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 05m 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 38% 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 February 2026. The most frequent departure time is 7:00PM, with 78% of daily flights leaving in the evening.

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 February 2026. The most frequent departure day is Mon, with 16% of weekly flights leaving on this day.

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

Southwest, United Airlines, and Alaska Airlines 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 February 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.

$159 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.

9:55 pm - 6:20 pm

HNL

MDW

16h 25m

1 stop

8:25 am - 4:30 pm

MDW

HNL

12h 05m

1 stop

$342Southwest

Wed, Feb 25 - Wed, Mar 4

11:35 pm - 2:58 pm

HNL

ORD

11h 23m

1 stop

8:20 am - 7:59 pm

ORD

HNL

15h 39m

1 stop

$342Alaska Airlines

Wed, Feb 25 - Wed, Mar 4

6:05 pm - 6:14 am

HNL

ORD

8h 09mnonstop

10:35 am - 9:06 pm

ORD

HNL

14h 31m

1 stop

$372United Airlines

Wed, Feb 25 - Wed, Mar 4

8:45 pm - 11:19 am

HNL

ORD

10h 34m

1 stop

12:54 pm - 8:21 pm

ORD

HNL

12h 27m

1 stop

$382United Airlines

Thu, Mar 5 - Sun, Mar 8

12:55 pm - 2:58 pm

HNL

ORD

22h 03m

1 stop

8:20 am - 6:59 pm

ORD

HNL

15h 39m

1 stop

$392Multiple Airlines

Mon, Mar 2 - Tue, Mar 10

9:40 pm - 10:51 am

HNL

ORD

33h 11m

2 stops

7:39 pm - 10:15 am

ORD

HNL

19h 36m

1 stop

$393Multiple Airlines

Mon, Mar 2 - Mon, Mar 9

10:30 pm - 2:53 pm

LIH

ORD

12h 23m

1 stop

7:00 am - 5:14 pm

ORD

LIH

14h 14m

1 stop

$424American Airlines

Wed, Feb 18 - Sun, Feb 22

10:30 pm - 1:33 pm

LIH

ORD

11h 03m

1 stop

7:00 am - 4:14 pm

ORD

LIH

14h 14m

1 stop

$453American Airlines

Mon, Feb 23 - Sun, Mar 8

4:10 pm - 12:43 pm

HNL

MDW

15h 33m

2 stops

1:23 pm - 9:45 pm

MDW

HNL

13h 22m

2 stops

$465Delta

Thu, Apr 30 - Wed, May 6

10:40 pm - 6:40 pm

LIH

MDW

16h 00m

2 stops

9:35 am - 6:50 pm

MDW

LIH

14h 15m

2 stops

$477Delta

Tue, Mar 3 - Tue, Mar 10

Alaska Airlines flights from Hawaii to Chicago

Our best Alaska Airlines deals on Hawaii to Chicago flight tickets

Alaska Airlines

Feb 25

HNL11:35 pmHonolulu

11h 23m

1 stop

ORD2:58 pmChicago O'Hare Intl

Mar 4

ORD8:20 amChicago O'Hare Intl

15h 39m

1 stop

HNL7:59 pmHonolulu

$342

Alaska Airlines

Apr 30

HNL10:00 pmHonolulu

16h 03m

1 stop

ORD7:03 pmChicago O'Hare Intl

May 6

ORD8:50 amChicago O'Hare Intl

17h 13m

2 stops

HNL9:03 pmHonolulu

$399

Alaska Airlines

Apr 30

HNL10:00 pmHonolulu

16h 03m

1 stop

ORD7:03 pmChicago O'Hare Intl

May 6

ORD8:50 amChicago O'Hare Intl

17h 13m

2 stops

HNL9:03 pmHonolulu

$419

United Airlines flights from Hawaii to Chicago

Our best United Airlines deals on Hawaii to Chicago flight tickets

United Airlines

Feb 25

HNL6:05 pmHonolulu

8h 09m

ORD6:14 amChicago O'Hare Intl

Mar 4

ORD10:35 amChicago O'Hare Intl

14h 31m

1 stop

HNL9:06 pmHonolulu

$372

United Airlines

Mar 5

HNL8:45 pmHonolulu

10h 34m

1 stop

ORD11:19 amChicago O'Hare Intl

Mar 8

ORD12:54 pmChicago O'Hare Intl

12h 27m

1 stop

HNL8:21 pmHonolulu

$382

United Airlines

Mar 3

LIH8:40 pmLihue

10h 39m

1 stop

ORD11:19 amChicago O'Hare Intl

Mar 10

ORD2:26 pmChicago O'Hare Intl

12h 31m

1 stop

LIH9:57 pmLihue

$422

Fly from

Fly to

Route

Depart

Return

Price

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 2/25

9:55 pm-6:20 pm

1 stop16h 25m

Chicago Midway

Wed 3/4

8:25 am-4:30 pm

1 stop12h 05m

$342

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 2/25

11:35 pm-2:58 pm

1 stop11h 23m

Chicago O'Hare Intl

Wed 3/4

8:20 am-7:59 pm

1 stop15h 39m

$342

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 2/25

6:05 pm-6:14 am

Nonstop8h 09m

Chicago O'Hare Intl

Wed 3/4

10:35 am-9:06 pm

1 stop14h 31m

$372

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 3/5

8:45 pm-11:19 am

1 stop10h 34m

Chicago O'Hare Intl

Sun 3/8

12:54 pm-8:21 pm

1 stop12h 27m

$382

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Mon 3/2

12:55 pm-2:58 pm

1 stop22h 03m

Chicago O'Hare Intl

Tue 3/10

8:20 am-6:59 pm

1 stop15h 39m

$392

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Mon 3/2

9:40 pm-10:51 am

2 stops33h 11m

Chicago O'Hare Intl

Mon 3/9

7:39 pm-10:15 am

1 stop19h 36m

$393

LihueChicago

LIH - ORD

LIHORD

Lihue

Wed 2/18

10:30 pm-2:53 pm

1 stop12h 23m

Chicago O'Hare Intl

Sun 2/22

7:00 am-5:14 pm

1 stop14h 14m

$424

LihueChicago

LIH - ORD

LIHORD

Lihue

Mon 2/23

10:30 pm-1:33 pm

1 stop11h 03m

Chicago O'Hare Intl

Sun 3/8

7:00 am-4:14 pm

1 stop14h 14m

$453

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 4/30

4:10 pm-12:43 pm

2 stops15h 33m

Chicago Midway

Wed 5/6

1:23 pm-9:45 pm

2 stops13h 22m

$465

LihueChicago

LIH - MDW

LIHMDW

Lihue

Tue 3/3

10:40 pm-6:40 pm

2 stops16h 00m

Chicago Midway

Tue 3/10

9:35 am-6:50 pm

2 stops14h 15m

$477

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 $472. If you’re not able to fly to Chicago in February, then September is your next best option. Flight prices from Hawaii to Chicago during September average around $558.

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 $798. 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 $1,030.

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 $847. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $870.

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 $792 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 $557 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 21% 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	$305
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 $305. The best round-trip flight deal from Hawaii to Chicago found on momondo in the last 72 hours is $464.

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 February 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 787-8 Dreamliner, making up 33.94% of the total bookings. Other popular models include Boeing 787-10 Dreamliner with 33.33%, Boeing 767-400 with 7.88%, and Boeing 767-300 (winglets) with 6.67%.

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 $282	Free Cancellation	Rating 7.9 8,138 reviews	Search Delta flights
Hawaiian Airlines	PriceFrom $322	Free Cancellation	Rating 7.8 2,831 reviews	Search Hawaiian Airlines flights
United Airlines	PriceFrom $410	Free Cancellation	Rating 7.4 9,236 reviews	Search United Airlines flights
American Airlines	PriceFrom $447	Free Cancellation	Rating 7.2 11,218 reviews	Search American Airlines flights
Alaska Airlines	PriceFrom $467	Free Cancellation	Rating 8.0 11,834 reviews	Search Alaska Airlines flights
Southwest	PriceFrom $581	Free Cancellation	Rating 8.0 4,272 reviews	Search Southwest flights

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Saint Joseph

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Valparaiso

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.

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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Fly into one of these airports located in Chicago

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Cheap flights from Hawaii to Chicago from $159

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 3/4. 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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Filter for what you want

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Find the cheapest flights from Hawaii to Chicago

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Alaska Airlines flights from Hawaii to Chicago

Our best Alaska Airlines deals on Hawaii to Chicago flight tickets

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Our best United 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?

The month of February is, on average, the cheapest month to fly to Chicago from Hawaii, with most prices found around $472. If you’re not able to fly to Chicago in February, then September is your next best option. Flight prices from Hawaii to Chicago during September average around $558.

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?

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 $847. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $870.

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?

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 21% on your flight if you consider stops on a Hawaii to Chicago flight.

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

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

What airlines fly to Chicago?

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 February 2026. The most frequent departure time is 7:00PM, with 78% of daily flights leaving in the evening.

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 February 2026. The most frequent departure day is Mon, with 16% of weekly flights leaving on this day.

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

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

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

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

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

What is the most popular plane model 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?

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

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

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

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

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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According to popular flight searches on momondo this year

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