Cheap Flights from Anchorage to Chicago
Browse current best options from Anchorage. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Anchorage
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Prices updated 5 days ago
402 airlines compared
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Fares are subject to change and may not be available for all dates. (Data last updated Jul 12, 2026.)
Today’s best flight deals from Anchorage to Chicago
Explore current cheapest deals departing from Anchorage to Chicago
Round trip
Sort by: Cheapest
July 15 - July 21
ANC - Chicago
$523
$333
Round trip
July 14 - July 20
ANC - Chicago
$522
$333
Round trip
July 15 - July 23
ANC - Chicago
$500
$333
Round trip
July 14 - July 23
ANC - Chicago
$495
$333
Round trip
July 15 - July 20
ANC - Chicago
$559
$333
Round trip
July 14 - July 16
ANC - Chicago
$631
$333
Round trip
July 21 - July 23
ANC - Chicago
$526
$333
Round trip
July 14 - July 21
ANC - Chicago
$523
$333
Round trip
July 22 - August 12
ANC - Chicago
$415
$349
Round trip
July 21 - August 12
ANC - Chicago
$421
$349
Round trip
Unlock all 500+ flight deals to Chicago and get alerts when great deals appear
Anchorage to Chicago: Overview
Insights for flights from Anchorage to Chicago
How much is a round trip from Anchorage to Chicago
Regular price: $346 - $575
Prices for flights from Anchorage to Chicago are currently within the regular range.
The regular price range for flights from Anchorage to Chicago is $346 to $575. The current lowest deal is $353 with Alaska Airlines, Inc. for travel from Aug 20-Aug 24.
now $353
Low $346
High $575
The cheapest time to fly from Anchorage to Chicago
The cheapest month to fly from Anchorage to Chicago is November, with a median price of $290. The most expensive month is April, with a median price of $868. Generally, prices are lower from March to November.
November
Flights from $290
April
Flights from $868
Direct flights from Anchorage to Chicago
Alaska Airlines, Inc.
Last-minute flights going from Anchorage to Chicago
Mon, Jul 13
ANC - Chicago
Anchorage (ANC) - Chicago (ORD)
Alaska Airlines, Inc.
$457
$367
One-way
Mon, Jul 13
ANC - Chicago
Anchorage (ANC) - Chicago (ORD)
Alaska Airlines, Inc.
$495
$370
One-way
Mon, Jul 13
ANC - Chicago
Anchorage (ANC) - Chicago (ORD)
Alaska Airlines, Inc.
$631
$370
One-way
Mon, Jul 13
ANC - Chicago
Anchorage (ANC) - Chicago (ORD)
Alaska Airlines, Inc.
$523
$370
One-way
Mon, Jul 13
ANC - Chicago
Anchorage (ANC) - Chicago (ORD)
Alaska Airlines, Inc.
$499
$370
One-way
Mon, Jul 13
ANC - Chicago
Anchorage (ANC) - Chicago (ORD)
Alaska Airlines, Inc.
$624
$370
One-way
Biggest price drops on these dates for flights from Anchorage to Chicago
Jul 5 - Jul 6
$633 → $391
38%
Sep 25 - Sep 27
$564 → $413
27%
Nov 13 - Nov 16
$538 → $413
23%
Sep 2 - Sep 9
$531 → $412
22%
Popular Airports to fly from Anchorage to Chicago
Anchorage - Chicago route insights
💸 Price insights
Recent fares are below the typical level
Recent fares from Anchorage to Chicago are below the typical level, with 31% good prices.
📅 Best time to fly
Fly in November for prices as low as $290
Historically, November is the cheapest month to fly, with median prices around $290.
⏱️ Flight duration
Direct flights take 6h 18m
The typical direct flight from Anchorage to Chicago takes 6h 18m, connecting flights average 9h 28m.
✈️ Airlines & availability
Alaska Airlines, Inc. offers direct flights
Alaska Airlines, Inc. offers direct flights on this route, with 37.5% of recent flights being direct.
🏆 Airline highlight
Alaska Airlines, Inc. has a $353 deal
Alaska Airlines, Inc. recently offered a deal for $353 from Anchorage to Chicago.
🎯 Booking tip
Deals are frequent on this route
Deals from Anchorage to Chicago are frequent, appearing often over the last 30 days.
Anchorage main airports to depart from
Ted Stevens Anchorage International (ANC)
Ted Stevens Anchorage International is a convenient departure airport for flights from Anchorage to Chicago.
📍 ~7 km from Anchorage city center (reachable by car)
💸 Flights from ~$353
Chicago main airports to arrive at
O Hare International (ORD)
O'Hare International Airport is a major hub, offering many flight options for travelers to Chicago.
📍 ~25 km from Chicago city center (reachable by car)
💸 Flights from ~$353
Chicago Midway International (MDW)
Chicago Midway International Airport is a convenient option for reaching the city of Chicago.
📍 ~14 km from Chicago city center (reachable by car)
💸 Flights from ~$411
Chicago Rockford International (RFD)
Chicago Rockford International Airport serves as an alternative arrival point for the Chicago area.
📍 ~126 km from Chicago city center (reachable by car)
💸 Flights from ~$767
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
General Mitchell International is a major international airport with significant carrier presence and direct flight options.
📍 ~135 km from Chicago (reachable by train or car)
💸 Flights from ~$347
Gerald R. Ford International (GRR)
Gerald R. Ford International is the second largest airport in Michigan with a robust domestic network.
📍 ~230 km from Chicago (reachable by car)
💸 Flights from ~$267
Dane County Regional (MSN)
Dane County Regional is a reliable regional hub with efficient operations and good amenities for travelers.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$598
South Bend International (SBN)
South Bend International is geographically the closest alternative airport to the Chicago metro area.
📍 ~120 km from Chicago (reachable by train or car)
💸 Flights from ~$597
Fort Wayne International (FWA)
Fort Wayne International offers multiple cabin classes and solid connectivity for travelers heading to eastern domestic destinations.
📍 ~240 km from Chicago (reachable by car)
💸 Flights from ~$669
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from Anchorage to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From ANC
Elite
Aug 12
Chicago, United States
94% AI deal score
$2,554
$1,269
Save $1,285
From ANC
Elite
Jun 19
Chicago, United States
94% AI deal score
$2,745
$1,320
Save $1,425
From ANC
Elite
Aug 12
Chicago, United States
94% AI deal score
$2,639
$1,329
Save $1,310
From ANC
Elite
Aug 12
Chicago, United States
93% AI deal score
$2,344
$1,269
Save $1,075
From ANC
Elite
Aug 12
Chicago, United States
93% AI deal score
$2,222
$1,269
Save $953
From ANC
Elite
Aug 31
Chicago, United States
93% AI deal score
$2,331
$1,311
Save $1,020
From ANC
Elite
Jul 15
Chicago, United States
93% AI deal score
$2,356
$1,324
Save $1,032
From ANC
Elite
Jul 13
Chicago, United States
93% AI deal score
$2,374
$1,366
Save $1,008
From ANC
Elite
Jul 13
Chicago, United States
93% AI deal score
$2,374
$1,366
Save $1,008
From ANC
Elite
Aug 12
Chicago, United States
93% AI deal score
$2,475
$1,389
Save $1,086
From ANC
Elite
Aug 14
Chicago, United States
93% AI deal score
$2,473
$1,389
Save $1,084
From ANC
Elite
Aug 10
Chicago, United States
93% AI deal score
$2,543
$1,389
Save $1,154
From ANC
Elite
Aug 11
Chicago, United States
93% AI deal score
$3,132
$1,269
Save $1,863
From ANC
Elite
Sep 01
Chicago, United States
93% AI deal score
$3,257
$1,269
Save $1,988
From ANC
Elite
Jun 24
Chicago, United States
93% AI deal score
$1,699
$1,055
Save $644
From ANC
Elite
Jun 19
Chicago, United States
93% AI deal score
$1,970
$1,141
Save $829
From ANC
Elite
Jun 21
Chicago, United States
93% AI deal score
$1,848
$1,141
Save $707
From ANC
Elite
Jun 17
Chicago, United States
93% AI deal score
$1,970
$1,162
Save $808
From ANC
Elite
Jun 18
Chicago, United States
93% AI deal score
$1,948
$1,198
Save $750
From ANC
Elite
Jul 17
Chicago, United States
92% AI deal score
$2,923
$1,217
Save $1,706
From ANC
Elite
Aug 17
Chicago, United States
92% AI deal score
$2,213
$1,311
Save $902
From ANC
Elite
Jul 13
Chicago, United States
92% AI deal score
$2,387
$1,366
Save $1,021
From ANC
Elite
Jul 15
Chicago, United States
92% AI deal score
$2,370
$1,366
Save $1,004
From ANC
Elite
Jul 15
Chicago, United States
92% AI deal score
$2,391
$1,366
Save $1,025
From ANC
Elite
Jul 15
Chicago, United States
92% AI deal score
$2,370
$1,366
Save $1,004
From ANC
Elite
Jul 13
Chicago, United States
92% AI deal score
$2,374
$1,379
Save $995
From ANC
Elite
Jul 13
Chicago, United States
92% AI deal score
$2,374
$1,379
Save $995
From ANC
Elite
Jul 15
Chicago, United States
92% AI deal score
$2,356
$1,379
Save $977
From ANC
Elite
Jul 15
Chicago, United States
92% AI deal score
$2,370
$1,379
Save $991
From ANC
Elite
Aug 10
Chicago, United States
92% AI deal score
$2,383
$1,389
Save $994
From ANC
Elite
Jul 20
Chicago, United States
92% AI deal score
$2,356
$1,389
Save $967
From ANC
Elite
Jul 20
Chicago, United States
92% AI deal score
$2,356
$1,389
Save $967
From ANC
Elite
Jul 29
Chicago, United States
92% AI deal score
$2,366
$1,389
Save $977
From ANC
Elite
Jul 16
Chicago, United States
92% AI deal score
$2,344
$1,389
Save $955
From ANC
Elite
Aug 26
Chicago, United States
92% AI deal score
$2,280
$1,389
Save $891
From ANC
Elite
Jul 17
Chicago, United States
92% AI deal score
$2,356
$1,389
Save $967
From ANC
Elite
Aug 10
Chicago, United States
92% AI deal score
$2,304
$1,389
Save $915
From ANC
Elite
Jul 29
Chicago, United States
92% AI deal score
$2,338
$1,389
Save $949
From ANC
Elite
Aug 11
Chicago, United States
92% AI deal score
$2,887
$1,269
Save $1,618
From ANC
Elite
Jul 07
Chicago, United States
92% AI deal score
$2,726
$1,269
Save $1,457
From ANC
Elite
Aug 11
Chicago, United States
92% AI deal score
$2,760
$1,269
Save $1,491
From ANC
Elite
Aug 12
Chicago, United States
92% AI deal score
$2,757
$1,269
Save $1,488
From ANC
Elite
Jul 07
Chicago, United States
92% AI deal score
$2,731
$1,311
Save $1,420
From ANC
Elite
Jul 07
Chicago, United States
92% AI deal score
$2,726
$1,311
Save $1,415
From ANC
Elite
Aug 31
Chicago, United States
92% AI deal score
$3,098
$1,311
Save $1,787
From ANC
Elite
Jul 13
Chicago, United States
92% AI deal score
$2,692
$1,313
Save $1,379
From ANC
Elite
Jul 13
Chicago, United States
92% AI deal score
$2,692
$1,313
Save $1,379
From ANC
Elite
Jul 08
Chicago, United States
92% AI deal score
$2,726
$1,324
Save $1,402
From ANC
Elite
Jul 07
Chicago, United States
92% AI deal score
$2,726
$1,324
Save $1,402
From ANC
Elite
Jul 01
Chicago, United States
92% AI deal score
$1,639
$1,098
Save $541
From ANC
Elite
Jun 18
Chicago, United States
92% AI deal score
$1,970
$1,262
Save $708
From ANC
Elite
Aug 04
Chicago, United States
91% AI deal score
$2,604
$1,187
Save $1,417
From ANC
Elite
Aug 17
Chicago, United States
91% AI deal score
$2,791
$1,307
Save $1,484
From ANC
Elite
Jul 15
Chicago, United States
91% AI deal score
$2,692
$1,324
Save $1,368
From ANC
Elite
Jul 15
Chicago, United States
91% AI deal score
$2,697
$1,324
Save $1,373
From ANC
Elite
Jul 13
Chicago, United States
91% AI deal score
$2,692
$1,343
Save $1,349
From ANC
Elite
Jul 08
Chicago, United States
91% AI deal score
$2,726
$1,354
Save $1,372
From ANC
Elite
Jul 15
Chicago, United States
91% AI deal score
$2,692
$1,354
Save $1,338
From ANC
Elite
Jul 13
Chicago, United States
91% AI deal score
$2,697
$1,355
Save $1,342
From ANC
Elite
Jul 13
Chicago, United States
91% AI deal score
$2,721
$1,355
Save $1,366
From ANC
Elite
Jul 08
Chicago, United States
91% AI deal score
$2,718
$1,366
Save $1,352
From ANC
Elite
Jul 08
Chicago, United States
91% AI deal score
$2,726
$1,366
Save $1,360
From ANC
Elite
Jul 13
Chicago, United States
91% AI deal score
$2,685
$1,368
Save $1,317
From ANC
Elite
Nov 11
Chicago, United States
91% AI deal score
$1,494
$999
Save $495
From ANC
Elite
Jun 24
Chicago, United States
91% AI deal score
$1,726
$1,198
Save $528
From ANC
Elite
Jul 17
Chicago, United States
90% AI deal score
$2,606
$1,462
Save $1,144
From ANC
Elite
Jun 17
Chicago, United States
90% AI deal score
$2,612
$1,717
Save $895
From ANC
Elite
Jun 22
Chicago, United States
90% AI deal score
$2,745
$1,717
Save $1,028
From ANC
Elite
Oct 22
Chicago, United States
90% AI deal score
$1,632
$1,112
Save $520
From ANC
Elite
Jul 26
Chicago, United States
90% AI deal score
$1,541
$1,137
Save $404
From ANC
Elite
Jul 15
Chicago, United States
90% AI deal score
$1,525
$1,137
Save $388
From ANC
Elite
Sep 06
Chicago, United States
89% AI deal score
$2,438
$1,568
Save $870
From ANC
Elite
Aug 10
Chicago, United States
89% AI deal score
$1,682
$1,214
Save $468
From ANC
Elite
Jul 02
Chicago, United States
89% AI deal score
$1,593
$1,243
Save $350
From ANC
Elite
Jun 30
Chicago, United States
88% AI deal score
$2,121
$1,595
Save $526
From ANC
Elite
Jul 17
Chicago, United States
88% AI deal score
$2,070
$1,449
Save $621
From ANC
Elite
Aug 27
Chicago, United States
88% AI deal score
$2,586
$1,675
Save $911
From ANC
Elite
Jul 27
Chicago, United States
88% AI deal score
$1,518
$1,219
Save $299
From ANC
Elite
Jul 21
Chicago, United States
88% AI deal score
$1,539
$1,225
Save $314
From ANC
Elite
Jul 20
Chicago, United States
88% AI deal score
$1,525
$1,233
Save $292
From ANC
Elite
Jul 17
Chicago, United States
88% AI deal score
$1,558
$1,257
Save $301
From ANC
Elite
Jul 17
Chicago, United States
88% AI deal score
$1,558
$1,257
Save $301
From ANC
Elite
Jul 20
Chicago, United States
87% AI deal score
$2,786
$1,669
Save $1,117
From ANC
Elite
Jul 26
Chicago, United States
87% AI deal score
$1,518
$1,274
Save $244
From ANC
Elite
Jul 01
Chicago, United States
87% AI deal score
$1,615
$1,382
Save $233
From ANC
Elite
Jul 05
Chicago, United States
86% AI deal score
$2,578
$1,838
Save $740
From ANC
Elite
Jul 30
Chicago, United States
83% AI deal score
$2,208
$1,838
Save $370
From ANC
Elite
Aug 10
Chicago, United States
82% AI deal score
$1,695
$1,327
Save $368
From ANC
Elite
Jul 17
Chicago, United States
79% AI deal score
$1,548
$1,409
Save $139
From ANC
Elite
Jul 17
Chicago, United States
77% AI deal score
$1,515
$1,460
Save $55
From ANC
Elite
Aug 09
Chicago, United States
76% AI deal score
$2,289
$1,989
Save $300
From ANC
Elite
Jul 20
Chicago, United States
75% AI deal score
$2,484
$2,223
Save $261
From ANC
Elite
Jul 18
Chicago, United States
75% AI deal score
$1,519
From ANC
Elite
Aug 07
Chicago, United States
72% AI deal score
$2,262
$2,228
Save $34
From ANC
Elite
Jul 30
Chicago, United States
67% AI deal score
$2,645
From ANC
Elite
Jul 29
Chicago, United States
66% AI deal score
$2,845