$277 Find Cheap Flights from Maui to Illinois - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Maui to Illinois departing on 8/20. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Useful Info

Good to know

Low seasonJanuary
Cheapest flight$277
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Kahului to Chicago Midway Airport

FAQs for booking flights from Maui to Illinois

  • How does KAYAK find such low prices on flights from Maui to Illinois?

    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 Illinois.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Maui to Illinois 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 Illinois?

    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 from Maui to Illinois with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Maui to Illinois?

    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 from Maui to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many airports are there in Illinois?

    There are 12 airports in Illinois. The busiest airport is Chicago O'Hare Airport (ORD), with 93% of all flights arriving there.

  • Which is the cheapest airport to fly into in Illinois?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Illinois is Chicago O'Hare Intl Airport (ORD), with an average flight price of $398.

  • What is the cheapest day to fly to Illinois?

    Based on KAYAK data, the cheapest day to fly to Illinois is Thursday where round-trip tickets can be as cheap as $541. On the other hand, the most expensive day to fly is Friday, where round-trip prices are $1,045 on average.

  • What is the cheapest time of day to fly to Illinois?

    The cheapest time of day to fly to Illinois is generally in the evening, when round-trip flights cost $766 on average. The most expensive time of day to fly to Illinois is generally in the evening, which is peak travel time and where the average cost of a ticket is $766.

  • What is the cheapest flight to Illinois?

    The cheapest ticket to Illinois from Maui found in the last 5 days was to Chicago O'Hare Intl Airport, at $864 round-trip. The most popular route is Kahului (OGG) to Chicago O'Hare Intl Airport (ORD) and the cheapest round-trip airline ticket found on this route in the last 5 days was $864.

  • What is the cheapest month to fly from Maui to Illinois?

    The cheapest month for flights from Maui to Illinois is April, when tickets cost $171 (return) on average. On the other hand, the most expensive months are July and June, when the average cost of round-trip tickets is $346 and $323 respectively.

  • How many cities have direct flights to Illinois?

    From Maui, there are direct flights to Illinois from 1 city. This city is Kahului and there are 2 direct flights each week.

  • How many direct flights to Illinois are there each day?

    There are around 1 direct flights from within Maui to Illinois every day. All flights depart in the afternoon.

  • How many direct flights to Illinois are there each week?

    Each week there are around 2 direct flights from within Maui to Illinois. The most common day for departures is Saturday, with 100% of flights taking off on this day.

  • How long is the flight to Illinois?

    An average nonstop flight from Maui to Illinois takes 19h 17m, covering a distance of 4098 miles. The shortest route is Kahului (OGG) to Chicago Midway Airport (MDW) with an average flight time of 10h 50m.

  • How many long-haul flights are there to Illinois each week?

    There are not any medium-haul (3-6 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Illinois. Instead, there are 2 long-haul flights (6-12 hour flight duration), with the most arriving from Kahului.

  • What are the most popular destinations in Illinois?

    Based on KAYAK flight searches, the most popular destination is Chicago (70% of total searches to Illinois). The next most popular destinations are St. Louis (18%) and Moline (7%). Searches for flights to Dubuque (5%) are also popular.

Reviews of the top 3 airlines serving from Maui to Illinois

 
Need help choosing which airline to fly with from Maui to Illinois? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
Alaska AirlinesOverall score based on 12607 reviews
7.8Comfort
7.1Food
7.0Entertainment
8.1Boarding
8.5Crew
Airline reviews

Great with American Poor with Alaska airlines. 3 hrs isn’t enough to transfer bags from one gate to another 5-6 gates away in the same terminal. Bags essential for cruise were unavailable Flights delayed cascading the problem. (Alaska Airlines responsibility). Very poor execution of operations that should be the simplest aspect of travel.

4.0 OkayDave, Jun 2026
FSD - ORD
Read more Alaska Airlines reviews

Great with American Poor with Alaska airlines. 3 hrs isn’t enough to transfer bags from one gate to another 5-6 gates away in the same terminal. Bags essential for cruise were unavailable Flights delayed cascading the problem. (Alaska Airlines responsibility). Very poor execution of operations that should be the simplest aspect of travel.

My flight was several times rescheduled and then finally canceled.

The flight kept getting delayed due to a maintenance issue. That happens, but there is no excuse for changing the gate FIVE TIMES, including one time nearly all the way across SeaTac. After we were delayed for 3+ hours, they did send us (via email) a $12 meal voucher...except you can't find a $12 meal anywhere in that airport, unless you consider a bag of M&M's and a bottle of water a meal. The plane had one problem after another but finally took off 4.5 hours late. This caused us to miss our hotel shuttle at ORD (they didn't run past midnight and it was 3 am) so we had to wait 25 minutes and pay for an Uber. I did get a $50 flight voucher from Alaska...big deal. Barely covers my Uber ride that I shouldn't have needed.

It was good. Too long for older people. Service and support was great! Friendly crew!

I'm not sure if you are going to ask me about the check in process. I could not get my boarding pass, so I had to stop at the American desk before security. I also had a difficult time downloading the app with the confirmation code for the two flights.

Worst first/business class I have ever flown after 75 years on planes. Barely acceptable seats, terrible food, uninterested attendants, unavailable WiFi. I’ll never fly this airline again.

Dropping off of the checked bags took way longer than it should have. The agent for the pre-tagged and ready to drop off line was gone and didn't come back for about 15 minutes. The other bag check lines were barely moving. Agents were standing around and not much was getting done. Everything else about the flight was great.

Check in online didn't accept my confirmation number so i could only check in with assistance at the airport and ended up with s creepy middle seat.

It was the most expensive Alaska Airlines ticket I’ve ever purchased. I had a middle seat with no legroom or space compared to any other middle seat I’ve hadThere was a silver box under the seat that took up 70% of my legroom on the most narrow 737 max the crew flat out would not help they would not help with bags they would not help with garbage there was no coffee,It was definitely not one of my better experiences on Alaska.

Why was I charged for a glass of wine on one flight and not on another? Why no movie or TVs? It was a long flight.

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Charging and entertainment didn't work. The meal was horrible. They only came by with the drink cart one time for the 8 hour flight. They did come by with water a couple times.

The planes can use an actual cleaning. The armrest and seats do not appear to be cleaned on this one and most other planes.

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

The flight de-boarded after being informed of a 3 hour delay. The gate agent said we could go to lounge. The flight ended up boarding 20 minutes later and I missed it.

I love the e fact that the staff communicated swiftly when my flight was delayed and gate number changed

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

Everything you need to know for your flight to Illinois

Cabin class types available on flights to Maui

Cabin classes available on flights to Maui. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.