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

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 Midway Airport. 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 Midway Airport?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport 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 Midway Airport?

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 Midway Airport 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 Midway Airport?

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 Midway Airport 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>

$208 Cheap Flights from Maui to Chicago Midway (MDW)

MDW

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

...and more

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

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Filter your dealsChoose cabin class, free Wi-Fi and more.

Cheapest round-trip

$657

Delta

Thu 2/19Wed 3/4

OGG - MDW • 2 stops

Cheapest one-way

$208

Multiple Airlines

Thu 2/26

OGG - MDW • 2 stops

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 Midway!

Flight Deals

Cheap Flights from Maui to Midway

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Maui to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

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

Round-trip

One-way

Last minute

Recent round-trip flight deals from Maui to Midway

Thu, Feb 19 - Wed, Mar 4

1:53 pm - 9:06 am

OGG

MDW

15h 13m2 stops

6:00 am - 8:26 pm

MDW

OGG

18h 26m2 stops

$657Delta

Sat, Feb 28 - Sun, Mar 8

12:45 pm - 5:05 am

OGG

MDW

12h 20m2 stops

7:10 am - 4:35 pm

MDW

OGG

14h 25m2 stops

$695Southwest

Sat, Feb 28 - Sun, Mar 8

12:45 pm - 5:05 am

OGG

MDW

12h 20m2 stops

5:00 am - 12:30 pm

MDW

OGG

12h 30m1 stop

$719Southwest

Thu, Feb 19 - Wed, Mar 4

5:10 pm - 9:56 am

OGG

MDW

12h 46m1 stop

6:00 am - 8:26 pm

MDW

OGG

18h 26m2 stops

$771Delta

Sat, Feb 28 - Sun, Mar 8

5:10 pm - 9:56 am

OGG

MDW

12h 46m1 stop

10:49 am - 6:40 pm

MDW

OGG

12h 51m1 stop

$892Delta

Useful Info

Low season	January
High season	July
Cheapest flight	$208

Best time to beat the crowds with an average 8% drop in price.

Most popular time to fly with an average 3% increase in price.

Flight from Kahului to Chicago Midway Airport

How does KAYAK find such low prices on flights from Maui to Chicago Midway Airport?
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 Midway Airport.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Maui to Chicago Midway Airport?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport 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 Midway Airport?
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 Midway Airport 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 Midway Airport?
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 Midway Airport 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

Saint John

Griffith

Everything you need to know for your flight to Midway

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Chicago Midway Airport (MDW)

MDW

$208 Find Cheap Flights from Maui to Chicago Midway Airport

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

Everything you should know

Cheap Flights from Maui to Midway

Recent round-trip flight deals from Maui to Midway

Recent one-way flight deals from Maui to Midway

Recent last minute flight deals from Maui to Midway

Good to know

FAQs for booking Maui to Chicago Midway Airport flights

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

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 Midway Airport.

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

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport 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 Midway Airport?

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 Midway Airport 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 Midway Airport?

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 Midway Airport 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 Midway?

Everything you need to know for your flight to Midway

Information on your arrival and departure airports

Cabin class types available on flights to Midway

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

Find direct flights for Midway

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