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$597+ Cheap flights from Midway (MDW) to Hilo (ITO)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ITO
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
1 adult, Economy
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Cheap flight deals from Midway to Hilo

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Hilo (ITO). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$674
(Southwest)

One-way from

$597
(Southwest)

Popular in

June

Cheapest in

November

Average price

$701
Provider with most accurate pricing for Chicago Midway-Hilo Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Hilo Intl flights.
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From Chicago Midway to Hilo Intl
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One-way flight from Chicago Midway to Hilo Intl
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Highest demand for flights based on searches. 12% potential increase in price ($119 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($38 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Midway to Hilo

Cheapest flights from Midway to Hilo
Explore the most affordable flight options available from Midway to Hilo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 29, 2025.

This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/77:55 amMDW - ITO
2 stops17h 45mSouthwest
Sat 12/136:55 pmITO - MDW
2 stops13h 45mSouthwest
Deal found 9/29$674
This Southwest deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:55 amMDW - ITO
2 stops16h 15mSouthwest
Sat 12/136:55 pmITO - MDW
2 stops13h 45mSouthwest
Deal found 9/27$724
This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/77:45 amMDW - ITO
2 stops17h 55mSouthwest
Wed 1/76:55 pmITO - MDW
2 stops15h 50mSouthwest
Deal found 9/29$944
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/105:40 amMDW - ITO
2 stops14h 00mSouthwest
Mon 10/136:55 pmITO - MDW
2 stops12h 30mSouthwest
Deal found 9/28$994
This Delta deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/276:00 amMDW - ITO
2 stops21h 17mDelta
Mon 9/2910:59 amITO - MDW
2 stops17h 41mDelta
Deal found 9/26$1,236
This Southwest deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:10 amMDW - ITO
2 stops17h 00mSouthwest
Sat 12/276:55 pmITO - MDW
2 stops15h 15mSouthwest
Deal found 9/27$1,319
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/96:00 amMDW - ITO
2 stops19h 31mDelta
Mon 10/136:55 pmITO - MDW
2 stops32h 45mDelta
Deal found 9/28$1,385
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/86:00 amMDW - ITO
2 stops18h 30mDelta
Sat 11/1511:16 amITO - MDW
2 stops21h 18mDelta
Deal found 9/27$1,403
This Delta deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/146:00 amMDW - ITO
2 stops15h 16mDelta
Sat 10/189:49 amITO - MDW
2 stops18h 06mDelta
Deal found 9/29$1,451
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/116:23 pmMDW - ITO
2 stops49h 30mDelta
Mon 10/137:49 pmITO - MDW
2 stops32h 06mDelta
Deal found 9/28$1,475
This Southwest deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/195:10 amMDW - ITO
2 stops17h 00mSouthwest
Fri 1/26:00 amITO - MDW
2 stops13h 50mSouthwest
Deal found 9/27$2,362

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Hilo that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 29, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Hilo that are best for you.

Fly from

Midway

Fly to

Hilo

Route

Depart

Return

Price

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sun 12/7

7:55 am-9:40 pm

2 stops17h 45m

Hilo Intl

Sat 12/13

6:55 pm-12:40 pm

2 stops13h 45m

$674

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sat 12/6

5:55 am-6:10 pm

2 stops16h 15m

Hilo Intl

Sat 12/13

6:55 pm-12:40 pm

2 stops13h 45m

$724

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Fri 11/7

7:45 am-9:40 pm

2 stops17h 55m

Hilo Intl

Wed 1/7

6:55 pm-2:45 pm

2 stops15h 50m

$944

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Mon 12/22

5:10 am-6:10 pm

2 stops17h 00m

Hilo Intl

Sat 12/27

6:55 pm-2:10 pm

2 stops15h 15m

$1,319

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Thu 10/9

6:00 am-8:31 pm

2 stops19h 31m

Hilo Intl

Mon 10/13

6:55 pm-8:40 am

2 stops32h 45m

$1,385

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sat 11/8

6:00 am-8:30 pm

2 stops18h 30m

Hilo Intl

Sat 11/15

11:16 am-12:34 pm

2 stops21h 18m

$1,403

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Tue 10/14

6:00 am-4:16 pm

2 stops15h 16m

Hilo Intl

Sat 10/18

9:49 am-8:55 am

2 stops18h 06m

$1,451

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sat 10/11

6:23 pm-2:53 pm

2 stops49h 30m

Hilo Intl

Mon 10/13

7:49 pm-8:55 am

2 stops32h 06m

$1,475

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Fri 12/19

5:10 am-6:10 pm

2 stops17h 00m

Hilo Intl

Fri 1/2

6:00 am-11:50 pm

2 stops13h 50m

$2,362

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Fri 10/10

5:40 am-2:40 pm

2 stops14h 00m

$597

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/28

Showing 1-10 of 12 results
1
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Compare providers for flights from Midway to Hilo

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Hilo in September.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Hilo flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Hilo flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Hilo flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Hilo flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Hilo flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to Hilo

Have a flexible travel schedule? Discover the best time to fly to Hilo from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Find useful and relevant information for your journey from Midway to Hilo. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Hilo from Chicago Midway?

    If you book a flight to Hilo from Chicago Midway, you will be flying to Hilo Intl, which is the city’s only airport. Hilo Intl (ITO) is located 3.0 mi from the center of Hilo. There are 0 flights from Chicago Midway to Hilo Intl per day from 0 different airlines.

  • How long is the flight from Chicago Midway Airport to Hilo?

    There are many flights that can get you from Chicago Midway Airport to Hilo in 17h 45m. Fly via Southwest to get the fastest option. Airlines will cover a distance of 4162 mi.

  • Can I find deals for flights from Midway to Hilo that include hotel bookings?

    Yes. In addition to deals on Midway to Hilo flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Hilo?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Hilo.

  • Can I find deals for business class flights from Midway to Hilo?

    Yes. Cheapflights offers flight deals from Midway to Hilo by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Hilo?

    Currently, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Hilo (average of $330). Flying from Chicago Midway Airport to Hilo in December is currently the most expensive (average of $726). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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