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Cheap flights from Hilo to Chicago from $343

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 7/22. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Hilo to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
8:45 pm - 11:59 pm
ITO
-
ORD
22h 14m
2 stops
Multiple Airlines Logo
7:00 am - 9:54 pm
ORD
-
ITO
18h 54m
2 stops
$565Multiple Airlines
Mon, Oct 26 - Mon, Nov 2
Multiple Airlines Logo
7:44 pm - 11:59 pm
ITO
-
ORD
23h 15m
2 stops
Multiple Airlines Logo
7:56 pm - 7:11 pm
ORD
-
ITO
27h 15m
2 stops
$653Multiple Airlines
Mon, Oct 26 - Mon, Nov 2
Multiple Airlines Logo
6:49 pm - 6:57 pm
ITO
-
ORD
19h 08m
2 stops
Multiple Airlines Logo
6:20 am - 9:59 pm
ORD
-
ITO
20h 39m
2 stops
$655Multiple Airlines
Thu, Aug 13 - Sun, Aug 16
Multiple Airlines Logo
6:00 am - 11:59 pm
ITO
-
ORD
12h 59m
2 stops
Multiple Airlines Logo
7:20 am - 5:27 pm
ORD
-
ITO
15h 07m
2 stops
$667Multiple Airlines
Tue, Oct 27 - Wed, Oct 28
Multiple Airlines Logo
6:00 am - 11:59 pm
ITO
-
ORD
12h 59m
2 stops
Multiple Airlines Logo
7:00 am - 8:13 pm
ORD
-
ITO
17h 13m
2 stops
$685Multiple Airlines
Mon, Oct 26 - Mon, Nov 2
Multiple Airlines Logo
8:30 am - 5:00 am
ITO
-
ORD
15h 30m
2 stops
Multiple Airlines Logo
7:20 am - 9:59 pm
ORD
-
ITO
19h 39m
2 stops
$759Multiple Airlines
Sat, Jul 11 - Fri, Jul 17
American Airlines Logo
3:45 pm - 7:10 am
ITO
-
ORD
10h 25m
1 stop
American Airlines Logo
10:00 am - 4:59 pm
ORD
-
ITO
10h 59m
1 stop
$769American Airlines
Mon, Oct 26 - Mon, Nov 2
American Airlines Logo
8:45 pm - 4:03 pm
ITO
-
ORD
14h 18m
2 stops
American Airlines Logo
10:00 am - 5:27 pm
ORD
-
ITO
11h 27m
1 stop
$778American Airlines
Mon, Oct 26 - Mon, Nov 2
Multiple Airlines Logo
7:44 pm - 6:19 pm
ITO
-
ORD
17h 35m
2 stops
Multiple Airlines Logo
6:00 am - 6:17 pm
ORD
-
ITO
17h 17m
2 stops
$780Multiple Airlines
Fri, Jul 3 - Wed, Jul 15
Multiple Airlines Logo
7:44 pm - 4:44 pm
ITO
-
ORD
16h 00m
2 stops
Multiple Airlines Logo
8:20 pm - 6:17 pm
ORD
-
ITO
26h 57m
2 stops
$833Multiple Airlines
Fri, Jul 3 - Wed, Jul 22

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United Airlines flights from Hilo to Chicago

Our best United Airlines deals on Hilo to Chicago flight tickets
United Airlines
Oct 27
ITO6:00 amHilo Intl
18h 04m
1 stop
ORD5:04 amChicago O'Hare Intl
Oct 28
ORD9:30 amChicago O'Hare Intl
11h 45m
1 stop
ITO4:15 pmHilo Intl
$918
United Airlines
Oct 27
ITO6:00 amHilo Intl
18h 04m
1 stop
ORD5:04 amChicago O'Hare Intl
Oct 28
ORD9:15 amChicago O'Hare Intl
14h 57m
2 stops
ITO7:12 pmHilo Intl
$927
United Airlines
Oct 27
ITO6:00 amHilo Intl
18h 27m
2 stops
ORD5:27 amChicago O'Hare Intl
Oct 28
ORD9:30 amChicago O'Hare Intl
11h 45m
1 stop
ITO4:15 pmHilo Intl
$1,000

American Airlines flights from Hilo to Chicago

Our best American Airlines deals on Hilo to Chicago flight tickets
American Airlines
Oct 26
ITO3:45 pmHilo Intl
10h 25m
1 stop
ORD7:10 amChicago O'Hare Intl
Nov 2
ORD10:00 amChicago O'Hare Intl
10h 59m
1 stop
ITO4:59 pmHilo Intl
$769
American Airlines
Oct 26
ITO8:45 pmHilo Intl
14h 18m
2 stops
ORD4:03 pmChicago O'Hare Intl
Nov 2
ORD10:00 amChicago O'Hare Intl
11h 27m
1 stop
ITO5:27 pmHilo Intl
$778

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 June 13, 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

Mon 10/26

8:45 pm-11:59 pm

2 stops22h 14m

Chicago O'Hare Intl

Mon 11/2

7:00 am-9:54 pm

2 stops18h 54m

$565

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Mon 10/26

7:44 pm-11:59 pm

2 stops23h 15m

Chicago O'Hare Intl

Mon 11/2

7:56 pm-7:11 pm

2 stops27h 15m

$653

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Thu 8/13

6:49 pm-6:57 pm

2 stops19h 08m

Chicago O'Hare Intl

Sun 8/16

6:20 am-9:59 pm

2 stops20h 39m

$655

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Tue 10/27

6:00 am-11:59 pm

2 stops12h 59m

Chicago O'Hare Intl

Wed 10/28

7:20 am-5:27 pm

2 stops15h 07m

$667

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Mon 10/26

6:00 am-11:59 pm

2 stops12h 59m

Chicago O'Hare Intl

Mon 11/2

7:00 am-8:13 pm

2 stops17h 13m

$685

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Sat 7/11

8:30 am-5:00 am

2 stops15h 30m

Chicago O'Hare Intl

Fri 7/17

7:20 am-9:59 pm

2 stops19h 39m

$759
Quickest round-trip

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Mon 10/26

3:45 pm-7:10 am

1 stop10h 25m

Chicago O'Hare Intl

Mon 11/2

10:00 am-4:59 pm

1 stop10h 59m

$769

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Mon 10/26

8:45 pm-4:03 pm

2 stops14h 18m

Chicago O'Hare Intl

Mon 11/2

10:00 am-5:27 pm

1 stop11h 27m

$778

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Fri 7/3

7:44 pm-6:19 pm

2 stops17h 35m

Chicago O'Hare Intl

Wed 7/15

6:00 am-6:17 pm

2 stops17h 17m

$780

HiloChicago

ITO - ORD

ITOORD

Hilo Intl

Fri 7/3

7:44 pm-4:44 pm

2 stops16h 00m

Chicago O'Hare Intl

Wed 7/22

8:20 pm-6:17 pm

2 stops26h 57m

$833

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

Can stopping save me money on Hilo to Chicago flights?

You could potentially save up to 43% 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 36m

Direct flights

None
The fastest flight from Hilo to Chicago takes 12h 36m
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 36m, 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
7.9
4,235 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
Portage
Benton Harbor
Saint Joseph
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