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Cheap flights from Hilo to Chicago from $289

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Hilo to Chicago departing on 8/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Hilo to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
8:23 am - 6:20 am
ITO
-
ORD
16h 57m
2 stops
Multiple Airlines Logo
8:00 am - 8:20 pm
ORD
-
ITO
17h 20m
2 stops
$622Multiple Airlines
Wed, Jun 3 - Sun, Sep 6
Multiple Airlines Logo
7:44 pm - 1:22 pm
ITO
-
ORD
12h 38m
2 stops
Multiple Airlines Logo
7:00 am - 6:20 pm
ORD
-
ITO
16h 20m
2 stops
$632Multiple Airlines
Tue, May 26 - Tue, Sep 1
Multiple Airlines Logo
8:23 am - 6:20 am
ITO
-
ORD
16h 57m
2 stops
Multiple Airlines Logo
9:20 am - 6:20 pm
ORD
-
ITO
14h 00m
2 stops
$665Multiple Airlines
Wed, Jun 3 - Thu, Sep 3
Multiple Airlines Logo
7:44 pm - 2:32 pm
ITO
-
ORD
13h 48m
2 stops
Multiple Airlines Logo
7:00 am - 6:20 pm
ORD
-
ITO
16h 20m
2 stops
$675Multiple Airlines
Tue, Jun 2 - Thu, Sep 3
Multiple Airlines Logo
8:23 am - 6:20 am
ITO
-
ORD
16h 57m
2 stops
Multiple Airlines Logo
9:20 am - 7:23 pm
ORD
-
ITO
15h 03m
2 stops
$695Multiple Airlines
Wed, Jun 3 - Sat, Sep 5
Multiple Airlines Logo
5:59 pm - 1:22 pm
ITO
-
ORD
14h 23m
2 stops
Multiple Airlines Logo
9:20 am - 8:20 pm
ORD
-
ITO
16h 00m
2 stops
$705Multiple Airlines
Tue, May 26 - Sat, Sep 5
Multiple Airlines Logo
7:44 pm - 1:22 pm
ITO
-
ORD
12h 38m
2 stops
Multiple Airlines Logo
7:00 am - 3:41 pm
ORD
-
ITO
13h 41m
2 stops
$718Multiple Airlines
Mon, Jun 1 - Mon, Sep 7
Multiple Airlines Logo
5:59 pm - 1:16 pm
ITO
-
ORD
14h 17m
2 stops
Multiple Airlines Logo
6:22 am - 10:09 pm
ORD
-
ITO
20h 47m
2 stops
$730Multiple Airlines
Wed, Jun 24 - Wed, Jul 8
Multiple Airlines Logo
7:44 pm - 2:32 pm
ITO
-
ORD
13h 48m
2 stops
Multiple Airlines Logo
9:20 am - 6:20 pm
ORD
-
ITO
14h 00m
2 stops
$748Multiple Airlines
Fri, May 29 - Tue, Sep 1
Multiple Airlines Logo
7:44 pm - 1:22 pm
ITO
-
ORD
12h 38m
2 stops
Multiple Airlines Logo
9:20 am - 6:20 pm
ORD
-
ITO
14h 00m
2 stops
$761Multiple Airlines
Mon, Jun 1 - Thu, Sep 3

United Airlines flights from Hilo to Chicago

Our best United Airlines deals on Hilo to Chicago flight tickets
United Airlines
May 31
ITO11:27 amHilo Intl
12h 24m
2 stops
ORD4:51 amChicago O'Hare Intl
Sep 1
ORD9:30 amChicago O'Hare Intl
11h 11m
1 stop
ITO3:41 pmHilo Intl
$1,010
United Airlines
Jun 2
ITO9:26 amHilo Intl
15h 20m
2 stops
ORD5:46 amChicago O'Hare Intl
Sep 3
ORD9:30 amChicago O'Hare Intl
12h 31m
1 stop
ITO5:01 pmHilo Intl
$1,023
United Airlines
May 31
ITO11:27 amHilo Intl
12h 24m
2 stops
ORD4:51 amChicago O'Hare Intl
Sep 3
ORD9:30 amChicago O'Hare Intl
12h 31m
1 stop
ITO5:01 pmHilo Intl
$1,053

American Airlines flights from Hilo to Chicago

Our best American Airlines deals on Hilo to Chicago flight tickets
American Airlines
Mar 18
ITO4:45 pmHilo Intl
13h 18m
2 stops
ORD11:03 amChicago O'Hare Intl
Mar 22
ORD9:55 amChicago O'Hare Intl
15h 33m
1 stop
ITO8:28 pmHilo Intl
$3,053
American Airlines
Mar 18
ITO3:09 pmHilo Intl
11h 16m
1 stop
ORD7:25 amChicago O'Hare Intl
Mar 22
ORD9:55 amChicago O'Hare Intl
15h 33m
1 stop
ITO8:28 pmHilo Intl
$4,145

momondo Fare Finder

 
Customize your flight search to find flights from Hilo to Chicago 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 March 3, 2026.
Use the filters below to find and compare flights from Hilo to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 6/3

8:23 am-6:20 am

2 stops16h 57m

Chicago O'Hare Intl

Sun 9/6

8:00 am-8:20 pm

2 stops17h 20m

$622

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Tue 5/26

7:44 pm-1:22 pm

2 stops12h 38m

Chicago O'Hare Intl

Tue 9/1

7:00 am-6:20 pm

2 stops16h 20m

$632

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 6/3

8:23 am-6:20 am

2 stops16h 57m

Chicago O'Hare Intl

Thu 9/3

9:20 am-6:20 pm

2 stops14h 00m

$665

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Tue 6/2

7:44 pm-2:32 pm

2 stops13h 48m

Chicago O'Hare Intl

Thu 9/3

7:00 am-6:20 pm

2 stops16h 20m

$675

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 6/3

8:23 am-6:20 am

2 stops16h 57m

Chicago O'Hare Intl

Sat 9/5

9:20 am-7:23 pm

2 stops15h 03m

$695

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Tue 5/26

5:59 pm-1:22 pm

2 stops14h 23m

Chicago O'Hare Intl

Sat 9/5

9:20 am-8:20 pm

2 stops16h 00m

$705

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Mon 6/1

7:44 pm-1:22 pm

2 stops12h 38m

Chicago O'Hare Intl

Mon 9/7

7:00 am-3:41 pm

2 stops13h 41m

$718

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 6/24

5:59 pm-1:16 pm

2 stops14h 17m

Chicago O'Hare Intl

Wed 7/8

6:22 am-10:09 pm

2 stops20h 47m

$730

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Fri 5/29

7:44 pm-2:32 pm

2 stops13h 48m

Chicago O'Hare Intl

Tue 9/1

9:20 am-6:20 pm

2 stops14h 00m

$748

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Mon 6/1

7:44 pm-1:22 pm

2 stops12h 38m

Chicago O'Hare Intl

Thu 9/3

9:20 am-6:20 pm

2 stops14h 00m

$761

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Hilo to Chicago

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 airlines fly to Chicago?

American Airlines, Southwest and Alaska Airlines are the top three most popular airlines that fly to Chicago from Hilo according to our data. American Airlines is the first choice among our users, with 33% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

When to book flights from Hilo to Chicago

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

Cheap Hilo to Chicago (ITO to CHI) flight deals and tips

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

Fastest flight time

14h 23m

Direct flights

None
The fastest flight from Hilo to Chicago takes 14h 23m
There are no direct flights from Hilo to Chicago. There are no popular flight routes from Hilo to Chicago.
Search flight deals

  • How far is Hilo Intl to Chicago by plane?

    A flight from Hilo Intl to Chicago will travel around 4170.2 mi. Flights usually cover this in 14h 23m, depending on flying conditions and air traffic around both airports.

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

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

  • How many operators does momondo search for flights from Hilo Intl Airport to Chicago?

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Hilo Intl Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago 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.

Best airlines flying from Hilo to Chicago

Compare and see reviews for airlines that fly from Hilo to Chicago with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $693Free CancellationRating
8.0
4,305 reviews
Search Southwest flights
Alaska AirlinesPriceFrom $699Free CancellationRating
8.0
11,982 reviews
Search Alaska Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Hilo.

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

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

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

momondo helps you find the best flight between Hilo and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Price alerts on flights to Chicago from Hilo are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport