$330 Cheap Flights from Chicago (MDW) to Hilo (ITO)

View $330 flight on Tue, May 19, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Hilo Intl. Airport (ITO)

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Cheap Flights from Chicago to Hilo (MDW-ITO)

Prices were available within the past 7 days and start at $330 for one-way flights and $635 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, May 19 - Sat, May 23
MDW
Chicago
ITO
Hawaii Island
$635 Roundtrip, found 6 days ago
$635
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, May 19 from Chicago to Hawaii Island, returning Sat, May 23, priced at $635 found 6 days ago
Southwest Airlines
Fri, Sep 18 - Fri, Sep 25
MDW
Chicago
ITO
Hawaii Island
$644 Roundtrip, found 4 days ago
$644
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Fri, Sep 18 from Chicago to Hawaii Island, returning Fri, Sep 25, priced at $644 found 4 days ago
Southwest Airlines
Tue, May 19 - Wed, May 20
MDW
Chicago
ITO
Hawaii Island
$645 Roundtrip, found 6 days ago
$645
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, May 19 from Chicago to Hawaii Island, returning Wed, May 20, priced at $645 found 6 days ago
Southwest Airlines
Fri, May 8 - Tue, May 12
MDW
Chicago
ITO
Hawaii Island
$649 Roundtrip, found 6 days ago
$649
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Fri, May 8 from Chicago to Hawaii Island, returning Tue, May 12, priced at $649 found 6 days ago
Southwest Airlines
Wed, Oct 7 - Tue, Oct 13
MDW
Chicago
ITO
Hawaii Island
$685 Roundtrip, found 8 hours ago
$685
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Wed, Oct 7 from Chicago to Hawaii Island, returning Tue, Oct 13, priced at $685 found 8 hours ago
Southwest Airlines
Fri, Sep 18 - Fri, Sep 25
MDW
Chicago
ITO
Hawaii Island
$694 Roundtrip, found 4 days ago
$694
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Fri, Sep 18 from Chicago to Hawaii Island, returning Fri, Sep 25, priced at $694 found 4 days ago
Southwest Airlines
Tue, May 19 - Fri, May 22
MDW
Chicago
ITO
Hawaii Island
$702 Roundtrip, found 12 hours ago
$702
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Tue, May 19 from Chicago to Hawaii Island, returning Fri, May 22, priced at $702 found 12 hours ago
Southwest Airlines
Mon, Oct 5 - Fri, Oct 9
MDW
Chicago
ITO
Hawaii Island
$704 Roundtrip, found 7 hours ago
$704
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Mon, Oct 5 from Chicago to Hawaii Island, returning Fri, Oct 9, priced at $704 found 7 hours ago
Southwest Airlines
Mon, May 4 - Mon, May 18
MDW
Chicago
ITO
Hawaii Island
$715 Roundtrip, just found
$715
Roundtrip
just found
Select Southwest Airlines flight, departing Mon, May 4 from Chicago to Hawaii Island, returning Mon, May 18, priced at $715 just found
Southwest Airlines
Tue, May 19 - Fri, May 22
MDW
Chicago
ITO
Hawaii Island
$725 Roundtrip, found 16 hours ago
$725
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Tue, May 19 from Chicago to Hawaii Island, returning Fri, May 22, priced at $725 found 16 hours ago

Frequently asked questions

How much does a flight from Chicago, IL (MDW-Midway Intl.) to Hilo, HI (ITO-Hilo Intl.) cost?
You can find cheap one-way flights from $330 and cheap return flights from $635 Chicago, IL (MDW-Midway Intl.) to Hilo, HI (ITO-Hilo Intl.) with Expedia. Return flights often range between $953 and $1394. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Chicago, IL (MDW-Midway Intl.) to Hilo, HI (ITO-Hilo Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Chicago, IL (MDW-Midway Intl.) to Hilo, HI (ITO-Hilo Intl.)?
The cheapest month to fly from MDW to ITO is May when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Chicago, IL (MDW-Midway Intl.) to Hilo, HI (ITO-Hilo Intl.)?
Enter MDW to ITO and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Chicago, IL (MDW-Midway Intl.) to Hilo, HI (ITO-Hilo Intl.)?
Southwest Airlines is one of the cheapest airlines offering connecting flights from Chicago, IL (MDW) to Hilo, HI (ITO), with round-trip tickets starting from around $868. This flight includes a layover in Las Vegas (LAS). Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Chicago, IL (MDW-Midway Intl.) to Hilo, HI (ITO-Hilo Intl.)?
To find a cheap flight from Chicago, IL (MDW-Midway Intl.) to Hilo, HI (ITO-Hilo Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Chicago, IL (MDW-Midway Intl.) to Hilo, HI (ITO-Hilo Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from Chicago, IL (MDW-Midway Intl.) to Hilo, HI (ITO-Hilo Intl.)?
The earliest flight from Chicago (MDW-Midway Intl.) to Hilo (ITO-Hilo Intl.) usually departs at around 5:10 AM, operated by Southwest Airlines. This seasonal service is active in June, allowing you to make the most of your time in Hawaii. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Chicago, IL (MDW-Midway Intl.) to Hilo, HI (ITO-Hilo Intl.)?
The busiest day for flights from Midway Intl. (MDW) to Hilo Intl. (ITO) is a Monday, with around 8 flights. This gives you plenty of options for your travel plans. A major airline on this route is Delta.
What are the most popular departure times for flights from Chicago, IL (MDW-Midway Intl.) to Hilo, HI (ITO-Hilo Intl.)?
For flights from Midway Intl. (MDW) to Hilo Intl. (ITO), the most popular departure times are in the early morning, from 6am to 9am. About 58% of passengers choose this time, likely because it allows for a full day of travel upon arrival. Southwest Airlines, Delta Airlines, and Alaska Airlines all provide flights during this window.
How long does it take to fly from Chicago, IL (MDW-Midway Intl.) to Hilo, HI (ITO-Hilo Intl.)?
A flight from MDW to ITO with a layover takes around 12 hours 20 minutes, with the route covering approximately 4,166 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (MDW-Midway Intl.) to Hilo, HI (ITO-Hilo Intl.)?
Select the "Business class" and "First class" filters when looking for MDW to ITO flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Chicago, IL (MDW-Midway Intl.) to Hilo, HI (ITO-Hilo Intl.) flight with Expedia?
It's easy to earn miles on a Chicago, IL (MDW-Midway Intl.) to Hilo, HI (ITO-Hilo Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Hilo from Midway Intl. (MDW)?
If you're planning to travel to Hilo from Midway Intl. (MDW), you can fly typically into Hilo Intl. (ITO) Some flights may connect through major hubs like Harry Reid Intl. (LAS), Sky Harbor Intl. (PHX), San Diego Intl. (SAN) before reaching Hilo. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Chicago, IL (MDW-Midway Intl.) to Hilo, HI (ITO-Hilo Intl.) at the last minute?
Typically, booking a last minute flight from Chicago, IL (MDW-Midway Intl.) to Hilo, HI (ITO-Hilo Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (MDW-Midway Intl.) to Hilo, HI (ITO-Hilo Intl.) flight and hotel package?
Securing a Chicago, IL (MDW-Midway Intl.) to Hilo, HI (ITO-Hilo Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (MDW-Midway Intl.) to Hilo, HI (ITO-Hilo Intl.)?
If you booked your Chicago, IL (MDW-Midway Intl.) to Hilo, HI (ITO-Hilo Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Midway Intl.
Destination airport
Hilo Intl.
Airlines serving
Southwest Airlines
Roundtrip price
$634
Distance
4165 mi

Book with confidence

Chicago to Hilo Flights

The cheapest times to fly from Chicago to Hilo

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Hilo are during the month of May. You can find some of the cheapest flights from Chicago to Hilo with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Hilo

Sunday is one of the best days to book for cheap flights from Chicago to Hilo: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Hilo

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Hilo in 2026. You can also book with separate airlines for your outbound and return journeys, from $330 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Hilo flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Hilo airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Hilo Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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