Cheap Flights from Anchorage, AK to Chicago, IL from $201

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On Cheapflightsplus.com you will find 7 direct and 268 connecting flights from Anchorage to Chicago. You can compare airfare deals from 4 airlines and multiple travel sites from $201, book and save on cheap plane tickets and last minute offers. Also check out ANC-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Anchorage to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $201 (one-way), $345 (round-trip).

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Best Flights from Anchorage to Chicago Today

Take a look at the list of non stop flights and flights with layovers from Anchorage to Chicago with the lowest price of $201. The fastest direct flight takes 6h 9m and the fastest connecting – 8h 3m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $201 Find flight	23:25 Anchorage Ted Stevens Anchorage	08:40+1 день Chicago O'Hare International	6h 15m	Hawaiian Airlines	HA4726
from $205 Find flight	23:25 Anchorage Ted Stevens Anchorage	08:40+1 день Chicago O'Hare International	6h 15m	Alaska Airlines	AS138
from $238 Find flight	23:26 Anchorage Ted Stevens Anchorage	08:40+1 день Chicago O'Hare International	6h 14m	Hawaiian Airlines	HA4725
from $213 Find flight	11:00 Anchorage Ted Stevens Anchorage	23:59 Chicago O'Hare International	9h 59m layover 2h 26m - Seattle	Alaska Airlines	AS130 AS538
from $225 Find flight	20:55 Anchorage Ted Stevens Anchorage	12:28+1 день Chicago O'Hare International	12h 33m layover 5h 28m - Minneapolis	Sun Country Airlines	SY474 SY1629
from $217 Find flight	05:05 Anchorage Ted Stevens Anchorage	23:59 Chicago O'Hare International	15h 54m layover 3h 45m - Portland 3h 26m - Seattle	Alaska Airlines	AS593 AS165 AS538
from $245 Find flight	02:50 Anchorage Ted Stevens Anchorage	18:18 Chicago O'Hare International	12h 28m layover 1h 0m - Seattle 1h 26m - San Francisco	Hawaiian Airlines	HA698 HA6903 HA7000

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on September 18, 2025

Flight Schedule Anchorage (Alaska) to Chicago (Illinois)

Full flight schedule will help you in detecting at what time planes fly from Anchorage to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.

Departure	Flight Details	Flight Duration	Price
01:29 — 18:18	01:29 — 06:00 AS54 Alaska Airlines Anchorage — Seattle 2h 5m stop 08:05 — 10:24 AS1166 Alaska Airlines Seattle — San Francisco 1h 31m stop 11:55 — 18:18 AS598 Alaska Airlines San Francisco — Chicago	13h 49m including layover	Find flight from$220
02:50 — 18:18	02:50 — 07:10 AS8088 Alaska Airlines Anchorage — Seattle 1h stop 08:05 — 10:24 AS1166 Alaska Airlines Seattle — San Francisco 1h 26m stop 11:55 — 18:18 AS598 Alaska Airlines San Francisco — Chicago	12h 28m including layover	Find flight from$220
05:05 — 23:59	05:05 — 09:40 AS593 Alaska Airlines Anchorage — Portland 3h 45m stop 13:25 — 14:24 AS165 Alaska Airlines Portland — Seattle 3h 26m stop 17:50 — 23:59 AS538 Alaska Airlines Seattle — Chicago	15h 54m including layover	Find flight from$217
11:00 — 23:59	11:00 — 15:28 AS130 Alaska Airlines Anchorage — Seattle 2h 26m stop 17:54 — 23:59 AS538 Alaska Airlines Seattle — Chicago	9h 59m including layover	Find flight from$213
13:25 — 11:32 +1 day	13:30 — 21:56 SY472 Sun Country Airlines Anchorage — Minneapolis 11h 58m stop 10:50 — 12:28 SY1629 Sun Country Airlines Minneapolis — Chicago	19h 7m including layover	Find flight from$233
20:49 — 05:58 +1 day	20:49 — 05:58 UA1127 United Airlines Anchorage — Chicago	6h 9m	Find flight from$248
20:55 — 12:28 +1 day	20:55 — 05:22 SY474 Sun Country Airlines Anchorage — Minneapolis 5h 28m stop 10:50 — 12:28 SY1629 Sun Country Airlines Minneapolis — Chicago	12h 33m including layover	Find flight from$225
20:55 — 15:45 +1 day	20:55 — 05:22 SY474 Sun Country Airlines Anchorage — Minneapolis 8h 44m stop 15:36 — 17:15 SY259 Sun Country Airlines Minneapolis — Chicago	15h 50m including layover	Find flight from$225
20:55 — 17:15 +1 day	20:55 — 05:22 SY474 Sun Country Airlines Anchorage — Minneapolis 10h 14m stop 15:36 — 17:15 SY261 Sun Country Airlines Minneapolis — Chicago	17h 20m including layover	Find flight from$233
20:57 — 06:09 +1 day	20:57 — 06:09 UA2740 United Airlines Anchorage — Chicago	6h 12m	Find flight from$243
23:25 — 08:40 +1 day	23:25 — 08:40 HA4726 Hawaiian Airlines Anchorage — Chicago	6h 15m	Find flight from$201
23:25 — 08:40 +1 day	23:25 — 08:40 AS138 Alaska Airlines Anchorage — Chicago	6h 15m	Find flight from$205
23:26 — 08:40 +1 day	23:26 — 08:40 HA4725 Hawaiian Airlines Anchorage — Chicago	6h 14m	Find flight from$238
23:26 — 08:40 +1 day	23:26 — 08:40 AS109 Alaska Airlines Anchorage — Chicago	6h 14m	Find flight from$241
23:59 — 09:08 +1 day	23:59 — 09:08 UA2632 United Airlines Anchorage — Chicago	6h 9m	Find flight from$246

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times - local. Updated on September 18, 2025

Flight Information

Below we will explain in detail what the flights cost on the destination from Anchorage to Chicago depends on and how to choose the most interesting flight option for you.

Distance between Anchorage and Chicago is 4591 miles. Time difference between the cities is 3h. Airplanes depart 00:29 to 23:59 from 4 Anchorage airports and arrive 00:29 to 23:59 to 7 Chicago airports. Average flight time is 6h 14m.

The fastest flight 6h 9m
Average flight time 6h 14m
The earliest flight 00:29
The latest flight 23:59
Distance 2853 ml

The cheapest months to travel to Chicago are august (from 201 $), october (from 217 $), july (from 225 $).

The most expensive months are december (from 292 $), september (from 243 $), july (from 225 $).

What is the lowest airfare Anchorage to Chicago?

The cheapest plane ticket found by our users is $201. This airfare is for economy class on one-way HA4726 flight by Hawaiian Airlines for August 28, 2025 which leaves Ted Stevens Anchorage in Anchorage at 23:25 am and arrives at Chicago O'Hare International at 08:40.

Economy class

$201

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Business class

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First class

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Popular Airlines on the Route

The flight Anchorage — Chicago is served by 4 regular airlines and 1 low-cost airline. Most of the flights on this route are operated by Alaska Airlines - 120 departures per week at the price of from $ 205 . And the most expensive tickets are offered by Alaska Airlines airline - from $ 7111.

Direct flights

There are 7 nonstop flights on the route. The fastest direct flight is UA2632 by United Airlines takes 6h 9m and the cheapest is HA4726 by Hawaiian Airlines for $201.

AS - Alaska Airlines

from $205

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HA - Hawaiian Airlines

from $201

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UA - United Airlines

from $243

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Connecting Flights

There are 268 flights with layovers on the route. The fastest connecting flight is AS59 by Alaska Airlines takes 8h 3m and the cheapest is HA4726 by Hawaiian Airlines for $213.

AS - Alaska Airlines

from $213

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SY - Sun Country Airlines

from $225

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HA - Hawaiian Airlines

from $235

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UA - United Airlines

from $248

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Airports

You can fly from Anchorage to Chicago from 4 airports (Bryant AAF, Merrill Field, Ted Stevens Anchorage, Elmendorf AFB).

Anchorage airports

Bryant AAF-FRN

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Merrill Field-MRI

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Ted Stevens Anchorage-ANC

from $201
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Elmendorf AFB-EDF

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Chicago airports

O'Hare International-ORD

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Midway-MDW

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Dupage County-DPA

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Chicago FSS-CHI

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Merrill C Meigs (closed)-CGX

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Pal-Waukee-PWK

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Chicago NAS-NOH

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Airplanes

There are flights to Chicago from Anchorage by 4 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.

Top Domestic Destinations from Anchorage

You may also consider searching for discounted plane tickets to some other popular places from Anchorage within United States.

Anchorage — Seattle

from $209

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Anchorage — Denver

from $66

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Anchorage — Las Vegas

from $80

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Anchorage — Chicago

from $56

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Anchorage — Honolulu

from $60

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Anchorage — Phoenix

from $74

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Anchorage — Boston

from $58

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Anchorage — Orlando

from $62

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Anchorage — Los Angeles

from $60

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Anchorage — Salt Lake City

from $66

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Top International Destinations from Anchorage

Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.

Anchorage — Vancouver

from $58

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How to book a plane ticket yourself?

Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.
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