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 Kahului to Chicago O'Hare Intl Airport is 7h 52m on average, while flying from Honolulu to Chicago O'Hare Intl Airport is 8h 04m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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 41% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 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 day?

The number of flights available between Hawaii and Chicago is 7 per day as of March 2026. The most frequent departure time is 5:00PM, with 66% of daily flights leaving in the afternoon.

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

The number of flights available between Hawaii and Chicago is 51 per week as of March 2026. The most frequent departure day is Sat, with 18% of weekly flights leaving on this day.

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

American Airlines, Alaska Airlines, and Southwest are the most popular carriers operating 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 6 as of March 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.

$182 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.

7:50 am - 11:59 pm

HNL

ORD

11h 09m

1 stop

2:03 pm - 8:55 pm

ORD

HNL

11h 52m

1 stop

$412Multiple Airlines

Wed, Sep 2 - Wed, Sep 16

3:40 pm - 12:26 pm

HNL

ORD

15h 46m

1 stop

12:46 pm - 9:20 pm

ORD

HNL

13h 34m

1 stop

$424Delta

Wed, Apr 29 - Wed, May 6

8:15 am - 5:00 am

HNL

MDW

15h 45m

1 stop

10:20 am - 9:10 pm

MDW

HNL

15h 50m

1 stop

$428Southwest

Wed, Aug 12 - Tue, Aug 18

12:31 pm - 12:45 pm

HNL

ORD

19h 14m

2 stops

12:46 pm - 9:20 pm

ORD

HNL

13h 34m

1 stop

$430Delta

Tue, Apr 28 - Wed, May 6

12:50 pm - 6:40 am

HNL

ORD

12h 50m

1 stop

8:50 am - 5:32 pm

ORD

HNL

13h 42m

1 stop

$478Alaska Airlines

Wed, Apr 29 - Mon, May 4

8:15 am - 5:00 am

HNL

MDW

15h 45m

1 stop

10:20 am - 9:10 pm

MDW

HNL

15h 50m

1 stop

$496Southwest

Wed, Aug 12 - Tue, Aug 18

9:30 pm - 5:41 pm

LIH

ORD

15h 11m

1 stop

6:00 am - 12:22 pm

ORD

LIH

11h 22m

1 stop

$512American Airlines

Mon, Apr 6 - Fri, Apr 10

10:30 pm - 6:50 pm

OGG

ORD

15h 20m

1 stop

2:10 pm - 9:30 pm

ORD

OGG

12h 20m

1 stop

$524Alaska Airlines

Thu, May 14 - Tue, May 19

2:12 pm - 5:47 am

LIH

ORD

10h 35m

1 stop

6:00 am - 12:22 pm

ORD

LIH

11h 22m

1 stop

$528American Airlines

Fri, Apr 24 - Fri, May 1

12:55 pm - 5:15 am

LIH

ORD

11h 20m

1 stop

7:00 am - 7:53 pm

ORD

LIH

17h 53m

2 stops

$578United Airlines

Thu, Apr 23 - Mon, Apr 27

Delta flights from Hawaii to Chicago

Our best Delta deals on Hawaii to Chicago flight tickets

Delta

Apr 29

HNL3:40 pmHonolulu

15h 46m

1 stop

ORD12:26 pmChicago O'Hare Intl

May 6

ORD12:46 pmChicago O'Hare Intl

13h 34m

1 stop

HNL9:20 pmHonolulu

$424

Delta

Apr 28

HNL12:31 pmHonolulu

19h 14m

2 stops

ORD12:45 pmChicago O'Hare Intl

May 6

ORD12:46 pmChicago O'Hare Intl

13h 34m

1 stop

HNL9:20 pmHonolulu

$430

Delta

Apr 28

HNL12:31 pmHonolulu

19h 14m

2 stops

ORD12:45 pmChicago O'Hare Intl

May 5

ORD8:50 amChicago O'Hare Intl

17h 30m

2 stops

HNL9:20 pmHonolulu

$435

Alaska Airlines flights from Hawaii to Chicago

Our best Alaska Airlines deals on Hawaii to Chicago flight tickets

Alaska Airlines

Apr 29

HNL12:50 pmHonolulu

12h 50m

1 stop

ORD6:40 amChicago O'Hare Intl

May 4

ORD8:50 amChicago O'Hare Intl

13h 42m

1 stop

HNL5:32 pmHonolulu

$478

Alaska Airlines

May 4

HNL3:54 pmHonolulu

27h 05m

1 stop

ORD11:59 pmChicago O'Hare Intl

May 11

ORD8:50 amChicago O'Hare Intl

13h 42m

1 stop

HNL5:32 pmHonolulu

$500

Alaska Airlines

May 14

OGG10:30 pmKahului

15h 20m

1 stop

ORD6:50 pmChicago O'Hare Intl

May 19

ORD2:10 pmChicago O'Hare Intl

12h 20m

1 stop

OGG9:30 pmKahului

$524

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 9/2

7:50 am-11:59 pm

1 stop11h 09m

Chicago O'Hare Intl

Wed 9/16

2:03 pm-8:55 pm

1 stop11h 52m

$412

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 4/29

3:40 pm-12:26 pm

1 stop15h 46m

Chicago O'Hare Intl

Wed 5/6

12:46 pm-9:20 pm

1 stop13h 34m

$424

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 8/12

8:15 am-5:00 am

1 stop15h 45m

Chicago Midway

Tue 8/18

10:20 am-9:10 pm

1 stop15h 50m

$428

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 4/28

12:31 pm-12:45 pm

2 stops19h 14m

Chicago O'Hare Intl

Wed 5/6

12:46 pm-9:20 pm

1 stop13h 34m

$430

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 4/29

12:50 pm-6:40 am

1 stop12h 50m

Chicago O'Hare Intl

Mon 5/4

8:50 am-5:32 pm

1 stop13h 42m

$478

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 8/12

8:15 am-5:00 am

1 stop15h 45m

Chicago Midway

Tue 8/18

10:20 am-9:10 pm

1 stop15h 50m

$496

LihueChicago

LIH - ORD

LIHORD

Lihue

Mon 4/6

9:30 pm-5:41 pm

1 stop15h 11m

Chicago O'Hare Intl

Fri 4/10

6:00 am-12:22 pm

1 stop11h 22m

$512

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 5/14

10:30 pm-6:50 pm

1 stop15h 20m

Chicago O'Hare Intl

Tue 5/19

2:10 pm-9:30 pm

1 stop12h 20m

$524

Quickest round-trip

LihueChicago

LIH - ORD

LIHORD

Lihue

Fri 4/24

2:12 pm-5:47 am

1 stop10h 35m

Chicago O'Hare Intl

Fri 5/1

6:00 am-12:22 pm

1 stop11h 22m

$528

LihueChicago

LIH - ORD

LIHORD

Lihue

Thu 4/23

12:55 pm-5:15 am

1 stop11h 20m

Chicago O'Hare Intl

Mon 4/27

7:00 am-7:53 pm

2 stops17h 53m

$578

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 February is, on average, the cheapest month to fly to Chicago from Hawaii, with most prices found around $382. If you’re not able to fly to Chicago in February, then January is your next best option. Flight prices from Hawaii to Chicago during January average around $527.

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 Monday when prices can be found for as low as $775. This is often the case because there is less demand to fly during this day of the week. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Hawaii to Chicago for around $992.

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 evening. Flights from Hawaii to Chicago during this time can be as low as $843. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $858.

What is the cheapest Hawaii to Chicago flight route?

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

How far in advance should I book a flight 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 $772 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 $512 on momondo.

What cabin class options are available on Hawaii to Chicago flights?

There are 4 cabin classes available to choose from on Hawaii to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Hawaii to Chicago flights?

You could potentially save up to 36% 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	$313
Fastest flight time	7h 52m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Hawaii in the past 72 hours is $313. The best round-trip flight deal from Hawaii to Chicago found on momondo in the last 72 hours is $649.

The fastest flight from Hawaii to Chicago takes 7h 52m

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

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 6 as of March 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 39.32% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 33.33%, Airbus A330 with 5.98%, and Boeing 767-400 with 5.98%.

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 $230	Free Cancellation	Rating 7.9 8,315 reviews	Search Delta flights
Hawaiian Airlines	PriceFrom $280	Free Cancellation	Rating 7.8 2,841 reviews	Search Hawaiian Airlines flights
American Airlines	PriceFrom $447	Free Cancellation	Rating 7.1 11,487 reviews	Search American Airlines flights
United Airlines	PriceFrom $447	Free Cancellation	Rating 7.4 9,458 reviews	Search United Airlines flights
Alaska Airlines	PriceFrom $467	Free Cancellation	Rating 7.9 12,093 reviews	Search Alaska Airlines flights
Southwest	PriceFrom $581	Free Cancellation	Rating 8.0 4,325 reviews	Search Southwest flights

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Portage

Lansing

Valparaiso

Schererville

Munster

Crown Point

Chesterton

Monticello

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 $182

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 4/16. 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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Delta flights from Hawaii to Chicago

Our best Delta deals on Hawaii to Chicago flight tickets

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Our best Alaska Airlines 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 to Chicago?

What cabin class options are available on Hawaii to Chicago flights?

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

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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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

Fly your favorite airline to Chicago

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

Cabin classes currently available on flights to Chicago

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

Popular cities in the United States

Popular flights according to clicks in the last 7 days on momondo

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