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

How many flights depart from Chicago to Maui on average per week?

As of July 2025, there are 2 flights per week flying from Chicago to Maui. The most common day of the week flights depart is Wed, with 50% of flights taking off on this day.

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 July 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.

$194 Cheap Flights from Chicago to Maui in 2025

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Find the cheapest flights from Chicago to Maui

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

8:20 am - 10:05 pmORD-OGG

18h 45m1 stop

11:09 pm - 11:59 pmOGG-ORD

19h 50m1 stop

$367Alaska Airlines

Find Deal

Tue, Oct 14 - Tue, Oct 21

8:20 am - 10:05 pmORD-OGG

18h 45m1 stop

6:00 am - 11:59 pmOGG-ORD

12h 59m2 stops

$372Alaska Airlines

Find Deal

Tue, Oct 14 - Tue, Oct 21

7:59 pm - 10:05 pmORD-OGG

31h 06m1 stop

11:09 pm - 2:50 pmOGG-ORD

10h 41m1 stop

$376Alaska Airlines

Find Deal

Tue, Oct 14 - Tue, Oct 21

2:59 pm - 10:48 pmORD-OGG

11h 49m1 stop

11:20 pm - 11:10 pmOGG-ORD

19h 50m1 stop

$377Alaska Airlines

Find Deal

Tue, Dec 9 - Mon, Dec 15

8:20 am - 10:05 pmORD-OGG

18h 45m1 stop

6:00 am - 11:59 pmOGG-ORD

12h 59m2 stops

$383Alaska Airlines

Find Deal

Wed, Oct 22 - Wed, Oct 29

9:00 am - 10:48 pmORD-OGG

17h 48m1 stop

11:20 pm - 1:59 pmOGG-ORD

10h 39m1 stop

$388Alaska Airlines

Find Deal

Tue, Dec 9 - Fri, Dec 12

6:10 am - 12:25 pmMDW-OGG

11h 15m1 stop

8:30 pm - 12:15 pmOGG-MDW

10h 45m1 stop

$480Southwest

Find Deal

Tue, Aug 19 - Tue, Sep 2

7:50 am - 4:35 pmMDW-OGG

13h 45m2 stops

8:25 pm - 11:45 amOGG-MDW

10h 20m1 stop

$485Southwest

Find Deal

Tue, Aug 26 - Tue, Sep 2

6:40 am - 1:00 pmMDW-OGG

11h 20m1 stop

8:25 pm - 2:30 pmOGG-MDW

13h 05m1 stop

$499Southwest

Find Deal

Tue, Aug 26 - Thu, Sep 4

6:00 am - 3:24 pmMDW-OGG

13h 24m1 stop

10:10 pm - 6:07 pmOGG-MDW

15h 57m2 stops

$612Delta

Find Deal

Sun, Nov 16 - Sun, Nov 23

Alaska Airlines flights from Chicago to Maui

Our best Alaska Airlines deals on Chicago to Maui flight tickets

Alaska Airlines

Oct 14

ORD8:20 amChicago O'Hare Intl

18h 45m

1 stop

OGG10:05 pmKahului

Oct 21

OGG11:09 pmKahului

19h 50m

1 stop

ORD11:59 pmChicago O'Hare Intl

$367

Find similar

Alaska Airlines

Oct 14

ORD8:20 amChicago O'Hare Intl

18h 45m

1 stop

OGG10:05 pmKahului

Oct 21

OGG6:00 amKahului

12h 59m

2 stops

ORD11:59 pmChicago O'Hare Intl

$372

Find similar

Alaska Airlines

Oct 14

ORD7:59 pmChicago O'Hare Intl

31h 06m

1 stop

OGG10:05 pmKahului

Oct 21

OGG11:09 pmKahului

10h 41m

1 stop

ORD2:50 pmChicago O'Hare Intl

$376

Find similar

Southwest flights from Chicago to Maui

Our best Southwest deals on Chicago to Maui flight tickets

Southwest

Aug 19

MDW6:10 amChicago Midway

11h 15m

1 stop

OGG12:25 pmKahului

Sep 2

OGG8:30 pmKahului

10h 45m

1 stop

MDW12:15 pmChicago Midway

$480

Find similar

Southwest

Aug 26

MDW7:50 amChicago Midway

13h 45m

2 stops

OGG4:35 pmKahului

Sep 2

OGG8:25 pmKahului

10h 20m

1 stop

MDW11:45 amChicago Midway

$485

Find similar

Southwest

Aug 26

MDW6:40 amChicago Midway

11h 20m

1 stop

OGG1:00 pmKahului

Sep 4

OGG8:25 pmKahului

13h 05m

1 stop

MDW2:30 pmChicago Midway

$499

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Fly from

Fly to

Route

Depart

Return

Price

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 10/14

8:20 am-10:05 pm

1 stop18h 45m

Kahului

Tue 10/21

11:09 pm-11:59 pm

1 stop19h 50m

$367

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 10/14

8:20 am-10:05 pm

1 stop18h 45m

Kahului

Tue 10/21

6:00 am-11:59 pm

2 stops12h 59m

$372

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 10/14

7:59 pm-10:05 pm

1 stop31h 06m

Kahului

Tue 10/21

11:09 pm-2:50 pm

1 stop10h 41m

$376

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 12/9

2:59 pm-10:48 pm

1 stop11h 49m

Kahului

Mon 12/15

11:20 pm-11:10 pm

1 stop19h 50m

$377

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Wed 10/22

8:20 am-10:05 pm

1 stop18h 45m

Kahului

Wed 10/29

6:00 am-11:59 pm

2 stops12h 59m

$383

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 12/9

9:00 am-10:48 pm

1 stop17h 48m

Kahului

Fri 12/12

11:20 pm-1:59 pm

1 stop10h 39m

$388

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 8/19

6:10 am-12:25 pm

1 stop11h 15m

Kahului

Tue 9/2

8:30 pm-12:15 pm

1 stop10h 45m

$480

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 8/26

7:50 am-4:35 pm

2 stops13h 45m

Kahului

Tue 9/2

8:25 pm-11:45 am

1 stop10h 20m

$485

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Tue 8/26

6:40 am-1:00 pm

1 stop11h 20m

Kahului

Thu 9/4

8:25 pm-2:30 pm

1 stop13h 05m

$499

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Sun 11/16

6:00 am-3:24 pm

1 stop13h 24m

Kahului

Sun 11/23

10:10 pm-6:07 pm

2 stops15h 57m

$612

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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 September is, on average, the cheapest month to fly to Maui from Chicago, with most prices found around $528. If you are unable to visit Maui during the month of September, then departing from Chicago during the month November is also very affordable. Most momondo users find prices during this month for around $529.

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 $1,043. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Maui is Wednesday, with ticket prices averaging around $1,327.

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 $1,131. 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 $776 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 $632 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	$194
Fastest flight time	8h 48m
Direct flights	Mon, Tue, Wed, Fri, Sat and Sun
Airports in Maui	1 airport

The best one-way flight to Maui from Chicago in the past 72 hours is $194. The best round-trip flight deal from Chicago to Maui found on momondo in the last 72 hours is $367.

The fastest flight from Chicago to Maui takes 8h 48m

Direct flights go from Chicago to Maui on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. The only airline offering direct flights is United Airlines.

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 July 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 (17.22% of total bookings). The next most popular plane models are Airbus A321neo (8.77%), Boeing 737-900 (7.92%), and Airbus A321-100/200 (6.72%).

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
Delta	PriceFrom $341	Free Cancellation	Rating 8.0 7,981 reviews	Search Delta flights
Hawaiian Airlines	PriceFrom $346	Free Cancellation	Rating 7.8 2,611 reviews	Search Hawaiian Airlines flights
American Airlines	PriceFrom $349	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Alaska Airlines	PriceFrom $425	Free Cancellation	Rating 8.0 10,000 reviews	Search Alaska Airlines flights
United Airlines	PriceFrom $492	Free Cancellation	Rating 7.4 8,900 reviews	Search United Airlines flights
Southwest	PriceFrom $498	Free Cancellation	Rating 8.0 4,246 reviews	Search Southwest 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.

An easier way to manage your Maui trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Find better results for your trip to Maui

Popular cities in Maui

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Flights to Atlantafrom $29

Flights to Dallasfrom $55

Flights to Seattlefrom $93

Cheap flights from Chicago to Maui from $194

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Maui departing on 10/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names and deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Chicago to Maui

Cheap round-trip flights

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Cheap last minute flights

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Alaska Airlines flights from Chicago to Maui

Our best Alaska Airlines deals on Chicago to Maui flight tickets

Southwest flights from Chicago to Maui

Our best Southwest deals on Chicago to Maui flight tickets

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Use the filters below to find and compare flights from Chicago to Maui that are best for you.

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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

What is the cheapest month to fly to Maui?

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

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

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?

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.

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

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

What airlines fly to Maui?

How many flights depart from Chicago to Maui on average per week?

As of July 2025, there are 2 flights per week flying from Chicago to Maui. The most common day of the week flights depart is Wed, with 50% of flights taking off on this day.

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

Fastest flight time

Direct flights

Airports in Maui

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

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

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

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

What is the most popular plane model from Chicago to Maui?

Best airlines flying from Chicago to Maui

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

Why use momondo?

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

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

How can momondo help me find flights 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?

An easier way to manage your Maui trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Maui

Popular cities in Maui

Popular flights according to clicks in the last 7 days on momondo