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Maui

Cheap flights from Chicago (CHI) to Maui

CHI — OGG
Oct 28 — Nov 41
Wed 10/28
Wed 11/4
1 adult, Economy
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Find flight deals from Chicago to Maui

Popular in

December

Cheapest in

January

Average price

$711

Good round-trip deal

$680 or less

Good one-way deal

$457 or less
Highest demand for flights based on searches. 6% potential increase in price ($55 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($33 potential savings vs. average RT price).
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Average for round-trip flights in September 2026
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Price to beat on a round-trip flight from Chicago (CHI) to Maui.
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Price to beat on a one-way flight from Chicago (CHI) to Maui.
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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 50 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, January is the cheapest month in which you can book a flight from Chicago to Maui (average of $676). Flying from Chicago to Maui in December is currently the most expensive (average of $1,210). 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
4,200 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

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
4,200 reviews
Southwest
8.0
Very good
4,200 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

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
12,981 reviews
Southwest
8.0
Very good
4,200 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

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
8,606 reviews
Southwest
8.0
Very good
4,200 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

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
7.4
Good
10,247 reviews
Southwest
8.0
Very good
4,200 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

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
12,098 reviews
Southwest
8.0
Very good
4,200 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Overall

8.0

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 $273 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 - Kapalua West Maui 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 $252. While the most popular route (Chicago O'Hare Intl - Kahului) can be booked for $567 on average, our data indicates $1,490 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, January is the cheapest month in which you can book a flight from Chicago to Maui (average of $676). Flying from Chicago to Maui in December is currently the most expensive (average of $1,210). 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
Alaska AirlinesCheapest$352Average$660FlexibilityNo cancel feeOn-time75%
DeltaCheapest$355Average$575FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$431Average$732FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$626Average$817FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$705Average$1,025FlexibilityNo cancel feeOn-time69%

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