HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Maui

Cheap flights from Chicago (CHI) to Maui

CHI — OGG
Dec 12 — Dec 191
Sat 12/12
Sat 12/19
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Maui 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.

Find flight deals from Chicago to Maui

Popular in

December

Cheapest in

May

Average price

$754

Good round-trip deal

$755 or less

Good one-way deal

$392 or less
Highest demand for flights based on searches. 3% potential increase in price ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Maui.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Maui.
Search Deals

Cheapflights Insights

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

How far ahead should I book a flight from Chicago to Maui?

The best time to book flights from Chicago to Maui is 83 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, February is the cheapest month in which you can book a flight from Chicago to Maui (average of $688). Flying from Chicago to Maui in December is currently the most expensive (average of $1,181). 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 FUK?

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

Reviews of airlines servicing Maui

Get a feel of what it's like to fly with Southwest,Alaska Airlines, andDelta from Chicago to Maui by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,219 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
4.0
Okay

Steven,Sep 2026

OGG - HNL

It was a red eye overnight which I prefer. But this time the seat was SOOOO uncomfortable that sleeping was difficult and painful
Southwest
8.0
Very good
4,219 reviews
Southwest
8.0
Very good
4,219 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
4.0
Okay

Steven,Sep 2026

OGG - HNL

It was a red eye overnight which I prefer. But this time the seat was SOOOO uncomfortable that sleeping was difficult and painful
Alaska Airlines
7.9
Good
13,158 reviews
Southwest
8.0
Very good
4,219 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
4.0
Okay

Steven,Sep 2026

OGG - HNL

It was a red eye overnight which I prefer. But this time the seat was SOOOO uncomfortable that sleeping was difficult and painful
Delta
7.8
Good
8,710 reviews
Southwest
8.0
Very good
4,219 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
4.0
Okay

Steven,Sep 2026

OGG - HNL

It was a red eye overnight which I prefer. But this time the seat was SOOOO uncomfortable that sleeping was difficult and painful
United Airlines
7.3
Good
10,482 reviews
Southwest
8.0
Very good
4,219 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
4.0
Okay

Steven,Sep 2026

OGG - HNL

It was a red eye overnight which I prefer. But this time the seat was SOOOO uncomfortable that sleeping was difficult and painful
American Airlines
7.0
Good
12,228 reviews
Southwest
8.0
Very good
4,219 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
4.0
Okay

Steven,Sep 2026

OGG - HNL

It was a red eye overnight which I prefer. But this time the seat was SOOOO uncomfortable that sleeping was difficult and painful

Related info for your journey

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

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $179. Users have also found prices from $202 and $262 on Delta and Alaska Airlines, respectively.

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

    Most travelers choose Chicago O'Hare Intl - Kahului, Chicago Midway - Kahului or Chicago O'Hare Intl - Hana when deciding on the best route from Chicago to Maui.

  • What are the cheapest flights from Chicago to Maui?

    Looking at all options, your cheapest flight can be booked for $283. While the most popular route (Chicago O'Hare Intl - Kahului) can be booked for $577 on average, our data indicates $743 when flying from Chicago to Maui.

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

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

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

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

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

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

    Currently, February is the cheapest month in which you can book a flight from Chicago to Maui (average of $688). Flying from Chicago to Maui in December is currently the most expensive (average of $1,181). 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

Top 5 airlines flying from Chicago to Maui

AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$355Average$579FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$361Average$677FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$433Average$759FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$626Average$817FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$660Average$1,032FlexibilityNo cancel feeOn-time69%

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.