$243 Cheap Flights from Hilo (ITO) to Chicago (MDW)

View $243 flight on Thu, Sep 4, 2025Opens in a new window

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

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Cheap Flights from Hilo to Chicago (ITO-MDW)

Prices were available within the past 7 days and start at $243 for one-way flights and $495 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Thu, Sep 4 - Tue, Sep 9
ITO
Hawaii Island
MDW
Chicago
$495 Roundtrip, found 4 hours ago
$495
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Thu, Sep 4 from Hawaii Island to Chicago, returning Tue, Sep 9, priced at $495 found 4 hours ago
Southwest Airlines
Thu, Sep 4 - Tue, Sep 9
ITO
Hawaii Island
MDW
Chicago
$504 Roundtrip, found 4 hours ago
$504
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Thu, Sep 4 from Hawaii Island to Chicago, returning Tue, Sep 9, priced at $504 found 4 hours ago
Southwest Airlines
Thu, Sep 4 - Tue, Sep 9
ITO
Hawaii Island
MDW
Chicago
$509 Roundtrip, found 4 hours ago
$509
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Thu, Sep 4 from Hawaii Island to Chicago, returning Tue, Sep 9, priced at $509 found 4 hours ago
Southwest Airlines
Thu, Sep 4 - Tue, Sep 9
ITO
Hawaii Island
MDW
Chicago
$527 Roundtrip, found 4 hours ago
$527
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Thu, Sep 4 from Hawaii Island to Chicago, returning Tue, Sep 9, priced at $527 found 4 hours ago
Southwest Airlines
Thu, Sep 4 - Tue, Sep 9
ITO
Hawaii Island
MDW
Chicago
$536 Roundtrip, found 4 hours ago
$536
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Thu, Sep 4 from Hawaii Island to Chicago, returning Tue, Sep 9, priced at $536 found 4 hours ago
Southwest Airlines
Thu, Sep 4 - Tue, Sep 9
ITO
Hawaii Island
MDW
Chicago
$541 Roundtrip, found 4 hours ago
$541
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Thu, Sep 4 from Hawaii Island to Chicago, returning Tue, Sep 9, priced at $541 found 4 hours ago
Southwest Airlines
Thu, Sep 4 - Tue, Sep 9
ITO
Hawaii Island
MDW
Chicago
$568 Roundtrip, found 4 hours ago
$568
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Thu, Sep 4 from Hawaii Island to Chicago, returning Tue, Sep 9, priced at $568 found 4 hours ago
Southwest Airlines
Thu, Aug 28 - Wed, Sep 3
ITO
Hawaii Island
MDW
Chicago
$574 Roundtrip, found 4 hours ago
$574
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Thu, Aug 28 from Hawaii Island to Chicago, returning Wed, Sep 3, priced at $574 found 4 hours ago
Southwest Airlines
Thu, Sep 4 - Tue, Sep 9
ITO
Hawaii Island
MDW
Chicago
$584 Roundtrip, found 4 hours ago
$584
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Thu, Sep 4 from Hawaii Island to Chicago, returning Tue, Sep 9, priced at $584 found 4 hours ago
Delta
Thu, Sep 4 - Tue, Sep 9
ITO
Hawaii Island
MDW
Chicago
$947 Roundtrip, found 4 hours ago
$947
Roundtrip
found 4 hours ago
Select Delta flight, departing Thu, Sep 4 from Hawaii Island to Chicago, returning Tue, Sep 9, priced at $947 found 4 hours ago
Flights from Hilo (ITO) to Chicago (MDW)
Origin airport
Hilo Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$494
Distance
4165 mi

Hilo to Chicago Flights

The cheapest times to fly from Hilo to Chicago

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 Hilo to Chicago are during the month of September. You can find some of the cheapest flights from Hilo to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Hilo to Chicago

Sunday is one of the best days to book for cheap flights from Hilo to Chicago: 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 Hilo to Chicago

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 Hilo to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $243 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 Hilo to Chicago 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 Hilo to Chicago 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.

 

Frequently asked questions

How much does a flight from Hilo Intl. Airport (ITO) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from ITO to MDW by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from ITO to MDW?
The cheapest flights from ITO to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from ITO to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from ITO to MDW. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Hilo Intl. Airport (ITO) to Midway Intl. Airport (MDW)?
Direct flights from Hilo Intl. Airport (ITO) to Midway Intl. Airport (MDW) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel details and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ITO to MDW?
Usually you'll find the greatest selection of flight options on a Friday. Tuesdays tend to be the quietest.* But this can change depending on the time of year, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Hilo Intl. Airport (ITO) to Midway Intl. Airport (MDW)?
Select a flight from Hilo Intl. Airport (ITO) to Midway Intl. Airport (MDW) that takes off before 3 PM to reduce the likelihood of delays and cancellations. Departures after this time are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Hilo Intl. Airport (ITO) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from ITO to MDW are typically more expensive. To secure the best prices, start searching for flights ahead of time. That being said, if you're flexible with your travel plans, it's possible to find a cheap fare just before your departure.
Is it cheaper to book an ITO to MDW flight and hotel package?
Opting for an ITO to MDW flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels in one place. Pick from our wide 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 Hilo Intl. Airport (ITO) to Midway Intl. Airport (MDW)?
In most cases, you can modify or cancel your ITO to MDW flight. However, there may be additional charges, especially if your booking was made over 24 hours ago. Check your itinerary for the airline's policies and fees on flight changes, or if you'd like further details, head to our Customer Service portal.

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*Available to One Key members.