What airlines fly to Hawaii?

United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Hawaii from Chicago according to our data. United Airlines is the first choice among our users, with 37% of people opting to fly with this airline when traveling to Hawaii. Keep in mind that there are 6 different airlines that fly to Hawaii on a routine basis, so you have a few additional options to choose from.

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

As of August 2025, there are 2 flights per day flying from Chicago to Hawaii. The most common time of day flights depart is 9:00AM, with 100% of flights taking off at noon.

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

15 flights are operational weekly from Chicago to Hawaii as of August 2025. The most popular departure day for this route is Sat, with 20% of flights per week taking off on this day.

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

Alaska Airlines, Hawaiian Airlines, and Delta are the most popular carriers operating from Chicago to Hawaii

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

Prices for flights from Chicago to Hawaii were last updated today.

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

The number of operators available for flights from Chicago to Hawaii is 6 as of August 2025.

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

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Hawaii.

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

The travel and health documents required for your trip to Hawaii 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 Hawaii. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$165 Cheap Flights from Chicago to Hawaii in 2025

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Chicago to Hawaii

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

2:05 pm - 11:55 amORD-LIH

25h 50m1 stop

11:00 am - 1:59 pmLIH-ORD

22h 59m1 stop

$422Alaska Airlines

Find Deal

Thu, Jan 29 - Tue, Feb 10

7:10 am - 3:58 pmORD-LIH

13h 48m1 stop

2:15 pm - 5:16 amLIH-ORD

11h 01m1 stop

$423United Airlines

Find Deal

Sun, Oct 26 - Sun, Nov 2

7:00 am - 5:57 pmORD-LIH

15h 57m2 stops

12:52 pm - 1:54 pmLIH-ORD

20h 02m2 stops

$426Alaska Airlines

Find Deal

Thu, Oct 30 - Fri, Oct 31

6:00 am - 12:14 pmORD-LIH

11h 14m1 stop

1:45 pm - 8:45 amLIH-ORD

14h 00m2 stops

$429American Airlines

Find Deal

Sun, Sep 28 - Mon, Oct 6

6:00 am - 12:14 pmORD-LIH

11h 14m1 stop

1:44 pm - 6:01 amLIH-ORD

11h 17m1 stop

$443American Airlines

Find Deal

Sun, Sep 7 - Wed, Sep 10

7:10 am - 5:29 pmORD-KOA

15h 19m1 stop

9:30 pm - 1:20 pmKOA-ORD

10h 50m1 stop

$447Delta

Find Deal

Wed, Sep 17 - Wed, Sep 24

6:15 am - 5:35 pmORD-KOA

16h 20m2 stops

9:30 pm - 1:20 pmKOA-ORD

10h 50m1 stop

$452Delta

Find Deal

Wed, Sep 17 - Wed, Sep 24

1:00 pm - 10:16 pmORD-LIH

13h 16m2 stops

2:16 pm - 5:16 amLIH-ORD

11h 00m1 stop

$465United Airlines

Find Deal

Sat, Nov 15 - Sat, Nov 22

5:25 am - 1:05 pmMDW-OGG

11h 40m1 stop

9:25 pm - 3:00 pmOGG-MDW

13h 35m1 stop

$506Southwest

Find Deal

Thu, Dec 11 - Tue, Dec 16

5:15 am - 4:05 pmMDW-OGG

14h 50m2 stops

9:35 pm - 1:40 pmOGG-MDW

12h 05m1 stop

$511Southwest

Find Deal

Thu, Dec 11 - Tue, Dec 16

Southwest flights from Chicago to Hawaii

Our best Southwest deals on Chicago to Hawaii flight tickets

Southwest

Dec 11

MDW5:25 amChicago Midway

11h 40m

1 stop

OGG1:05 pmKahului

Dec 16

OGG9:25 pmKahului

13h 35m

1 stop

MDW3:00 pmChicago Midway

$506

Find similar

Southwest

Dec 11

MDW5:15 amChicago Midway

14h 50m

2 stops

OGG4:05 pmKahului

Dec 16

OGG9:35 pmKahului

12h 05m

1 stop

MDW1:40 pmChicago Midway

$511

Find similar

Southwest

Nov 5

MDW5:15 amChicago Midway

14h 55m

2 stops

LIH4:10 pmLihue

Nov 10

LIH9:10 pmLihue

12h 30m

1 stop

MDW1:40 pmChicago Midway

$533

Find similar

American Airlines flights from Chicago to Hawaii

Our best American Airlines deals on Chicago to Hawaii flight tickets

American Airlines

Sep 28

ORD6:00 amChicago O'Hare Intl

11h 14m

1 stop

LIH12:14 pmLihue

Oct 6

LIH1:45 pmLihue

14h 00m

2 stops

ORD8:45 amChicago O'Hare Intl

$429

Find similar

American Airlines

Sep 7

ORD6:00 amChicago O'Hare Intl

11h 14m

1 stop

LIH12:14 pmLihue

Sep 10

LIH1:44 pmLihue

11h 17m

1 stop

ORD6:01 amChicago O'Hare Intl

$443

Find similar

American Airlines

Sep 11

ORD6:00 amChicago O'Hare Intl

11h 14m

1 stop

LIH12:14 pmLihue

Sep 18

LIH9:40 pmLihue

13h 18m

1 stop

ORD3:58 pmChicago O'Hare Intl

$453

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Thu 1/29

2:05 pm-11:55 am

1 stop25h 50m

Lihue

Tue 2/10

11:00 am-1:59 pm

1 stop22h 59m

$422

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Sun 10/26

7:10 am-3:58 pm

1 stop13h 48m

Lihue

Sun 11/2

2:15 pm-5:16 am

1 stop11h 01m

$423

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Thu 10/30

7:00 am-5:57 pm

2 stops15h 57m

Lihue

Fri 10/31

12:52 pm-1:54 pm

2 stops20h 02m

$426

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Sun 9/28

6:00 am-12:14 pm

1 stop11h 14m

Lihue

Mon 10/6

1:45 pm-8:45 am

2 stops14h 00m

$429

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Sun 9/7

6:00 am-12:14 pm

1 stop11h 14m

Lihue

Wed 9/10

1:44 pm-6:01 am

1 stop11h 17m

$443

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 9/17

7:10 am-5:29 pm

1 stop15h 19m

Kona Intl

Wed 9/24

9:30 pm-1:20 pm

1 stop10h 50m

$447

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 9/17

6:15 am-5:35 pm

2 stops16h 20m

Kona Intl

Wed 9/24

9:30 pm-1:20 pm

1 stop10h 50m

$452

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Sat 11/15

1:00 pm-10:16 pm

2 stops13h 16m

Lihue

Sat 11/22

2:16 pm-5:16 am

1 stop11h 00m

$465

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 12/11

5:25 am-1:05 pm

1 stop11h 40m

Kahului

Tue 12/16

9:25 pm-3:00 pm

1 stop13h 35m

$506

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 12/11

5:15 am-4:05 pm

2 stops14h 50m

Kahului

Tue 12/16

9:35 pm-1:40 pm

1 stop12h 05m

$511

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 Chicago to Hawaii

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 Hawaii?

If you don’t want to visit Hawaii in October, then you should wait until January to fly from Chicago, when ticket prices are also cheap, with an average price of $633.

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

On average, the least expensive day to fly to Hawaii from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $1,072. However, this price may fluctuate depending on the airline, the season, and holidays. Flights from Chicago to Hawaii on a Friday will generally be more expensive and average around $1,143. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

Our data shows that the cheapest Chicago to Hawaii flights are usually those with departure times in the afternoon. Our users have found flights to Hawaii in the afternoon for as low as $631. Flights at noon are often more expensive with an average ticket price of $1,224.

What is the cheapest Chicago to Hawaii flight route?

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

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

You are more likely to see cheaper flights to Hawaii from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Hawaii for around $798 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Hawaii from Chicago for as low as $677 on momondo.

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

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

You could potentially save up to 17% on your flight if you consider stops on a Chicago to Hawaii flight.

Cheap Chicago to Hawaii flight deals and tips

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

Best Price Found	$462
Fastest flight time	8h 48m
Direct flights	Every day
Airports in Hawaii	2 airports

The best one-way flight to Hawaii from Chicago in the past 72 hours is $462. The best round-trip flight deal from Chicago to Hawaii found on momondo in the last 72 hours is $840.

The fastest flight from Chicago to Hawaii takes 8h 48m

Direct flights go from Chicago to Hawaii every day.

There are 2 airports near Hawaii: Honolulu (HNL), Kahului (OGG)

Search flight deals

When did momondo last update prices for flights from Chicago to Hawaii?
Prices for flights from Chicago to Hawaii were last updated today.
How many operators does momondo search for flights from Chicago to Hawaii?
The number of operators available for flights from Chicago to Hawaii is 6 as of August 2025.
How old do you have to be to fly from Chicago to Hawaii?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Hawaii.
What documentation or ID do you need to fly to Hawaii?
The travel and health documents required for your trip to Hawaii 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 Hawaii. 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 Chicago to Hawaii?
Based on momondo bookings for flights between Chicago and Hawaii, the leading plane model is Boeing 787-10 Dreamliner, making up 59.37% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 37.97%, Airbus A321neo with 0.73%, and Boeing 737-900 with 0.60%.

Best airlines flying from Chicago to Hawaii

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

Airline	Rating	Free Cancellation	Price
Hawaiian Airlines	PriceFrom $231	Free Cancellation	Rating 7.8 2,679 reviews	Search Hawaiian Airlines flights
Delta	PriceFrom $341	Free Cancellation	Rating 7.9 7,981 reviews	Search Delta flights
American Airlines	PriceFrom $357	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Alaska Airlines	PriceFrom $421	Free Cancellation	Rating 8.0 10,000 reviews	Search Alaska Airlines flights
Southwest	PriceFrom $424	Free Cancellation	Rating 8.0 4,243 reviews	Search Southwest flights
United Airlines	PriceFrom $435	Free Cancellation	Rating 7.4 8,940 reviews	Search United Airlines flights

Why use momondo?

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

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 Chicago to Hawaii for you.

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

Yes. All flights to Hawaii from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once all potential Chicago to Hawaii flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Yes. momondo can track prices for Chicago to Hawaii flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Hawaii 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.

Start using Trips

Find my bookings

Get notified when prices go down

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

1 adult

Sat 8/30

Sat 9/6

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Hawaii

Popular cities in Hawaii

Flights to New Yorkfrom $37

Flights to Los Angelesfrom $37

Flights to Miamifrom $38

Flights to Chicagofrom $37

Flights to Orlandofrom $37

Flights to Las Vegasfrom $33

Flights to San Franciscofrom $37

Flights to Washington, D.C.from $37

Flights to Bostonfrom $58

Flights to Atlantafrom $37

Flights to Dallasfrom $38

Flights to Seattlefrom $45

Cheap flights from Chicago to Hawaii from $165

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Hawaii departing on 9/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Chicago to Hawaii

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Southwest flights from Chicago to Hawaii

Our best Southwest deals on Chicago to Hawaii flight tickets

American Airlines flights from Chicago to Hawaii

Our best American Airlines deals on Chicago to Hawaii flight tickets

momondo Fare Finder

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

See travel insights to Hawaii from

How to get the cheapest flight ticket from Chicago to Hawaii

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 Hawaii?

If you don’t want to visit Hawaii in October, then you should wait until January to fly from Chicago, when ticket prices are also cheap, with an average price of $633.

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

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

Our data shows that the cheapest Chicago to Hawaii flights are usually those with departure times in the afternoon. Our users have found flights to Hawaii in the afternoon for as low as $631. Flights at noon are often more expensive with an average ticket price of $1,224.

What is the cheapest Chicago to Hawaii flight route?

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

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

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

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

You could potentially save up to 17% on your flight if you consider stops on a Chicago to Hawaii flight.

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

Alaska Airlines, Hawaiian Airlines, and Delta are the most popular carriers operating from Chicago to Hawaii

What airlines fly to Hawaii?

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

As of August 2025, there are 2 flights per day flying from Chicago to Hawaii. The most common time of day flights depart is 9:00AM, with 100% of flights taking off at noon.

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

15 flights are operational weekly from Chicago to Hawaii as of August 2025. The most popular departure day for this route is Sat, with 20% of flights per week taking off on this day.

Cheap Chicago to Hawaii flight deals and tips

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

Best Price Found

Fastest flight time

Direct flights

Airports in Hawaii

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

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

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

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

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

Best airlines flying from Chicago to Hawaii

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

Why use momondo?

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

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

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

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

An easier way to manage your Hawaii 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 Hawaii

Popular cities in Hawaii

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