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.

$383 Cheap Flights from Chicago Midway Airport to Hilo in 2026/27

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.

10:00 am - 9:50 pmMDW Chicago Midway-ITO Hilo Intl

15h 50m2 stops Los Angeles Honolulu

11:35 am - 5:50 amITO Hilo Intl-MDW Chicago Midway

14h 15m2 stops Honolulu Oakland

$581Southwest

Thu, Jan 7 - Tue, Jan 12

10:20 am - 9:50 pmMDW Chicago Midway-ITO Hilo Intl

15h 30m2 stops Oakland Honolulu

9:30 pm - 4:25 pmITO Hilo Intl-MDW Chicago Midway

14h 55m1 stop Las Vegas Harry Reid Intl

$700Southwest

Mon, Feb 22 - Mon, Mar 1

10:20 am - 9:50 pmMDW Chicago Midway-ITO Hilo Intl

15h 30m2 stops Oakland Honolulu

6:55 pm - 11:20 amITO Hilo Intl-MDW Chicago Midway

12h 25m2 stops Honolulu Phoenix Sky Harbor Intl

$705Southwest

Mon, Feb 22 - Mon, Mar 1

10:00 am - 9:50 pmMDW Chicago Midway-ITO Hilo Intl

15h 50m2 stops Los Angeles Honolulu

6:55 pm - 11:20 amITO Hilo Intl-MDW Chicago Midway

12h 25m2 stops Honolulu Phoenix Sky Harbor Intl

$725Southwest

Thu, Jan 7 - Mon, Jan 18

10:00 am - 9:50 pmMDW Chicago Midway-ITO Hilo Intl

15h 50m2 stops Los Angeles Honolulu

9:30 pm - 12:35 pmITO Hilo Intl-MDW Chicago Midway

11h 05m1 stop Las Vegas Harry Reid Intl

$740Southwest

Thu, Jan 7 - Mon, Jan 18

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

$754Southwest

Mon, Nov 2 - Fri, Nov 6

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

11h 35m1 stop Las Vegas Harry Reid Intl

9:25 pm - 2:15 pmITO Hilo Intl-MDW Chicago Midway

12h 50m1 stop Las Vegas Harry Reid Intl

$754Southwest

Thu, Nov 5 - Mon, Nov 9

10:15 am - 9:50 pmMDW Chicago Midway-ITO Hilo Intl

15h 35m2 stops Los Angeles Honolulu

9:30 pm - 4:25 pmITO Hilo Intl-MDW Chicago Midway

14h 55m1 stop Las Vegas Harry Reid Intl

$760Southwest

Sat, Jan 23 - Sun, Jan 31

10:05 am - 9:50 pmMDW Chicago Midway-ITO Hilo Intl

15h 45m2 stops Oakland Honolulu

9:25 pm - 2:15 pmITO Hilo Intl-MDW Chicago Midway

12h 50m1 stop Las Vegas Harry Reid Intl

$760Southwest

Thu, Nov 5 - Mon, Nov 9

5:45 am - 6:10 pmMDW Chicago Midway-ITO Hilo Intl

16h 25m2 stops Las Vegas Harry Reid Intl Honolulu

9:25 pm - 12:15 pmITO Hilo Intl-MDW Chicago Midway

10h 50m1 stop Las Vegas Harry Reid Intl

$760Southwest

Mon, Nov 2 - Fri, Nov 6

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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

Jan 7

MDW10:00 amChicago Midway

15h 50m

2 stops

ITO9:50 pmHilo Intl

Jan 12

ITO11:35 amHilo Intl

14h 15m

2 stops

MDW5:50 amChicago Midway

$581

Southwest

Feb 22

MDW10:20 amChicago Midway

15h 30m

2 stops

ITO9:50 pmHilo Intl

Mar 1

ITO9:30 pmHilo Intl

14h 55m

1 stop

MDW4:25 pmChicago Midway

$700

Southwest

Feb 22

MDW10:20 amChicago Midway

15h 30m

2 stops

ITO9:50 pmHilo Intl

Mar 1

ITO6:55 pmHilo Intl

12h 25m

2 stops

MDW11:20 amChicago Midway

$705

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 Chicago Midway - ITO Hilo Intl

MDWITO

Chicago Midway

Thu 1/7

10:00 am-9:50 pm

2 stops15h 50m

Hilo Intl

Tue 1/12

11:35 am-5:50 am

2 stops14h 15m

$581

ChicagoHilo

MDW Chicago Midway - ITO Hilo Intl

MDWITO

Chicago Midway

Mon 2/22

10:20 am-9:50 pm

2 stops15h 30m

Hilo Intl

Mon 3/1

9:30 pm-4:25 pm

1 stop14h 55m

$700

ChicagoHilo

MDW Chicago Midway - ITO Hilo Intl

MDWITO

Chicago Midway

Mon 2/22

10:20 am-9:50 pm

2 stops15h 30m

Hilo Intl

Mon 3/1

6:55 pm-11:20 am

2 stops12h 25m

$705

ChicagoHilo

MDW Chicago Midway - ITO Hilo Intl

MDWITO

Chicago Midway

Thu 1/7

10:00 am-9:50 pm

2 stops15h 50m

Hilo Intl

Mon 1/18

6:55 pm-11:20 am

2 stops12h 25m

$725

ChicagoHilo

MDW Chicago Midway - ITO Hilo Intl

MDWITO

Chicago Midway

Thu 1/7

10:00 am-9:50 pm

2 stops15h 50m

Hilo Intl

Mon 1/18

9:30 pm-12:35 pm

1 stop11h 05m

$740

Quickest round-trip

ChicagoHilo

MDW Chicago Midway - ITO Hilo Intl

MDWITO

Chicago Midway

Mon 11/2

5:45 am-1:20 pm

1 stop11h 35m

Hilo Intl

Fri 11/6

9:25 pm-2:10 pm

1 stop12h 45m

$754

ChicagoHilo

MDW Chicago Midway - ITO Hilo Intl

MDWITO

Chicago Midway

Thu 11/5

5:45 am-1:20 pm

1 stop11h 35m

Hilo Intl

Mon 11/9

9:25 pm-2:15 pm

1 stop12h 50m

$754

ChicagoHilo

MDW Chicago Midway - ITO Hilo Intl

MDWITO

Chicago Midway

Sat 1/23

10:15 am-9:50 pm

2 stops15h 35m

Hilo Intl

Sun 1/31

9:30 pm-4:25 pm

1 stop14h 55m

$760

ChicagoHilo

MDW Chicago Midway - ITO Hilo Intl

MDWITO

Chicago Midway

Thu 11/5

10:05 am-9:50 pm

2 stops15h 45m

Hilo Intl

Mon 11/9

9:25 pm-2:15 pm

1 stop12h 50m

$760

ChicagoHilo

MDW Chicago Midway - ITO Hilo Intl

MDWITO

Chicago Midway

Mon 11/2

5:45 am-6:10 pm

2 stops16h 25m

Hilo Intl

Fri 11/6

9:25 pm-12:15 pm

1 stop10h 50m

$760

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 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	$383
Fastest flight time	11h 30m
Direct flights	None

The best one-way flight to Hilo from Chicago Midway Airport in the past 72 hours is $383. The best round-trip flight deal from Chicago Midway Airport to Hilo found on momondo in the last 72 hours is $581.

The fastest flight from Chicago Midway Airport to Hilo takes 11h 30m

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 30m.
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.