Cheap Flights from Anchorage, AK to Chicago, IL from $156

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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 $156, 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: $156 (one-way), $268 (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 $156. The fastest direct flight takes 6h 9m and the fastest connecting – 8h 3m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $156 Find flight	23:25 Anchorage Ted Stevens Anchorage	08:40+1 день Chicago O'Hare International	6h 15m	Hawaiian Airlines	HA4726
from $159 Find flight	23:25 Anchorage Ted Stevens Anchorage	08:40+1 день Chicago O'Hare International	6h 15m	Alaska Airlines	AS138
from $186 Find flight	23:26 Anchorage Ted Stevens Anchorage	08:40+1 день Chicago O'Hare International	6h 14m	Hawaiian Airlines	HA4725
from $189 Find flight	20:57 Anchorage Ted Stevens Anchorage	06:09+1 день Chicago O'Hare International	6h 12m	United Airlines	UA2740
from $189 Find flight	23:26 Anchorage Ted Stevens Anchorage	08:40+1 день Chicago O'Hare International	6h 14m	Alaska Airlines	AS109
from $166 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 $175 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 $182 Find flight	13:25 Anchorage Ted Stevens Anchorage	11:32+1 день Chicago O'Hare International	19h 7m layover 11h 58m - Minneapolis	Sun Country Airlines	SY472 SY1629
from $183 Find flight	02:50 Anchorage Ted Stevens Anchorage	14:13 Chicago O'Hare International	8h 23m layover 0h 53m - Seattle	Hawaiian Airlines	HA698 HA6820
from $183 Find flight	00:29 Anchorage Ted Stevens Anchorage	12:07 Chicago O'Hare International	8h 38m layover 1h 0m - Seattle	Hawaiian Airlines	HA4751 HA6816
from $183 Find flight	11:16 Anchorage Ted Stevens Anchorage	23:59 Chicago O'Hare International	9h 43m layover 2h 3m - Seattle	Hawaiian Airlines	HA4744 HA6819
from $183 Find flight	01:29 Anchorage Ted Stevens Anchorage	14:13 Chicago O'Hare International	9h 44m layover 2h 3m - Seattle	Hawaiian Airlines	HA4738 HA6820
from $169 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 $171 Find flight	02:50 Anchorage Ted Stevens Anchorage	18:18 Chicago O'Hare International	12h 28m layover 1h 0m - Seattle 1h 26m - San Francisco	Alaska Airlines	AS8088 AS1166 AS598
from $171 Find flight	01:29 Anchorage Ted Stevens Anchorage	18:18 Chicago O'Hare International	13h 49m layover 2h 5m - Seattle 1h 31m - San Francisco	Alaska Airlines	AS54 AS1166 AS598
from $191 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 June 06, 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
20:49 — 05:58 +1 day	20:49 — 05:58 UA1127 United Airlines Anchorage — Chicago	6h 9m	Find flight from$193
20:57 — 06:09 +1 day	20:57 — 06:09 UA2740 United Airlines Anchorage — Chicago	6h 12m	Find flight from$189
23:25 — 08:40 +1 day	23:25 — 08:40 HA4726 Hawaiian Airlines Anchorage — Chicago	6h 15m	Find flight from$156
23:25 — 08:40 +1 day	23:25 — 08:40 AS138 Alaska Airlines Anchorage — Chicago	6h 15m	Find flight from$159
23:26 — 08:40 +1 day	23:26 — 08:40 HA4725 Hawaiian Airlines Anchorage — Chicago	6h 14m	Find flight from$186
23:26 — 08:40 +1 day	23:26 — 08:40 AS109 Alaska Airlines Anchorage — Chicago	6h 14m	Find flight from$189
23:59 — 09:08 +1 day	23:59 — 09:08 UA2632 United Airlines Anchorage — Chicago	6h 9m	Find flight from$192
00:29 — 12:07	00:29 — 05:00 HA4751 Hawaiian Airlines Anchorage — Seattle 1h stop 06:00 — 12:07 HA6816 Hawaiian Airlines Seattle — Chicago	8h 38m including layover	Find flight from$183
00:29 — 14:13	00:29 — 05:00 HA4751 Hawaiian Airlines Anchorage — Seattle 3h 3m stop 08:03 — 14:13 HA6820 Hawaiian Airlines Seattle — Chicago	10h 44m including layover	Find flight from$183
01:29 — 14:13	01:29 — 06:00 HA4738 Hawaiian Airlines Anchorage — Seattle 2h 3m stop 08:03 — 14:13 HA6820 Hawaiian Airlines Seattle — Chicago	9h 44m including layover	Find flight from$183
02:50 — 14:13	02:50 — 07:10 HA698 Hawaiian Airlines Anchorage — Seattle 53m stop 08:03 — 14:13 HA6820 Hawaiian Airlines Seattle — Chicago	8h 23m including layover	Find flight from$183
04:40 — 22:04	04:40 — 09:09 HA4741 Hawaiian Airlines Anchorage — Seattle 6h 50m stop 15:59 — 22:04 HA6821 Hawaiian Airlines Seattle — Chicago	14h 24m including layover	Find flight from$191
05:00 — 16:59	05:00 — 09:30 HA4754 Hawaiian Airlines Anchorage — Seattle 1h 22m stop 10:52 — 16:59 HA6818 Hawaiian Airlines Seattle — Chicago	8h 59m including layover	Find flight from$184
06:00 — 23:59	06:00 — 10:31 HA4710 Hawaiian Airlines Anchorage — Seattle 7h 19m stop 17:50 — 23:59 HA6819 Hawaiian Airlines Seattle — Chicago	14h 59m including layover	Find flight from$189
06:00 — 19:42	06:00 — 10:31 HA4741 Hawaiian Airlines Anchorage — Seattle 3h 14m stop 13:45 — 19:42 HA6817 Hawaiian Airlines Seattle — Chicago	10h 42m including layover	Find flight from$190
07:15 — 19:42	07:15 — 11:50 HA4736 Hawaiian Airlines Anchorage — Seattle 1h 55m stop 13:45 — 19:42 HA6817 Hawaiian Airlines Seattle — Chicago	9h 27m including layover	Find flight from$190
08:00 — 23:59	04:40 — 09:09 HA4741 Hawaiian Airlines Anchorage — Seattle 5h 22m stop 17:55 — 23:59 HA6819 Hawaiian Airlines Seattle — Chicago	12h 59m including layover	Find flight from$189
08:45 — 22:04	08:45 — 13:17 AS48 Alaska Airlines Anchorage — Seattle 2h 42m stop 15:59 — 22:04 AS941 Alaska Airlines Seattle — Chicago	10h 19m including layover	Find flight from$189
09:00 — 23:59	08:45 — 13:17 HA4737 Hawaiian Airlines Anchorage — Seattle 4h 16m stop 17:55 — 23:59 HA6819 Hawaiian Airlines Seattle — Chicago	11h 59m including layover	Find flight from$189
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$166
11:16 — 23:59	10:35 — 15:04 HA4744 Hawaiian Airlines Anchorage — Seattle 2h 3m stop 17:54 — 23:59 HA6819 Hawaiian Airlines Seattle — Chicago	9h 43m including layover	Find flight from$183
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$182
13:30 — 17:09 +1 day	13:20 — 21:46 SY472 Sun Country Airlines Anchorage — Minneapolis 17h 34m stop 15:36 — 17:15 SY261 Sun Country Airlines Minneapolis — Chicago	24h 39m including layover	Find flight from$193
16:00 — 06:21 +1 day	16:00 — 20:31 HA4702 Hawaiian Airlines Anchorage — Seattle 3h 46m stop 00:17 — 06:21 HA6538 Hawaiian Airlines Seattle — Chicago	11h 21m including layover	Find flight from$183
16:34 — 06:21 +1 day	16:34 — 21:05 HA4749 Hawaiian Airlines Anchorage — Seattle 3h 12m stop 00:17 — 06:21 HA6538 Hawaiian Airlines Seattle — Chicago	10h 47m including layover	Find flight from$183
17:30 — 06:21 +1 day	17:30 — 22:00 HA4750 Hawaiian Airlines Anchorage — Seattle 2h 17m stop 00:17 — 06:21 HA6538 Hawaiian Airlines Seattle — Chicago	9h 51m including layover	Find flight from$183
17:30 — 06:21 +1 day	17:30 — 22:00 AS143 Alaska Airlines Anchorage — Seattle 2h 17m stop 00:17 — 06:21 AS384 Alaska Airlines Seattle — Chicago	9h 51m including layover	Find flight from$189
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$175
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$175
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$171
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$171
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$169
09:10 — 23:59	09:10 — 13:45 AS198 Alaska Airlines Anchorage — Portland 1h 55m stop 15:40 — 16:36 AS2249 Alaska Airlines Portland — Seattle 1h 19m stop 17:55 — 23:59 AS538 Alaska Airlines Seattle — Chicago	11h 49m including layover	Find flight from$193

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

*Departure and arrival times - local. Updated on June 6, 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 209 $), october (from 226 $), july (from 234 $).

The most expensive months are december (from 304 $), september (from 253 $), july (from 234 $).

What is the lowest airfare Anchorage to Chicago?

The cheapest plane ticket found by our users is $156. This airfare is for economy class on one-way HA4726 flight by Hawaiian Airlines for August 27, 2025 which leaves Ted Stevens Anchorage in Anchorage at 23:25 am and arrives at Chicago O'Hare International at 08:40.

Economy class

$156

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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 $ 159 . And the most expensive tickets are offered by Alaska Airlines airline - from $ 5556.

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 $156.

AS - Alaska Airlines

from $159

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HA - Hawaiian Airlines

from $156

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UA - United Airlines

from $189

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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 $166.

AS - Alaska Airlines

from $166

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SY - Sun Country Airlines

from $175

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HA - Hawaiian Airlines

from $183

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UA - United Airlines

from $194

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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 $156
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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?

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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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