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

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Flight deals from Maui Kahului to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from Maui Kahului to Chicago? Find the lowest prices on one-way and round-trip tickets right here.

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 October.

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.

Kahului to Chicago: Flight information

The things to know before you go.
Cheapest flight found$277
Cheapest month to flyOctober
Average flight time7 hrs, 56 mins
Most popular airlineUnited
Average flights per week7

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

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a round-trip flight from Maui Kahului to Chicago is $671. 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.
United and Lufthansa fly direct from Maui Kahului to Chicago.
There are 21 flights per week flying from Maui Kahului to Chicago, as of June 2025.
The cheapest month to fly from Maui Kahului to Chicago is usually June 2025.
If you're flying from Maui Kahului Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 15.8 miles away from the center of Chicago. We've found flights to this airport from $671.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Maui Kahului Airport to Chicago on Tuesday, July 1, 2025.
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 June, the average temperature is usually around 66°F. July is typically the warmest month in Chicago, when it usually averages around 80°F. You can expect the least rain in January. The coldest month is January, with temperatures averaging 18°F. The rainiest month is August.
Currently, Alaska Airlines offers the cheapest flight tickets to Chicago.

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

  • Jump on a direct flight from Kahului Airport to Chicago and you'll be in the air for an average of 9 hours 15 minutes.

  • Chicago is five hours ahead of Kahului, where Kahului Airport is located. Chicago follows the UTC-5 timezone.

  • Kahului Airport (OGG) to O'Hare International Airport (ORD) is the most popular route, with three departures a week to pick from. If you have things to do before leaving, the last flight from OGG to ORD is with United Airlines at 18:20. Opt for the first departure operated by United Airlines at 17:05 if you want to fly out earlier.

  • For a stress-free journey, arrive at the airport two hours ahead of international flights and an hour before domestic departures. This leaves you with plenty of time to board your OGG to Chicago flight.

  • If you're jetting off during a public holiday or another peak period, give yourself more time. A good rule is two hours before domestic flights and up to four hours before international departures. Queues at check-in and security will be longer.

  • You can book a direct Kahului Airport to Chicago ticket. Start your journey at OGG and end it at O'Hare International Airport (ORD).

  • Check out the promotions from United Airlines. This carrier has direct flights from Kahului Airport to Chicago.

  • OGG is around 2 miles from central Kahului. If you're driving, catching a cab or ride-sharing from the center, it'll take 10 minutes or so to get there, depending on traffic. If you're planning to take public transport, expect the journey time to be around 25 minutes.

  • Booked an early flight from Kahului Airport to Chicago? Avoid the stress of rushing to the terminal (and get some extra shut-eye) by choosing one of these stays close to OGG:

  • Kahului Airport maintains a solid on-time record, so you're less likely to experience disruptions. Departures from OGG arrive at their destination as scheduled 86.31% of the time.

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

  • The lowest price we've seen for a one-way Kahului Airport to Chicago flight is $277. The cheapest price for a return flight is $671. Bear in mind fares may change due to availability at the time of booking.

  • To score cheap flights from OGG to Chicago, book your trip six months ahead of your departure date.

  • October is the best month for picking up an incredible deal on Kahului Airport to Chicago tickets. If you'd like to travel during a different time of year, the 'Whole month' tool will give you the lowest prices for each month.

  • Stay on top of deals for cheap flights from OGG to Chicago by creating a Price Alert. We'll send you an email or push notification on the app when a lower fare becomes available.

  • Tailor your trip with filters. Pick your ideal departure and arrival times, airlines and total journey duration. You can also sort the results by 'Best,' 'Fastest' or 'Cheapest' flights from Kahului Airport to Chicago.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) to the center of Chicago takes about 35 minutes to reach by car. The center is roughly 25 miles away.

  • Getting to the center by public transport takes around 55 minutes.

  • Consider staying in a hotel near ORD if you're coming in on a late flight from Kahului Airport to Chicago. Check in to one of these options and make your first night all about rest:

  • Travel at your own speed with an O'Hare International Airport rental car. Pick up a set of wheels from Routes Car Rentals, Dollar or Budget and find adventure across Chicago and beyond.

  • For the lowest price, reserve your vehicle from O'Hare International Airport about four weeks in advance of your flight from OGG to Chicago.

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

Chicago Midway International Airport (MDW)

  • Central Chicago is located around 12 miles from Chicago Midway International Airport (MDW). After your flight from Kahului Airport to Chicago has landed and you've made your way through the terminal, the drive should take about 20 minutes.

  • If you travel by public transport, you'll get to the city center in 45 minutes or so.

  • There are some great places ready to welcome you near MDW. Tuck yourself in and get cozy after your OGG to Chicago flight at one of these well-located options:

  • The quickest way to get to where you're going is with a Chicago Midway International Airport rental car. Collect your wheels from Dollar, Hertz or Budget and make a speedy getaway.

  • Get what you want, not just what's left over. Securing your ride from MDW four weeks ahead of time often means better prices and a greater selection of vehicles.

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

Chicago Rockford International Airport (RFD)

  • Find your way to the city center after your flight from Kahului Airport to Chicago has touched down. Central Chicago is about 85 miles from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 25 minutes to get to by car.

  • The journey will take roughly 4 hours 15 minutes by public transport.

  • If you don't want to make the journey to the center, choose a hotel close to RFD. Settle in at one of these options after your OGG to Chicago flight:

  • Whether you'd like a zippy compact for a solo adventure or a roomy SUV to fit the whole crew comfortably, you'll find the perfect Chicago Rockford International Airport rental car for your needs. Explore the types of wheels available from names such as Budget, Alamo and National.

  • Booking at least a few weeks in advance of your flight from Kahului Airport to Chicago is always a good idea. Along with better deals, you'll likely have a better variety of makes and models to choose from at RFD.

  • The street address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

  • Visit Chicago in peak season if you prefer a busy atmosphere, but remember that prices are usually higher. Alternatively, book flights from Kahului Airport to Chicago during the off-season when prices are cheaper and it's not as busy.

  • The warmest month in Chicago is July, with temperatures ranging between 59ºF and 84ºF. Book your Kahului Airport to Chicago plane ticket then if that's your definition of good weather.

  • If you'd rather travel in cooler conditions, search for a cheap ticket from OGG to Chicago in January when temperatures average between 10ºF and 37ºF.

More about Chicago

  • When it comes to searching for somewhere to rest your head, you'll find the top stays in Chicago right here. Browse these options after locking in your flight from Kahului Airport to Chicago:

  • There are so many things to discover in this city it can be tricky to work out where to start. Art Institute of Chicago, Millennium Park and LandShark Beer Garden at Navy Pier are popular attractions which should be on any good Chicago itinerary.

Explore more of United States

  • Columbus is just one of the many places in United States waiting to be discovered once you've seen the sights of Chicago. Around 280 miles away to the south-east, its best attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • If you're interested in discovering another well-known destination in United States, consider Indianapolis, roughly 160 miles south-east of Chicago. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are the start of reasons to visit.

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