Cheap flights from Chicago Midway Airport to Hilo from $377

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Hilo departing on 9/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to Hilo

Cheap round-trip flights

Southwest Logo
5:55 am - 6:10 pmMDW-ITO
16h 15m2 stops
Southwest Logo
6:55 pm - 12:40 pmITO-MDW
13h 45m2 stops
$704Southwest
Find Deal
Sat, Nov 15 - Sat, Dec 6
Southwest Logo
8:20 am - 6:10 pmMDW-ITO
13h 50m2 stops
Southwest Logo
6:55 pm - 12:30 pmITO-MDW
13h 35m2 stops
$784Southwest
Find Deal
Sat, Feb 7 - Sat, Feb 14
Southwest Logo
6:10 am - 2:40 pmMDW-ITO
13h 30m2 stops
Southwest Logo
6:55 pm - 12:15 pmITO-MDW
12h 20m2 stops
$834Southwest
Find Deal
Tue, Sep 23 - Tue, Sep 30
Delta Logo
6:00 am - 4:56 pmMDW-ITO
15h 56m2 stops
Delta Logo
12:20 pm - 8:40 amITO-MDW
15h 20m2 stops
$912Delta
Find Deal
Tue, Sep 23 - Tue, Sep 30
Delta Logo
6:00 am - 5:31 pmMDW-ITO
15h 31m2 stops
Delta Logo
1:46 pm - 9:52 amITO-MDW
16h 06m2 stops
$914Delta
Find Deal
Wed, Nov 12 - Tue, Nov 18
Delta Logo
6:00 am - 4:56 pmMDW-ITO
15h 56m2 stops
Delta Logo
12:20 pm - 9:40 amITO-MDW
16h 20m2 stops
$952Delta
Find Deal
Tue, Sep 23 - Tue, Sep 30
Southwest Logo
7:50 am - 6:10 pmMDW-ITO
14h 20m2 stops
Southwest Logo
6:55 pm - 11:55 amITO-MDW
13h 00m2 stops
$994Southwest
Find Deal
Sun, Jan 4 - Fri, Jan 9
Delta Logo
9:20 am - 10:17 pmMDW-ITO
41h 57m2 stops
Delta Logo
9:43 am - 5:35 pmITO-MDW
26h 52m2 stops
$1,008Delta
Find Deal
Sat, Sep 27 - Mon, Sep 29
Southwest Logo
5:25 am - 6:10 pmMDW-ITO
16h 45m2 stops
Southwest Logo
6:55 pm - 3:00 pmITO-MDW
16h 05m2 stops
$1,024Southwest
Find Deal
Wed, Dec 17 - Tue, Dec 23
Delta Logo
6:00 am - 7:20 pmMDW-ITO
18h 20m2 stops
Delta Logo
12:32 pm - 8:40 amITO-MDW
15h 08m2 stops
$1,036Delta
Find Deal
Tue, Oct 7 - Thu, Oct 16

Delta flights from Chicago Midway Airport to Hilo

Our best Delta deals on Chicago Midway Airport to Hilo flight tickets
Delta
Sep 23
MDW6:00 amChicago Midway
15h 56m
2 stops
ITO4:56 pmHilo Intl
Sep 30
ITO12:20 pmHilo Intl
15h 20m
2 stops
MDW8:40 amChicago Midway
Delta
Nov 12
MDW6:00 amChicago Midway
15h 31m
2 stops
ITO5:31 pmHilo Intl
Nov 18
ITO1:46 pmHilo Intl
16h 06m
2 stops
MDW9:52 amChicago Midway
Delta
Sep 23
MDW6:00 amChicago Midway
15h 56m
2 stops
ITO4:56 pmHilo Intl
Sep 30
ITO12:20 pmHilo Intl
16h 20m
2 stops
MDW9:40 amChicago Midway

Southwest flights from Chicago Midway Airport to Hilo

Our best Southwest deals on Chicago Midway Airport to Hilo flight tickets
Southwest
Nov 15
MDW5:55 amChicago Midway
16h 15m
2 stops
ITO6:10 pmHilo Intl
Dec 6
ITO6:55 pmHilo Intl
13h 45m
2 stops
MDW12:40 pmChicago Midway
Southwest
Sep 2
MDW6:10 amChicago Midway
13h 30m
2 stops
ITO2:40 pmHilo Intl
Sep 15
ITO6:55 pmHilo Intl
13h 20m
2 stops
MDW1:15 pmChicago Midway
Southwest
Feb 7
MDW8:20 amChicago Midway
13h 50m
2 stops
ITO6:10 pmHilo Intl
Feb 14
ITO6:55 pmHilo Intl
13h 35m
2 stops
MDW12:30 pmChicago Midway

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated August 28, 2025.
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

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sat 11/15

5:55 am-6:10 pm

2 stops16h 15m

Hilo Intl

Sat 12/6

6:55 pm-12:40 pm

2 stops13h 45m

$704

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sat 2/7

8:20 am-6:10 pm

2 stops13h 50m

Hilo Intl

Sat 2/14

6:55 pm-12:30 pm

2 stops13h 35m

$784

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Tue 9/23

6:10 am-2:40 pm

2 stops13h 30m

Hilo Intl

Tue 9/30

6:55 pm-12:15 pm

2 stops12h 20m

$834

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Tue 9/23

6:00 am-4:56 pm

2 stops15h 56m

Hilo Intl

Tue 9/30

12:20 pm-8:40 am

2 stops15h 20m

$912

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Wed 11/12

6:00 am-5:31 pm

2 stops15h 31m

Hilo Intl

Tue 11/18

1:46 pm-9:52 am

2 stops16h 06m

$914

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Tue 9/23

6:00 am-4:56 pm

2 stops15h 56m

Hilo Intl

Tue 9/30

12:20 pm-9:40 am

2 stops16h 20m

$952

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sun 1/4

7:50 am-6:10 pm

2 stops14h 20m

Hilo Intl

Fri 1/9

6:55 pm-11:55 am

2 stops13h 00m

$994

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sat 9/27

9:20 am-10:17 pm

2 stops41h 57m

Hilo Intl

Mon 9/29

9:43 am-5:35 pm

2 stops26h 52m

$1,008

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Wed 12/17

5:25 am-6:10 pm

2 stops16h 45m

Hilo Intl

Tue 12/23

6:55 pm-3:00 pm

2 stops16h 05m

$1,024

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Tue 10/7

6:00 am-7:20 pm

2 stops18h 20m

Hilo Intl

Thu 10/16

12:32 pm-8:40 am

2 stops15h 08m

$1,036

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 11 resultsSorted by cheapest first
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See travel insights to Hilo from

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

What is the cheapest day to depart on your flight to Hilo?

The cheapest day to depart from Chicago Midway Airport to Hilo is on a Monday. Travelers who choose to depart for Hilo on a Monday will often find tickets for as low as $778. Flights from Chicago Midway Airport to Hilo on a Saturday will generally be more expensive and average around $1,059. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Hilo?

Our data shows that the cheapest Chicago Midway Airport to Hilo flights are usually those with departure times in the morning. Our users have found flights to Hilo in the morning for as low as $849. In contrast, the most expensive time of day to depart to Hilo is in the evening when prices are around $1,423.

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

Direct flights

None
There are no direct flights from Chicago Midway Airport to Hilo. There are no popular flight routes 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 13h 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.

Traveling to a place near Hilo?

Book flights to Hilo if you plan to visit one of these locations
Mountain View

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.

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1 adult
Tue 9/2
Tue 9/9

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