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Cheap flights from Chicago to Hilo from $417

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Hilo departing on 11/12. 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 Chicago to Hilo (CHI-ITO)

Cheap round-trip flights

Alaska Airlines Logo
7:59 pm - 10:19 pmORD-ITO
30h 20m2 stops
Alaska Airlines Logo
9:00 pm - 11:59 pmITO-ORD
22h 59m2 stops
$417Alaska Airlines
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Wed, Nov 12 - Tue, Nov 18
Alaska Airlines Logo
7:59 pm - 8:30 pmORD-ITO
28h 31m2 stops
Alaska Airlines Logo
7:43 pm - 11:59 pmITO-ORD
24h 16m2 stops
$437Alaska Airlines
Find Deal
Wed, Nov 12 - Tue, Nov 18
Alaska Airlines Logo
10:00 am - 10:19 pmORD-ITO
16h 19m2 stops
Alaska Airlines Logo
9:00 pm - 1:54 pmITO-ORD
12h 54m2 stops
$438Alaska Airlines
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Wed, Nov 5 - Tue, Nov 18
Alaska Airlines Logo
9:20 am - 4:04 pmORD-ITO
34h 44m2 stops
Alaska Airlines Logo
11:56 am - 5:01 amITO-ORD
13h 05m2 stops
$457Alaska Airlines
Find Deal
Tue, Nov 11 - Wed, Nov 19
Southwest Logo
7:45 am - 6:10 pmMDW-ITO
15h 25m2 stops
Southwest Logo
6:55 pm - 4:50 pmITO-MDW
16h 55m2 stops
$652Southwest
Find Deal
Fri, Oct 24 - Fri, Oct 31
Southwest Logo
7:15 am - 9:40 pmORD-ITO
18h 25m2 stops
Southwest Logo
3:30 pm - 3:00 pmITO-ORD
18h 30m2 stops
$759Southwest
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Sat, Nov 29 - Tue, Mar 10
United Airlines Logo
9:35 am - 8:30 pmORD-ITO
14h 55m1 stop
United Airlines Logo
7:43 pm - 6:08 amITO-ORD
30h 25m1 stop
$784United Airlines
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Tue, Nov 11 - Wed, Nov 19
United Airlines Logo
9:35 am - 7:01 pmORD-ITO
13h 26m1 stop
United Airlines Logo
7:43 pm - 6:08 amITO-ORD
30h 25m1 stop
$786United Airlines
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Mon, Nov 3 - Mon, Nov 10
Delta Logo
9:20 am - 8:30 pmMDW-ITO
40h 10m2 stops
Delta Logo
1:32 pm - 5:35 pmITO-MDW
23h 03m2 stops
$926Delta
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Sat, Sep 27 - Mon, Sep 29
Delta Logo
9:20 am - 8:30 pmMDW-ITO
40h 10m2 stops
Delta Logo
1:32 pm - 1:03 pmITO-MDW
18h 31m2 stops
$945Delta
Find Deal
Sat, Sep 27 - Mon, Sep 29

Southwest flights from Chicago to Hilo

Our best Southwest deals on Chicago to Hilo flight tickets
Southwest
Oct 24
MDW7:45 amChicago Midway
15h 25m
2 stops
ITO6:10 pmHilo Intl
Oct 31
ITO6:55 pmHilo Intl
16h 55m
2 stops
MDW4:50 pmChicago Midway
$652
Find similar
Southwest
Nov 29
ORD7:15 amChicago O'Hare Intl
18h 25m
2 stops
ITO9:40 pmHilo Intl
Mar 10
ITO3:30 pmHilo Intl
18h 30m
2 stops
ORD3:00 pmChicago O'Hare Intl
$759
Find similar
Southwest
Sep 1
ORD6:15 amChicago O'Hare Intl
16h 55m
2 stops
ITO6:10 pmHilo Intl
Sep 5
ITO6:00 amHilo Intl
12h 40m
2 stops
ORD11:40 pmChicago O'Hare Intl
$764
Find similar

Alaska Airlines flights from Chicago to Hilo

Our best Alaska Airlines deals on Chicago to Hilo flight tickets
Alaska Airlines
Nov 12
ORD7:59 pmChicago O'Hare Intl
30h 20m
2 stops
ITO10:19 pmHilo Intl
Nov 18
ITO9:00 pmHilo Intl
22h 59m
2 stops
ORD11:59 pmChicago O'Hare Intl
$417
Find similar
Alaska Airlines
Nov 12
ORD7:59 pmChicago O'Hare Intl
28h 31m
2 stops
ITO8:30 pmHilo Intl
Nov 18
ITO7:43 pmHilo Intl
24h 16m
2 stops
ORD11:59 pmChicago O'Hare Intl
$437
Find similar
Alaska Airlines
Nov 5
ORD10:00 amChicago O'Hare Intl
16h 19m
2 stops
ITO10:19 pmHilo Intl
Nov 18
ITO9:00 pmHilo Intl
12h 54m
2 stops
ORD1:54 pmChicago O'Hare Intl
$438
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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 17, 2025.
Use the filters below to find and compare flights from Chicago to Hilo that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Wed 11/12

7:59 pm-10:19 pm

2 stops30h 20m

Hilo Intl

Tue 11/18

9:00 pm-11:59 pm

2 stops22h 59m

$417

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Wed 11/12

7:59 pm-8:30 pm

2 stops28h 31m

Hilo Intl

Tue 11/18

7:43 pm-11:59 pm

2 stops24h 16m

$437

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Wed 11/5

10:00 am-10:19 pm

2 stops16h 19m

Hilo Intl

Tue 11/18

9:00 pm-1:54 pm

2 stops12h 54m

$438

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Tue 11/11

9:20 am-4:04 pm

2 stops34h 44m

Hilo Intl

Wed 11/19

11:56 am-5:01 am

2 stops13h 05m

$457

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Fri 10/24

7:45 am-6:10 pm

2 stops15h 25m

Hilo Intl

Fri 10/31

6:55 pm-4:50 pm

2 stops16h 55m

$652

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Sat 11/29

7:15 am-9:40 pm

2 stops18h 25m

Hilo Intl

Tue 3/10

3:30 pm-3:00 pm

2 stops18h 30m

$759

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Tue 11/11

9:35 am-8:30 pm

1 stop14h 55m

Hilo Intl

Wed 11/19

7:43 pm-6:08 am

1 stop30h 25m

$784

ChicagoHilo

ORD - ITO

ORDITO

Chicago O'Hare Intl

Mon 11/3

9:35 am-7:01 pm

1 stop13h 26m

Hilo Intl

Mon 11/10

7:43 pm-6:08 am

1 stop30h 25m

$786

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sat 9/27

9:20 am-8:30 pm

2 stops40h 10m

Hilo Intl

Mon 9/29

1:32 pm-5:35 pm

2 stops23h 03m

$926

ChicagoHilo

MDW - ITO

MDWITO

Chicago Midway

Sat 9/27

9:20 am-8:30 pm

2 stops40h 10m

Hilo Intl

Mon 9/29

1:32 pm-1:03 pm

2 stops18h 31m

$945

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 Hilo from

How to get the cheapest flight ticket from Chicago 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 month to fly to Hilo?

The month of November is, on average, the cheapest month to fly to Hilo from Chicago, with most prices found around $558. If you’re not able to fly to Hilo in November, then September is your next best option. Flight prices from Chicago to Hilo during September average around $701.

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

The cheapest day to depart from Chicago 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 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 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.

Can stopping save me money on Chicago to Hilo flights?

You could potentially save up to 42% on your flight if you consider stops on a Chicago to Hilo flight.

When to book flights from Chicago to Hilo

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

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

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

Best Price Found

$574

Fastest flight time

11h 29m

Direct flights

None

Airports in Hilo

1 airport
The best one-way flight to Hilo from Chicago in the past 72 hours is $574. The best round-trip flight deal from Chicago to Hilo found on momondo in the last 72 hours is $417.
The fastest flight from Chicago to Hilo takes 11h 29m
There are no direct flights from Chicago to Hilo. Popular non-direct routes for this connection are Chicago Midway Airport - Hilo Intl Airport and Chicago O'Hare Intl Airport - Hilo Intl Airport.
There is 1 airport near Hilo: Hilo Intl (ITO)
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  • How far is Chicago to Hilo Intl by plane?

    Hilo Intl is 4170.2 mi away from Chicago. By plane, this route typically takes 13h 25m.

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

    Prices for flights from Chicago to Hilo Intl Airport refresh daily.

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago 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.

  • What is the most popular airline from Chicago to Hilo?

Best airlines flying from Chicago to Hilo

Compare and see reviews for airlines that fly from Chicago to Hilo with momondo
Airline
Rating
Free Cancellation
Price
Alaska AirlinesPriceFrom $553Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $598Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
United AirlinesPriceFrom $747Free CancellationRating
7.4
8,919 reviews
Search United Airlines flights

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?

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 Hilo from Chicago.

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

Yes. momondo enables you to select and highlight flights to Hilo from Chicago with this policy.

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

momondo helps you find the best flight between Chicago and Hilo 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 Chicago to Hilo right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Hilo from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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