HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Hawaii

$205+ Cheap flights from Chicago (CHI) to Hawaii

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HNL
Aug 2 — Aug 91
Sat 8/2
Sat 8/9
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Hawaii with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Hawaii

Keep the following information in mind while searching for Chicago to Hawaii flight deals. Data was last updated July 28, 2025.

Round-trip from

$409
(Alaska Airlines)

One-way from

$205
(Hawaiian Airlines)

Popular in

December

Cheapest in

February

Average price

$866

Good round-trip deal

$922 or less

Good one-way deal

$520 or less
From Chicago (CHI) to Hawaii
Search Deals
One-way flight from Chicago (CHI) to Hawaii
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Hawaii.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Hawaii.
Search Deals

Find flight deals from Chicago to Hawaii

Cheapest flights from Chicago to Hawaii
Explore the most affordable flight options available from Chicago to Hawaii. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 28, 2025.

This Alaska Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/99:00 amORD - LIH
1 stop33h 46mAlaska Airlines
Fri 12/1211:00 amLIH - ORD
1 stop32h 10mAlaska Airlines
Deal found 7/28$405
This Alaska Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/108:00 amORD - KOA
1 stop13h 00mAlaska Airlines
Fri 9/1912:16 pmKOA - ORD
1 stop11h 44mAlaska Airlines
Deal found 7/26$409
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/96:00 amORD - LIH
1 stop11h 14mAmerican Airlines
Tue 9/161:44 pmLIH - ORD
1 stop11h 28mAmerican Airlines
Deal found 7/26$410
This Alaska Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/49:20 amORD - ITO
2 stops15h 10mAlaska Airlines
Mon 11/109:00 pmITO - ORD
2 stops17h 59mAlaska Airlines
Deal found 7/27$419
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/177:10 amORD - KOA
1 stop15h 19mDelta
Thu 9/259:30 pmKOA - ORD
1 stop14h 45mDelta
Deal found 7/26$423
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/27:37 amORD - LIH
1 stop16h 26mDelta
Sun 11/910:45 pmLIH - ORD
1 stop10h 43mDelta
Deal found 7/27$423
This American Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/36:00 amORD - OGG
1 stop10h 44mAmerican Airlines
Tue 9/99:29 pmOGG - ORD
2 stops12h 41mAmerican Airlines
Deal found 7/28$466
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/37:45 amORD - OGG
2 stops14h 23mDelta
Tue 9/99:10 pmOGG - ORD
2 stops15h 20mDelta
Deal found 7/28$472
This Alaska Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/309:20 amORD - HNL
1 stop12h 35mAlaska Airlines
Wed 11/129:00 amHNL - ORD
1 stop10h 59mAlaska Airlines
Deal found 7/28$474
This Alaska Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/107:55 pmORD - OGG
1 stop22h 40mAlaska Airlines
Sat 12/1311:20 pmOGG - ORD
1 stop19h 50mAlaska Airlines
Deal found 7/27$475
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/266:40 amMDW - OGG
1 stop11h 20mSouthwest
Tue 9/28:25 pmOGG - MDW
1 stop11h 50mSouthwest
Deal found 7/27$481
This Hawaiian Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/152:54 pmORD - OGG
1 stop11h 56mHawaiian Airlines
Wed 11/198:45 amOGG - ORD
1 stop11h 39mHawaiian Airlines
Deal found 7/28$484

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Hawaii that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 28, 2025.
Use the filters below to find and compare flights from Chicago to Hawaii that are best for you.

Fly from

Chicago

Fly to

Hawaii

Route

Depart

Return

Price

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 9/10

8:00 am-4:00 pm

1 stop13h 00m

Kona Intl

Fri 9/19

12:16 pm-5:00 am

1 stop11h 44m

$409

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Tue 9/9

6:00 am-12:14 pm

1 stop11h 14m

Lihue

Tue 9/16

1:44 pm-6:12 am

1 stop11h 28m

$410

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Tue 9/9

1:01 pm-9:30 pm

1 stop13h 29m

Lihue

Tue 12/9

11:00 am-6:55 pm

1 stop27h 55m

$414

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 9/17

7:10 am-5:29 pm

1 stop15h 19m

Kona Intl

Thu 9/25

9:30 pm-5:15 pm

1 stop14h 45m

$423

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Sat 9/27

12:05 pm-10:17 pm

2 stops15h 12m

Hilo Intl

Mon 9/29

7:00 pm-4:49 pm

2 stops16h 49m

$464

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Wed 9/3

6:00 am-11:44 am

1 stop10h 44m

Kahului

Tue 9/9

9:29 pm-3:10 pm

2 stops12h 41m

$466

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Wed 9/3

7:45 am-5:08 pm

2 stops14h 23m

Kahului

Tue 9/9

9:10 pm-5:30 pm

2 stops15h 20m

$472

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Wed 10/15

8:20 am-9:05 pm

1 stop17h 45m

Honolulu

Wed 10/29

12:35 pm-6:59 pm

1 stop25h 24m

$472

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 9/17

9:20 am-8:30 pm

2 stops16h 10m

Honolulu

Wed 9/24

4:10 pm-12:28 pm

2 stops15h 18m

$474

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Sat 10/25

10:00 am-10:05 pm

1 stop17h 05m

Kahului

Sat 11/8

11:59 pm-11:59 pm

1 stop20h 00m

$478

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/25

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Chicago to Hawaii

Have a flexible travel schedule? Discover the best time to fly to Hawaii from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Hawaii

What is the cheapest month to book a flight from Chicago to Hawaii?

Currently, November is the cheapest month in which you can book a flight from Chicago to Hawaii (average of $469). Flying from Chicago to Hawaii in June is currently the most expensive (average of $687). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to HI?

Find hourly flight availability from Chicago to Hawaii. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 28, 2025.

When flying from Chicago to Hawaii, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Chicago to Hawaii

Explore weekly flight availability from Chicago to Hawaii. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 28, 2025.

The most flights from CHI to USHI are scheduled on a Monday (3 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

How much does it cost to fly round-trip from Chicago to Hawaii?

Reviews of airlines servicing Hawaii

Get insights into the airlines that provide service to Hawaii. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Hawaii. Reviews last updated July 28, 2025.
See what other customers who have flown with Alaska Airlines, Southwest, and Delta from Chicago to Hawaii have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,237 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,971 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Hawaiian Airlines
7.8
Good
2,604 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,893 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

Chicago to Hawaii Travel Guide

When you're looking for a tropical escape from the hustle and bustle of the Windy City, Hawaii makes a great choice. With their perfect weather and laid-back lifestyle, the Hawaiian Islands can help you relax and recharge. Whether you want to kick back with a book on Hulopoe Beach or hike through the jungle on the Manoa Falls Trail, the friendly locals and well-developed infrastructure make your journey a breeze. A direct flight between Chicago and Hawaii reduces travel time, so you can reach the islands quickly.

Hawaii is the perfect island vacation spot for travelers from Chicago: it's accessible by a direct flight, and it requires no passport or customs. Once you arrive on Oahu or Maui, you'll be greeted with balmy breezes and smiling locals. If you're longing for sunshine and sunbathing, head for the islands' many stunning beaches. On Maui, try Kaanapali Beach or Wailea Beach, and on the Big Island, check out the unusual Punaluu Black Sand Beach. If you're visiting Honolulu, the famous Waikiki Beach is a must-see. When you're ready to get out into the wild, check out the lava flows at Hawaii Volcanoes National Park or hike through the otherworldly landscapes of Haleakala National Park. Cool off in Hanakapiai Falls, or marvel at the steep cliffs of the Na Pali Coast.

If you're dreaming of a vacation to sunny Hawaii, start planning today. Use the Cheapflights search engine to browse a wide variety of fares on nonstop flights between Chicago and Honolulu or Kahului.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Hawaii. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What alternative but sustainable transport option can I use to travel from Chicago to Hawaii?

    Hawaii is situated about 4194 mi from Chicago. Therefore, flights offer the most sustainable mode that passengers can use to travel from their origin to their destination. This is so because flights offer direct transport services to many passengers in one trip. Unfortunately, there are no other sustainable modes of getting from Chicago to Hawaii because of the Pacific Ocean crossing. Therefore, flights are the only sustainable way to get you to Hawaii from Chicago.

  • What can I do to reduce my carbon footprint when flying from Chicago to Hawaii?

    If you are a passenger looking to travel sustainably from Chicago to Hawaii, consider settling for a direct flight. The route is serviced by several direct flights as well as others with one or two stopovers. Direct flights utilize less fuel for the journey than those with one or more stopovers. This is so because flights involving several stopovers do not use the shortest route and consume more fuel when landing and taking off from multiple destinations. Therefore, fly directly from the origin to the destination to reduce your carbon footprint.

  • What information is necessary for identifying a sustainable airline for my trip from Chicago to Hawaii?

    If you need to identify a sustainable airline for flying from Chicago to Hawaii, think about looking for the SAF certification. SAF-certified airlines have engines that are designed to use fossil-based fuel rather than conventional petroleum-based fuel. Fossil fuel is more sustainable because its production does not emit carbon gases into the atmosphere as opposed to petroleum-based fuel. Therefore, flying in a SAF-certified airline is a great way to promote the sustainability of the environment.

  • How long is the flight from Chicago to Hawaii?

    When you're traveling from Chicago, it's possible to fly direct to two different cities in Hawaii. The flight to Honolulu lasts approximately nine hours from gate to gate, and the flight to Kahului takes slightly longer than nine hours.

  • Which airlines operate flights from Chicago to Hawaii?

    United Airlines is the only carrier that flies direct between Chicago and the state of Hawaii. United flies to the island of Oahu and the island of Maui.

  • How frequent are flights between Chicago and Hawaii?

    There is one flight per day from Chicago to Honolulu, and one daily flight to the city of Kahului. Both flights leave from O'Hare International Airport.

  • Which airports serve Chicago to Hawaii?

    Direct flights from Chicago to Hawaii leave from the O'Hare International Airport. If you're visiting Honolulu, you'll land at the Honolulu International Airport, and if you are traveling to Kahului, expect to land at the Kahului Airport. All three airports provide a variety of ground transportation options.

  • Which direct flight route between Chicago and Hawaii is cheapest?

    You can get the best fares when traveling between Chicago and Honolulu, with flights to Kahului close behind. Prices drop dramatically when you book your departing and returning flights together on a round-trip ticket.

  • How busy are the airports in Chicago and Hawaii?

    Flying to Hawaii from Chicago means you will start your journey at O'Hare International Airport (ORD) on the northwest side of the city. O’Hare is in the top 10 busiest airports in the world and is a major hub for airlines like United and American Airlines. In Hawaii, the three largest international airports are Hilo International Airport (ITO) which serves as the destination airport for most of east Hawaii. The next is Daniel K. Inouye International Airport, also known as Honolulu International Airport (HNL), and is also located on the northwest side of the city center. Honolulu International Airport is the largest airport serving Hawaii and the major hub for Hawaiian Airlines. Lastly, is Ellison Onizuka Kona International Airport (KOA) or Kona International Airport. This airport serves the west side of Hawaii.

  • Which airlines fly directly from Chicago to Hawaii?

    Unfortunately, direct flights from Chicago to Hawaii are not currently available, but there are plenty of flight options to choose from. If you fly from Chicago to Hilo International Airport, you will most likely have one stopover. Most flights are operated by United Airlines on this common flight route. From Chicago to Honolulu, the major airline most commonly operating this route is Delta Airlines. Finally, if you’re headed to the west area of Hawaii, you’ll most likely fly into Kona International Airport. The main airline operating this flight path is American Airlines. All these airlines have differing hub cities, which means the stopover city will be unique to the airline that is operating the flight.

  • What are the stopover options between Chicago to Hawaii?

    Flights from Chicago to Hawaii include at least one stopover, and that stopover city depends on what airlines you’re flying with and which destination you land at in Hawaii. From Hilo International from Chicago, you will most likely have a stopover in Los Angeles (LAX) before heading to your final destination. If you’re flying into Honolulu International Airport (HNL) with Delta Airlines, there are a few common stopover cities including Seattle, Salt Lake City, and Atlanta. Flights with American Airlines from Chicago to Kona International Airport have stopovers in cities including Phoenix and Dallas.

  • Do I need a passport or visa to fly from Chicago to Hawaii?

    No, you will not need a passport or visa as an American citizen heading from Chicago to Hawaii. You will however need a valid driver’s license from the state you live in. If you don’t have a driver’s license you will need a valid identification card from your home state. Both your driver’s license or identification card will need to be valid for the length of your travel, otherwise, you will need to renew either before heading on your journey.

  • What are the cheapest airlines to fly from Chicago to Hawaii one-way?

    To fly one-way, consider booking your trip with Hawaiian Airlines, which is currently one of the cheapest options available, starting at $205. American Airlines flights start at $211 while deals on Alaska Airlines start at $217 one-way.

  • What are the most popular routes from Chicago to Hawaii?

    While some choose either Chicago O'Hare Intl - Kahului or Chicago Midway - Honolulu, Chicago O'Hare Intl - Honolulu is the most popular route from Chicago to Hawaii.

  • What are the cheapest flights from Chicago to Hawaii?

    Looking at all options, your cheapest flight can be booked for $412. While the most popular route (Chicago O'Hare Intl - Honolulu) can be booked for $444 on average our data indicates $2,111 when flying from Chicago to Hawaii.

  • Can I find deals for flights from Chicago to Hawaii that include hotel bookings?

    Yes. In addition to deals on Chicago to Hawaii flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Hawaii?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Hawaii.

  • Can I find deals for business class flights from Chicago to Hawaii?

    Yes. Cheapflights offers flight deals from Chicago to Hawaii by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Hawaii?

    Currently, November is the cheapest month in which you can book a flight from Chicago to Hawaii (average of $469). Flying from Chicago to Hawaii in June is currently the most expensive (average of $687). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Hawaii

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Newark flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to Seattle flights
O'Hare Intl to Denver flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Orlando flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Boston flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Miami flights
Midway to Las Vegas flights
Midway to Newark flights
Midway to LaGuardia flights
O'Hare Intl to Tampa flights
O'Hare Intl to San Diego flights
O'Hare Intl to Philadelphia flights
O'Hare Intl to Portland flights
O'Hare Intl to Reagan-National flights
St. Louis to Las Vegas flights
Midway to John F Kennedy Intl flights
O'Hare Intl to Ontario flights
O'Hare Intl to Honolulu flights
O'Hare Intl to Atlanta flights
O'Hare Intl to Salt Lake City flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to Dulles Intl flights
Midway to Dallas/Fort Worth flights
O'Hare Intl to Austin flights
O'Hare Intl to Baltimore flights
O'Hare Intl to Nashville flights
Midway to Orlando flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to New Orleans flights
Midway to Seattle flights
St. Louis to Seattle flights
Midway to Atlanta flights
O'Hare Intl to George Bush Intcntl flights
Midway to Miami flights
Midway to Tampa flights
O'Hare Intl to Charlotte flights
O'Hare Intl to Love Field flights
O'Hare Intl to Portland flights
O'Hare Intl to Hobby flights
O'Hare Intl to Knoxville flights
O'Hare Intl to Charleston flights
O'Hare Intl to San Antonio flights

Top 6 airlines flying from Chicago to Hawaii

Discover the top 6 airlines that operate flights from Chicago to Hawaii. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$316Average$566FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$346Average$739FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$349Average$663FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$420Average$714FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$424Average$771FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$425Average$937FlexibilityNo cancel feeOn-time69%

Helpful tips for your next trip to Hawaii

Get useful tips and recommendations to enhance your travel experience on your next trip to Hawaii. Learn about must-visit attractions, local customs, transportation options, weather conditions, and other valuable tips to make your trip more enjoyable and hassle-free.
  • American Airlines is one of the airlines that gets passengers from Chicago to Hawaii. It does so sustainably by ensuring it has fuel-efficient planes in its fleet servicing the route.
  • Chicago is committed to promoting environmental sustainability. As a result, the city requires the airports operating in the region to monitor their carbon emissions to ensure they are within acceptable standards.
  • The O’Hare International Airport (ORD) will be your departure airport if you are traveling from Chicago to Hawaii. The airport is known to have an elaborate waste collection mechanism that sorts plastics and other non-biodegradable materials ready for reuse or recycling.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.