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

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:10 am - 12:35 pmMDW Chicago Midway-ITO Hilo Intl

12h 25m1 stop Las Vegas Harry Reid Intl

8:45 pm - 1:25 pmITO Hilo Intl-MDW Chicago Midway

11h 40m1 stop Las Vegas Harry Reid Intl

$494Southwest

Thu, Oct 22 - Mon, Oct 26

5:10 am - 12:35 pmMDW Chicago Midway-ITO Hilo Intl

12h 25m1 stop Las Vegas Harry Reid Intl

11:40 am - 5:55 amITO Hilo Intl-MDW Chicago Midway

13h 15m2 stops Honolulu Oakland

$500Southwest

Thu, Oct 22 - Mon, Oct 26

5:45 am - 1:20 pmMDW Chicago Midway-ITO Hilo Intl

11h 35m1 stop Las Vegas Harry Reid Intl

11:35 am - 5:55 amITO Hilo Intl-MDW Chicago Midway

14h 20m2 stops Honolulu Oakland

$560Southwest

Fri, Nov 27 - Sun, Dec 6

5:45 am - 1:20 pmMDW Chicago Midway-ITO Hilo Intl

11h 35m1 stop Las Vegas Harry Reid Intl

9:25 pm - 2:10 pmITO Hilo Intl-MDW Chicago Midway

12h 45m1 stop Las Vegas Harry Reid Intl

$614Southwest

Fri, Nov 27 - Sun, Dec 6

5:10 am - 12:35 pmMDW Chicago Midway-ITO Hilo Intl

12h 25m1 stop Las Vegas Harry Reid Intl

8:45 pm - 3:45 pmITO Hilo Intl-MDW Chicago Midway

14h 00m1 stop Las Vegas Harry Reid Intl

$660Southwest

Mon, Oct 5 - Mon, Oct 12

5:25 am - 2:35 pmMDW Chicago Midway-ITO Hilo Intl

14h 10m2 stops San Diego Honolulu

8:45 pm - 3:45 pmITO Hilo Intl-MDW Chicago Midway

14h 00m1 stop Las Vegas Harry Reid Intl

$666Southwest

Mon, Oct 5 - Mon, Oct 12

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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

Oct 22

MDW5:10 amChicago Midway

12h 25m

1 stop

ITO12:35 pmHilo Intl

Oct 26

ITO8:45 pmHilo Intl

11h 40m

1 stop

MDW1:25 pmChicago Midway

$494

Southwest

Oct 22

MDW5:10 amChicago Midway

12h 25m

1 stop

ITO12:35 pmHilo Intl

Oct 26

ITO11:40 amHilo Intl

13h 15m

2 stops

MDW5:55 amChicago Midway

$500

Southwest

Nov 27

MDW5:45 amChicago Midway

11h 35m

1 stop

ITO1:20 pmHilo Intl

Dec 6

ITO11:35 amHilo Intl

14h 20m

2 stops

MDW5:55 amChicago Midway

$560

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

Quickest round-trip

ChicagoHilo

MDW Chicago Midway - ITO Hilo Intl

MDWITO

Chicago Midway

Thu 10/22

5:10 am-12:35 pm

1 stop12h 25m

Hilo Intl

Mon 10/26

8:45 pm-1:25 pm

1 stop11h 40m

$494

ChicagoHilo

MDW Chicago Midway - ITO Hilo Intl

MDWITO

Chicago Midway

Thu 10/22

5:10 am-12:35 pm

1 stop12h 25m

Hilo Intl

Mon 10/26

11:40 am-5:55 am

2 stops13h 15m

$500

ChicagoHilo

MDW Chicago Midway - ITO Hilo Intl

MDWITO

Chicago Midway

Fri 11/27

5:45 am-1:20 pm

1 stop11h 35m

Hilo Intl

Sun 12/6

11:35 am-5:55 am

2 stops14h 20m

$560

ChicagoHilo

MDW Chicago Midway - ITO Hilo Intl

MDWITO

Chicago Midway

Fri 11/27

5:45 am-1:20 pm

1 stop11h 35m

Hilo Intl

Sun 12/6

9:25 pm-2:10 pm

1 stop12h 45m

$614

ChicagoHilo

MDW Chicago Midway - ITO Hilo Intl

MDWITO

Chicago Midway

Mon 10/5

5:10 am-12:35 pm

1 stop12h 25m

Hilo Intl

Mon 10/12

8:45 pm-3:45 pm

1 stop14h 00m

$660

ChicagoHilo

MDW Chicago Midway - ITO Hilo Intl

MDWITO

Chicago Midway

Mon 10/5

5:25 am-2:35 pm

2 stops14h 10m

Hilo Intl

Mon 10/12

8:45 pm-3:45 pm

1 stop14h 00m

$666

Cheapest one-way

Quickest one-way

ChicagoHilo

MDW Chicago Midway - ITO Hilo Intl

MDWITO

Chicago Midway

Fri 11/27

5:45 am-1:20 pm

1 stop11h 35m

$247

ChicagoHilo

MDW Chicago Midway - ITO Hilo Intl

MDWITO

Chicago Midway

Fri 11/27

10:15 am-9:50 pm

2 stops15h 35m

$358

ChicagoHilo

MDW Chicago Midway - ITO Hilo Intl

MDWITO

Chicago Midway

Wed 9/9

8:20 pm-12:35 pm

2 stops21h 15m

$378

ChicagoHilo

MDW Chicago Midway - ITO Hilo Intl

MDWITO

Chicago Midway

Mon 10/5

5:10 am-12:35 pm

1 stop12h 25m

$413

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 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

Best Price Found	$247
Fastest flight time	11h 35m
Direct flights	None

The best one-way flight to Hilo from Chicago Midway Airport in the past 72 hours is $247. The best round-trip flight deal from Chicago Midway Airport to Hilo found on momondo in the last 72 hours is $494.

The fastest flight from Chicago Midway Airport to Hilo takes 11h 35m

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 11h 35m.
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.