What airlines fly to Maui?

United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Maui from Chicago according to our data. United Airlines is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Maui. Keep in mind that there are 6 different airlines that fly to Maui on a routine basis, so you have a few additional options to choose from.

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

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

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

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

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

There are 6 operators available for flights from Chicago to Maui as of October 2025.

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

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 Maui.

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

The travel and health documents you'll need for your trip to Maui may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Maui. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$188 Cheap Flights from Chicago to Maui in 2025/26

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Find the cheapest flights from Chicago to Maui

Round-trip

One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

9:00 am - 10:59 pmORD-OGG

17h 59m1 stop

11:59 pm - 2:29 pmOGG-ORD

10h 30m1 stop

$425Alaska Airlines

Find Deal

Tue, Jan 27 - Sat, Feb 7

9:00 am - 6:51 amORD-OGG

25h 51m2 stops

6:00 am - 11:37 pmOGG-ORD

13h 37m2 stops

$426Alaska Airlines

Find Deal

Sat, Jan 17 - Wed, Jan 21

9:06 pm - 12:19 pmORD-OGG

19h 13m1 stop

4:04 pm - 12:13 amOGG-ORD

28h 09m1 stop

$427Multiple Airlines

Find Deal

Sat, Dec 6 - Sun, Dec 7

9:00 am - 8:30 pmORD-OGG

15h 30m2 stops

11:59 pm - 2:29 pmOGG-ORD

10h 30m1 stop

$428Alaska Airlines

Find Deal

Wed, Jan 28 - Tue, Feb 10

7:30 am - 7:15 pmORD-OGG

15h 45m2 stops

10:00 pm - 1:22 pmOGG-ORD

11h 22m1 stop

$429Delta

Find Deal

Sat, Jan 24 - Sat, Jan 31

9:00 am - 10:21 pmORD-OGG

17h 21m2 stops

11:59 pm - 2:29 pmOGG-ORD

10h 30m1 stop

$430Alaska Airlines

Find Deal

Tue, Jan 27 - Sat, Feb 7

9:06 pm - 12:19 pmORD-OGG

19h 13m1 stop

4:04 pm - 12:13 amOGG-ORD

28h 09m1 stop

$432Multiple Airlines

Find Deal

Sun, Dec 7 - Sun, Dec 14

6:45 am - 3:24 pmORD-OGG

12h 39m1 stop

10:00 pm - 1:22 pmOGG-ORD

11h 22m1 stop

$442Delta

Find Deal

Thu, Jan 1 - Thu, Jan 8

5:10 am - 2:50 pmMDW-OGG

13h 40m2 stops

9:25 pm - 2:45 pmOGG-MDW

13h 20m1 stop

$560Southwest

Find Deal

Tue, Feb 17 - Tue, Feb 24

5:15 am - 1:10 pmMDW-OGG

11h 55m1 stop

9:35 pm - 1:40 pmOGG-MDW

12h 05m1 stop

$563Southwest

Find Deal

Wed, Dec 3 - Wed, Dec 10

Delta flights from Chicago to Maui

Our best Delta deals on Chicago to Maui flight tickets

Delta

Jan 24

ORD7:30 amChicago O'Hare Intl

15h 45m

2 stops

OGG7:15 pmKahului

Jan 31

OGG10:00 pmKahului

11h 22m

1 stop

ORD1:22 pmChicago O'Hare Intl

$429

Find similar

Delta

Jan 1

ORD6:45 amChicago O'Hare Intl

12h 39m

1 stop

OGG3:24 pmKahului

Jan 8

OGG10:00 pmKahului

11h 22m

1 stop

ORD1:22 pmChicago O'Hare Intl

$442

Find similar

Delta

Jan 7

ORD7:30 amChicago O'Hare Intl

15h 45m

2 stops

OGG7:15 pmKahului

Jan 13

OGG9:05 pmKahului

16h 16m

2 stops

ORD5:21 pmChicago O'Hare Intl

$453

Find similar

Alaska Airlines flights from Chicago to Maui

Our best Alaska Airlines deals on Chicago to Maui flight tickets

Alaska Airlines

Jan 27

ORD9:00 amChicago O'Hare Intl

17h 59m

1 stop

OGG10:59 pmKahului

Feb 7

OGG11:59 pmKahului

10h 30m

1 stop

ORD2:29 pmChicago O'Hare Intl

$425

Find similar

Alaska Airlines

Jan 17

ORD9:00 amChicago O'Hare Intl

25h 51m

2 stops

OGG6:51 amKahului

Jan 21

OGG6:00 amKahului

13h 37m

2 stops

ORD11:37 pmChicago O'Hare Intl

$426

Find similar

Alaska Airlines

Jan 28

ORD9:00 amChicago O'Hare Intl

15h 30m

2 stops

OGG8:30 pmKahului

Feb 10

OGG11:59 pmKahului

10h 30m

1 stop

ORD2:29 pmChicago O'Hare Intl

$428

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 1/27

9:00 am-10:59 pm

1 stop17h 59m

Kahului

Sat 2/7

11:59 pm-2:29 pm

1 stop10h 30m

$425

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Sat 1/17

9:00 am-6:51 am

2 stops25h 51m

Kahului

Wed 1/21

6:00 am-11:37 pm

2 stops13h 37m

$426

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Sat 12/6

9:06 pm-12:19 pm

1 stop19h 13m

Kahului

Sun 12/7

4:04 pm-12:13 am

1 stop28h 09m

$427

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Wed 1/28

9:00 am-8:30 pm

2 stops15h 30m

Kahului

Tue 2/10

11:59 pm-2:29 pm

1 stop10h 30m

$428

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Sat 1/24

7:30 am-7:15 pm

2 stops15h 45m

Kahului

Sat 1/31

10:00 pm-1:22 pm

1 stop11h 22m

$429

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 1/27

9:00 am-10:21 pm

2 stops17h 21m

Kahului

Sat 2/7

11:59 pm-2:29 pm

1 stop10h 30m

$430

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Sun 12/7

9:06 pm-12:19 pm

1 stop19h 13m

Kahului

Sun 12/14

4:04 pm-12:13 am

1 stop28h 09m

$432

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Thu 1/1

6:45 am-3:24 pm

1 stop12h 39m

Kahului

Thu 1/8

10:00 pm-1:22 pm

1 stop11h 22m

$442

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 2/17

5:10 am-2:50 pm

2 stops13h 40m

Kahului

Tue 2/24

9:25 pm-2:45 pm

1 stop13h 20m

$560

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Wed 12/3

5:15 am-1:10 pm

1 stop11h 55m

Kahului

Wed 12/10

9:35 pm-1:40 pm

1 stop12h 05m

$563

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 Maui

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 Maui?

The month of October is, on average, the cheapest month to fly to Maui from Chicago, with most prices found around $591. If you are unable to visit Maui during the month of October, then departing from Chicago during the month September is also very affordable. Most momondo users find prices during this month for around $609.

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

On average, the least expensive day to fly to Maui from Chicago is on a Monday. momondo users have found tickets for Monday departures for as low as $1,033. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Maui is Friday, with ticket prices averaging around $1,142.

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

Flying to Maui from Chicago in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $531 when looking at flights departing in the afternoon. Flights to Maui are more costly in the morning, with an average ticket price of $1,096. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago to Maui flight route?

Fly from Chicago O'Hare Intl to Kahului for the best Chicago - Maui flight prices

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

You are more likely to see cheaper flights to Maui from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Maui for around $800 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Maui from Chicago for as low as $684 on momondo.

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

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

No. A direct flight is the cheapest option for a flight between Chicago to Maui.

Cheap Chicago to Maui flight deals and tips

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

Best Price Found	$522
Fastest flight time	9h 15m
Direct flights	Every day
Airports in Maui	1 airport

The best one-way flight to Maui from Chicago in the past 72 hours is $522. The best round-trip flight deal from Chicago to Maui found on momondo in the last 72 hours is $772.

The fastest flight from Chicago to Maui takes 9h 15m

Direct flights go from Chicago to Maui every day.

There is 1 airport near Maui: Kahului (OGG)

Search flight deals

When did momondo last update prices for flights from Chicago to Maui?
Prices for flights from Chicago to Maui were last updated today.
How many operators does momondo search for flights from Chicago to Maui?
There are 6 operators available for flights from Chicago to Maui as of October 2025.
How old do you have to be to fly from Chicago to Maui?
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 Maui.
What documentation or ID do you need to fly to Maui?
The travel and health documents you'll need for your trip to Maui may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Maui. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to Maui?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Maui is Boeing 737-800 (20.19% of total bookings). The next most popular plane models are Airbus A321neo (12.88%), Boeing 737-900 (9.32%), and Airbus A320neo (7.52%).

Best airlines flying from Chicago to Maui

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

Airline	Rating	Free Cancellation	Price
Hawaiian Airlines	PriceFrom $357	Free Cancellation	Rating 7.8 2,797 reviews	Search Hawaiian Airlines flights
Delta	PriceFrom $357	Free Cancellation	Rating 7.9 7,993 reviews	Search Delta flights
Alaska Airlines	PriceFrom $401	Free Cancellation	Rating 8.0 11,214 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $407	Free Cancellation	Rating 7.2 11,030 reviews	Search American Airlines flights
Southwest	PriceFrom $479	Free Cancellation	Rating 8.0 4,242 reviews	Search Southwest flights
United Airlines	PriceFrom $580	Free Cancellation	Rating 7.4 8,998 reviews	Search United Airlines flights

Why use momondo?

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

It is quick and easy to find Chicago to Maui flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Maui that suits you.

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

Flights from Chicago to Maui with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Maui.

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

Yes momondo offers price alerts on flights to Maui from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.