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$527+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ITO
ago. 19 — ago. 261
mar. 8/19
mar. 8/26
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 agosto 14, 2025.

Round-trip from

$652
(Southwest)

One-way from

$527
(Delta)

Popular in

June

Cheapest in

November

Average price

$883
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 August 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 agosto 14, 2025.

This Southwest deal was found by Cheapflights users on 8/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/247:45 amMDW - ITO
2 stops15h 25mSouthwest
vie. 10/316:55 pmITO - MDW
2 stops16h 55mSouthwest
Deal found 8/13$652
This Southwest deal was found by Cheapflights users on 8/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/255:15 amMDW - ITO
2 stops17h 55mSouthwest
lun. 9/86:55 pmITO - MDW
2 stops14h 00mSouthwest
Deal found 8/13$754
This Southwest deal was found by Cheapflights users on 8/14. 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.
dom. 8/175:30 amMDW - ITO
2 stops14h 10mSouthwest
dom. 8/316:00 amITO - MDW
2 stops12h 25mSouthwest
Deal found 8/14$944
This Delta deal was found by Cheapflights users on 8/13. 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.
sáb. 9/271:43 pmMDW - ITO
2 stops35h 47mDelta
lun. 9/2912:20 pmITO - MDW
2 stops24h 15mDelta
Deal found 8/13$945
This Delta deal was found by Cheapflights users on 8/12. 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.
jue. 9/46:00 amMDW - ITO
2 stops14h 59mDelta
mar. 9/912:20 pmITO - MDW
2 stops16h 14mDelta
Deal found 8/12$954
This Southwest deal was found by Cheapflights users on 8/12. 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.
vie. 8/155:15 amMDW - ITO
2 stops17h 55mSouthwest
vie. 8/226:55 pmITO - MDW
2 stops16h 50mSouthwest
Deal found 8/12$1,069
This Delta deal was found by Cheapflights users on 8/12. 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.
mié. 8/276:00 amMDW - ITO
2 stops15h 56mDelta
dom. 8/319:43 amITO - MDW
2 stops18h 07mDelta
Deal found 8/12$1,296
This Delta deal was found by Cheapflights users on 8/12. 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.
sáb. 11/86:00 amMDW - ITO
2 stops15h 31mDelta
sáb. 11/1511:56 amITO - MDW
2 stops21h 13mDelta
Deal found 8/12$1,309
This Southwest deal was found by Cheapflights users on 8/12. 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.
sáb. 12/278:45 amMDW - ITO
2 stops13h 25mSouthwest
lun. 1/56:55 pmITO - MDW
2 stops13h 40mSouthwest
Deal found 8/12$1,424
This Southwest deal was found by Cheapflights users on 8/14. 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.
dom. 12/287:45 amMDW - ITO
2 stops14h 25mSouthwest
dom. 1/46:55 pmITO - MDW
2 stops14h 10mSouthwest
Deal found 8/14$1,896

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 agosto 14, 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

vie. 10/24

7:45 am-6:10 pm

2 stops15h 25m

Hilo Intl

vie. 10/31

6:55 pm-4:50 pm

2 stops16h 55m

$652

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

mar. 8/26

6:10 am-6:10 pm

2 stops17h 00m

Hilo Intl

mar. 9/9

6:55 pm-1:15 pm

2 stops13h 20m

$754

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

lun. 8/25

5:15 am-6:10 pm

2 stops17h 55m

Hilo Intl

lun. 9/8

6:55 pm-1:55 pm

2 stops14h 00m

$754

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

dom. 8/17

5:30 am-2:40 pm

2 stops14h 10m

Hilo Intl

dom. 8/31

6:00 am-11:25 pm

2 stops12h 25m

$944

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

sáb. 9/27

9:20 am-8:30 pm

2 stops40h 10m

Hilo Intl

lun. 9/29

9:43 am-5:35 pm

2 stops26h 52m

$945

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

jue. 9/4

6:00 am-3:59 pm

2 stops14h 59m

Hilo Intl

mar. 9/9

12:20 pm-9:34 am

2 stops16h 14m

$954

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

mié. 8/27

6:00 am-4:56 pm

2 stops15h 56m

Hilo Intl

dom. 8/31

9:43 am-8:50 am

2 stops18h 07m

$1,296

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

sáb. 11/8

6:00 am-5:31 pm

2 stops15h 31m

Hilo Intl

sáb. 11/15

11:56 am-1:09 pm

2 stops21h 13m

$1,309

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

vie. 9/5

6:00 am-4:56 pm

2 stops15h 56m

$527

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

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.

  • 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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