How long does it take to fly to Chicago?

Average flight duration from Hawaii to Chicago depends on which airport you fly into and out of. Flying from Honolulu to Chicago O'Hare Intl Airport is 8h 04m on average, while flying from Kahului to Chicago O'Hare Intl Airport is 10h 04m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

What is the cheapest airline that flies from Hawaii to Chicago?

Delta, Southwest, and United Airlines are the most popular carriers operating from Hawaii to Chicago

How many flights depart from Hawaii to Chicago on average per day?

The number of flights available between Hawaii and Chicago is 2 per day as of May 2026. The most frequent departure time is 4:00PM, with 100% of daily flights leaving in the afternoon.

What airlines fly to Chicago?

United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Chicago from Hawaii according to our data. United Airlines is the first choice among our users, with 43% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How many flights depart from Hawaii to Chicago on average per week?

The number of flights available between Hawaii and Chicago is 16 per week as of May 2026. The most frequent departure day is Sat, with 25% of weekly flights leaving on this day.

When did momondo last update prices for flights from Hawaii to Chicago?

Prices for flights from Hawaii to Chicago are updated daily.

How many operators does momondo search for flights from Hawaii to Chicago?

The number of operators available for flights from Hawaii to Chicago is 5 as of May 2026.

How old do you have to be to fly from Hawaii to Chicago?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Hawaii to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$212 Cheap Flights from Hawaii to Chicago in 2026

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Find the cheapest flights from Hawaii to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:31 pm - 1:41 pm

LIH

ORD

12h 10m

1 stop

6:25 am - 5:41 pm

ORD

LIH

16h 16m

2 stops

$430Delta

Sun, Aug 16 - Mon, Aug 24

8:31 pm - 1:41 pm

LIH

ORD

12h 10m

1 stop

6:25 am - 5:41 pm

ORD

LIH

16h 16m

2 stops

$460Delta

Sun, Aug 16 - Thu, Aug 27

9:40 pm - 10:59 pm

LIH

ORD

20h 19m

1 stop

11:47 am - 8:08 pm

ORD

LIH

13h 21m

1 stop

$482American Airlines

Thu, Aug 13 - Sun, Aug 23

8:31 pm - 1:41 pm

LIH

ORD

12h 10m

1 stop

6:25 am - 5:41 pm

ORD

LIH

16h 16m

2 stops

$490Delta

Sun, Aug 16 - Fri, Aug 21

6:00 am - 11:57 pm

KOA

ORD

12h 57m

2 stops

6:01 am - 2:51 pm

ORD

KOA

13h 50m

1 stop

$500Multiple Airlines

Thu, Sep 24 - Mon, Sep 28

12:50 pm - 6:20 am

OGG

ORD

12h 30m

1 stop

7:49 pm - 11:29 am

ORD

OGG

20h 40m

1 stop

$509Multiple Airlines

Thu, May 28 - Tue, Jun 2

12:35 pm - 6:22 am

KOA

ORD

12h 47m

1 stop

6:01 am - 2:51 pm

ORD

KOA

13h 50m

1 stop

$524Alaska Airlines

Thu, Sep 24 - Mon, Sep 28

9:51 pm - 2:21 pm

LIH

ORD

11h 30m

1 stop

6:00 am - 8:21 pm

ORD

LIH

19h 21m

1 stop

$534American Airlines

Fri, May 22 - Sun, May 31

8:10 am - 4:30 am

HNL

MDW

15h 20m

1 stop

10:10 am - 9:15 pm

MDW

HNL

16h 05m

1 stop

$554Southwest

Wed, Sep 9 - Sun, Sep 20

8:10 am - 4:30 am

HNL

MDW

15h 20m

1 stop

7:10 am - 9:10 pm

MDW

HNL

19h 00m

2 stops

$560Southwest

Wed, Sep 9 - Sun, Sep 20

Southwest flights from Hawaii to Chicago

Our best Southwest deals on Hawaii to Chicago flight tickets

Southwest

Sep 9

HNL8:10 amHonolulu

15h 20m

1 stop

MDW4:30 amChicago Midway

Sep 20

MDW10:10 amChicago Midway

16h 05m

1 stop

HNL9:15 pmHonolulu

$554

Southwest

Sep 9

HNL8:10 amHonolulu

15h 20m

1 stop

MDW4:30 amChicago Midway

Sep 20

MDW7:10 amChicago Midway

19h 00m

2 stops

HNL9:10 pmHonolulu

$560

Southwest

Aug 20

KOA8:35 pmKona Intl

10h 30m

1 stop

MDW12:05 pmChicago Midway

Aug 26

MDW6:50 amChicago Midway

10h 50m

1 stop

KOA12:40 pmKona Intl

$569

United Airlines flights from Hawaii to Chicago

Our best United Airlines deals on Hawaii to Chicago flight tickets

United Airlines

May 20

LIH1:16 pmLihue

12h 04m

1 stop

ORD6:20 amChicago O'Hare Intl

May 24

ORD6:13 amChicago O'Hare Intl

12h 03m

1 stop

LIH1:16 pmLihue

$578

United Airlines

May 28

KOA1:52 pmKona Intl

10h 06m

1 stop

ORD4:58 amChicago O'Hare Intl

Jun 2

ORD6:00 amChicago O'Hare Intl

10h 42m

1 stop

KOA11:42 amKona Intl

$633

United Airlines

Jun 9

OGG8:00 pmKahului

10h 23m

1 stop

ORD11:23 amChicago O'Hare Intl

Jun 11

ORD12:45 pmChicago O'Hare Intl

11h 32m

1 stop

OGG7:17 pmKahului

$634

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

LihueChicago

LIH - ORD

LIHORD

Lihue

Sun 8/16

8:31 pm-1:41 pm

1 stop12h 10m

Chicago O'Hare Intl

Mon 8/24

6:25 am-5:41 pm

2 stops16h 16m

$430

LihueChicago

LIH - ORD

LIHORD

Lihue

Sun 8/16

8:31 pm-1:41 pm

1 stop12h 10m

Chicago O'Hare Intl

Thu 8/27

6:25 am-5:41 pm

2 stops16h 16m

$460

LihueChicago

LIH - ORD

LIHORD

Lihue

Thu 8/13

9:40 pm-10:59 pm

1 stop20h 19m

Chicago O'Hare Intl

Sun 8/23

11:47 am-8:08 pm

1 stop13h 21m

$482

LihueChicago

LIH - ORD

LIHORD

Lihue

Sun 8/16

8:31 pm-1:41 pm

1 stop12h 10m

Chicago O'Hare Intl

Fri 8/21

6:25 am-5:41 pm

2 stops16h 16m

$490

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 9/24

6:00 am-11:57 pm

2 stops12h 57m

Chicago O'Hare Intl

Mon 9/28

6:01 am-2:51 pm

1 stop13h 50m

$500

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 5/28

12:50 pm-6:20 am

1 stop12h 30m

Chicago O'Hare Intl

Tue 6/2

7:49 pm-11:29 am

1 stop20h 40m

$509

Quickest round-trip

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 9/24

12:35 pm-6:22 am

1 stop12h 47m

Chicago O'Hare Intl

Mon 9/28

6:01 am-2:51 pm

1 stop13h 50m

$524

LihueChicago

LIH - ORD

LIHORD

Lihue

Fri 5/22

9:51 pm-2:21 pm

1 stop11h 30m

Chicago O'Hare Intl

Sun 5/31

6:00 am-8:21 pm

1 stop19h 21m

$534

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 9/9

8:10 am-4:30 am

1 stop15h 20m

Chicago Midway

Sun 9/20

10:10 am-9:15 pm

1 stop16h 05m

$554

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 9/9

8:10 am-4:30 am

1 stop15h 20m

Chicago Midway

Sun 9/20

7:10 am-9:10 pm

2 stops19h 00m

$560

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Hawaii to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Hawaii, with most prices found around $204. If you’re not able to fly to Chicago in November, then August is your next best option. Flight prices from Hawaii to Chicago during August average around $215.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $762. This is often the case because there is less demand to fly during this day of the week. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Hawaii to Chicago for around $1,015.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Hawaii to Chicago during this time can be as low as $835. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $838.

What is the cheapest Hawaii to Chicago flight route?

Fly from Honolulu to Chicago O'Hare Intl for the best Hawaii - Chicago flight prices

How far in advance should I book a flight from Hawaii to Chicago?

You are more likely to see cheaper flights to Chicago from Hawaii when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $766 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Hawaii for as low as $448 on momondo.

Can stopping save me money on Hawaii to Chicago flights?

You could potentially save up to 58% on your flight if you consider stops on a Hawaii to Chicago flight.

Cheap Hawaii to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Hawaii to Chicago

Best Price Found	$345
Fastest flight time	8h 04m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Hawaii in the past 72 hours is $345. The best round-trip flight deal from Hawaii to Chicago found on momondo in the last 72 hours is $751.

The fastest flight from Hawaii to Chicago takes 8h 04m

Direct flights go from Hawaii to Chicago every day.

There are 3 airports in Chicago. From Hawaii there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

Frequently asked questions about flying from Hawaii to Chicago

When did momondo last update prices for flights from Hawaii to Chicago?
Prices for flights from Hawaii to Chicago are updated daily.
How many operators does momondo search for flights from Hawaii to Chicago?
The number of operators available for flights from Hawaii to Chicago is 5 as of May 2026.
How old do you have to be to fly from Hawaii to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Hawaii to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Hawaii to Chicago?
Based on momondo bookings for flights between Hawaii and Chicago, the leading plane model is Boeing 787-10 Dreamliner, making up 53.27% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 24.30%, Airbus A330-200 with 4.67%, and Boeing 787-9 Dreamliner with 2.80%.

Best airlines flying from Hawaii to Chicago

Compare and see reviews for airlines that fly from Hawaii to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $218	Free Cancellation	Rating 7.9 8,457 reviews	Search Delta flights
Hawaiian Airlines	PriceFrom $335	Free Cancellation	Rating 7.8 2,837 reviews	Search Hawaiian Airlines flights
American Airlines	PriceFrom $447	Free Cancellation	Rating 7.1 11,670 reviews	Search American Airlines flights
United Airlines	PriceFrom $447	Free Cancellation	Rating 7.4 9,694 reviews	Search United Airlines flights
Alaska Airlines	PriceFrom $465	Free Cancellation	Rating 7.9 12,349 reviews	Search Alaska Airlines flights
Southwest	PriceFrom $581	Free Cancellation	Rating 7.9 4,303 reviews	Search Southwest flights

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Munster

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Crown Point

Monticello

Chesterton

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Hawaii to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Hawaii to Chicago for you.

Can I find flights from Hawaii to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Hawaii with this policy.

How can momondo help me find flights from Hawaii to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Hawaii.

I’m not ready to book a flight from Hawaii to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Hawaii. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Cheap flights from Hawaii to Chicago from $212

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Hawaii to Chicago departing on 5/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Southwest flights from Hawaii to Chicago

Our best Southwest deals on Hawaii to Chicago flight tickets

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How to get the cheapest flight ticket from Hawaii to Chicago

What is the cheapest month to fly to Chicago?

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

What is the cheapest Hawaii to Chicago flight route?

How far in advance should I book a flight from Hawaii to Chicago?

Can stopping save me money on Hawaii to Chicago flights?

What is the cheapest airline that flies from Hawaii to Chicago?

What airlines fly to Chicago?

How many flights depart from Hawaii to Chicago on average per day?

How many flights depart from Hawaii to Chicago on average per week?

How long does it take to fly to Chicago?

Cheap Hawaii to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Hawaii to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying from Hawaii to Chicago

Best airlines flying from Hawaii to Chicago

Compare and see reviews for airlines that fly from Hawaii to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago

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Airlines are sorted and displayed according to clicks in the past 7 days on momondo

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List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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