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Cheap flights from Hawaii to Chicago from $164

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Hawaii to Chicago departing on 2/5. 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 Hawaii to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Alaska Airlines Logo
11:59 pm - 11:37 pm
OGG
-
ORD
19h 38m1 stop
Alaska Airlines Logo
9:00 am - 10:59 pm
ORD
-
OGG
17h 59m1 stop
$343Alaska Airlines
Tue, Jan 13 - Tue, Jan 20
Alaska Airlines Logo
11:59 pm - 2:29 pm
OGG
-
ORD
10h 30m1 stop
Alaska Airlines Logo
9:00 am - 10:59 pm
ORD
-
OGG
17h 59m1 stop
$361Alaska Airlines
Thu, Jan 15 - Mon, Jan 19
Multiple Airlines Logo
1:39 pm - 2:29 pm
LIH
-
ORD
20h 50m2 stops
Multiple Airlines Logo
3:44 pm - 1:45 pm
ORD
-
LIH
26h 01m1 stop
$368Multiple Airlines
Wed, Jan 21 - Sun, Jan 25
Multiple Airlines Logo
4:05 pm - 2:29 pm
OGG
-
ORD
18h 24m2 stops
Multiple Airlines Logo
9:00 am - 10:59 pm
ORD
-
OGG
17h 59m1 stop
$369Multiple Airlines
Tue, Jan 13 - Tue, Jan 20
American Airlines Logo
7:00 pm - 7:00 am
HNL
-
ORD
8h 00mnonstop
American Airlines Logo
10:00 am - 3:21 pm
ORD
-
HNL
9h 21mnonstop
$404American Airlines
Thu, Jan 15 - Tue, Jan 20
Delta Logo
4:50 pm - 9:53 am
HNL
-
MDW
13h 03m1 stop
Delta Logo
6:00 am - 3:10 pm
MDW
-
HNL
13h 10m1 stop
$423Delta
Wed, Jan 28 - Tue, Feb 3
Delta Logo
5:15 pm - 12:46 pm
HNL
-
MDW
15h 31m2 stops
Delta Logo
6:00 am - 3:10 pm
MDW
-
HNL
13h 10m1 stop
$429Delta
Wed, Jan 28 - Tue, Feb 3
American Airlines Logo
7:00 pm - 7:00 am
HNL
-
ORD
8h 00mnonstop
American Airlines Logo
10:00 am - 3:21 pm
ORD
-
HNL
9h 21mnonstop
$440American Airlines
Thu, Jan 15 - Thu, Jan 22
Southwest Logo
9:55 pm - 12:35 pm
HNL
-
MDW
10h 40m1 stop
Southwest Logo
8:25 am - 4:30 pm
MDW
-
HNL
12h 05m1 stop
$450Southwest
Wed, Jan 28 - Tue, Feb 3
Southwest Logo
12:30 pm - 5:05 am
HNL
-
MDW
12h 35m2 stops
Southwest Logo
8:25 am - 4:30 pm
MDW
-
HNL
12h 05m1 stop
$455Southwest
Wed, Jan 28 - Tue, Feb 3

Alaska Airlines flights from Hawaii to Chicago

Our best Alaska Airlines deals on Hawaii to Chicago flight tickets
Alaska Airlines
Jan 13
OGG11:59 pmKahului
19h 38m
1 stop
ORD11:37 pmChicago O'Hare Intl
Jan 20
ORD9:00 amChicago O'Hare Intl
17h 59m
1 stop
OGG10:59 pmKahului
$343
Find similar
Alaska Airlines
Jan 15
OGG11:59 pmKahului
10h 30m
1 stop
ORD2:29 pmChicago O'Hare Intl
Jan 19
ORD9:00 amChicago O'Hare Intl
17h 59m
1 stop
OGG10:59 pmKahului
$361
Find similar
Alaska Airlines
Jan 15
OGG11:59 pmKahului
19h 38m
1 stop
ORD11:37 pmChicago O'Hare Intl
Jan 19
ORD9:00 amChicago O'Hare Intl
17h 59m
1 stop
OGG10:59 pmKahului
$362
Find similar

United Airlines flights from Hawaii to Chicago

Our best United Airlines deals on Hawaii to Chicago flight tickets
United Airlines
Dec 30
LIH8:30 pmLihue
10h 55m
1 stop
ORD11:25 amChicago O'Hare Intl
Jan 2
ORD6:15 amChicago O'Hare Intl
12h 33m
1 stop
LIH2:48 pmLihue
$453
Find similar
United Airlines
Dec 31
LIH8:30 pmLihue
10h 55m
1 stop
ORD11:25 amChicago O'Hare Intl
Jan 2
ORD6:15 amChicago O'Hare Intl
12h 33m
1 stop
LIH2:48 pmLihue
$486
Find similar
United Airlines
Dec 31
LIH2:29 pmLihue
10h 58m
1 stop
ORD5:27 amChicago O'Hare Intl
Jan 4
ORD8:45 amChicago O'Hare Intl
12h 19m
1 stop
LIH5:04 pmLihue
$514
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Hawaii 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 December 18, 2025.
Use the filters below to find and compare flights from Hawaii to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 1/13

11:59 pm-11:37 pm

1 stop19h 38m

Chicago O'Hare Intl

Tue 1/20

9:00 am-10:59 pm

1 stop17h 59m

$343

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Thu 1/15

11:59 pm-2:29 pm

1 stop10h 30m

Chicago O'Hare Intl

Mon 1/19

9:00 am-10:59 pm

1 stop17h 59m

$361

LihueChicago

LIH - ORD

LIHORD

Lihue

Wed 1/21

1:39 pm-2:29 pm

2 stops20h 50m

Chicago O'Hare Intl

Sun 1/25

3:44 pm-1:45 pm

1 stop26h 01m

$368

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Tue 1/13

4:05 pm-2:29 pm

2 stops18h 24m

Chicago O'Hare Intl

Tue 1/20

9:00 am-10:59 pm

1 stop17h 59m

$369

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 1/15

7:00 pm-7:00 am

Nonstop8h 00m

Chicago O'Hare Intl

Tue 1/20

10:00 am-3:21 pm

Nonstop9h 21m

$404

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/28

4:50 pm-9:53 am

1 stop13h 03m

Chicago Midway

Tue 2/3

6:00 am-3:10 pm

1 stop13h 10m

$423

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/28

5:15 pm-12:46 pm

2 stops15h 31m

Chicago Midway

Tue 2/3

6:00 am-3:10 pm

1 stop13h 10m

$429

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 1/15

7:00 pm-7:00 am

Nonstop8h 00m

Chicago O'Hare Intl

Thu 1/22

10:00 am-3:21 pm

Nonstop9h 21m

$440

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/28

9:55 pm-12:35 pm

1 stop10h 40m

Chicago Midway

Tue 2/3

8:25 am-4:30 pm

1 stop12h 05m

$450

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/28

12:30 pm-5:05 am

2 stops12h 35m

Chicago Midway

Tue 2/3

8:25 am-4:30 pm

1 stop12h 05m

$455

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 Hawaii 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

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Hawaii, with most prices found around $558. If you’re not able to fly to Chicago in September, then May is your next best option. Flight prices from Hawaii to Chicago during May average around $598.

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

The cheapest day to depart on your flight to Chicago is on a Monday when prices can be found for as low as $809. This is often the case because there is less demand to fly during this day of the week. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Hawaii to Chicago for around $1,141.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Hawaii to Chicago during this time can be as low as $618. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $881.

What is the cheapest Hawaii to Chicago flight route?

Fly from Kahului to Chicago O'Hare Intl for the best Hawaii - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Hawaii when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $807 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Hawaii for as low as $563 on momondo.

What cabin class options are available on Hawaii to Chicago flights?

There are 4 cabin classes available to choose from on Hawaii to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Hawaii to Chicago flights?

You could potentially save up to 44% on your flight if you consider stops on a Hawaii to Chicago flight.

Cheap Hawaii to Chicago flight deals and tips

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

Best Price Found

$292

Fastest flight time

7h 52m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Hawaii in the past 72 hours is $292. The best round-trip flight deal from Hawaii to Chicago found on momondo in the last 72 hours is $554.
The fastest flight from Hawaii to Chicago takes 7h 52m
Direct flights go from Hawaii to Chicago every day.
There are 3 airports in Chicago. From Hawaii there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

  • When did momondo last update prices for flights from Hawaii to Chicago?

    Prices for flights from Hawaii to Chicago are updated daily.

  • How many operators does momondo search for flights from Hawaii to Chicago?

  • How old do you have to be to fly from Hawaii 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 Hawaii to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Hawaii to Chicago?

Best airlines flying from Hawaii to Chicago

Compare and see reviews for airlines that fly from Hawaii to Chicago with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $305Free CancellationRating
7.9
8,009 reviews
Search Delta flights
Hawaiian AirlinesPriceFrom $322Free CancellationRating
7.8
2,820 reviews
Search Hawaiian Airlines flights
United AirlinesPriceFrom $424Free CancellationRating
7.4
9,095 reviews
Search United Airlines flights
American AirlinesPriceFrom $455Free CancellationRating
7.2
11,054 reviews
Search American Airlines flights
Alaska AirlinesPriceFrom $468Free CancellationRating
8.0
11,479 reviews
Search Alaska Airlines flights
SouthwestPriceFrom $581Free CancellationRating
7.9
4,251 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
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Hawaii to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Hawaii to Chicago for you.

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

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

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Hawaii.

I’m not ready to book a flight from Hawaii to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Hawaii. 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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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