What is the cheapest airline that flies from Chicago Midway to Hilo Intl?

Southwest is the most popular carrier operating from Chicago Midway to Hilo Intl

When did momondo last update prices for flights from Chicago Midway Airport to Hilo Intl Airport?

Prices for flights from Chicago Midway Airport to Hilo Intl Airport are updated daily.

How old do you have to be to fly from Chicago Midway Airport to Hilo Intl Airport?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Hilo Intl Airport.

What documentation or ID do you need to fly to Hilo Intl Airport?

The necessary travel and health documents for your Hilo Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$247 Cheap Flights from Chicago Midway Airport to Hilo in 2026

Find the cheapest flights from Chicago Midway Airport to Hilo

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:20 pm - 12:35 pm

MDW

ITO

21h 15m

2 stops

8:45 pm - 11:55 am

ITO

MDW

10h 10m

1 stop

$595Southwest

Wed, Aug 19 - Mon, Aug 24

8:20 pm - 12:35 pm

MDW

ITO

21h 15m

2 stops

6:55 pm - 11:55 am

ITO

MDW

12h 00m

2 stops

$600Southwest

Wed, Aug 19 - Mon, Aug 24

6:40 am - 12:35 pm

MDW

ITO

10h 55m

1 stop

8:45 pm - 12:05 pm

ITO

MDW

10h 20m

1 stop

$689Southwest

Mon, Aug 10 - Fri, Aug 14

8:20 pm - 12:35 pm

MDW

ITO

21h 15m

2 stops

8:45 pm - 1:30 pm

ITO

MDW

11h 45m

1 stop

$695Southwest

Wed, Aug 12 - Mon, Aug 17

8:20 pm - 12:35 pm

MDW

ITO

21h 15m

2 stops

8:45 pm - 2:45 pm

ITO

MDW

13h 00m

2 stops

$700Southwest

Wed, Aug 12 - Mon, Aug 17

6:40 am - 12:35 pm

MDW

ITO

10h 55m

1 stop

8:45 pm - 2:20 pm

ITO

MDW

12h 35m

2 stops

$741Southwest

Mon, Aug 10 - Fri, Aug 14

6:40 am - 12:35 pm

MDW

ITO

10h 55m

1 stop

6:55 pm - 1:35 pm

ITO

MDW

13h 40m

2 stops

$756Southwest

Thu, Aug 13 - Tue, Aug 18

5:45 am - 2:30 pm

MDW

ITO

13h 45m

2 stops

6:00 am - 11:30 pm

ITO

MDW

12h 30m

2 stops

$811Southwest

Mon, Jul 6 - Fri, Jul 10

5:45 am - 1:20 pm

MDW

ITO

11h 35m

1 stop

9:25 pm - 12:05 pm

ITO

MDW

10h 40m

1 stop

$835Southwest

Mon, Nov 23 - Mon, Nov 30

5:45 am - 1:20 pm

MDW

ITO

11h 35m

1 stop

9:25 pm - 2:55 pm

ITO

MDW

13h 30m

2 stops

$841Southwest

Mon, Nov 23 - Mon, Nov 30

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Southwest flights from Chicago Midway Airport to Hilo

Our best Southwest deals on Chicago Midway Airport to Hilo flight tickets

Southwest

Aug 19

MDW8:20 pmChicago Midway

21h 15m

2 stops

ITO12:35 pmHilo Intl

Aug 24

ITO8:45 pmHilo Intl

10h 10m

1 stop

MDW11:55 amChicago Midway

$595

Southwest

Aug 19

MDW8:20 pmChicago Midway

21h 15m

2 stops

ITO12:35 pmHilo Intl

Aug 24

ITO6:55 pmHilo Intl

12h 00m

2 stops

MDW11:55 amChicago Midway

$600

Southwest

Aug 10

MDW6:40 amChicago Midway

10h 55m

1 stop

ITO12:35 pmHilo Intl

Aug 14

ITO8:45 pmHilo Intl

10h 20m

1 stop

MDW12:05 pmChicago Midway

$689

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Hilo that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Wed 8/19

8:20 pm-12:35 pm

2 stops21h 15m

Hilo Intl

Mon 8/24

8:45 pm-11:55 am

1 stop10h 10m

$595

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Wed 8/19

8:20 pm-12:35 pm

2 stops21h 15m

Hilo Intl

Mon 8/24

6:55 pm-11:55 am

2 stops12h 00m

$600

Quickest round-trip

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Mon 8/10

6:40 am-12:35 pm

1 stop10h 55m

Hilo Intl

Fri 8/14

8:45 pm-12:05 pm

1 stop10h 20m

$689

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Wed 8/12

8:20 pm-12:35 pm

2 stops21h 15m

Hilo Intl

Mon 8/17

8:45 pm-1:30 pm

1 stop11h 45m

$695

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Wed 8/12

8:20 pm-12:35 pm

2 stops21h 15m

Hilo Intl

Mon 8/17

8:45 pm-2:45 pm

2 stops13h 00m

$700

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Mon 8/10

6:40 am-12:35 pm

1 stop10h 55m

Hilo Intl

Fri 8/14

8:45 pm-2:20 pm

2 stops12h 35m

$741

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Thu 8/13

6:40 am-12:35 pm

1 stop10h 55m

Hilo Intl

Tue 8/18

6:55 pm-1:35 pm

2 stops13h 40m

$756

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Mon 7/6

5:45 am-2:30 pm

2 stops13h 45m

Hilo Intl

Fri 7/10

6:00 am-11:30 pm

2 stops12h 30m

$811

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Mon 11/23

5:45 am-1:20 pm

1 stop11h 35m

Hilo Intl

Mon 11/30

9:25 pm-12:05 pm

1 stop10h 40m

$835

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Mon 11/23

5:45 am-1:20 pm

1 stop11h 35m

Hilo Intl

Mon 11/30

9:25 pm-2:55 pm

2 stops13h 30m

$841

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago Midway Airport to Hilo

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Can stopping save me money on Chicago Midway Airport to Hilo flights?

You could potentially save up to 22% on your flight if you consider stops on a Chicago Midway Airport to Hilo flight.

When to book flights from Chicago Midway Airport to Hilo

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Hilo according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago Midway Airport to Hilo (MDW to ITO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Hilo

Fastest flight time	10h 55m
Direct flights	None

The fastest flight from Chicago Midway Airport to Hilo takes 10h 55m

There are no direct flights from Chicago Midway Airport to Hilo. There are no popular flight routes from Chicago Midway Airport to Hilo.

Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Hilo

How far is Chicago Midway to Hilo Intl by plane?
The straight-line distance from Chicago Midway to Hilo Intl is 4164.2 mi. A reasonable flight in good conditions will take 10h 55m.
When did momondo last update prices for flights from Chicago Midway Airport to Hilo Intl Airport?
Prices for flights from Chicago Midway Airport to Hilo Intl Airport are updated daily.
How old do you have to be to fly from Chicago Midway Airport to Hilo Intl Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Hilo Intl Airport.
What documentation or ID do you need to fly to Hilo Intl Airport?
The necessary travel and health documents for your Hilo Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Hilo?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Hilo. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Hilo with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Hilo flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Hilo?

Once you have performed a search for Chicago to Hilo flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Hilo right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Hilo now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Hilo and let you know when they change.