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Cheap Flights from Chicago (MDW) to Kahului (OGG)

Compare Chicago Midway to Maui Kahului flight deals

Find the cheapest month or even day of the year to fly to Maui Kahului

Book the best Maui Kahului fare with no extra fees

Flight deals from Chicago Midway to Maui Kahului

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Maui Kahului Airport? If you want to travel next month, return fares start from $754. Find the lowest prices on one-way and return tickets right here.
Kahului.$514 per passenger.Departing Wed, 28 Oct, returning Tue, 3 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 28 Oct, arriving in Maui Kahului.Inbound indirect flight with Southwest Airlines, departs from Maui Kahului on Tue, 3 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $514, select.
Kahului.$621 per passenger.Departing Tue, 12 Jan, returning Thu, 21 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 12 Jan, arriving in Maui Kahului.Inbound indirect flight with Delta, departs from Maui Kahului on Thu, 21 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $621, select.
Kahului.$631 per passenger.Departing Mon, 8 Feb, returning Fri, 12 Feb.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 8 Feb, arriving in Maui Kahului.Inbound indirect flight with Southwest Airlines, departs from Maui Kahului on Fri, 12 Feb, arriving in Chicago Midway.Price includes taxes and charges.From $631, select.
Kahului.$641 per passenger.Departing Wed, 21 Oct, returning Wed, 28 Oct.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 21 Oct, arriving in Maui Kahului.Inbound indirect flight with Southwest Airlines, departs from Maui Kahului on Wed, 28 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $641, select.
Kahului.$643 per passenger.Departing Wed, 4 Nov, returning Mon, 9 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 4 Nov, arriving in Maui Kahului.Inbound indirect flight with Southwest Airlines, departs from Maui Kahului on Mon, 9 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $643, select.
Kahului.$696 per passenger.Departing Tue, 25 Aug, returning Tue, 1 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 25 Aug, arriving in Maui Kahului.Inbound indirect flight with Southwest Airlines, departs from Maui Kahului on Tue, 1 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $696, select.
Kahului.$709 per passenger.Departing Tue, 18 Aug, returning Fri, 28 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 18 Aug, arriving in Maui Kahului.Inbound indirect flight with Southwest Airlines, departs from Maui Kahului on Fri, 28 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $709, select.
Kahului.$746 per passenger.Departing Sun, 30 Aug, returning Mon, 26 Oct.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 30 Aug, arriving in Maui Kahului.Inbound indirect flight with Southwest Airlines, departs from Maui Kahului on Mon, 26 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $746, select.
Kahului.$754 per passenger.Departing Tue, 15 Sep, returning Tue, 22 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 15 Sep, arriving in Maui Kahului.Inbound indirect flight with Southwest Airlines, departs from Maui Kahului on Tue, 22 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $754, select.
Kahului.$793 per passenger.Departing Mon, 7 Dec, returning Mon, 14 Dec.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon, 7 Dec, arriving in Maui Kahului.Inbound indirect flight with Delta, departs from Maui Kahului on Mon, 14 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $793, select.
Kahului.$796 per passenger.Departing Mon, 22 Feb, returning Wed, 3 Mar.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 22 Feb, arriving in Maui Kahului.Inbound indirect flight with Southwest Airlines, departs from Maui Kahului on Wed, 3 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $796, select.
Kahului.$801 per passenger.Departing Mon, 28 Sep, returning Wed, 7 Oct.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 28 Sep, arriving in Maui Kahului.Inbound indirect flight with Southwest Airlines, departs from Maui Kahului on Wed, 7 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $801, select.
Kahului.$867 per passenger.Departing Sun, 31 Jan, returning Sun, 14 Feb.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sun, 31 Jan, arriving in Maui Kahului.Inbound indirect flight with Delta, departs from Maui Kahului on Sun, 14 Feb, arriving in Chicago Midway.Price includes taxes and charges.From $867, select.
Kahului.$895 per passenger.Departing Mon, 1 Mar, returning Mon, 8 Mar.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon, 1 Mar, arriving in Maui Kahului.Inbound indirect flight with Delta, departs from Maui Kahului on Mon, 8 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $895, select.
Kahului.$927 per passenger.Departing Fri, 27 Nov, returning Fri, 4 Dec.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Fri, 27 Nov, arriving in Maui Kahului.Inbound indirect flight with Southwest Airlines, departs from Maui Kahului on Fri, 4 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $927, select.
Kahului.$993 per passenger.Departing Thu, 6 Aug, returning Wed, 4 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Thu, 6 Aug, arriving in Maui Kahului.Inbound indirect flight with Southwest Airlines, departs from Maui Kahului on Wed, 4 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $993, select.

Find the cheapest month to fly from Chicago Midway to Maui Kahului

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Maui Kahului flights are currently cheapest in January.
Aug
from $709
Sep
from $754
Oct
from $641
Nov
from $643
Dec
from $793
Jan
from $621
Feb
from $631
Mar
from $895
Apr
from $1,475
May
from $1,129
Jun
from $1,245
Jul
Find prices

Chicago Midway to Maui Kahului: Alternative routes

Compare routes from Chicago Midway to Kahului below. You may find an airport to fly into that's cheaper, faster, or easier than Maui Kahului.

Maui Kahului

5km from central Kahului
ClosestCheapest
from $515
Search flights

Kapalua

22km from central Kahului
Search flights

Hana

49km from central Kahului
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Lanai City

50km from central Kahului
from $3,168
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Kalaupapa

62km from central Kahului
Search flights

Hoolehua

70km from central Kahului
from $1,491
Search flights

Chicago to Kahului: Flight information

The things to know before you go.
Cheapest flight found$514
Cheapest month to flyOctober

Finding cheap flights from Chicago Midway to Maui Kahului: Frequently asked questions

The best price we found for a return flight from Chicago Midway to Maui Kahului is $515. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Chicago Midway to Maui Kahului. But we found flights with one or more stops from $515.
As of August 2026, there are no flights flying from Chicago Midway to Maui Kahului.
The cheapest month to fly from Chicago Midway to Maui Kahului is usually October.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Maui Kahului Airport on Wednesday, 28 October 2026.
No airlines currently offer direct flights between Chicago Midway Airport and Maui Kahului Airport. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Maui Kahului but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Kahului is around 40 days in advance, so don’t leave your flight to the last minute.

Currently, Southwest Airlines offers the cheapest flight tickets to Maui Kahului.

Travelling from Chicago Midway Airport (MDW) to Maui Kahului Airport (OGG): what you need to know

  • The timezone in Kahului is UTC-10, which is four hours behind Chicago.

  • Give yourself plenty of time to make your MDW to OGG flight. As a rule of thumb, arrive two hours before international departures and an hour ahead for domestic flights.

  • Flying during a peak month such as July? Major public holidays and other popular periods can mean longer queues and delays at airport checkpoints. Play things extra safe and arrive up to four hours before international flights and two hours before a domestic departure.

  • Think about adding a stopover when booking your ticket from Chicago Midway Airport to Maui Kahului Airport. Just uncheck 'Direct flights only' to break up your trip, or even explore someplace new along the way. Here are some options between MDW and OGG:

    • Denver International Airport

    • Los Angeles International Airport

    • Phoenix Sky Harbour Airport

Handy information about Chicago Midway Airport (MDW)

  • MDW's address is 5700 South Cicero.

  • Of all flights departing from Chicago Midway Airport, 76% land on time at their destination.

  • Central Chicago to Chicago Midway Airport is approximately 16 kilometres. Depending on traffic, it'll take about 25 minutes to get there if you're ride-sharing, catching a taxi or driving.

  • You can expect a trip time of around 30 minutes on public transport.

  • Booked an early flight from Chicago Midway Airport to Maui Kahului Airport? Avoid the hassle of rushing to the airport (and sneak in some extra precious sleep) by picking one of these stays close to MDW:

Arriving at Maui Kahului Airport (OGG)

  • If you're getting in on a late Chicago Midway Airport to Maui Kahului Airport flight, nothing beats the convenience of staying near the terminal. Grab your suitcases from the carousel and then be resting not long after at one of these hotels near OGG:

  • Pick up a Maui Kahului Airport rental car and discover Kahului and beyond with your own wheels. Dollar, Thrifty and Ace Rent a Car are top providers to choose from here.

  • Reserving your ride from Maui Kahului Airport about four weeks in advance increases your chances of getting a good deal.

Getting from Maui Kahului Airport (OGG) to central Kahului

  • Maui Kahului Airport is approximately 3 kilometres from central Kahului. The drive time takes around 10 minutes.

  • When travelling by public transport, expect a journey time of around 20 minutes.

When to fly to Maui Kahului Airport (OGG)

  • July is the busiest month for flights from Chicago Midway Airport to Maui Kahului Airport. To steer clear of the crowds, head to Kahului in March.

  • Book your flight from Chicago Midway Airport to Maui Kahului Airport for September if you want to visit Kahului during its warmest month. Expect temperatures of between 23ºC (73ºF) and 29ºC (84ºF).

  • February has average temperatures of between 19ºC (66ºF) and 25ºC (77ºF). Look for cheap tickets from MDW to OGG sometime around then if you want to travel when it's cooler.

Explore more of the United States

  • You've seen Kahului, now it's time to explore more of the United States. Journey about 153 kilometres west to Honolulu to check off its top sights. From Pacific Ocean to Waikiki Beach and Pearl Harbour, there's plenty to keep you on the go.

Plan smart, explore more

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Plan the rest of your trip from Chicago to Kahului

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.