HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$258+ Cheap flights from Maui to Chicago (CHI)

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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Maui to Chicago 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 Maui to Chicago

Keep the following information in mind while searching for Maui to Chicago flight deals. Data was last updated May 1, 2025.

Round-trip from

$665
(Hawaiian Airlines)

One-way from

$258
(Delta)

Good round-trip deal

$560 or less

Good one-way deal

$465 or less
From Maui to Chicago (CHI)
Search Deals
One-way flight from Maui to Chicago (CHI)
Search Deals
Price to beat on a round-trip flight from Maui to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Maui to Chicago (CHI).
Search Deals

Find flight deals from Maui to Chicago

Cheapest flights from Maui to Chicago
Explore the most affordable flight options available from Maui to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

This Hawaiian Airlines deal was found by Cheapflights users on 4/30. 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.
Tue 6/2410:34 pmOGG - ORD
1 stop13h 25mHawaiian Airlines
Wed 7/301:03 pmORD - OGG
1 stop13h 31mHawaiian Airlines
Deal found 4/30$665
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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 6/249:00 pmOGG - ORD
2 stops14h 59mAlaska Airlines
Wed 7/306:00 amORD - OGG
1 stop12h 40mAlaska Airlines
Deal found 4/30$671
This Delta deal was found by Cheapflights users on 4/30. 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.
Thu 5/159:30 pmOGG - MDW
2 stops16h 15mDelta
Mon 5/199:20 amMDW - OGG
2 stops15h 05mDelta
Deal found 4/30$822
This Delta deal was found by Cheapflights users on 4/30. 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.
Thu 5/158:50 pmOGG - ORD
2 stops14h 55mDelta
Mon 5/197:10 amORD - OGG
2 stops17h 15mDelta
Deal found 4/30$822

Cheapflights Fare Finder

Customize your flight search to find flights from Maui to Chicago 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 May 1, 2025.
Use the filters below to find and compare flights from Maui to Chicago that are best for you.

Fly from

Maui

Fly to

Chicago

Route

Depart

Return

Price

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 6/24

10:34 pm-4:59 pm

1 stop13h 25m

Chicago O'Hare Intl

Wed 7/30

1:03 pm-9:34 pm

1 stop13h 31m

$665

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 6/24

9:00 pm-4:59 pm

2 stops14h 59m

Chicago O'Hare Intl

Wed 7/30

6:00 am-1:40 pm

1 stop12h 40m

$671

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 5/15

9:30 pm-6:45 pm

2 stops16h 15m

Chicago Midway

Mon 5/19

9:20 am-7:25 pm

2 stops15h 05m

$822

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 5/15

8:50 pm-4:45 pm

2 stops14h 55m

Chicago O'Hare Intl

Mon 5/19

7:10 am-7:25 pm

2 stops17h 15m

$822

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 5/20

9:30 pm-5:25 pm

1 stop14h 55m

$258

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 5/19

11:13 pm-6:55 pm

2 stops14h 42m

$266

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Thu 8/14

8:30 pm-1:25 pm

1 stop11h 55m

$308

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 5/19

11:55 am-5:40 am

1 stop12h 45m

$308

KahuluiChicago

OGG - MDW

OGGMDW

Kahului

Tue 5/20

8:50 pm-5:45 pm

2 stops15h 55m

$309

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Sat 5/31

1:49 pm-5:53 am

1 stop11h 04m

$334

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 13 results
1
2

Best time to book a flight from Maui to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Maui 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 Maui to Chicago

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

Currently, August is the cheapest month in which you can book a flight from Maui to Chicago (average of $245). Flying from Maui to Chicago in March is currently the most expensive (average of $321). 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 FUK to CHI?

Find hourly flight availability from Maui to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 1, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Maui to Chicago as you normally would.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated May 1, 2025.
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,972 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,294 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,934 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,408 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Related info for your journey

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

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

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $258. Users have also found prices from $266 and $308 on Alaska Airlines and Southwest, respectively.

  • What are the cheapest flights from Maui to Chicago?

    The cheapest flight price from Maui to Chicago is $320. On average you can expect to pay $716. The most popular route, (Kahului - Chicago O'Hare Intl), can usually be booked for $548.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Maui to Chicago 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 Maui to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Maui to Chicago (average of $245). Flying from Maui to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Maui?

Book flights to Maui if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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.

Top 5 airlines flying from Maui to Chicago

Discover the top 5 airlines that operate flights from Maui to Chicago. 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$282Average$541FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$322Average$802FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$349Average$538FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$432Average$727FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$495Average$637FlexibilityNo cancel feeOn-time75%

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.