ITO - ORD

$343 Find Cheap Flights from Hilo to Chicago - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Hilo to O'Hare Intl departing on 7/22. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hilo to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hilo to Chicago, as well as popular online travel agencies
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$525
Multiple Airlines
Wed 9/16Wed 9/30
ITO - ORD • 2 stops
Cheapest one-way
$343
Multiple Airlines
Wed 7/22
ITO - ORD • 2 stops
Top airlines
American Airlines
Cheapest • from $769 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Hilo and O'Hare Intl. You'll need at least 1 connection.
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to O'Hare Intl!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Hilo to O'Hare Intl (ITO-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hilo to O'Hare Intl that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Hilo to O'Hare Intl

Wed, Sep 16 - Wed, Sep 30
Multiple Airlines Logo
9:26 am - 1:22 pm
ITO
-
ORD
22h 56m
2 stops
Multiple Airlines Logo
7:20 am - 7:12 pm
ORD
-
ITO
16h 52m
2 stops
$525Multiple 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
7:49 pm - 5:27 pm
ORD
-
ITO
26h 38m
2 stops
$653Multiple Airlines
Thu, Aug 13 - Sun, Aug 16
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
Mon, Oct 26 - Mon, Nov 2
Multiple Airlines Logo
6:00 am - 11:59 pm
ITO
-
ORD
12h 59m
2 stops
Multiple Airlines Logo
7:56 pm - 6:20 pm
ORD
-
ITO
26h 24m
2 stops
$684Multiple 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
7:20 am - 4:15 pm
ORD
-
ITO
13h 55m
2 stops
$685Multiple Airlines
Mon, Oct 26 - Mon, Nov 2
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
11:27 am - 6:01 am
ITO
-
ORD
13h 34m
2 stops
American Airlines Logo
10:00 am - 5:27 pm
ORD
-
ITO
11h 27m
1 stop
$778American Airlines
Sun, Jul 5 - Sun, Jul 12
Multiple Airlines Logo
2:59 pm - 1:13 pm
ITO
-
ORD
17h 14m
2 stops
Multiple Airlines Logo
6:00 am - 6:17 pm
ORD
-
ITO
17h 17m
2 stops
$810Multiple Airlines
Wed, Jun 24 - Wed, Jul 8
Multiple Airlines Logo
8:45 pm - 11:36 pm
ITO
-
ORD
21h 51m
2 stops
Multiple Airlines Logo
8:20 pm - 2:27 pm
ORD
-
ITO
23h 07m
2 stops
$845Multiple Airlines
Tue, Jun 30 - Fri, Jul 31
Multiple Airlines Logo
8:45 pm - 11:36 pm
ITO
-
ORD
21h 51m
2 stops
Multiple Airlines Logo
6:20 am - 9:59 pm
ORD
-
ITO
20h 39m
2 stops
$871Multiple Airlines
Booking Insights

KAYAK's insights & trends for Hilo to O'Hare Intl flights

Get data-powered insights and trends into flights from Hilo to O'Hare Intl to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Hilo to Chicago?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 5 days.

In the past 5 days, the cheapest round-trip tickets from Hilo to Chicago were found on American Airlines ($769) and United Airlines ($928).

Find deals

Good to know

Cheapest flight$343
Flight from Hilo to Chicago

When to book flights from Hilo to O'Hare Intl

Are your dates flexible? Find out the best times to travel from Hilo to O'Hare Intl based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Hilo to Chicago flights

  • What is the cheapest flight from Hilo to Chicago O'Hare Intl Airport?

    In the last 5 days, the lowest price for a flight from Hilo to Chicago O'Hare Intl Airport was $343 for a one-way ticket and $525 for a round-trip.

  • Do I need a passport to fly between Hilo and Chicago?

    No

  • Which aircraft models fly most regularly from Hilo to Chicago?

    We unfortunately don’t have that data for this specific route.

  • How does KAYAK find such low prices on flights from Hilo to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hilo to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hilo to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Hilo is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Hilo to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Hilo with another airline. Booking your flights between Hilo and ORD can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hilo to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Hilo up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Hilo to O'Hare Intl

 
See real verified KAYAK customer reviews for airlines flying from Hilo to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Hilo to O'Hare Intl? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
SouthwestOverall score based on 4235 reviews
8.6Crew
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
Airline reviews

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

10.0 ExcellentAnonymous, Jun 2026
OKC - LAS
Read more Southwest reviews

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

Everything you need to know for your flight from Hilo to O'Hare Intl

Information on your arrival and departure airports

Hilo (ITO)
O'Hare Intl (ORD)