Compare fares from different airlines, check the flight schedule and travel time — and book your Anchorage — Chicago ticket online at the best price.

The route has direct flights — around 75 flights per week, flights are operated by Alaska Airlines, United Airlines, American Airlines, a nonstop flight takes about 6 h 14 min, the distance between the cities is around 4,598 km.

Planning your trip? You may find our Chicago travel guide, how to get from the airport into town and Chicago weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

Facts about this route

from $164Min. price
OctoberCheapest
JulyPeak season
YesDirect flights
4,598 kmDistance
6 h 14 minTravel time
3Airlines
75 / wkFlights

Flight schedule from Anchorage to Chicago

The table shows direct flights from Anchorage to Chicago on the selected date. The flight takes approximately 6 h 14 min. Regular flights are operated by Alaska Airlines, United Airlines and American Airlines. Departures from Ted Stevens Anchorage International Airport airports, arrivals at O'Hare International Airport, Chicago Midway International Airport and Midway International Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

Today
Any time
Last update: 14 Aug 2026

Flight ticket prices by day: Anchorage — Chicago

Below is a calendar of the lowest flight ticket prices for Anchorage — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $164 in October, and the most expensive are around $264 in July. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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Prices by month

Average one-way fares from Anchorage to Chicago by month. Tickets are usually cheapest in October (around $350) and priciest in January (about $423) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$423highMay$387mediumSep$357low
Feb$411highJun$405highOct$350low
Mar$363lowJul$417highNov$369medium
Apr$375mediumAug$375mediumDec$405high

Some values are estimated based on seasonality.

When to fly

Weather in Chicago: it is warmest in July (up to 27 °C on average) and coolest in January (around 0 °C). The driest month is November.

Tickets are usually cheapest in October and most expensive in July. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · Chicago

Dry and wet days · Chicago

Wind speed and direction · Chicago

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How to get the best deal on a Anchorage — Chicago ticket

  • Book ahead: fares for Anchorage — Chicago are usually lower 3–8 weeks before departure than at the last minute.
  • Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
  • The cheapest month to fly to Chicago is usually October — plan your trip around it if your dates are flexible.
  • Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
  • Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
  • Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
  • Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Airlines

Flights on the Anchorage — Chicago route are operated by 3 airlines; Alaska Airlines runs the most flights (around 60% of all flights). Compare carriers, flight shares and schedules below.

  • Alaska AirlinesAS
    15x/week
    WebsiteFleet: 31545M pax/year
    • Direct flight ANC → ORD15x/week
      Duration
      6h 15m
      Days
      MTWTFSS
    60.0%Open →
  • United AirlinesUA
    7x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight ANC → ORD7x/week
      Duration
      6h 12m
      Days
      MTWTFSS
    29.3%Open →
  • American AirlinesAA
    3x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight ANC → ORD3x/week
      Duration
      6h 29m
      Days
      MTWTFSS
    10.7%Open →

Cities and airports on the Anchorage — Chicago route

Flights Anchorage — Chicago depart from Ted Stevens Anchorage International Airport and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Anchorage

ANC
United States
About the cityHow to get thereWeatherAll about the country United States
Arrival

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

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Frequently asked questions about the Anchorage — Chicago flight

How long is the flight from Anchorage to Chicago?

A nonstop Anchorage — Chicago flight takes about 6 h 14 min — the distance between the cities is around 4,598 km.

How far is it from Anchorage to Chicago?

The distance from Anchorage to Chicago is about 4,598 km, which a nonstop flight covers in around 6 h 14 min.

Are there direct flights from Anchorage to Chicago?

Yes, there are nonstop flights Anchorage — Chicago — around 75 flights per week.

Which airlines fly from Anchorage to Chicago?

Airlines operating Anchorage — Chicago include Alaska Airlines, United Airlines, American Airlines. See the full list with schedules in the "Airlines" section on this page.

Which airports do Anchorage — Chicago flights use?

Flights from Anchorage depart from Ted Stevens Anchorage International Airport, and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Anchorage to Chicago?

The price of a Anchorage — Chicago ticket depends on your travel date, season and demand: it is usually cheapest to fly in October, and most expensive in July. Tickets typically cost between $164 and $264. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights Anchorage — Chicago?

Flights Anchorage — Chicago are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is October. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Anchorage to Chicago?

To catch a low fare Anchorage — Chicago, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually October.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

Where else you can fly from Anchorage

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SeattleFairbanksPortlandDenverLos AngelesJuneauMinneapolisNew York CityKenaiPhoenixSan FranciscoHonoluluVancouverDallasSalt Lake CityNomeLas VegasWashington, D.C.HoustonDetroitTaipeiKailua-KonaKotzebueHong KongBethelUtqiagvikKodiakFrankfurt am MainSan DiegoSeoulSacramentoSpokaneCordovaAtlantaBoiseSitkaKahuluiTokyoKetchikanOsaka

Where else you can fly from Chicago

See all
New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverNashvilleLondonIndianapolisSan DiegoMontrealMilwaukeeSt. LouisCharlottePhiladelphiaColumbusKansas CityPhoenixMiamiLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochester

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