Cheap Flights from Anchorage, AK to Chicago, IL from $198
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
Best Flights from Anchorage to Chicago Today
Price | Departure | Arrival | Flight Duration | Airline | Flight |
---|---|---|---|---|---|
from $198 | 23:25 Anchorage Ted Stevens Anchorage | 08:40+1 день Chicago O'Hare International | 6h 15m | Hawaiian Airlines | HA4726 |
from $202 | 23:25 Anchorage Ted Stevens Anchorage | 08:40+1 день Chicago O'Hare International | 6h 15m | Alaska Airlines | AS138 |
from $235 | 23:26 Anchorage Ted Stevens Anchorage | 08:40+1 день Chicago O'Hare International | 6h 14m | Hawaiian Airlines | HA4725 |
from $210 | 11:00 Anchorage Ted Stevens Anchorage | 23:59 Chicago O'Hare International | 9h 59m layover 2h 26m - Seattle | Alaska Airlines | AS130 AS538 |
from $221 | 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 $214 | 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 $241 | 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 |
Flight Schedule Anchorage (Alaska) to Chicago (Illinois)
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 |
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.
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 Airlinesfrom $202Find
- HA - Hawaiian Airlinesfrom $198Find
- UA - United Airlinesfrom $239Find
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 Airlinesfrom $210Find
- SY - Sun Country Airlinesfrom $221Find
- HA - Hawaiian Airlinesfrom $231Find
- UA - United Airlinesfrom $245Find
Airports
You can fly from Anchorage to Chicago from 4 airports (Bryant AAF, Merrill Field, Ted Stevens Anchorage, Elmendorf AFB).
Anchorage airports
- Bryant AAF-FRNFind
- Merrill Field-MRIFind
- Ted Stevens Anchorage-ANCfrom $198Find
- Elmendorf AFB-EDFFind
Chicago airports
- O'Hare International-ORDFind
- Midway-MDWFind
- Dupage County-DPAFind
- Chicago FSS-CHIFind
- Merrill C Meigs (closed)-CGXFind
- Pal-Waukee-PWKFind
- Chicago NAS-NOHFind
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
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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.
- from $58Find
How to book a plane ticket yourself?

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