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Hilo

$660+ Cheap flights from Midway (MDW) to Hilo (ITO)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ITO
Mar 14 — Mar 211
Sat 3/14
Sat 3/21
1 adult, Economy
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Cheap 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 February 12, 2026.

This Southwest deal was found by Cheapflights users on 2/9. 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.
Wed 8/126:50 am
MDW
-
ITO
2 stops19h 55m
Southwest
Mon 8/178:45 pm
ITO
-
MDW
1 stop11h 50m
Southwest
Deal found 2/9$660
This Southwest deal was found by Cheapflights users on 2/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:45 am
MDW
-
ITO
2 stops14h 25m
Southwest
Mon 3/26:55 pm
ITO
-
MDW
2 stops13h 40m
Southwest
Deal found 2/11$725
This Southwest deal was found by Cheapflights users on 2/10. 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.
Wed 6/310:00 am
MDW
-
ITO
2 stops13h 10m
Southwest
Wed 6/108:00 am
ITO
-
MDW
2 stops16h 00m
Southwest
Deal found 2/10$815
This Southwest deal was found by Cheapflights users on 2/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/1610:05 am
MDW
-
ITO
2 stops16h 35m
Southwest
Fri 3/206:55 pm
ITO
-
MDW
2 stops12h 50m
Southwest
Deal found 2/11$860
This Southwest deal was found by Cheapflights users on 2/8. 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 5/217:50 am
MDW
-
ITO
2 stops15h 20m
Southwest
Sun 5/246:55 pm
ITO
-
MDW
2 stops12h 40m
Southwest
Deal found 2/8$875
This Southwest deal was found by Cheapflights users on 2/10. 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 4/710:20 am
MDW
-
ITO
2 stops16h 25m
Southwest
Sat 4/116:00 am
ITO
-
MDW
2 stops12h 05m
Southwest
Deal found 2/10$910
This Delta deal was found by Cheapflights users on 2/12. 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.
Fri 3/136:00 am
MDW
-
ITO
2 stops16h 29m
Delta
Sat 3/219:58 am
ITO
-
MDW
2 stops21h 31m
Delta
Deal found 2/12$1,645
This Delta deal was found by Cheapflights users on 2/11. 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.
Fri 3/276:00 am
MDW
-
ITO
2 stops16h 27m
Delta
Sat 4/49:58 am
ITO
-
MDW
2 stops21h 04m
Delta
Deal found 2/11$2,052

Find 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 February 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$725
(Southwest)
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
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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 February 12, 2026.
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

Mon 3/16

10:05 am-9:40 pm

2 stops16h 35m

Hilo Intl

Fri 3/20

6:55 pm-12:45 pm

2 stops12h 50m

$860

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Tue 4/7

10:20 am-9:45 pm

2 stops16h 25m

Hilo Intl

Sat 4/11

6:00 am-11:05 pm

2 stops12h 05m

$910

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Fri 3/13

6:00 am-5:29 pm

2 stops16h 29m

Hilo Intl

Sat 3/21

9:58 am-12:29 pm

2 stops21h 31m

$1,645

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Fri 3/27

6:00 am-5:27 pm

2 stops16h 27m

Hilo Intl

Sat 4/4

9:58 am-12:02 pm

2 stops21h 04m

$2,052

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/11

  • 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 16h 29m. 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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