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 24 days ago
486,190 searches this week
171 airlines compared
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Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)
Today’s best flight deals from Anchorage to Chicago
Explore current cheapest deals departing from Anchorage to Chicago
Round trip
Sort by: Cheapest
June 30 - July 28
ANC - Chicago
$382
$367
Round trip
August 27 - August 31
ANC - Chicago
$411
$373
Round trip
August 26 - August 31
ANC - Chicago
$408
$373
Round trip
September 3 - September 7
ANC - Chicago
$395
$373
Round trip
July 29 - August 5
ANC - Chicago
$412
$373
Round trip
August 10 - August 12
ANC - Chicago
$421
$373
Round trip
August 11 - August 13
ANC - Chicago
$417
$373
Round trip
August 10 - August 18
ANC - Chicago
$381
$373
Round trip
August 10 - August 17
ANC - Chicago
$392
$373
Round trip
July 16 - July 20
ANC - Chicago
$439
$373
Round trip
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Route Intelligence — 486,190 Searches this Week
Insights for flights from Anchorage to Chicago
How much is a round trip from Anchorage to Chicago
Regular price: $340 - $562
Prices are currently within the regular range for flights from Anchorage to Chicago.
The regular price range for flights from Anchorage to Chicago is between $340 and $562. The current lowest deal is $367 with Alaska Airlines, Inc. for travel from Jun 30-Jul 28.
now $367
Low $340
High $562
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 July, with a median price of $685. Prices are generally lower from May to November.
November
Flights from $290
July
Flights from $685
Direct flights from Anchorage to Chicago
Alaska Airlines, Inc.
Last-minute flights going from Anchorage to Chicago
Wed, Jun 17
ANC - Chicago
Anchorage (ANC) - Chicago (MDW)
$727
$469
One-way
Wed, Jun 17
ANC - Chicago
Anchorage (ANC) - Chicago (MDW)
$715
$474
One-way
Thu, Jun 18
ANC - Chicago
Anchorage (ANC) - Chicago (ORD)
United Airlines
$598
$450
One-way
Thu, Jun 18
ANC - Chicago
Anchorage (ANC) - Chicago (ORD)
Deutsche Luft Hansa
$617
$468
One-way
Thu, Jun 18
ANC - Chicago
Anchorage (ANC) - Chicago (ORD)
Alaska Airlines, Inc.
$602
$475
One-way
Fri, Jun 19
ANC - Chicago
Anchorage (ANC) - Chicago (ORD)
$613
$512
One-way
Biggest price drops on these dates for flights from Anchorage to Chicago
Jun 17 - Jun 19
$727 → $469
36%
Jun 17 - Jun 21
$715 → $474
34%
Dec 20 - Dec 28
$564 → $406
28%
Jun 18 - Jun 20
$617 → $468
24%
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 a median price of $482.
📅 Best time to fly
November is historically the cheapest month to fly.
Historically, November is the cheapest month to fly, with a median price of $290.
⏱️ Flight duration
Flights from Anchorage to Chicago take 13h 5m.
The median flight duration from Anchorage to Chicago is 13 hours and 5 minutes.
✈️ Airlines & availability
Connecting flights are dominant on this route.
Connecting flights make up 64.7% of deals, with a median of 2 stopovers.
🏆 Airline highlight
Alaska Airlines, Inc. offers direct flights.
Alaska Airlines, Inc. is one airline offering direct flights from Anchorage to Chicago.
🎯 Booking tip
Deals appear frequently for this route.
Deals for flights from Anchorage to Chicago appear frequently, about once per day.
Anchorage main airports to depart from
Ted Stevens Anchorage International (ANC)
Ted Stevens Anchorage International Airport is a great option for flights from Anchorage to Chicago.
📍 ~10 km from Anchorage (reachable by car)
💸 Flights from ~$367
Chicago main airports to arrive at
O Hare International (ORD)
O'Hare International Airport is a major hub, offering extensive connections for your flight to Chicago.
📍 ~25 km from Chicago city center (reachable by car or public transport).
💸 Flights from ~$367
Chicago Midway International (MDW)
Chicago Midway International Airport provides a convenient arrival option for your trip to Chicago.
📍 ~15 km from Chicago city center (reachable by car or public transport).
💸 Flights from ~$392
Chicago Rockford International (RFD)
Chicago Rockford International Airport offers an alternative arrival point for flights to the Chicago area.
📍 ~120 km from Chicago city center (reachable by car).
💸 Flights from ~$776
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
Consider MKE for excellent proximity to Chicago with high-frequency flight options and direct rail access.
📍 ~135 km from Chicago (reachable by car, train)
💸 Flights from ~$336
South Bend International (SBN)
SBN is geographically the closest alternative to the Chicago area with direct commuter rail connections.
📍 ~120 km from Chicago (reachable by car, train)
💸 Flights from ~$633
Gerald R. Ford International (GRR)
GRR is a major regional hub offering a wide range of cabin classes for travelers on Chicago's eastern side.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$256
Dane County Regional (MSN)
MSN is a reliable regional airport with consistent service levels and less congestion than major Chicago hubs.
📍 ~205 km from Chicago (reachable by car)
💸 Flights from ~$611
Fort Wayne International (FWA)
FWA offers stable regional service and is an alternative for travelers in the southeastern Chicago suburbs.
📍 ~235 km from Chicago (reachable by car)
💸 Flights from ~$794
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