How does KAYAK find such low prices on flights from Maui to Chicago?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Maui to Chicago. Visit our flight page for the latest deals!>/a>

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Maui to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Maui is likely to change within 7 days, so travelers know whether to wait or book now. Visit our flight page for the latest deals!>/a>

What is the Hacker Fare option on flights from Maui to Chicago?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Maui with another airline. Visit our flight page for the latest deals!>/a>

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Maui to Chicago?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Maui up to 3 days before/after your preferred dates. You can then pick the flights that suit you best. Visit our flight page for the latest deals!>/a>

$182 CHEAP FLIGHTS from Maui to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

...and more

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41,299,237 searches in the past 7 days on KAYAK

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Cheapest round-trip

$432

Alaska Airlines

Wed 2/18Sun 2/22

OGG - ORD • 1 stop

Cheapest non-stop

$1,015

United Airlines

Thu 3/12Thu 3/19

OGG - ORD • Non-stop

Start a new search

KAYAK searches 100s of sites at once to find you the best travel deals.

We hope you love your trip to Chicago!

Flight Deals

Cheap Flights from Maui to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Maui to Chicago

Wed, Feb 18 - Sun, Feb 22

11:54 pm - 11:59 pm

OGG

ORD

20h 05m

1 stop

8:20 am - 2:52 pm

ORD

OGG

34h 32m

1 stop

$432Alaska Airlines

Sun, Feb 22 - Wed, Feb 25

11:54 pm - 11:59 pm

OGG

ORD

20h 05m

1 stop

3:07 pm - 11:46 pm

ORD

OGG

12h 39m

1 stop

$455Alaska Airlines

Sun, Feb 22 - Wed, Feb 25

11:54 pm - 11:59 pm

OGG

ORD

20h 05m

1 stop

8:20 am - 10:21 pm

ORD

OGG

18h 01m

2 stops

$460Multiple Airlines

Wed, Feb 18 - Sun, Feb 22

11:54 pm - 11:59 pm

OGG

ORD

20h 05m

1 stop

8:20 am - 7:56 am

ORD

OGG

27h 36m

2 stops

$470Multiple Airlines

Wed, Feb 18 - Sun, Feb 22

11:54 pm - 11:59 pm

OGG

ORD

20h 05m

1 stop

8:20 am - 2:52 pm

ORD

OGG

34h 32m

1 stop

$494Alaska Airlines

Wed, Feb 18 - Sun, Feb 22

11:54 pm - 2:58 pm

OGG

ORD

11h 04m

1 stop

8:20 am - 7:56 am

ORD

OGG

27h 36m

2 stops

$532Multiple Airlines

Fri, Feb 13 - Tue, Feb 17

9:25 pm - 5:00 pm

OGG

MDW

15h 35m

1 stop

8:10 am - 4:25 pm

MDW

OGG

12h 15m

1 stop

$714Southwest

Fri, Mar 13 - Thu, Mar 19

12:59 pm - 8:53 am

OGG

MDW

14h 54m

2 stops

2:05 pm - 11:30 am

MDW

OGG

26h 25m

2 stops

$717Delta

Fri, Feb 13 - Tue, Feb 17

9:35 pm - 1:30 pm

OGG

MDW

11h 55m

1 stop

8:10 am - 6:10 pm

MDW

OGG

14h 00m

2 stops

$720Southwest

Sat, Mar 14 - Sat, Mar 21

12:59 pm - 8:53 am

OGG

MDW

14h 54m

2 stops

6:00 am - 7:23 pm

MDW

OGG

18h 23m

2 stops

$1,938Delta

Useful Info

High season	May
Cheapest flight	$182

Most popular time to fly with an average 15% increase in price.

Flight from Kahului to Chicago O'Hare Airport

How does KAYAK find such low prices on flights from Maui to Chicago?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Maui to Chicago.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Maui to Chicago?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Maui is likely to change within 7 days, so travelers know whether to wait or book now.
What is the Hacker Fare option on flights from Maui to Chicago?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Maui with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Maui to Chicago?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Maui up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Merrillville

Saint Joseph

Hammond

Portage

Lansing

Valparaiso

Chesterton

Schererville

Munster

Porter

Monticello

Griffith

Saint John

Everything you need to know for your flight to Chicago

Cabin class

Complete your trip

Direct Flights

Flights to other cities

Origins

Other airports

Return flight deals

Cabin class types available on flights to Maui

First Class flights to Chicagofrom $329

Business Class flights to Chicagofrom $242

Premium Economy Class flights to Chicagofrom $182

Economy Class flights to Chicagofrom $50

$182 Find Cheap Flights from Maui to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

Everything you should know

Cheap Flights from Maui to Chicago

Recent round-trip flight deals from Maui to Chicago

Recent one-way flight deals from Maui to Chicago

Recent last minute flight deals from Maui to Chicago

Recent direct flight deals from Maui to Chicago

Good to know

FAQs for booking flights from Maui to Chicago

How does KAYAK find such low prices on flights from Maui to Chicago?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Maui to Chicago.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Maui to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Maui is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights from Maui to Chicago?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Maui with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Maui to Chicago?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Maui up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Traveling to a place near Chicago?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Maui

Complete your trip to Chicago with a hotel stay or car rental

Find direct flights for Chicago

Flights to other popular destinations

Flights from domestic origins to Maui

Choose which airport to fly into in Chicago

Find deals for your return flight