What airlines fly to Chicago?

United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Chicago from Honolulu 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.

Which airport is the most popular layover for flights between Honolulu and Chicago?

Portland (PDX) was the most common stop: 67% of momondo users choosing 1-stop flights on this route connected there.

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

Delta, American Airlines, and Southwest are the most popular carriers operating from Honolulu to Chicago

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

The number of flights available between Honolulu and Chicago is 18 per week as of December 2025. The most frequent departure day is Mon, with 33% of weekly flights leaving on this day.

Which layover airport offers the lowest fares from Honolulu to Chicago?

Flights via Portland (PDX) offer the lowest average round-trip price of $761.

Which layover airport has the shortest connection time from Honolulu to Chicago?

Portland (PDX) has the shortest average layover time for this route: 0h 50m.

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

As of December 2025, there are 2 flights per day flying from Honolulu to Chicago. The most common time of day flights depart is 7:00PM, with 100% of flights taking off in the evening.

Which layover airport has the shortest travel time from Honolulu to Chicago?

Flights connecting via Portland (PDX) have the shortest average one-way travel time: 10h 23m.

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

Prices for flights from Honolulu Airport to Chicago refresh daily.

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

As of December 2025, there are 6 operators available to choose from for flights from Honolulu Airport to Chicago.

How old do you have to be to fly from Honolulu Airport 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 Honolulu Airport 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.

$263 Cheap Flights from Honolulu to Chicago in 2025/26

Q: What is the typical price of a round-trip flight between Honolulu and Chicago?

Prices are currently low for flights on this route. Typical prices usually range from $683 to $818. The lowest price recently found on this route was $404.

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Find the cheapest flights from Honolulu to Chicago

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One-way

Last minute

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Cheap round-trip flights

Enter your travel dates to find the best prices.

7:00 pm - 7:00 am

HNL

ORD

8h 00mnonstop

10:00 am - 3:21 pm

ORD

HNL

9h 21mnonstop

$404American Airlines

Thu, Jan 15 - Tue, Jan 20

8:17 am - 11:37 pm

HNL

ORD

11h 20m1 stop

9:00 am - 6:53 pm

ORD

HNL

13h 53m1 stop

$410Multiple Airlines

Wed, Jan 28 - Wed, Feb 4

8:17 am - 11:37 pm

HNL

ORD

11h 20m1 stop

3:44 pm - 9:21 pm

ORD

HNL

33h 37m1 stop

$422Multiple Airlines

Thu, Jan 15 - Tue, Jan 20

11:16 pm - 2:29 pm

HNL

ORD

11h 13m1 stop

9:00 am - 6:53 pm

ORD

HNL

13h 53m1 stop

$423Alaska Airlines

Wed, Jan 21 - Sun, Jan 25

4:50 pm - 9:53 am

HNL

MDW

13h 03m1 stop

6:00 am - 3:10 pm

MDW

HNL

13h 10m1 stop

$423Delta

Wed, Jan 28 - Tue, Feb 3

5:15 pm - 12:46 pm

HNL

MDW

15h 31m2 stops

6:00 am - 3:10 pm

MDW

HNL

13h 10m1 stop

$429Delta

Wed, Jan 28 - Tue, Feb 3

5:15 pm - 8:40 am

HNL

ORD

11h 25m1 stop

7:20 am - 9:28 pm

ORD

HNL

18h 08m2 stops

$429Delta

Tue, Jan 13 - Tue, Jan 20

8:17 am - 11:37 pm

HNL

ORD

11h 20m1 stop

9:00 am - 9:21 pm

ORD

HNL

16h 21m1 stop

$433Multiple Airlines

Thu, Jan 15 - Thu, Jan 22

9:55 pm - 12:35 pm

HNL

MDW

10h 40m1 stop

8:25 am - 4:30 pm

MDW

HNL

12h 05m1 stop

$450Southwest

Wed, Jan 28 - Tue, Feb 3

12:30 pm - 5:05 am

HNL

MDW

12h 35m2 stops

8:25 am - 4:30 pm

MDW

HNL

12h 05m1 stop

$455Southwest

Wed, Jan 28 - Tue, Feb 3

Alaska Airlines flights from Honolulu to Chicago

Our best Alaska Airlines deals on Honolulu to Chicago flight tickets

Alaska Airlines

Jan 21

HNL11:16 pmHonolulu

11h 13m

1 stop

ORD2:29 pmChicago O'Hare Intl

Jan 25

ORD9:00 amChicago O'Hare Intl

13h 53m

1 stop

HNL6:53 pmHonolulu

$423

Find similar

Alaska Airlines

Feb 1

HNL11:16 pmHonolulu

20h 21m

1 stop

ORD11:37 pmChicago O'Hare Intl

Feb 5

ORD9:00 amChicago O'Hare Intl

13h 53m

1 stop

HNL6:53 pmHonolulu

$473

Find similar

Alaska Airlines

Apr 1

HNL10:00 amHonolulu

14h 00m

1 stop

ORD5:00 amChicago O'Hare Intl

Apr 8

ORD3:20 pmChicago O'Hare Intl

11h 59m

1 stop

HNL10:19 pmHonolulu

$591

Find similar

Delta flights from Honolulu to Chicago

Our best Delta deals on Honolulu to Chicago flight tickets

Delta

Jan 13

HNL5:15 pmHonolulu

11h 25m

1 stop

ORD8:40 amChicago O'Hare Intl

Jan 20

ORD7:20 amChicago O'Hare Intl

18h 08m

2 stops

HNL9:28 pmHonolulu

$429

Find similar

Delta

Jan 28

HNL9:35 pmHonolulu

16h 09m

2 stops

ORD5:44 pmChicago O'Hare Intl

Feb 4

ORD8:50 amChicago O'Hare Intl

16h 38m

2 stops

HNL9:28 pmHonolulu

$434

Find similar

Delta

Jan 15

HNL5:15 pmHonolulu

11h 53m

1 stop

MDW9:08 amChicago Midway

Jan 22

MDW9:32 amChicago Midway

15h 56m

2 stops

HNL9:28 pmHonolulu

$465

Find similar

Fly from

Fly to

Route

Depart

Return

Price

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 1/15

7:00 pm-7:00 am

Nonstop8h 00m

Chicago O'Hare Intl

Tue 1/20

10:00 am-3:21 pm

Nonstop9h 21m

$404

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 1/28

8:17 am-11:37 pm

1 stop11h 20m

Chicago O'Hare Intl

Wed 2/4

9:00 am-6:53 pm

1 stop13h 53m

$410

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 1/15

8:17 am-11:37 pm

1 stop11h 20m

Chicago O'Hare Intl

Tue 1/20

3:44 pm-9:21 pm

1 stop33h 37m

$422

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 1/21

11:16 pm-2:29 pm

1 stop11h 13m

Chicago O'Hare Intl

Sun 1/25

9:00 am-6:53 pm

1 stop13h 53m

$423

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/28

4:50 pm-9:53 am

1 stop13h 03m

Chicago Midway

Tue 2/3

6:00 am-3:10 pm

1 stop13h 10m

$423

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/28

5:15 pm-12:46 pm

2 stops15h 31m

Chicago Midway

Tue 2/3

6:00 am-3:10 pm

1 stop13h 10m

$429

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 1/13

5:15 pm-8:40 am

1 stop11h 25m

Chicago O'Hare Intl

Tue 1/20

7:20 am-9:28 pm

2 stops18h 08m

$429

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 1/15

8:17 am-11:37 pm

1 stop11h 20m

Chicago O'Hare Intl

Thu 1/22

9:00 am-9:21 pm

1 stop16h 21m

$433

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/28

9:55 pm-12:35 pm

1 stop10h 40m

Chicago Midway

Tue 2/3

8:25 am-4:30 pm

1 stop12h 05m

$450

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/28

12:30 pm-5:05 am

2 stops12h 35m

Chicago Midway

Tue 2/3

8:25 am-4:30 pm

1 stop12h 05m

$455

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Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Honolulu 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

Layovers

Other information

What is the typical price of a round-trip flight between Honolulu and Chicago?

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Honolulu, with most prices found around $558. If you’re not able to fly to Chicago in September, then May is your next best option. Flight prices from Honolulu to Chicago during May average around $598.

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 $809. 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 Honolulu to Chicago for around $1,141.

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 at noon. Flights from Honolulu to Chicago during this time can be as low as $618. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $881.

What is the cheapest Honolulu to Chicago flight route?

Fly from Honolulu to Chicago O'Hare Intl for the best Honolulu - 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 Honolulu when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $807 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Honolulu for as low as $563 on momondo.

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

There are 4 cabin classes available to choose from on Honolulu 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 Honolulu to Chicago flights?

You could potentially save up to 8% on your flight if you consider stops on a Honolulu to Chicago flight.

How have Honolulu to Chicago flight prices changed over time?

As of December 2025, prices for Honolulu to Chicago flights are approximately 0% more expensive when compared to flights at the same time last year.

When to book flights from Honolulu to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Honolulu to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Honolulu to Chicago (HNL to CHI) flight deals and tips

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

Best Price Found	$345
Fastest flight time	8h 10m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Honolulu in the past 72 hours is $345. The best round-trip flight deal from Honolulu to Chicago found on momondo in the last 72 hours is $677.

The fastest flight from Honolulu to Chicago takes 8h 10m

Direct flights go from Honolulu to Chicago every day.

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

Search flight deals

How far is Honolulu to Chicago by plane?
The straight-line distance from Honolulu to Chicago is 4246.2 mi. By plane, this route typically takes 8h 10m.
When did momondo last update prices for flights from Honolulu Airport to Chicago?
Prices for flights from Honolulu Airport to Chicago refresh daily.
How many operators does momondo search for flights from Honolulu Airport to Chicago?
As of December 2025, there are 6 operators available to choose from for flights from Honolulu Airport to Chicago.
How old do you have to be to fly from Honolulu Airport 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 Honolulu Airport 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 Honolulu to Chicago?
Based on momondo bookings for flights between Honolulu and Chicago, the leading plane model is Boeing 787-10 Dreamliner, making up 36.36% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 33.12%, Airbus A330-200 with 7.79%, and Boeing 767-300 (winglets) with 7.14%.
What is the most popular airline from Honolulu to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Honolulu to Chicago is American Airlines (29% of total bookings). The next most popular airlines are United Airlines (25%), Alaska Airlines (17%), and Southwest (14%).

Best airlines flying from Honolulu to Chicago

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

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $305	Free Cancellation	Rating 7.9 8,009 reviews	Search Delta flights
Hawaiian Airlines	PriceFrom $335	Free Cancellation	Rating 7.8 2,820 reviews	Search Hawaiian Airlines flights
American Airlines	PriceFrom $479	Free Cancellation	Rating 7.2 11,054 reviews	Search American Airlines flights
Alaska Airlines	PriceFrom $512	Free Cancellation	Rating 8.0 11,479 reviews	Search Alaska Airlines flights
Southwest	PriceFrom $581	Free Cancellation	Rating 7.9 4,251 reviews	Search Southwest flights
United Airlines	PriceFrom $717	Free Cancellation	Rating 7.4 9,095 reviews	Search United Airlines flights

Alaska Airlines Flights From Honolulu to Chicago
Alaska Airlines is one of the most popular airlines flying from Honolulu to Chicago, operating 7 flights/week on average for this route. A good Alaska Airlines flight deal for Honolulu to Chicago starts from $512 round-trip, up to an average price of $778. Our users have rated Alaska Airlines at 8.0/10.
United Airlines Flights From Honolulu to Chicago
The best United Airlines deal for Honolulu to Chicago flight tickets found on momondo in the last 72 hours was $717, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $1,049 round-trip. United Airlines operates 5 flights out of Honolulu into Chicago in an average week, so prices vary by time and availability. 9,095 United Airlines reviews by users on momondo have scored the airline at 7.4/10.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Honolulu to Chicago. momondo saves you time and could save you money on your trip.

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

All flight searches from Honolulu to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Honolulu to Chicago.

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

Price alerts on flights to Chicago from Honolulu are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Cheap flights from Honolulu to Chicago from $263

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Honolulu to Chicago departing on 1/17. 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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Alaska Airlines flights from Honolulu to Chicago

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Our best Delta deals on Honolulu to Chicago flight tickets

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Use the filters below to find and compare flights from Honolulu to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Honolulu to Chicago

What is the typical price of a round-trip flight between Honolulu and Chicago?

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Honolulu, with most prices found around $558. If you’re not able to fly to Chicago in September, then May is your next best option. Flight prices from Honolulu to Chicago during May average around $598.

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 at noon. Flights from Honolulu to Chicago during this time can be as low as $618. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $881.

What is the cheapest Honolulu to Chicago flight route?

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

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

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

There are 4 cabin classes available to choose from on Honolulu 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 Honolulu to Chicago flights?

You could potentially save up to 8% on your flight if you consider stops on a Honolulu to Chicago flight.

How have Honolulu to Chicago flight prices changed over time?

As of December 2025, prices for Honolulu to Chicago flights are approximately 0% more expensive when compared to flights at the same time last year.

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

Delta, American Airlines, and Southwest are the most popular carriers operating from Honolulu to Chicago

What airlines fly to Chicago?

Which airport is the most popular layover for flights between Honolulu and Chicago?

Portland (PDX) was the most common stop: 67% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Honolulu to Chicago?

Flights via Portland (PDX) offer the lowest average round-trip price of $761.

Which layover airport has the shortest travel time from Honolulu to Chicago?

Flights connecting via Portland (PDX) have the shortest average one-way travel time: 10h 23m.

Which layover airport has the shortest connection time from Honolulu to Chicago?

Portland (PDX) has the shortest average layover time for this route: 0h 50m.

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

As of December 2025, there are 2 flights per day flying from Honolulu to Chicago. The most common time of day flights depart is 7:00PM, with 100% of flights taking off in the evening.

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

The number of flights available between Honolulu and Chicago is 18 per week as of December 2025. The most frequent departure day is Mon, with 33% of weekly flights leaving on this day.

When to book flights from Honolulu to Chicago

Cheap Honolulu to Chicago (HNL to CHI) flight deals and tips

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

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

How far is Honolulu to Chicago by plane?

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

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

How old do you have to be to fly from Honolulu Airport to Chicago?

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

What is the most popular plane model from Honolulu to Chicago?

What is the most popular airline from Honolulu to Chicago?

Best airlines flying from Honolulu to Chicago

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

Alaska Airlines Flights From Honolulu to Chicago

United Airlines Flights From Honolulu to Chicago

Traveling to a place near Chicago?

Why use momondo?

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

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

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

I’m not ready to book a flight from Honolulu 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