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Cheap flights from Hilo to Chicago from $373

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 5/5. 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
6:00 am - 11:57 pm
ITO
-
ORD
12h 57m
2 stops
Multiple Airlines Logo
7:00 am - 4:12 pm
ORD
-
ITO
14h 12m
2 stops
$720Multiple Airlines
Tue, Aug 25 - Wed, Aug 26
Multiple Airlines Logo
6:00 am - 11:57 pm
ITO
-
ORD
12h 57m
2 stops
Multiple Airlines Logo
7:00 am - 3:13 pm
ORD
-
ITO
13h 13m
2 stops
$735Multiple Airlines
Tue, Aug 25 - Wed, Aug 26
Multiple Airlines Logo
7:42 am - 6:40 am
ITO
-
ORD
17h 58m
2 stops
Multiple Airlines Logo
6:00 am - 5:39 pm
ORD
-
ITO
16h 39m
2 stops
$745Multiple Airlines
Thu, May 7 - Mon, May 11
Multiple Airlines Logo
7:59 pm - 6:57 pm
ITO
-
ORD
17h 58m
2 stops
Multiple Airlines Logo
7:20 am - 3:13 pm
ORD
-
ITO
12h 53m
2 stops
$800Multiple Airlines
Tue, Jun 9 - Tue, Jul 28
Multiple Airlines Logo
10:56 am - 6:40 am
ITO
-
ORD
14h 44m
2 stops
Multiple Airlines Logo
6:00 am - 7:13 pm
ORD
-
ITO
18h 13m
2 stops
$810Multiple Airlines
Sun, May 3 - Thu, May 7
Multiple Airlines Logo
1:59 pm - 2:32 pm
ITO
-
ORD
19h 33m
2 stops
Multiple Airlines Logo
7:40 am - 6:14 pm
ORD
-
ITO
15h 34m
2 stops
$845Multiple Airlines
Fri, May 15 - Wed, May 20
Multiple Airlines Logo
4:47 pm - 6:57 pm
ITO
-
ORD
21h 10m
2 stops
Multiple Airlines Logo
5:42 pm - 7:03 am
ORD
-
ITO
18h 21m
2 stops
$886Multiple Airlines
Wed, Jun 24 - Wed, Jul 8
Multiple Airlines Logo
7:02 pm - 6:57 pm
ITO
-
ORD
18h 55m
2 stops
Multiple Airlines Logo
7:20 am - 6:17 pm
ORD
-
ITO
15h 57m
3 stops
$896Multiple Airlines
Wed, Jun 24 - Wed, Jul 8
Multiple Airlines Logo
6:44 pm - 4:56 pm
ITO
-
ORD
17h 12m
2 stops
Multiple Airlines Logo
2:10 pm - 10:12 pm
ORD
-
ITO
13h 02m
2 stops
$916Multiple Airlines
Fri, May 15 - Wed, May 20
Multiple Airlines Logo
11:27 am - 12:03 pm
ITO
-
ORD
19h 36m
2 stops
Multiple Airlines Logo
8:02 am - 6:17 pm
ORD
-
ITO
15h 15m
2 stops
$925Multiple Airlines
Wed, Jul 1 - Wed, Jul 15

United Airlines flights from Hilo to Chicago

Our best United Airlines deals on Hilo to Chicago flight tickets
United Airlines
Aug 25
ITO9:26 amHilo Intl
14h 19m
2 stops
ORD4:45 amChicago O'Hare Intl
Aug 26
ORD9:30 amChicago O'Hare Intl
12h 56m
1 stop
ITO5:26 pmHilo Intl
$1,017
United Airlines
Aug 25
ITO9:26 amHilo Intl
14h 19m
2 stops
ORD4:45 amChicago O'Hare Intl
Aug 26
ORD9:30 amChicago O'Hare Intl
11h 42m
1 stop
ITO4:12 pmHilo Intl
$1,047
United Airlines
May 5
ITO10:56 amHilo Intl
13h 44m
2 stops
ORD5:40 amChicago O'Hare Intl
May 9
ORD12:40 pmChicago O'Hare Intl
14h 53m
2 stops
ITO10:33 pmHilo Intl
$1,123

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 April 23, 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

Cheapest round-trip

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Tue 8/25

6:00 am-11:57 pm

2 stops12h 57m

Chicago O'Hare Intl

Wed 8/26

7:00 am-4:12 pm

2 stops14h 12m

$720
Quickest round-trip

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Tue 8/25

6:00 am-11:57 pm

2 stops12h 57m

Chicago O'Hare Intl

Wed 8/26

7:00 am-3:13 pm

2 stops13h 13m

$735

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Thu 5/7

7:42 am-6:40 am

2 stops17h 58m

Chicago O'Hare Intl

Mon 5/11

6:00 am-5:39 pm

2 stops16h 39m

$745

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Tue 6/9

7:59 pm-6:57 pm

2 stops17h 58m

Chicago O'Hare Intl

Tue 7/28

7:20 am-3:13 pm

2 stops12h 53m

$800

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Sun 5/3

10:56 am-6:40 am

2 stops14h 44m

Chicago O'Hare Intl

Thu 5/7

6:00 am-7:13 pm

2 stops18h 13m

$810

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Fri 5/15

1:59 pm-2:32 pm

2 stops19h 33m

Chicago O'Hare Intl

Wed 5/20

7:40 am-6:14 pm

2 stops15h 34m

$845

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 6/24

4:47 pm-6:57 pm

2 stops21h 10m

Chicago O'Hare Intl

Wed 7/8

5:42 pm-7:03 am

2 stops18h 21m

$886

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 6/24

7:02 pm-6:57 pm

2 stops18h 55m

Chicago O'Hare Intl

Wed 7/8

7:20 am-6:17 pm

3 stops15h 57m

$896

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Fri 5/15

6:44 pm-4:56 pm

2 stops17h 12m

Chicago O'Hare Intl

Wed 5/20

2:10 pm-10:12 pm

2 stops13h 02m

$916

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Wed 7/1

11:27 am-12:03 pm

2 stops19h 36m

Chicago O'Hare Intl

Wed 7/15

8:02 am-6:17 pm

2 stops15h 15m

$925

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 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

Can stopping save me money on Hilo to Chicago flights?

You could potentially save up to 46% on your flight if you consider stops on a Hilo to Chicago flight.

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

12h 57m

Direct flights

None
The fastest flight from Hilo to Chicago takes 12h 57m
There are no direct flights from Hilo to Chicago. There are no popular flight routes from Hilo to Chicago.
Search flight deals

Frequently asked questions about flying from Hilo to Chicago

  • 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 12h 57m, 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 $679Free CancellationRating
8.0
4,327 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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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Sat 5/23
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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