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$547+ 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 12/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ITO
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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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 November 13, 2025.

This Southwest deal was found by Cheapflights users on 11/12. 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.
Thu 12/45:15 amMDW - ITO
2 stops16h 55mSouthwest
Thu 12/256:55 pmITO - MDW
2 stops13h 20mSouthwest
Deal found 11/12$674
This Southwest deal was found by Cheapflights users on 11/12. 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 12/127:55 amMDW - ITO
2 stops17h 45mSouthwest
Tue 12/166:55 pmITO - MDW
2 stops12h 40mSouthwest
Deal found 11/12$759
This Delta deal was found by Cheapflights users on 11/13. 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.
Fri 12/56:00 amMDW - ITO
2 stops15h 39mDelta
Thu 12/1112:05 pmITO - MDW
2 stops17h 49mDelta
Deal found 11/13$860
This Southwest deal was found by Cheapflights users on 11/10. 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.
Tue 12/305:10 amMDW - ITO
2 stops17h 00mSouthwest
Mon 1/126:55 pmITO - MDW
2 stops15h 50mSouthwest
Deal found 11/10$899
This Southwest deal was found by Cheapflights users on 11/12. 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.
Thu 12/185:30 amMDW - ITO
2 stops16h 40mSouthwest
Sun 12/216:55 pmITO - MDW
2 stops13h 20mSouthwest
Deal found 11/12$1,009
This Delta deal was found by Cheapflights users on 11/12. 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 11/276:00 amMDW - ITO
2 stops17h 13mDelta
Mon 12/110:55 amITO - MDW
2 stops21h 00mDelta
Deal found 11/12$1,157
This Delta deal was found by Cheapflights users on 11/10. 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.
Mon 11/246:00 amMDW - ITO
2 stops18h 28mDelta
Fri 11/283:02 pmITO - MDW
2 stops13h 59mDelta
Deal found 11/10$1,663
This Delta deal was found by Cheapflights users on 11/11. 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 12/256:00 amMDW - ITO
2 stops15h 29mDelta
Sat 1/33:44 pmITO - MDW
2 stops15h 22mDelta
Deal found 11/11$3,258

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 November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$537
(Southwest)

Popular in

December

Cheapest in

November

Average price

$558
Provider with most accurate pricing for Chicago Midway-Hilo Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Hilo Intl flights.
Search Deals
From Chicago Midway to Hilo Intl
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($62 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($40 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 13, 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

Thu 12/4

5:15 am-6:10 pm

2 stops16h 55m

Hilo Intl

Thu 12/25

6:55 pm-12:15 pm

2 stops13h 20m

$674

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Mon 12/8

5:15 am-6:10 pm

2 stops16h 55m

Hilo Intl

Mon 12/15

6:00 am-10:55 pm

2 stops12h 55m

$674

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Fri 12/12

7:55 am-9:40 pm

2 stops17h 45m

Hilo Intl

Tue 12/16

6:55 pm-11:35 am

2 stops12h 40m

$759

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Fri 12/5

6:00 am-5:39 pm

2 stops15h 39m

Hilo Intl

Thu 12/11

12:05 pm-9:54 am

2 stops17h 49m

$860

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Tue 12/30

5:10 am-6:10 pm

2 stops17h 00m

Hilo Intl

Mon 1/12

6:55 pm-2:45 pm

2 stops15h 50m

$899

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Thu 12/18

5:30 am-6:10 pm

2 stops16h 40m

Hilo Intl

Sun 12/21

6:55 pm-12:15 pm

2 stops13h 20m

$1,009

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Thu 11/27

6:00 am-7:13 pm

2 stops17h 13m

Hilo Intl

Mon 12/1

10:55 am-11:55 am

2 stops21h 00m

$1,157

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Mon 11/24

6:00 am-8:28 pm

2 stops18h 28m

Hilo Intl

Fri 11/28

3:02 pm-9:01 am

2 stops13h 59m

$1,663

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Thu 12/25

6:00 am-5:29 pm

2 stops15h 29m

Hilo Intl

Sat 1/3

3:44 pm-11:06 am

2 stops15h 22m

$3,258

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Mon 12/29

5:10 am-6:10 pm

2 stops17h 00m

$547

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 11 results
1
2

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 November.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Hilo flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 15h 39m. Fly via Southwest or Delta to get the fastest option. Airlines will cover a distance of 4162 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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.

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