Are there direct flights from Chicago to Honolulu?

Direct flights from Chicago to Honolulu are not common, historically accounting for only 1.2% of all flights on this route. When connecting flights are taken, travelers typically experience a median of 2 stopovers. This suggests that most journeys between these two cities will involve at least one layover.

What's the flight time from Chicago to Honolulu?

The typical direct flight time from Chicago to Honolulu is approximately 9 hours and 28 minutes, covering a distance of 6819 kilometers. For flights with one stop, the median travel time increases significantly to about 14 hours and 23 minutes. This difference highlights the convenience of direct routes when available.

Are there frequently good prices on flights from Chicago to Honolulu?

Historically, good prices on flights from Chicago to Honolulu are considered frequent. This route consistently offers opportunities for favorable deals. Travelers can typically find competitive pricing across the trailing quarter for this destination.

Flights From Chicago

To Honolulu

Cheap Flights from Chicago to Honolulu

Browse current best options from Chicago. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Chicago

RatePunk searches hundreds of travel sites at once for deals on flights to Honolulu

Prices updated 7 days ago

483 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Oct 26, 2026.)

Today’s best flight deals from Chicago to Honolulu

Explore current cheapest deals departing from Chicago to Honolulu

2026-12-08 – 2026-12-15
CHI - Honolulu
92% AI deal score
$615
$380
Round trip
2026-12-07 – 2026-12-10
CHI - Honolulu
93% AI deal score
$644
$380
Round trip
2027-02-03 – 2027-02-24
CHI - Honolulu
76% AI deal score
$381
$412
Round trip
2027-02-09 – 2027-02-24
CHI - Honolulu
76% AI deal score
$382
$412
Round trip
2027-02-02 – 2027-02-23
CHI - Honolulu
76% AI deal score
$381
$412
Round trip
2027-02-10 – 2027-02-24
CHI - Honolulu
76% AI deal score
$389
$412
Round trip
2027-02-09 – 2027-03-02
CHI - Honolulu
76% AI deal score
$382
$412
Round trip
2027-02-03 – 2027-02-25
CHI - Honolulu
76% AI deal score
$381
$412
Round trip
2027-02-03 – 2027-02-26
CHI - Honolulu
76% AI deal score
$381
$412
Round trip
2027-02-02 – 2027-02-26
CHI - Honolulu
76% AI deal score
$381
$412
Round trip

Chicago to Honolulu: Overview

Insights for flights from Chicago to Honolulu

Most itineraries for cheap flights from Chicago to Honolulu connect at least once, with only 1.2% of recent fares being non-stop. For connecting itineraries, the typical number of connections is 2.

Right now, fares to Honolulu from Chicago are typically $738–$1492, with a median of $1018. Current fares are below the typical level. There are currently no recent fares classified as a good price.

When is the cheapest time to fly from Chicago to Honolulu? The data indicates that September is the most affordable month, with a median fare of $707. Following closely are June, with a median of $710, and February, with a median of $753.

A typical journey from Chicago to Honolulu takes about 9h 23m, including connections. This is a long-haul route, covering a distance of 6819 km.

How much is a round trip from Chicago to Honolulu

Regular price: $573 - $780

Prices for flights from Chicago to Honolulu are currently within the regular range.

Regular prices for this route typically range from $573 to $780. The current lowest deal is $619 with Alaska Airlines, Inc., for travel from Oct 27-Oct 31.

now $619

Low $573

High $780

The cheapest time to fly from Chicago to Honolulu

The cheapest month to fly from Chicago to Honolulu is May, with a median price of $335. The most expensive month is November, with a median price of $1478. Prices are generally lower from February to September.

May

Cheapest

Flights from $335

November

Most Expensive

Flights from $1,478

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to Honolulu

United Airlines

Last-minute flights going from Chicago to Honolulu

Sun, Nov 1

⌛ Last-Minute

MDW - Honolulu

Chicago (MDW) - Honolulu (HNL)

Southwest Airlines

$694

$623

One-way

Mon, Nov 2

⌛ Last-Minute

MDW - Honolulu

Chicago (MDW) - Honolulu (HNL)

Southwest Airlines

$564

$588

One-way

Tue, Nov 3

⌛ Last-Minute

MDW - Honolulu

Chicago (MDW) - Honolulu (HNL)

Southwest Airlines

$545

$588

One-way

Tue, Nov 3

⌛ Last-Minute

MDW - Honolulu

Chicago (MDW) - Honolulu (HNL)

Southwest Airlines

$576

$588

One-way

Tue, Nov 3

⌛ Last-Minute

ORD - Honolulu

Chicago (ORD) - Honolulu (HNL)

American Airlines

$558

$648

One-way

Thu, Nov 5

⌛ Last-Minute

ORD - Honolulu

Chicago (ORD) - Honolulu (HNL)

Alaska Airlines, Inc.

$461

$588

One-way

Biggest price drops on these dates for flights from Chicago to Honolulu

3 nights

Dec 7 - Dec 10

$644 → $419

35%

4 nights

Dec 6 - Dec 10

$644 → $437

32%

4 nights

Dec 7 - Dec 11

$644 → $458

29%

5 nights

Dec 5 - Dec 10

$635 → $457

28%

Popular Airports to fly from Chicago to Honolulu

Chicago - Honolulu route insights

💸 Price insights

Recent fares are below the typical level

Recent fares from Chicago to Honolulu are below the typical level, with deals around $619.

📅 Best time to fly

September is historically cheapest

Historically, the cheapest month to fly from Chicago to Honolulu is September, with a median price of $707.

⏱️ Flight duration

Direct flights take 9h 23m

Direct flights from Chicago to Honolulu typically take 9h 23m, while connecting flights average 24h 32m.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights are dominant on this route, with only 1.2% of recent flights being direct.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines has offered direct flights from Chicago to Honolulu recently.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from Chicago to Honolulu are frequent, appearing often over the last 30 days.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International Airport offers a wide range of flights from Chicago to Honolulu.

📍 ~25 km from Chicago city center (reachable by car or train)

💸 Flights from ~$427

Honolulu main airports to arrive at

Daniel K. Inouye International (HNL)

Cheapest

Daniel K. Inouye International Airport is a primary gateway to Honolulu from Chicago.

📍 ~7 km from Honolulu (reachable by car)

💸 Flights from ~$427

Airports nearby Honolulu used as alternative

Kahului (OGG)

Honolulu, United States

91% AI deal score

$2,535

$1,888

Save $647

Alaska Airlines, Inc.

Business Class

From ORD

Honolulu, United States

90% AI deal score

$2,823

$2,279

Save $544

Porter Airlines, +1

Business Class

From ORD

Elite

Dec 04

Honolulu, United States

89% AI deal score

$2,247

$1,888

Save $359

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Feb 17

Honolulu, United States

89% AI deal score

$2,128

$1,846

Save $282

Alaska Airlines, Inc.

Business Class

From ORD

Elite

Feb 17

Honolulu, United States

89% AI deal score

$2,126

$1,846

Save $280

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to Honolulu

Historically, booking flights from Chicago to Honolulu 60+ days in advance typically yields the best prices. Across the trailing quarter, prices for this booking window averaged around $1140. In contrast, booking within 0-6 days of departure saw average prices rise to $1230. Even booking 28-59 days out showed a higher average price of $1333, indicating that earlier booking is generally more economical for this route.

Based on historical data from the trailing 90 days, a good price for a flight from Chicago to Honolulu is considered to be $738 or less. The median price for this route historically stands at $1018. Prices tend to increase significantly, with 75% of observed prices being $1492 or higher. Aiming for a price below $738 would represent a favorable deal.

Historically, the cheapest months to fly from Chicago to Honolulu are September, with a median price of $707, and June, with a median price of $710. February also shows a relatively low median price of $753. The annual median price for this route is $1018, indicating that these months offer significant savings compared to the yearly average.

Related routes

More routes from Chicago

Flights from Chicago to Houston Flights from Chicago to Huntsville Flights from Chicago to Hyderabad Flights from Chicago to Indianapolis Flights from Chicago to Islamabad Flights from Chicago to Istanbul Flights from Chicago to Jacksonville Flights from Chicago to Jakarta Flights from Chicago to Jeddah Flights from Chicago to Johannesburg Flights from Chicago to Karachi Flights from Chicago to Kuala Lumpur

Flights to Honolulu from other cities

Flights from Dallas to Honolulu Flights from Denver to Honolulu Flights from Hobart to Honolulu Flights from Hong Kong to Honolulu Flights from Houston to Honolulu Flights from Istanbul to Honolulu Flights from Las Vegas to Honolulu Flights from Los Angeles to Honolulu Flights from Madrid to Honolulu Flights from Melbourne to Honolulu Flights from New York to Honolulu Flights from Oakland to Honolulu

Chicago to Honolulu: Overview

Insights for flights from Chicago to Honolulu

A typical journey from Chicago to Honolulu takes about 9h 23m, including connections. This is a long-haul route, covering a distance of 6819 km.

How much is a round trip from Chicago to Honolulu

Regular price: $573 - $780

Prices for flights from Chicago to Honolulu are currently within the regular range.

Regular prices for this route typically range from $573 to $780. The current lowest deal is $619 with Alaska Airlines, Inc., for travel from Oct 27-Oct 31.

now $619

Low $573

High $780

The cheapest time to fly from Chicago to Honolulu

May

Cheapest

Flights from $335

November

Most Expensive

Flights from $1,478

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to Honolulu

United Airlines

Last-minute flights going from Chicago to Honolulu

Sun, Nov 1

⌛ Last-Minute

MDW - Honolulu

Chicago (MDW) - Honolulu (HNL)

Southwest Airlines

$694

$623

One-way

Mon, Nov 2

⌛ Last-Minute

MDW - Honolulu

Chicago (MDW) - Honolulu (HNL)

Southwest Airlines

$564

$588

One-way

Tue, Nov 3

⌛ Last-Minute

MDW - Honolulu

Chicago (MDW) - Honolulu (HNL)

Southwest Airlines

$545

$588

One-way

Tue, Nov 3

⌛ Last-Minute

MDW - Honolulu

Chicago (MDW) - Honolulu (HNL)

Southwest Airlines

$576

$588

One-way

Tue, Nov 3

⌛ Last-Minute

ORD - Honolulu

Chicago (ORD) - Honolulu (HNL)

American Airlines

$558

$648

One-way

Thu, Nov 5

⌛ Last-Minute

ORD - Honolulu

Chicago (ORD) - Honolulu (HNL)

Alaska Airlines, Inc.

$461

$588

One-way

Biggest price drops on these dates for flights from Chicago to Honolulu

3 nights

Dec 7 - Dec 10

$644 → $419

35%

4 nights

Dec 6 - Dec 10

$644 → $437

32%

4 nights

Dec 7 - Dec 11

$644 → $458

29%

5 nights

Dec 5 - Dec 10

$635 → $457

28%

Popular Airports to fly from Chicago to Honolulu

Chicago - Honolulu route insights

💸 Price insights

Recent fares are below the typical level

Recent fares from Chicago to Honolulu are below the typical level, with deals around $619.

📅 Best time to fly

September is historically cheapest

Historically, the cheapest month to fly from Chicago to Honolulu is September, with a median price of $707.

⏱️ Flight duration

Direct flights take 9h 23m

Direct flights from Chicago to Honolulu typically take 9h 23m, while connecting flights average 24h 32m.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights are dominant on this route, with only 1.2% of recent flights being direct.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines has offered direct flights from Chicago to Honolulu recently.

🎯 Booking tip

Deals are frequent on this route

Deals for flights from Chicago to Honolulu are frequent, appearing often over the last 30 days.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International Airport offers a wide range of flights from Chicago to Honolulu.

📍 ~25 km from Chicago city center (reachable by car or train)

💸 Flights from ~$427

Honolulu main airports to arrive at

Daniel K. Inouye International (HNL)

Cheapest

Daniel K. Inouye International Airport is a primary gateway to Honolulu from Chicago.

📍 ~7 km from Honolulu (reachable by car)

💸 Flights from ~$427

Airports nearby Honolulu used as alternative

Kahului (OGG)

Kahului Airport is a major secondary hub in Hawaii, offering extensive direct connections to the US mainland and Canada.

Honolulu, United States

89% AI deal score

$2,126

$1,846

Save $280

Alaska Airlines, Inc.

Business Class

Frequently Asked Questions About Flights to Honolulu

Cheap Flights from Chicago to Honolulu

Today’s best flight deals from Chicago to Honolulu

Chicago to Honolulu: Overview

Insights for flights from Chicago to Honolulu

How much is a round trip from Chicago to Honolulu

The cheapest time to fly from Chicago to Honolulu

Direct flights from Chicago to Honolulu

Last-minute flights going from Chicago to Honolulu

Biggest price drops on these dates for flights from Chicago to Honolulu

Popular Airports to fly from Chicago to Honolulu

Chicago - Honolulu route insights

Recent fares are below the typical level

September is historically cheapest

Direct flights take 9h 23m

Connecting flights are dominant

United Airlines offers direct flights

Deals are frequent on this route

Chicago main airports to depart from

Honolulu main airports to arrive at

Airports nearby Honolulu used as alternative

Business & First Class Flight Deals to Honolulu

Best Elite deals to Honolulu

Feb 23

Dec 04

Nov 01

Dec 04

Feb 17

Feb 17

Jan 27

Jan 21

Dec 02

Dec 04

Feb 17

Feb 17

Frequently Asked Questions About Flights to Honolulu

How early should I book Chicago to Honolulu flights to get the cheapest price?

What is a good price for a flight from Chicago to Honolulu?

When is the cheapest time of year to fly from Chicago to Honolulu?

Are there direct flights from Chicago to Honolulu?

What's the flight time from Chicago to Honolulu?

Are there frequently good prices on flights from Chicago to Honolulu?

Related routes

More routes from Chicago

Flights to Honolulu from other cities

Chicago to Honolulu: Overview

Insights for flights from Chicago to Honolulu

How much is a round trip from Chicago to Honolulu

The cheapest time to fly from Chicago to Honolulu

Direct flights from Chicago to Honolulu

Last-minute flights going from Chicago to Honolulu

Biggest price drops on these dates for flights from Chicago to Honolulu

Popular Airports to fly from Chicago to Honolulu

Chicago - Honolulu route insights

Recent fares are below the typical level

September is historically cheapest

Direct flights take 9h 23m

Connecting flights are dominant

United Airlines offers direct flights

Deals are frequent on this route

Chicago main airports to depart from

Honolulu main airports to arrive at

Airports nearby Honolulu used as alternative

Business & First Class Flight Deals to Honolulu

Best Elite deals to Honolulu

Feb 23

Dec 04

Nov 01

Dec 04

Feb 17

Feb 17

Jan 27

Jan 21

Dec 02

Dec 04

Feb 17

Feb 17

Frequently Asked Questions About Flights to Honolulu

How early should I book Chicago to Honolulu flights to get the cheapest price?

What is a good price for a flight from Chicago to Honolulu?

When is the cheapest time of year to fly from Chicago to Honolulu?