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

Portland (PDX) was the most common stop: 44% of momondo users choosing 1-stop flights on this route connected there.

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 34% 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 Honolulu to Chicago on average per day?

As of August 2025, there are 3 flights per day flying from Honolulu to Chicago. The most common time of day flights depart is 5:00PM, with 100% of flights taking off in the afternoon.

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

Southwest, Hawaiian Airlines, and Alaska Airlines 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 21 per week as of August 2025. The most frequent departure day is Mon, with 14% of weekly flights leaving on this day.

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.

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

Flights connecting via San Diego (SAN) have the shortest average one-way travel time: 10h 20m.

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

Flights via San Diego (SAN) offer the lowest average round-trip price of $418.

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 August 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.

$205 Cheap Flights from Honolulu to Chicago in 2025

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Find the cheapest flights from Honolulu to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

8:00 am - 1:30 amHNL-MDW

13h 30m1 stop

7:45 am - 4:15 pmMDW-HNL

12h 30m1 stop

$409Southwest

Find Deal

Thu, Nov 6 - Sun, Nov 9

9:25 pm - 4:20 pmHNL-MDW

14h 55m2 stops

7:45 am - 4:15 pmMDW-HNL

12h 30m1 stop

$414Southwest

Find Deal

Thu, Nov 6 - Sun, Nov 9

10:20 pm - 6:59 pmHNL-ORD

15h 39m1 stop

7:59 pm - 9:05 pmORD-HNL

30h 06m1 stop

$417Alaska Airlines

Find Deal

Tue, Oct 7 - Tue, Oct 14

10:20 pm - 2:50 pmHNL-ORD

11h 30m1 stop

8:20 am - 9:05 pmORD-HNL

17h 45m1 stop

$419Alaska Airlines

Find Deal

Tue, Oct 7 - Wed, Oct 15

8:00 am - 11:59 pmHNL-ORD

10h 59m1 stop

7:00 am - 1:43 pmORD-HNL

11h 43m1 stop

$421Hawaiian Airlines

Find Deal

Wed, Oct 29 - Fri, Oct 31

3:25 pm - 9:56 amHNL-ORD

13h 31m1 stop

7:37 am - 7:09 pmORD-HNL

16h 32m1 stop

$423Delta

Find Deal

Mon, Sep 22 - Thu, Oct 23

10:42 pm - 5:15 pmHNL-ORD

13h 33m1 stop

6:15 am - 6:57 pmORD-HNL

17h 42m2 stops

$428Delta

Find Deal

Wed, Sep 10 - Sat, Sep 20

4:50 pm - 8:40 amHNL-MDW

10h 50m1 stop

9:35 am - 9:26 pmMDW-HNL

15h 51m2 stops

$429Delta

Find Deal

Fri, Oct 31 - Tue, Nov 4

7:50 am - 12:04 amHNL-ORD

11h 14m1 stop

2:07 pm - 8:50 pmORD-HNL

11h 43m1 stop

$441Hawaiian Airlines

Find Deal

Sat, Sep 13 - Sat, Sep 20

11:02 pm - 3:51 pmHNL-ORD

11h 49m1 stop

6:55 am - 7:33 pmORD-HNL

17h 38m1 stop

$481American Airlines

Find Deal

Tue, Sep 9 - Wed, Sep 17

Hawaiian Airlines flights from Honolulu to Chicago

Our best Hawaiian Airlines deals on Honolulu to Chicago flight tickets

Hawaiian Airlines

Oct 29

HNL8:00 amHonolulu

10h 59m

1 stop

ORD11:59 pmChicago O'Hare Intl

Oct 31

ORD7:00 amChicago O'Hare Intl

11h 43m

1 stop

HNL1:43 pmHonolulu

$421

Find similar

Hawaiian Airlines

Sep 13

HNL7:50 amHonolulu

11h 14m

1 stop

ORD12:04 amChicago O'Hare Intl

Sep 20

ORD2:07 pmChicago O'Hare Intl

11h 43m

1 stop

HNL8:50 pmHonolulu

$441

Find similar

Alaska Airlines flights from Honolulu to Chicago

Our best Alaska Airlines deals on Honolulu to Chicago flight tickets

Alaska Airlines

Oct 7

HNL10:20 pmHonolulu

15h 39m

1 stop

ORD6:59 pmChicago O'Hare Intl

Oct 14

ORD7:59 pmChicago O'Hare Intl

30h 06m

1 stop

HNL9:05 pmHonolulu

$417

Find similar

Alaska Airlines

Oct 7

HNL10:20 pmHonolulu

11h 30m

1 stop

ORD2:50 pmChicago O'Hare Intl

Oct 15

ORD8:20 amChicago O'Hare Intl

17h 45m

1 stop

HNL9:05 pmHonolulu

$419

Find similar

Alaska Airlines

Oct 6

HNL10:20 pmHonolulu

20h 39m

1 stop

ORD11:59 pmChicago O'Hare Intl

Oct 14

ORD3:50 pmChicago O'Hare Intl

34h 15m

1 stop

HNL9:05 pmHonolulu

$432

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Fly from

Fly to

Route

Depart

Return

Price

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 11/6

8:00 am-1:30 am

1 stop13h 30m

Chicago Midway

Sun 11/9

7:45 am-4:15 pm

1 stop12h 30m

$409

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 11/6

9:25 pm-4:20 pm

2 stops14h 55m

Chicago Midway

Sun 11/9

7:45 am-4:15 pm

1 stop12h 30m

$414

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 10/7

10:20 pm-6:59 pm

1 stop15h 39m

Chicago O'Hare Intl

Tue 10/14

7:59 pm-9:05 pm

1 stop30h 06m

$417

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 10/7

10:20 pm-2:50 pm

1 stop11h 30m

Chicago O'Hare Intl

Wed 10/15

8:20 am-9:05 pm

1 stop17h 45m

$419

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 10/29

8:00 am-11:59 pm

1 stop10h 59m

Chicago O'Hare Intl

Fri 10/31

7:00 am-1:43 pm

1 stop11h 43m

$421

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Mon 9/22

3:25 pm-9:56 am

1 stop13h 31m

Chicago O'Hare Intl

Thu 10/23

7:37 am-7:09 pm

1 stop16h 32m

$423

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 9/10

10:42 pm-5:15 pm

1 stop13h 33m

Chicago O'Hare Intl

Sat 9/20

6:15 am-6:57 pm

2 stops17h 42m

$428

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Fri 10/31

4:50 pm-8:40 am

1 stop10h 50m

Chicago Midway

Tue 11/4

9:35 am-9:26 pm

2 stops15h 51m

$429

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Sat 9/13

7:50 am-12:04 am

1 stop11h 14m

Chicago O'Hare Intl

Sat 9/20

2:07 pm-8:50 pm

1 stop11h 43m

$441

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 9/9

11:02 pm-3:51 pm

1 stop11h 49m

Chicago O'Hare Intl

Wed 9/17

6:55 am-7:33 pm

1 stop17h 38m

$481

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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 cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Honolulu, with most prices found around $561. If you’re not able to fly to Chicago in November, then October is your next best option. Flight prices from Honolulu to Chicago during October average around $573.

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 $841. 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 $1,074.

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 evening when prices are around $939.

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 $804 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 $690 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.

How have Honolulu to Chicago flight prices changed over time?

As of August 2025, prices for Honolulu to Chicago flights are approximately 6% cheaper 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	$205
Fastest flight time	8h 16m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Honolulu in the past 72 hours is $205. The best round-trip flight deal from Honolulu to Chicago found on momondo in the last 72 hours is $409.

The fastest flight from Honolulu to Chicago takes 8h 16m

Direct flights go from Honolulu to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

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 10h 15m.
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 August 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 48.54% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 11.65%, Airbus A330-200 with 9.71%, and Airbus A330 with 8.74%.
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 (35% of total bookings). The next most popular airlines are United Airlines (23%), Alaska Airlines (15%), 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 $231	Free Cancellation	Rating 8.0 7,981 reviews	Search Delta flights
Hawaiian Airlines	PriceFrom $335	Free Cancellation	Rating 7.8 2,611 reviews	Search Hawaiian Airlines flights
American Airlines	PriceFrom $426	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Alaska Airlines	PriceFrom $457	Free Cancellation	Rating 8.0 10,000 reviews	Search Alaska Airlines flights
Southwest	PriceFrom $606	Free Cancellation	Rating 8.0 4,246 reviews	Search Southwest flights
United Airlines	PriceFrom $780	Free Cancellation	Rating 7.4 8,900 reviews	Search United Airlines flights

United Airlines Flights From Honolulu to Chicago
United Airlines is one of the most popular airlines flying from Honolulu to Chicago, operating 7 flights/week on average for this route. A good United Airlines flight deal for Honolulu to Chicago starts from $780 round-trip, up to an average price of $1,082. Our users have rated United Airlines at 7.4/10.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

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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Find better results for your trip to the United States

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Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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Flights to San Franciscofrom $49

Flights to Washington, D.C.from $49

Flights to Bostonfrom $77

Flights to Atlantafrom $29

Flights to Dallasfrom $55

Flights to Seattlefrom $93

Flights to Denverfrom $49

Cheap flights from Honolulu to Chicago from $205

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 9/18. 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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Big names and deals

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Hawaiian Airlines flights from Honolulu to Chicago

Our best Hawaiian Airlines deals on Honolulu to Chicago flight tickets

Alaska Airlines flights from Honolulu to Chicago

Our best Alaska Airlines 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

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

What is the cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Honolulu, with most prices found around $561. If you’re not able to fly to Chicago in November, then October is your next best option. Flight prices from Honolulu to Chicago during October average around $573.

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 evening when prices are around $939.

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.

How have Honolulu to Chicago flight prices changed over time?

As of August 2025, prices for Honolulu to Chicago flights are approximately 6% cheaper when compared to flights at the same time last year.

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

Southwest, Hawaiian Airlines, and Alaska Airlines 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: 44% 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 San Diego (SAN) offer the lowest average round-trip price of $418.

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

Flights connecting via San Diego (SAN) have the shortest average one-way travel time: 10h 20m.

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 August 2025, there are 3 flights per day flying from Honolulu to Chicago. The most common time of day flights depart is 5:00PM, with 100% of flights taking off in the afternoon.

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

The number of flights available between Honolulu and Chicago is 21 per week as of August 2025. The most frequent departure day is Mon, with 14% 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

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

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