Cheap Flights from Chicago to Honolulu
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Deals from
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RatePunk searches hundreds of travel sites at once for deals on flights to Honolulu
Prices updated 24 days ago
486,190 searches this week
171 airlines compared
80%+ AI score for best value
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 Chicago to Honolulu
Explore current cheapest deals departing from Chicago to Honolulu
Round trip
Sort by: Cheapest
August 18 - August 26
MDW - Honolulu
$620
$554
Round trip
August 24 - August 28
MDW - Honolulu
$651
$554
Round trip
August 31 - September 9
MDW - Honolulu
$616
$554
Round trip
September 9 - September 16
MDW - Honolulu
$568
$554
Round trip
September 28 - September 29
MDW - Honolulu
$612
$554
Round trip
October 5 - October 13
MDW - Honolulu
$591
$554
Round trip
October 18 - October 22
MDW - Honolulu
$623
$554
Round trip
October 27 - October 28
MDW - Honolulu
$634
$554
Round trip
November 1 - November 6
MDW - Honolulu
$601
$554
Round trip
November 3 - November 10
MDW - Honolulu
$594
$554
Round trip
Unlock all 500+ flight deals to Honolulu and get alerts when great deals appear
Route Intelligence — 486,190 Searches this Week
Insights for flights from Chicago to Honolulu
How much is a round trip from Chicago to Honolulu
Regular price: $459 - $893
Prices are currently within the regular range.
The regular price range for flights from Chicago to Honolulu is $459 to $893. The current lowest deal is $467 with Alaska Airlines, Inc. for travel from Nov 4-Nov 9.
now $467
Low $459
High $893
The cheapest time to fly from Chicago to Honolulu
The cheapest month to fly from Chicago to Honolulu is March, with a median price of $583. The most expensive month is June, with a median price of $1196. Prices are generally lower from February to November.
March
Flights from $583
June
Flights from $1,196
Direct flights from Chicago to Honolulu
American Airlines
Last-minute flights going from Chicago to Honolulu
Thu, Jun 18
MDW - Honolulu
Chicago (MDW) - Honolulu (HNL)
$734
$710
One-way
Thu, Jun 18
MDW - Honolulu
Chicago (MDW) - Honolulu (HNL)
$849
$779
One-way
Thu, Jun 18
MDW - Honolulu
Chicago (MDW) - Honolulu (HNL)
$840
$807
One-way
Fri, Jun 19
MDW - Honolulu
Chicago (MDW) - Honolulu (HNL)
$837
$763
One-way
Fri, Jun 19
MDW - Honolulu
Chicago (MDW) - Honolulu (HNL)
$846
$826
One-way
Sat, Jun 20
MDW - Honolulu
Chicago (MDW) - Honolulu (HNL)
$846
$763
One-way
Biggest price drops on these dates for flights from Chicago to Honolulu
Jul 23 - Jul 30
$744 → $630
15%
Jul 27 - Aug 3
$741 → $630
15%
Aug 24 - Aug 28
$651 → $554
15%
Jun 20 - Jun 22
$846 → $763
10%
Popular Airports to fly from Chicago to Honolulu
Chicago - Honolulu route insights
💸 Price insights
Recent fares are near the typical level
Recent fares for Chicago to Honolulu are near the typical level, with a median price of $779.
📅 Best time to fly
March is historically the cheapest month to fly
Historically, March is the cheapest month to fly from Chicago to Honolulu, with a median price of $583.
⏱️ Flight duration
Flights typically take 26h 46m
Flights from Chicago to Honolulu typically take 26 hours and 46 minutes, including layovers.
✈️ Airlines & availability
Connecting flights are dominant on this route
Only 5.2% of recent deals are direct, making connecting flights dominant for this route.
🏆 Airline highlight
American Airlines offers direct flights
American Airlines is one of the airlines that has offered direct flights on the Chicago to Honolulu route.
🎯 Booking tip
Deals appear frequently for this route
Deals for flights from Chicago to Honolulu appear frequently, with over one deal per day.
Chicago main airports to depart from
O Hare International (ORD)
O'Hare International Airport offers flights to Honolulu, with prices starting from $467.
📍 ~25 km from Chicago city center (reachable by car or train).
💸 Flights from ~$467
Chicago Midway International (MDW)
Chicago Midway International Airport is an alternative for flights to Honolulu, with prices from $519.
📍 ~14 km from Chicago city center (reachable by car or train).
💸 Flights from ~$519
Chicago Rockford International (RFD)
Chicago Rockford International Airport is another option for flights to Honolulu, with prices from $802.
📍 ~120 km from Chicago city center (reachable by car).
💸 Flights from ~$802
Honolulu main airports to arrive at
Daniel K. Inouye International (HNL)
Daniel K. Inouye International Airport is a key arrival point for flights from Chicago to Honolulu.
📍 ~10 km from Honolulu (reachable by car)
💸 Flights from ~$467
Airports nearby Honolulu used as alternative
Kahului (OGG)
Kahului Airport is a useful alternative for its extensive transpacific and domestic flight options, offering a full range of cabin classes.
📍 ~170 km from Honolulu (reachable by inter-island flight or ferry)
💸 Flights from ~$513
Lihue (LIH)
Lihue Airport is a major gateway for Kauai with direct connections to several US West Coast hubs and reliable commercial service.
📍 ~170 km from Honolulu (requires inter-island transit)
💸 Flights from ~$424
Kona International (KOA)
Kona International Airport is the primary international gateway for the Big Island, with a strong selection of direct flights.
📍 ~200 km from Honolulu (requires additional flight time)
💸 Flights from ~$463
Hilo International (ITO)
Hilo International Airport is a secondary major airport on the Big Island, offering a less crowded alternative to Kona.
📍 ~290 km from Honolulu (requires inter-island flight)
💸 Flights from ~$527
Molokai (MKK)
Molokai Airport is geographically the closest candidate airport to Honolulu, useful for specific regional connections within the islands.
📍 ~70 km from Honolulu (reachable by inter-island flight)
💸 Flights from ~$928
Business & First Class Flight Deals to Honolulu
Discover luxury on the budget with premium cabin class on flights from Chicago to Honolulu.
Elite
Best Elite deals to Honolulu
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From ORD
Elite
Nov 26
Honolulu, United States
92% AI deal score
$2,861
$1,950
Save $911
From ORD
Elite
Nov 26
Honolulu, United States
92% AI deal score
$2,866
$1,950
Save $916
From ORD
Elite
Jun 29
Honolulu, United States
92% AI deal score
$2,985
$2,010
Save $975
From ORD
Elite
Nov 26
Honolulu, United States
91% AI deal score
$2,596
$1,950
Save $646
From ORD
Elite
Nov 26
Honolulu, United States
91% AI deal score
$2,812
$1,950
Save $862
From ORD
Elite
Nov 16
Honolulu, United States
91% AI deal score
$2,568
$1,950
Save $618
From ORD
Elite
Nov 03
Honolulu, United States
91% AI deal score
$2,570
$1,950
Save $620
From ORD
Elite
Nov 16
Honolulu, United States
91% AI deal score
$2,604
$1,950
Save $654
From ORD
Elite
Nov 16
Honolulu, United States
91% AI deal score
$2,597
$1,950
Save $647
From ORD
Elite
Nov 26
Honolulu, United States
91% AI deal score
$2,596
$1,950
Save $646
From ORD
Elite
Nov 26
Honolulu, United States
91% AI deal score
$2,721
$1,950
Save $771
From ORD
Elite
Nov 16
Honolulu, United States
91% AI deal score
$2,636
$1,950
Save $686
From ORD
Elite
Nov 03
Honolulu, United States
91% AI deal score
$2,570
$1,950
Save $620
From ORD
Elite
Nov 03
Honolulu, United States
91% AI deal score
$2,836
$1,950
Save $886
From ORD
Elite
Nov 17
Honolulu, United States
91% AI deal score
$2,667
$1,950
Save $717
From MDW
Elite
Nov 01
Honolulu, United States
91% AI deal score
$3,675
$1,968
Save $1,707
From ORD
Elite
Nov 16
Honolulu, United States
90% AI deal score
$2,500
$1,950
Save $550
From ORD
Elite
Nov 16
Honolulu, United States
90% AI deal score
$2,500
$1,950
Save $550
From ORD
Elite
Nov 03
Honolulu, United States
90% AI deal score
$2,526
$1,950
Save $576
From ORD
Elite
Nov 16
Honolulu, United States
90% AI deal score
$2,698
$1,950
Save $748
From ORD
Elite
Nov 03
Honolulu, United States
90% AI deal score
$2,702
$1,950
Save $752
From ORD
Elite
Nov 16
Honolulu, United States
90% AI deal score
$2,728
$1,950
Save $778
From ORD
Elite
Oct 28
Honolulu, United States
90% AI deal score
$2,561
$1,950
Save $611
From ORD
Elite
Nov 16
Honolulu, United States
90% AI deal score
$2,535
$1,950
Save $585
From ORD
Elite
Nov 16
Honolulu, United States
90% AI deal score
$2,500
$1,950
Save $550
From ORD
Elite
Oct 21
Honolulu, United States
90% AI deal score
$2,566
$1,950
Save $616
From MDW
Elite
Nov 01
Honolulu, United States
90% AI deal score
$3,362
$1,998
Save $1,364
From ORD
Elite
Jul 09
Honolulu, United States
90% AI deal score
$2,588
$2,009
Save $579
From ORD
Elite
Jul 08
Honolulu, United States
90% AI deal score
$2,588
$2,010
Save $578
From ORD
Elite
Nov 03
Honolulu, United States
89% AI deal score
$2,498
$1,950
Save $548
From ORD
Elite
Nov 03
Honolulu, United States
89% AI deal score
$2,501
$1,950
Save $551
From ORD
Elite
Oct 28
Honolulu, United States
89% AI deal score
$2,485
$1,950
Save $535
From ORD
Elite
Oct 28
Honolulu, United States
89% AI deal score
$2,485
$1,950
Save $535
From ORD
Elite
Oct 28
Honolulu, United States
89% AI deal score
$2,492
$1,950
Save $542
From ORD
Elite
Nov 03
Honolulu, United States
89% AI deal score
$2,474
$1,950
Save $524
From ORD
Elite
Oct 28
Honolulu, United States
89% AI deal score
$2,485
$1,950
Save $535
From ORD
Elite
Jul 14
Honolulu, United States
89% AI deal score
$2,293
$1,957
Save $336
From ORD
Elite
Jul 09
Honolulu, United States
89% AI deal score
$2,378
$1,958
Save $420
From ORD
Elite
Jul 16
Honolulu, United States
89% AI deal score
$2,293
$1,958
Save $335
From ORD
Elite
Aug 04
Honolulu, United States
89% AI deal score
$2,543
$1,973
Save $570
From MDW
Elite
Oct 29
Honolulu, United States
89% AI deal score
$3,502
$2,158
Save $1,344
From ORD
Elite
Jun 27
Honolulu, United States
89% AI deal score
$3,056
$2,605
Save $451
From ORD
Elite
Jul 14
Honolulu, United States
88% AI deal score
$2,212
$1,958
Save $254
From MDW
Elite
Oct 02
Honolulu, United States
88% AI deal score
$2,862
$2,003
Save $859
From ORD
Elite
Oct 16
Honolulu, United States
88% AI deal score
$2,732
$2,222
Save $510
From ORD
Elite
Oct 25
Honolulu, United States
88% AI deal score
$2,739
$2,275
Save $464
From ORD
Elite
Jul 21
Honolulu, United States
88% AI deal score
$2,699
$2,295
Save $404
From ORD
Elite
Jul 09
Honolulu, United States
88% AI deal score
$2,688
$2,300
Save $388
From MDW
Elite
Nov 01
Honolulu, United States
87% AI deal score
$3,357
$2,330
Save $1,027
From MDW
Elite
Sep 07
Honolulu, United States
86% AI deal score
$2,943
$2,123
Save $820
From MDW
Elite
Nov 08
Honolulu, United States
86% AI deal score
$3,675
$2,548
Save $1,127
From MDW
Elite
Nov 07
Honolulu, United States
84% AI deal score
$3,357
$2,544
Save $813
From MDW
Elite
Nov 11
Honolulu, United States
84% AI deal score
$3,360
$2,544
Save $816
From ORD
Elite
Aug 04
Honolulu, United States
83% AI deal score
$2,179
$1,911
Save $268
From ORD
Elite
Jun 19
Honolulu, United States
83% AI deal score
$3,427
$3,110
Save $317
From ORD
Elite
Jul 02
Honolulu, United States
82% AI deal score
$2,831
$2,595
Save $236
From ORD
Elite
Jun 29
Honolulu, United States
81% AI deal score
$2,801
$2,605
Save $196
From ORD
Elite
Jun 19
Honolulu, United States
81% AI deal score
$3,469
$3,249
Save $220
From ORD
Elite
Jun 22
Honolulu, United States
80% AI deal score
$3,069
$2,746
Save $323
From ORD
Elite
Oct 26
Honolulu, United States
80% AI deal score
$2,738
$2,489
Save $249
From ORD
Elite
Jul 02
Honolulu, United States
80% AI deal score
$2,758
$2,595
Save $163
From ORD
Elite
Jul 03
Honolulu, United States
80% AI deal score
$2,758
$2,605
Save $153
From ORD
Elite
Jul 31
Honolulu, United States
80% AI deal score
$2,805
$2,605
Save $200
From ORD
Elite
Jun 23
Honolulu, United States
79% AI deal score
$2,996
$2,746
Save $250
From MDW
Elite
Oct 12
Honolulu, United States
79% AI deal score
$3,124
$2,509
Save $615
From ORD
Elite
Sep 30
Honolulu, United States
79% AI deal score
$2,512
$2,275
Save $237
From ORD
Elite
Oct 20
Honolulu, United States
79% AI deal score
$2,731
$2,542
Save $189
From ORD
Elite
Jul 23
Honolulu, United States
79% AI deal score
$2,752
$2,595
Save $157
From ORD
Elite
Jul 08
Honolulu, United States
79% AI deal score
$2,740
$2,595
Save $145
From ORD
Elite
Jul 08
Honolulu, United States
79% AI deal score
$2,783
$2,605
Save $178
From ORD
Elite
Jul 24
Honolulu, United States
79% AI deal score
$2,771
$2,605
Save $166
From ORD
Elite
Jul 14
Honolulu, United States
78% AI deal score
$2,693
$2,593
Save $100
From ORD
Elite
Jul 06
Honolulu, United States
78% AI deal score
$2,702
$2,595
Save $107
From ORD
Elite
Jul 23
Honolulu, United States
78% AI deal score
$2,699
$2,595
Save $104
From ORD
Elite
Jul 22
Honolulu, United States
78% AI deal score
$2,717
$2,595
Save $122
From ORD
Elite
Oct 24
Honolulu, United States
78% AI deal score
$2,739
$2,605
Save $134
From ORD
Elite
Jul 10
Honolulu, United States
78% AI deal score
$2,710
$2,605
Save $105
From ORD
Elite
Oct 23
Honolulu, United States
77% AI deal score
$2,705
$2,605
Save $100
From ORD
Elite
Jul 11
Honolulu, United States
77% AI deal score
$2,694
$2,615
Save $79
From ORD
Elite
Aug 07
Honolulu, United States
76% AI deal score
$2,344
From MDW
Elite
Aug 06
Honolulu, United States
76% AI deal score
$2,901
$2,560
Save $341
From ORD
Elite
Aug 06
Honolulu, United States
76% AI deal score
$2,346
$2,295
Save $51
From ORD
Elite
Sep 28
Honolulu, United States
76% AI deal score
$2,613
$2,595
Save $18
From ORD
Elite
Oct 01
Honolulu, United States
76% AI deal score
$2,770
From ORD
Elite
Oct 01
Honolulu, United States
76% AI deal score
$2,812
$2,780
Save $32
From MDW
Elite
Aug 06
Honolulu, United States
75% AI deal score
$2,651
$2,470
Save $181
From ORD
Elite
Aug 26
Honolulu, United States
75% AI deal score
$2,595
From ORD
Elite
Aug 17
Honolulu, United States
75% AI deal score
$2,595
From ORD
Elite
Aug 13
Honolulu, United States
75% AI deal score
$2,800
From ORD
Elite
Jul 21
Honolulu, United States
75% AI deal score
$2,800
From ORD
Elite
Aug 06
Honolulu, United States
75% AI deal score
$2,800
From ORD
Elite
Dec 07
Honolulu, United States
75% AI deal score
$2,882
From ORD
Elite
Dec 02
Honolulu, United States
75% AI deal score
$2,882
From ORD
Elite
Oct 23
Honolulu, United States
75% AI deal score
$2,892
From ORD
Elite
Jul 07
Honolulu, United States
75% AI deal score
$2,935
From ORD
Elite
Oct 27
Honolulu, United States
75% AI deal score
$3,047
From ORD
Elite
Oct 27
Honolulu, United States
75% AI deal score
$3,047
From ORD
Elite
Oct 06
Honolulu, United States
75% AI deal score
$3,110
From ORD
Elite
Oct 07
Honolulu, United States
75% AI deal score
$3,110
From ORD
Elite
Nov 08
Honolulu, United States
74% AI deal score
$2,759