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Cheap Flights from Chicago to Maui Kahului

Compare Chicago to Maui Kahului flight deals

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

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Flight deals from Chicago to Maui Kahului Airport

Looking for a cheap last-minute deal or the best return flight from Chicago to Maui Kahului Airport? If you want to travel next month, return fares start from R 7,977. Find the lowest prices on one-way and return tickets right here.
Kahului.R 3,988 per passenger.Departing Wed, 29 Apr.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 29 Apr, arriving in Maui Kahului.Price includes taxes and charges.From R 3,988, select.
Kahului.R 3,992 per passenger.Departing Wed, 6 May.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 6 May, arriving in Maui Kahului.Price includes taxes and charges.From R 3,992, select.
Kahului.R 4,768 per passenger.Departing Wed, 19 Aug.One-way flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departs from Chicago O'Hare International on Wed, 19 Aug, arriving in Maui Kahului.Price includes taxes and charges.From R 4,768, select.
Kahului.R 5,724 per passenger.Departing Wed, 14 Oct.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 14 Oct, arriving in Maui Kahului.Price includes taxes and charges.From R 5,724, select.
Kahului.R 6,033 per passenger.Departing Mon, 2 Nov.One-way flight with Alaska Airlines.Outbound indirect flight with Alaska Airlines, departs from Chicago O'Hare International on Mon, 2 Nov, arriving in Maui Kahului.Price includes taxes and charges.From R 6,033, select.
Kahului.R 6,050 per passenger.Departing Wed, 17 Jun.One-way flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Chicago Midway on Wed, 17 Jun, arriving in Maui Kahului.Price includes taxes and charges.From R 6,050, select.
Kahului.R 6,239 per passenger.Departing Tue, 7 Jul.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Tue, 7 Jul, arriving in Maui Kahului.Price includes taxes and charges.From R 6,239, select.
Kahului.R 8,267 per passenger.Departing Tue, 15 Dec.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Tue, 15 Dec, arriving in Maui Kahului.Price includes taxes and charges.From R 8,267, select.
Kahului.R 8,610 per passenger.Departing Sat, 15 Aug.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 15 Aug, arriving in Maui Kahului.Price includes taxes and charges.From R 8,610, select.
Kahului.R 9,128 per passenger.Departing Sat, 9 May.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 9 May, arriving in Maui Kahului.Price includes taxes and charges.From R 9,128, select.
Kahului.R 9,593 per passenger.Departing Sat, 27 Jun.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 27 Jun, arriving in Maui Kahului.Price includes taxes and charges.From R 9,593, select.
Kahului.R 9,705 per passenger.Departing Sat, 17 Oct.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 17 Oct, arriving in Maui Kahului.Price includes taxes and charges.From R 9,705, select.
Kahului.R 10,478 per passenger.Departing Sat, 4 Jul.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 4 Jul, arriving in Maui Kahului.Price includes taxes and charges.From R 10,478, select.
Kahului.R 11,423 per passenger.Departing Sat, 11 Apr.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 11 Apr, arriving in Maui Kahului.Price includes taxes and charges.From R 11,423, select.
Kahului.R 16,347 per passenger.Departing Thu, 24 Dec.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Thu, 24 Dec, arriving in Maui Kahului.Price includes taxes and charges.From R 16,347, select.

Find the cheapest month to fly from Chicago to Maui Kahului

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Maui Kahului flights are currently cheapest in April.
Apr
from R 3,988
May
from R 3,992
Jun
from R 6,050
Jul
from R 6,239
Aug
from R 4,768
Sep
Find prices
Oct
from R 5,724
Nov
from R 6,033
Dec
from R 8,267
Jan
Find prices
Feb
Find prices
Mar
Find prices

Direct flights from Chicago to Maui Kahului

Chicago to Maui Kahului: Alternative routes

Compare routes from Chicago 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 R 3,988
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 R 9,719
Search flights

Kalaupapa

62km from central Kahului
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Hoolehua

70km from central Kahului
from R 10,381
Search flights

Chicago to Kahului: Flight information

The things to know before you go.
Cheapest flight foundR 3,988
Cheapest month to flyApril
Average flight time9 hrs, 25 mins
Most popular airlineUnited
Average flights per week6

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

The best price we found for a return flight from Chicago to Maui Kahului is R 7,977. 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.
9 hours and 25 minutes is the average flight time from Chicago to Maui Kahului.
United and American Airlines fly direct from Chicago to Maui Kahului.
As of April 2026, there are 13 flights per week flying from Chicago to Maui Kahului.
The cheapest month to fly from Chicago to Maui Kahului is usually April.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Maui Kahului Airport on Wednesday, 29 April 2026.
Yes – the average flight time is 9 hours and 25 minutes.
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.

Travelling from Chicago to Kahului Airport (OGG): What you need to know

  • Start planning your holiday by checking out where you'll catch your flight from Chicago to Kahului Airport (OGG). Explore the options for leaving from O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW), two of the city's main airports.

  • The average length of a direct Chicago to Kahului Airport flight is 9 hours 15 minutes.

  • Kahului Airport is located in Kahului. The city runs on the UTC-10 timezone and is five hours behind Chicago.

  • You can choose from 3 direct flights a week between O'Hare International Airport (ORD) and Kahului Airport (OGG). This is the busiest route, with United Airlines offering a 9:20am departure from ORD to OGG.

  • To ensure you catch your flight from Chicago to OGG, leave plenty of time to check in and drop off your luggage. Turning up two hours ahead of international departures and one hour before domestic flights is the general rule.

  • Delays at security and check-in are likely if you're flying during high season, so give yourself even more breathing space. The recommendation for peak periods? Arrive up to four hours early for international flights and at least two hours for domestic departures.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) is a convenient option for travelling directly to your destination. Nonstop flights from Chicago to Kahului Airport (OGG) operate out of this terminal.

  • United Airlines is a well-known carrier that operates direct flights from Chicago to Kahului Airport taking off from ORD.

  • United Airlines sees the most traveller bookings for flights from ORD to OGG.

  • United Airlines takes the lead in punctuality. An exceptional 96.77% of its departures on this route arrive as scheduled.

  • Located around 40 kilometres from central Chicago, ORD can be reached in about 35 minutes by car (depending on traffic). The journey on public transport will take roughly 55 minutes.

  • Want an easy start to your trip? Stay near O'Hare International Airport. Whether you're boarding an early flight from Chicago to Kahului Airport or want to avoid feeling rushed, these hotels are the ideal choice:

  • Of the departures from O'Hare International Airport, 74.85% land on time at their destination.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Using public transport, you can travel from central Chicago to MDW in about 45 minutes. The airport is roughly 19 kilometres away, and making the journey by car will take approximately 20 minutes.

  • Kick off your holiday early with an extra night away from home. Before catching your Chicago to OGG flight, stay in one of these hotels near Chicago Midway International Airport:

  • 77.88% of flights departing Chicago Midway International Airport arrive according to schedule.

  • You'll find MDW at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • The journey to RFD from central Chicago is around 4 hours 15 minutes on public transport. If you're planning to travel by car, it'll take you roughly 1 hour 25 minutes to cover the 137 kilometres or so.

  • Sleep a little longer and still make your Chicago to Kahului Airport flight with plenty of time to spare. These accommodation options near Chicago Rockford International Airport make it a breeze to get to the terminal if you're setting off early:

  • Airports have an on-time performance rating that measures how often flights arrive at their destinations as expected. At RFD, that rate is 76.19%.

  • You'll find Chicago Rockford International Airport at 2 Airport Cir.

About Kahului Airport (OGG)

  • Have a late flight from Chicago to Kahului Airport? Don't let it end in exhaustion. Stay at one of these hotels near OGG and give yourself a well-earned lights-out:

  • Get your adventure underway by picking up a Kahului Airport rental car. Grab a set of wheels from Dollar, Thrifty or Ace Rent a Car and explore beyond Kahului's usual tourist stops.

  • To get the best deal, reserve your ride around four weeks in advance of your Chicago to Kahului Airport flight.

Getting from Kahului Airport (OGG) to central Kahului

  • Kahului Airport to the centre of Kahului is about 3 kilometres. If you're taking a cab or renting a car, do some research to make your trip as easy as possible. Journey times will vary depending on the time of day and traffic conditions.

  • It'll take around 25 minutes if you're travelling by public transport.

How to find the cheapest flights from Chicago to Kahului Airport (OGG)

  • R 3,988 is the lowest price for a one-way ticket from Chicago to Kahului Airport. A return flight starts from R 7,977. These fares can change based on demand.

  • Book six months before travelling. Pricing trends show that this is the ideal window for finding cheap flights from Chicago to OGG.

  • The best month for picking up cheap Chicago to Kahului Airport tickets is November. Use the 'Whole month' tool to compare prices, then choose the dates with the lowest fares.

  • There's no need to check back in every day to find out if prices have dropped when you set up a Price Alert. We'll notify you as soon as a better deal is available on plane tickets from Chicago to OGG.

  • Lock in a cheap flight from Chicago to Kahului Airport by using filters. Choose your ideal departure time, duration and airlines, then sort the results by 'Cheapest' for the best deals.

The best time to fly from Chicago to Kahului Airport (OGG)

  • It's time to figure out when to book your flight from Chicago to Kahului Airport (OGG). July is the busiest month to visit Kahului. If you like things a bit more low-key, think about going in May.

  • The warmest month in Kahului is August, with temperatures ranging between 22ºC (72ºF) and 29ºC (84ºF). Book your Chicago to OGG plane ticket then if that's your ideal forecast.

  • February has temperatures of between 18ºC (64ºF) and 25ºC (77ºF). Search for cheap tickets from Chicago to Kahului Airport around that time if you like travelling in cooler conditions.

More about Kahului

  • After booking your flight from Chicago to Kahului Airport, find a hotel that offers a good mix of location and comfort. Make one of these options your base for exploring Kahului:

  • There are so many things to discover in this city, it can be tricky to know where to begin. West Maui Circle Drive, Palaau State Park and Maui Nui Botanical Gardens are top attractions which should feature on any well-planned Kahului itinerary.

Explore more of the United States

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

  • Pearl City is another must-experience destination in the United States and is around 177 kilometres west of Kahului. No trip is complete without visiting USS Utah Memorial, Mānana Ridge Trail and Sunset Memorial Park.

Plan the rest of your trip from Chicago to Kahului

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.