ITO - ORD

$416 Find Cheap Flights from Hilo to Chicago

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 3/15. 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
Travelers love KAYAK
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Everything you should know

Cheapest round-trip
$761
Multiple Airlines
Tue 6/2Tue 9/1
ITO - ORD • 2 stops
Cheapest one-way
$416
Multiple Airlines
Sun 3/15
ITO - ORD • 2 stops
Top airlines
Southwest
Cheapest • from $790 (round-trip)
Alaska Airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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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

Tue, Jun 2 - Tue, Sep 1
Multiple Airlines Logo
9:46 am - 2:47 pm
ITO
-
ORD
24h 01m
2 stops
Multiple Airlines Logo
7:55 pm - 3:23 pm
ORD
-
ITO
24h 28m
2 stops
$761Multiple Airlines
Thu, Feb 12 - Tue, Feb 17
Southwest Logo
6:00 am - 10:35 pm
ITO
-
ORD
12h 35m
2 stops
Southwest Logo
7:15 am - 9:40 pm
ORD
-
ITO
18h 25m
2 stops
$790Southwest
Thu, Jun 4 - Wed, Sep 2
Multiple Airlines Logo
6:49 pm - 2:47 pm
ITO
-
ORD
14h 58m
2 stops
Multiple Airlines Logo
7:55 pm - 3:23 pm
ORD
-
ITO
24h 28m
2 stops
$798Multiple Airlines
Sat, Feb 14 - Thu, Feb 19
Multiple Airlines Logo
8:54 am - 2:58 pm
ITO
-
ORD
26h 04m
2 stops
Multiple Airlines Logo
8:20 am - 9:24 pm
ORD
-
ITO
17h 04m
2 stops
$801Multiple Airlines
Wed, Jun 24 - Wed, Jul 8
Multiple Airlines Logo
8:38 am - 6:20 am
ITO
-
ORD
16h 42m
2 stops
Multiple Airlines Logo
6:00 am - 8:20 pm
ORD
-
ITO
19h 20m
2 stops
$810Multiple Airlines
Fri, Feb 13 - Tue, Feb 17
Multiple Airlines Logo
8:40 am - 2:58 pm
ITO
-
ORD
26h 18m
2 stops
Multiple Airlines Logo
3:07 pm - 5:41 pm
ORD
-
ITO
30h 34m
2 stops
$872Multiple Airlines
Sat, Feb 14 - Thu, Feb 19
Delta Logo
1:45 pm - 9:41 am
ITO
-
ORD
15h 56m
2 stops
Delta Logo
6:30 am - 7:59 pm
ORD
-
ITO
17h 29m
2 stops
$898Delta
Thu, Feb 12 - Tue, Feb 17
United Airlines Logo
7:41 pm - 2:50 pm
ITO
-
ORD
15h 09m
2 stops
United Airlines Logo
9:30 am - 6:34 pm
ORD
-
ITO
13h 04m
1 stop
$900United Airlines
Fri, Feb 13 - Tue, Feb 17
Multiple Airlines Logo
9:00 pm - 2:58 pm
ITO
-
ORD
13h 58m
2 stops
Multiple Airlines Logo
3:07 pm - 5:41 pm
ORD
-
ITO
30h 34m
2 stops
$939Multiple Airlines
Tue, Jun 2 - Tue, Sep 1
United Airlines Logo
12:14 pm - 6:15 am
ITO
-
ORD
13h 01m
1 stop
United Airlines Logo
9:30 am - 5:01 pm
ORD
-
ITO
12h 31m
1 stop
$956United 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 72 hours.

In the past 3 days, the cheapest round-trip tickets from Hilo to Chicago were found on Southwest ($790) and Delta ($898).

Good to know

Cheapest flight$416
Most popular time to fly and prices are also 41% lower on average.
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 3 days, the lowest price for a flight from Hilo to Chicago O'Hare Intl Airport was $416 for a one-way ticket and $761 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.

  • Which airline alliances offer flights from Hilo to Chicago?

    oneworld is the only airline alliance operating flights between Hilo and Chicago.

  • Which is the best airline for flights from Hilo to Chicago, Southwest or Alaska Airlines?

    The two airlines most popular with KAYAK users for flights from Hilo to Chicago are Southwest and Alaska Airlines. With an average price for the route of $768 and an overall rating of 8.0, Southwest is the most popular choice. Alaska Airlines is also a great choice for the route, with an average price of $979 and an overall rating of 8.0.

  • 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 airlines 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.
8.0
Alaska AirlinesOverall score based on 11808 reviews
8.1Boarding
7.8Comfort
7.1Food
8.5Crew
7.0Entertainment
Airline reviews

Worst first/business class I have ever flown after 75 years on planes. Barely acceptable seats, terrible food, uninterested attendants, unavailable WiFi. I’ll never fly this airline again.

4.0 OkayJerry, Jan 2026
SAN - ORD
Read more Alaska Airlines reviews

Worst first/business class I have ever flown after 75 years on planes. Barely acceptable seats, terrible food, uninterested attendants, unavailable WiFi. I’ll never fly this airline again.

I paid for WiFi but it never really worked. That was frustrating.

Dropping off of the checked bags took way longer than it should have. The agent for the pre-tagged and ready to drop off line was gone and didn't come back for about 15 minutes. The other bag check lines were barely moving. Agents were standing around and not much was getting done. Everything else about the flight was great.

I flew Hawaiian Airlines three times during my trip. Each time, when we went to baggage claim, it took about 45 minutes to an hour to receive our luggage.

The kiosk was fast. I got in and got my baggage tag right away. There was a long lines at baggaged check in But it moved fast and checked my baggage with no problem. The flight was good. The flight attendants were very helpful, friendly and always smiling.

We were very late to take off, late exit plane, and luggage took a long time.

Boarding passes could not be received online, even after online check-in. While they appeared on the Alaska.com app, they did not transfer to inbox or messages and were not available at all on the Alaska.com app following the check-in process. There was no choice other than to get boarding passes at the airport counter.

Alaska Airlines has horrible customer service. After sitting in a packed airplane for over an hour, they decided to cancel our flight and had us deplane. Instead of helping us nearby, we had to ride two trains (in Seattle Airport), from the S-Gates to the C-Gates; only to stand in a line for 3 and a half hours. Throughout the 3 hours, there was often 1 agent at the customer service counter to help the passengers trying to get information and accommodation on a flight that they cancelled. Do better!

Short trip from Honolulu to Kauai. Not a major issue. Only concern was the drop off of the luggage for departure. Only one person handling all of the passengers. She was busting her butt.

I know airlines have to save money, but a little more legroom would be nice. I’m a small person and I just felt cramped after a few hours. However, I loved everything else! Free Alaska Airlines wifi, free movies, yummy snacks, and the crew was so helpful and accommodating!

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

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

Information on your arrival and departure airports