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

Compare Maui Kahului to Chicago flight deals

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Flight deals from Maui Kahului to Chicago

Looking for a cheap last-minute deal or the best return flight from Maui Kahului Airport to Chicago? If you want to travel next month, return fares start from $793. Find the lowest prices on one-way and return tickets right here.
Chicago.$621 per passenger.Departing Wed, 13 Jan, returning Tue, 26 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Maui Kahului on Wed, 13 Jan, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 26 Jan, arriving in Maui Kahului.Price includes taxes and charges.From $621, select.
Chicago.$715 per passenger.Departing Thu, 27 Aug, returning Tue, 1 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Maui Kahului on Thu, 27 Aug, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 1 Sep, arriving in Maui Kahului.Price includes taxes and charges.From $715, select.
Chicago.$793 per passenger.Departing Tue, 13 Oct, returning Tue, 20 Oct.Return flight with Delta.Outbound indirect flight with Delta, departs from Maui Kahului on Tue, 13 Oct, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Tue, 20 Oct, arriving in Maui Kahului.Price includes taxes and charges.From $793, select.
Chicago.$793 per passenger.Departing Mon, 14 Dec, returning Tue, 12 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Maui Kahului on Mon, 14 Dec, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Tue, 12 Jan, arriving in Maui Kahului.Price includes taxes and charges.From $793, select.
Chicago.$793 per passenger.Departing Fri, 21 Aug, returning Tue, 25 Aug.Return flight with Delta.Outbound indirect flight with Delta, departs from Maui Kahului on Fri, 21 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Tue, 25 Aug, arriving in Maui Kahului.Price includes taxes and charges.From $793, select.
Chicago.$891 per passenger.Departing Sun, 13 Sep, returning Thu, 17 Sep.Return flight with Delta.Outbound indirect flight with Delta, departs from Maui Kahului on Sun, 13 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Thu, 17 Sep, arriving in Maui Kahului.Price includes taxes and charges.From $891, select.
Chicago.$1,137 per passenger.Departing Thu, 30 Jul, returning Mon, 3 Aug.Return flight with Delta.Outbound indirect flight with Delta, departs from Maui Kahului on Thu, 30 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Mon, 3 Aug, arriving in Maui Kahului.Price includes taxes and charges.From $1,137, select.
Chicago.$1,312 per passenger.Departing Wed, 6 Jan, returning Wed, 20 Jan.Return flight with United.Outbound direct flight with United departs from Maui Kahului on Wed, 6 Jan, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Wed, 20 Jan, arriving in Maui Kahului.Price includes taxes and charges.From $1,312, select.
Chicago.$1,367 per passenger.Departing Sat, 12 Dec, returning Sun, 10 Jan.Return flight with United.Outbound direct flight with United departs from Maui Kahului on Sat, 12 Dec, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sun, 10 Jan, arriving in Maui Kahului.Price includes taxes and charges.From $1,367, select.
Chicago.$1,481 per passenger.Departing Sat, 29 Aug, returning Sat, 5 Sep.Return flight with United.Outbound direct flight with United departs from Maui Kahului on Sat, 29 Aug, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sat, 5 Sep, arriving in Maui Kahului.Price includes taxes and charges.From $1,481, select.
Chicago.$1,674 per passenger.Departing Sat, 5 Sep, returning Sat, 12 Sep.Return flight with United.Outbound direct flight with United departs from Maui Kahului on Sat, 5 Sep, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sat, 12 Sep, arriving in Maui Kahului.Price includes taxes and charges.From $1,674, select.
Chicago.$1,810 per passenger.Departing Wed, 9 Dec, returning Wed, 16 Dec.Return flight with United.Outbound indirect flight with United, departs from Maui Kahului on Wed, 9 Dec, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Wed, 16 Dec, arriving in Maui Kahului.Price includes taxes and charges.From $1,810, select.

Find the cheapest month to fly from Maui Kahului to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Maui Kahului to Chicago flights are currently cheapest in January.
Jul
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Aug
from $793
Sep
from $891
Oct
from $793
Nov
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Dec
from $1,810
Jan
from $621
Feb
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Mar
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Apr
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May
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Jun
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Direct flights from Maui Kahului to Chicago

Alternative Maui Kahului to Chicago routes

Looking for the cheapest, fastest or easiest route from Maui Kahului to Chicago? You could fly into the following airports instead.

Chicago Midway

14km from central Chicago
ClosestCheapest
from $621
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Chicago O'Hare International

25km from central Chicago
Cheapest
from $621
Search flights

Chicago Rockford

127km from central Chicago
Search flights

Kahului to Chicago: Flight information

The things to know before you go.
Cheapest flight found$621
Cheapest month to flyJanuary
Average flight time7 hrs, 56 mins
Most popular airlineAmerican Airlines
Average flights per week9

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

There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.
The best price we found for a return flight from Maui Kahului to Chicago is $621. 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.
7 hours and 56 minutes is the average flight time from Maui Kahului to Chicago.
American Airlines, Lufthansa and United fly direct from Maui Kahului to Chicago.
As of July 2026, there are 9 flights per week flying from Maui Kahului to Chicago.
The cheapest month to fly from Maui Kahului to Chicago is usually January.
If you're flying from Maui Kahului Airport, the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the centre of Chicago. We've found flights into this airport from $621.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Maui Kahului Airport to Chicago on Wednesday, 13 January 2027.
Yes – the average flight time is 7 hours and 56 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 Chicago 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 Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

In July, the average temperature is usually around 22°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Delta and United offer the cheapest flight tickets to Chicago.

Flying from Kahului Airport (OGG) to Chicago: what you need to know

  • The average duration of a direct flight from Kahului Airport to Chicago is 9 hours 20 minutes.

  • Kahului Airport is located in Kahului. Following the UTC-6 timezone, Chicago is four hours ahead of Kahului.

  • The busiest route is from Kahului Airport (OGG) to Chicago O'Hare International Airport (ORD). You can select from three weekly services between these two airports. If you'd like to take off as soon as possible, the earliest flight from OGG to ORD is the 17:05 United Airlines option. If you're planning to fly out later on, the final departure is at 18:20 with United Airlines.

  • Allow plenty of time to get on your OGG to Chicago flight. As a general rule, turn up two hours before international departures and an hour ahead for domestic flights.

  • Be prepared for longer lines in popular months such as July. Arriving up to four hours ahead of an international flight and two hours for a domestic departure is a smart move.

  • Begin your trip at OGG and travel nonstop to Chicago O'Hare International Airport (ORD). That's where you can expect to land when searching for Kahului Airport to Chicago tickets.

  • Book your ticket with United Airlines. This popular carrier offers direct flights from Kahului Airport to Chicago.

  • The journey from central Kahului to OGG takes around 20 minutes by public transport. If you drive, ride-share or take a taxi, you'll cover the 3 kilometres in 10 minutes or so, depending on traffic.

  • Want a hassle-free start to your journey? Stay near OGG. Whether you've booked an early flight from Kahului Airport to Chicago or want to avoid feeling rushed, these hotels are a convenient choice:

  • Kahului Airport maintains a strong on-time record, so flight disruptions are less likely. Departures from OGG land on schedule 83% of the time.

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

  • $311 is currently the lowest price for a one-way Kahului Airport to Chicago flight. Return plane tickets start from $621. These prices can change depending on demand.

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

  • October is the best month for picking up a fantastic deal on Kahului Airport to Chicago tickets. If you need to travel at a different time of year, the 'Whole month' tool will show you the lowest prices across every month.

  • There's no need to check back in every day to see if fares have dropped when you create a Price Alert. We'll notify you the moment there's an extra saving on cheap flights from OGG to Chicago.

  • Choose your preferred arrival and departure times, airlines and number of stops with our filters. Then, sort the results for your flight from Kahului Airport to Chicago by 'Cheapest,' 'Fastest' or 'Best.'

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Chicago O'Hare International Airport (ORD) to central Chicago takes about 30 minutes to reach by car. The centre is roughly 27 kilometres away.

  • It typically takes 45 minutes when travelling by public transport.

  • Consider staying in a hotel near ORD if you have a late flight from Kahului Airport to Chicago. Settle into one of these accommodation options and make arrival day easier:

  • Reserving your ride from Chicago O'Hare International Airport around four weeks before your flight from OGG to Chicago can help you lock in the best possible rate.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Central Chicago is located around 16 kilometres from Chicago Midway International Airport (MDW). Once your flight from Kahului Airport to Chicago has touched down and you've made your way to arrivals, expect a drive of around 25 minutes.

  • If you travel by public transport, the ride to the centre will take you 30 minutes or so.

  • After stepping off your OGG to Chicago flight, rest your head at a hotel close to MDW. These are some great options that'll help you slip into relaxation mode:

  • Get exactly what you want. Securing your ride from MDW four weeks ahead of time often means better prices and a wider range of vehicles.

  • Chicago Midway International Airport can be found at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Make your way to the city centre after your flight from Kahului Airport to Chicago has touched down. Central Chicago is about 145 kilometres from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 40 minutes to get to by car.

  • Public transport can take you there in roughly 2 hours.

  • Choose a hotel near RFD and get from baggage claim to your bed in a snap. Whether you're coming in on a late OGG to Chicago flight or just want to keep your travel plans simple, these stays will have you settling in quickly:

  • Rental agencies sometimes offer promotions on early bookings, so book your vehicle from RFD ahead of your flight from Kahului Airport to Chicago. A little prep work can make a big difference in cost.

  • Chicago Rockford International Airport's official address is 2 Airport Cir.

Best time to go to Chicago

  • July is the busiest month for flights from Kahului Airport to Chicago. To avoid the crowds, visit Chicago in January.

  • Book a Kahului Airport to Chicago plane ticket with a departure in July to explore the city during its warmest month. You can expect temperatures to range from 16ºC (61ºF) to 28ºC (82ºF).

  • If you like travelling in cooler conditions, look for a cheap ticket from OGG to Chicago in January when temperatures average between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

Explore more of the United States

  • You've seen Chicago, now it's time to explore other corners of the United States. Travel around 451 kilometres southeast to Columbus to tick off its popular sights. From Franklin Park Conservatory and Botanical Gardens to Whetstone Park / Park of Roses and Ohio Theatre, you've got a jam-packed schedule ahead.

  • Indianapolis is another sought-after destination in the United States and is around 257 kilometres southeast of Chicago. No trip is complete without dropping by Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

Plan smart, explore more

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Plan the rest of your trip from Kahului to Chicago

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