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

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

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 37% 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.

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

As of April 2026, there are 4 flights per week flying from Chicago to Maui. The most common day of the week flights depart is Wed, with 25% 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 April 2026.

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.

$235 Cheap Flights from Chicago to Maui in 2026

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Find the cheapest flights from Chicago to Maui

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:50 am - 8:52 pm

ORD

OGG

17h 02m

1 stop

12:37 pm - 1:13 pm

OGG

ORD

19h 36m

1 stop

$494Alaska Airlines

Sun, May 3 - Fri, May 8

7:35 am - 2:14 pm

ORD

OGG

11h 39m

1 stop

8:00 pm - 4:29 pm

OGG

ORD

15h 29m

2 stops

$496Delta

Tue, May 5 - Wed, May 13

6:24 am - 7:35 pm

ORD

OGG

18h 11m

2 stops

10:00 pm - 7:20 pm

OGG

ORD

16h 20m

2 stops

$497Delta

Wed, May 27 - Wed, Jun 3

6:55 am - 2:10 pm

MDW

OGG

12h 15m

1 stop

8:25 pm - 11:55 am

OGG

MDW

10h 30m

1 stop

$500Southwest

Fri, May 1 - Mon, May 4

7:12 am - 5:48 pm

ORD

OGG

15h 36m

1 stop

9:05 pm - 1:45 pm

OGG

ORD

11h 40m

1 stop

$500Delta

Fri, May 8 - Thu, May 14

9:23 am - 7:35 pm

MDW

OGG

15h 12m

2 stops

10:00 pm - 5:56 pm

OGG

MDW

14h 56m

2 stops

$501Delta

Thu, May 28 - Wed, Jun 3

8:50 am - 7:32 pm

ORD

OGG

15h 42m

2 stops

9:05 pm - 6:05 pm

OGG

ORD

16h 00m

2 stops

$501Delta

Tue, May 5 - Thu, May 14

7:15 am - 5:36 pm

ORD

OGG

15h 21m

1 stop

8:00 pm - 11:52 am

OGG

ORD

10h 52m

1 stop

$502Delta

Sun, May 3 - Tue, May 12

10:05 am - 4:05 pm

MDW

OGG

11h 00m

1 stop

12:40 pm - 5:00 am

OGG

MDW

11h 20m

1 stop

$505Southwest

Mon, May 4 - Sat, May 9

8:50 am - 8:52 pm

ORD

OGG

17h 02m

1 stop

12:37 pm - 1:13 pm

OGG

ORD

19h 36m

1 stop

$505Alaska Airlines

Sat, May 9 - Mon, May 11

Delta flights from Chicago to Maui

Our best Delta deals on Chicago to Maui flight tickets

Delta

May 5

ORD7:35 amChicago O'Hare Intl

11h 39m

1 stop

OGG2:14 pmKahului

May 13

OGG8:00 pmKahului

15h 29m

2 stops

ORD4:29 pmChicago O'Hare Intl

$496

Delta

May 27

ORD6:24 amChicago O'Hare Intl

18h 11m

2 stops

OGG7:35 pmKahului

Jun 3

OGG10:00 pmKahului

16h 20m

2 stops

ORD7:20 pmChicago O'Hare Intl

$497

Delta

May 8

ORD7:12 amChicago O'Hare Intl

15h 36m

1 stop

OGG5:48 pmKahului

May 14

OGG9:05 pmKahului

11h 40m

1 stop

ORD1:45 pmChicago O'Hare Intl

$500

Southwest flights from Chicago to Maui

Our best Southwest deals on Chicago to Maui flight tickets

Southwest

May 1

MDW6:55 amChicago Midway

12h 15m

1 stop

OGG2:10 pmKahului

May 4

OGG8:25 pmKahului

10h 30m

1 stop

MDW11:55 amChicago Midway

$500

Southwest

May 4

MDW10:05 amChicago Midway

11h 00m

1 stop

OGG4:05 pmKahului

May 9

OGG12:40 pmKahului

11h 20m

1 stop

MDW5:00 amChicago Midway

$505

Southwest

May 1

MDW5:25 amChicago Midway

13h 45m

1 stop

OGG2:10 pmKahului

May 4

OGG8:25 pmKahului

12h 45m

2 stops

MDW2:10 pmChicago Midway

$506

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Sun 5/3

8:50 am-8:52 pm

1 stop17h 02m

Kahului

Fri 5/8

12:37 pm-1:13 pm

1 stop19h 36m

$494

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 5/5

7:35 am-2:14 pm

1 stop11h 39m

Kahului

Wed 5/13

8:00 pm-4:29 pm

2 stops15h 29m

$496

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Wed 5/27

6:24 am-7:35 pm

2 stops18h 11m

Kahului

Wed 6/3

10:00 pm-7:20 pm

2 stops16h 20m

$497

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Fri 5/1

6:55 am-2:10 pm

1 stop12h 15m

Kahului

Mon 5/4

8:25 pm-11:55 am

1 stop10h 30m

$500

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Fri 5/8

7:12 am-5:48 pm

1 stop15h 36m

Kahului

Thu 5/14

9:05 pm-1:45 pm

1 stop11h 40m

$500

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Thu 5/28

9:23 am-7:35 pm

2 stops15h 12m

Kahului

Wed 6/3

10:00 pm-5:56 pm

2 stops14h 56m

$501

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 5/5

8:50 am-7:32 pm

2 stops15h 42m

Kahului

Thu 5/14

9:05 pm-6:05 pm

2 stops16h 00m

$501

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Sun 5/3

7:15 am-5:36 pm

1 stop15h 21m

Kahului

Tue 5/12

8:00 pm-11:52 am

1 stop10h 52m

$502

Quickest round-trip

ChicagoKahului

MDW - OGG

MDWOGG

Chicago Midway

Mon 5/4

10:05 am-4:05 pm

1 stop11h 00m

Kahului

Sat 5/9

12:40 pm-5:00 am

1 stop11h 20m

$505

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Sat 5/9

8:50 am-8:52 pm

1 stop17h 02m

Kahului

Mon 5/11

12:37 pm-1:13 pm

1 stop19h 36m

$505

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 $581. If you are unable to visit Maui during the month of October, then departing from Chicago during the month January is also very affordable. Most momondo users find prices during this month for around $624.

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 Sunday. momondo users have found tickets for Sunday departures for as low as $973. 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 $1,258.

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 $805 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 $642 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	$517
Fastest flight time	8h 56m
Direct flights	Sun
Airports in Maui	3 airports

The best one-way flight to Maui from Chicago in the past 72 hours is $517. The best round-trip flight deal from Chicago to Maui found on momondo in the last 72 hours is $954.

The fastest flight from Chicago to Maui takes 8h 56m

Direct flights go from Chicago to Maui on Sunday. There are no airlines offering direct flights.

There are 3 airports in Maui. From Chicago there are direct flights to Kahului (OGG).

Search flight deals

Frequently asked questions about flying 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 April 2026.
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 Airbus A321neo (16.85% of total bookings). The next most popular plane models are Boeing 737-800 (15.07%), Airbus A321-100/200 (8.37%), and Boeing 737-900 (7.72%).

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
Hawaiian Airlines	PriceFrom $307	Free Cancellation	Rating 7.8 2,838 reviews	Search Hawaiian Airlines flights
Delta	PriceFrom $355	Free Cancellation	Rating 7.9 8,390 reviews	Search Delta flights
Alaska Airlines	PriceFrom $363	Free Cancellation	Rating 7.9 12,192 reviews	Search Alaska Airlines flights
American Airlines	PriceFrom $422	Free Cancellation	Rating 7.1 11,559 reviews	Search American Airlines flights
Southwest	PriceFrom $568	Free Cancellation	Rating 8.0 4,337 reviews	Search Southwest flights
United Airlines	PriceFrom $743	Free Cancellation	Rating 7.4 9,554 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.

An easier way to manage your Maui trip

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Flights to New Yorkfrom $55

Flights to Los Angelesfrom $53

Flights to Orlandofrom $48

Flights to Miamifrom $57

Flights to Chicagofrom $58

Flights to San Franciscofrom $84

Flights to Las Vegasfrom $45

Flights to Washington, D.C.from $56

Flights to Bostonfrom $70

Flights to Atlantafrom $48

Flights to Dallasfrom $59

Flights to Fort Lauderdalefrom $49

Cheap flights from Chicago to Maui from $235

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 5/4. 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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How to get the cheapest flight ticket from Chicago to Maui

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 Chicago to Maui flight route?

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

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

Can stopping save me money on Chicago to Maui flights?

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

What airlines fly to Maui?

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

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

Frequently asked questions about flying 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?

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

Chicago flight routes

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