Cheap Flights from Anchorage, AK to Chicago, IL from $198

Return flight: Chicago – Anchorage

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 $198, 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: $198 (one-way), $340 (round-trip).
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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 Arrival 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$217
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$217
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$214
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$210
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$230
20:49 — 05:58
+1 day
20:49 — 05:58 UA1127 United Airlines
Anchorage — Chicago
6h 9m
Find flight
from$244
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$221
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$221
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$230
20:57 — 06:09
+1 day
20:57 — 06:09 UA2740 United Airlines
Anchorage — Chicago
6h 12m
Find flight
from$239
23:25 — 08:40
+1 day
23:25 — 08:40 HA4726 Hawaiian Airlines
Anchorage — Chicago
6h 15m
Find flight
from$198
23:25 — 08:40
+1 day
23:25 — 08:40 AS138 Alaska Airlines
Anchorage — Chicago
6h 15m
Find flight
from$202
23:26 — 08:40
+1 day
23:26 — 08:40 HA4725 Hawaiian Airlines
Anchorage — Chicago
6h 14m
Find flight
from$235
23:26 — 08:40
+1 day
23:26 — 08:40 AS109 Alaska Airlines
Anchorage — Chicago
6h 14m
Find flight
from$238
23:59 — 09:08
+1 day
23:59 — 09:08 UA2632 United Airlines
Anchorage — Chicago
6h 9m
Find flight
from$242
*Departure and arrival times - local. Updated on September 15, 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 198 $), october (from 214 $), july (from 221 $).

The most expensive months are december (from 288 $), september (from 239 $), july (from 221 $).

What is the lowest airfare Anchorage to Chicago?

The cheapest plane ticket found by our users is $198. 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
$198
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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 $ 202 . And the most expensive tickets are offered by Alaska Airlines airline - from $ 7001.

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 $198.

  • AS - Alaska Airlines
    from $202
    Find
  • HA - Hawaiian Airlines
    from $198
    Find
  • UA - United Airlines
    from $239
    Find
See more direct flights

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 $210.

  • AS - Alaska Airlines
    from $210
    Find
  • SY - Sun Country Airlines
    from $221
    Find
  • HA - Hawaiian Airlines
    from $231
    Find
  • UA - United Airlines
    from $245
    Find
See more connecting flights

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 $198
    Find
  • Elmendorf AFB-EDF
    Find

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
    Find
  • Chicago NAS-NOH
    Find

How to book a plane ticket yourself?

How to book an air 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.

    To find a plane ticket, please select dates.

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