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Cheap flights from Chicago to Hawaii from $140

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Hawaii departing on 1/13. 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 Hawaii

Cheap round-trip flights

Enter your travel dates to find the best prices.
Alaska Airlines Logo
8:20 am - 12:47 pm
ORD
-
LIH
32h 27m1 stop
Alaska Airlines Logo
4:50 pm - 11:59 pm
LIH
-
ORD
27h 09m1 stop
$277Alaska Airlines
Tue, Feb 24 - Tue, Mar 3
Southwest Logo
6:10 am - 1:15 pm
MDW
-
KOA
12h 05m1 stop
Southwest Logo
10:00 am - 5:45 am
KOA
-
MDW
14h 45m1 stop
$282Southwest
Tue, Apr 21 - Tue, May 5
Alaska Airlines Logo
3:44 pm - 8:30 pm
ORD
-
LIH
32h 46m2 stops
Alaska Airlines Logo
10:25 am - 11:37 pm
LIH
-
ORD
33h 12m1 stop
$282Alaska Airlines
Tue, Feb 3 - Tue, Feb 10
Southwest Logo
6:15 am - 1:15 pm
ORD
-
KOA
12h 00m1 stop
Southwest Logo
8:25 pm - 1:55 pm
KOA
-
ORD
12h 30m1 stop
$282Southwest
Tue, Apr 21 - Tue, May 5
Alaska Airlines Logo
8:20 am - 6:17 am
ORD
-
LIH
25h 57m2 stops
Alaska Airlines Logo
4:50 pm - 11:59 pm
LIH
-
ORD
27h 09m1 stop
$284Alaska Airlines
Tue, Feb 24 - Tue, Mar 3
Alaska Airlines Logo
8:20 am - 6:17 am
ORD
-
LIH
25h 57m2 stops
Alaska Airlines Logo
2:56 pm - 2:58 pm
LIH
-
ORD
20h 02m1 stop
$285Alaska Airlines
Wed, Feb 25 - Mon, Mar 2
Southwest Logo
6:10 am - 1:15 pm
MDW
-
KOA
12h 05m1 stop
Southwest Logo
10:00 am - 5:00 am
KOA
-
MDW
14h 00m2 stops
$287Southwest
Tue, Apr 21 - Tue, May 5
Southwest Logo
5:10 am - 2:30 pm
MDW
-
KOA
14h 20m2 stops
Southwest Logo
8:25 pm - 4:15 pm
KOA
-
MDW
14h 50m1 stop
$288Southwest
Mon, May 4 - Thu, May 7
Delta Logo
7:30 am - 6:47 pm
ORD
-
KOA
15h 17m1 stop
Delta Logo
9:55 pm - 1:22 pm
KOA
-
ORD
11h 27m1 stop
$310Delta
Tue, Jan 20 - Tue, Feb 3
Delta Logo
6:00 am - 7:55 pm
MDW
-
LIH
17h 55m2 stops
Delta Logo
10:55 pm - 5:37 pm
LIH
-
MDW
14h 42m2 stops
$374Delta
Tue, Feb 24 - Tue, Mar 3

Southwest flights from Chicago to Hawaii

Our best Southwest deals on Chicago to Hawaii flight tickets
Southwest
Apr 21
MDW6:10 amChicago Midway
12h 05m
1 stop
KOA1:15 pmKona Intl
May 5
KOA10:00 amKona Intl
14h 45m
1 stop
MDW5:45 amChicago Midway
$282
Find similar
Southwest
Apr 21
MDW6:10 amChicago Midway
12h 05m
1 stop
KOA1:15 pmKona Intl
May 5
KOA10:00 amKona Intl
14h 00m
2 stops
MDW5:00 amChicago Midway
$287
Find similar
Southwest
May 4
MDW5:10 amChicago Midway
14h 20m
2 stops
KOA2:30 pmKona Intl
May 7
KOA8:25 pmKona Intl
14h 50m
1 stop
MDW4:15 pmChicago Midway
$288
Find similar

Alaska Airlines flights from Chicago to Hawaii

Our best Alaska Airlines deals on Chicago to Hawaii flight tickets
Alaska Airlines
Feb 24
ORD8:20 amChicago O'Hare Intl
32h 27m
1 stop
LIH12:47 pmLihue
Mar 3
LIH4:50 pmLihue
27h 09m
1 stop
ORD11:59 pmChicago O'Hare Intl
$277
Find similar
Alaska Airlines
Feb 3
ORD3:44 pmChicago O'Hare Intl
32h 46m
2 stops
LIH8:30 pmLihue
Feb 10
LIH10:25 amLihue
33h 12m
1 stop
ORD11:37 pmChicago O'Hare Intl
$282
Find similar
Alaska Airlines
Feb 24
ORD8:20 amChicago O'Hare Intl
25h 57m
2 stops
LIH6:17 amLihue
Mar 3
LIH4:50 pmLihue
27h 09m
1 stop
ORD11:59 pmChicago O'Hare Intl
$284
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Hawaii 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 5, 2025.
Use the filters below to find and compare flights from Chicago to Hawaii that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Tue 2/24

8:20 am-12:47 pm

1 stop32h 27m

Lihue

Tue 3/3

4:50 pm-11:59 pm

1 stop27h 09m

$277

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 4/21

6:10 am-1:15 pm

1 stop12h 05m

Kona Intl

Tue 5/5

10:00 am-5:45 am

1 stop14h 45m

$282

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Tue 2/3

3:44 pm-8:30 pm

2 stops32h 46m

Lihue

Tue 2/10

10:25 am-11:37 pm

1 stop33h 12m

$282

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 4/21

6:15 am-1:15 pm

1 stop12h 00m

Kona Intl

Tue 5/5

8:25 pm-1:55 pm

1 stop12h 30m

$282

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Tue 2/24

8:20 am-6:17 am

2 stops25h 57m

Lihue

Tue 3/3

4:50 pm-11:59 pm

1 stop27h 09m

$284

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Wed 2/25

8:20 am-6:17 am

2 stops25h 57m

Lihue

Mon 3/2

2:56 pm-2:58 pm

1 stop20h 02m

$285

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Tue 4/21

6:10 am-1:15 pm

1 stop12h 05m

Kona Intl

Tue 5/5

10:00 am-5:00 am

2 stops14h 00m

$287

ChicagoKailua-Kona

MDW - KOA

MDWKOA

Chicago Midway

Mon 5/4

5:10 am-2:30 pm

2 stops14h 20m

Kona Intl

Thu 5/7

8:25 pm-4:15 pm

1 stop14h 50m

$288

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 1/20

7:30 am-6:47 pm

1 stop15h 17m

Kona Intl

Tue 2/3

9:55 pm-1:22 pm

1 stop11h 27m

$310

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Tue 2/24

6:00 am-7:55 pm

2 stops17h 55m

Lihue

Tue 3/3

10:55 pm-5:37 pm

2 stops14h 42m

$374

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 Hawaii from

How to get the cheapest flight ticket from Chicago to Hawaii

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 Hawaii?

If you don’t want to visit Hawaii in February, then you should wait until January to fly from Chicago, when ticket prices are also cheap, with an average price of $653.

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

On average, the least expensive day to fly to Hawaii from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $999. However, this price may fluctuate depending on the airline, the season, and holidays. Flights from Chicago to Hawaii on a Saturday will generally be more expensive and average around $1,126. 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 Hawaii?

Our data shows that the cheapest Chicago to Hawaii flights are usually those with departure times in the afternoon. Our users have found flights to Hawaii in the afternoon for as low as $631. Flights at noon are often more expensive with an average ticket price of $1,260.

What is the cheapest Chicago to Hawaii flight route?

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

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

You are more likely to see cheaper flights to Hawaii from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Hawaii for around $829 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Hawaii from Chicago for as low as $743 on momondo.

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

There are 4 cabin classes available to choose from on Chicago to Hawaii 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 Chicago to Hawaii flights?

You could potentially save up to 5% on your flight if you consider stops on a Chicago to Hawaii flight.

Cheap Chicago to Hawaii flight deals and tips

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

Best Price Found

$326

Fastest flight time

9h 04m

Direct flights

Every day

Airports in Hawaii

3 airports
The best one-way flight to Hawaii from Chicago in the past 72 hours is $326. The best round-trip flight deal from Chicago to Hawaii found on momondo in the last 72 hours is $680.
The fastest flight from Chicago to Hawaii takes 9h 04m
Direct flights go from Chicago to Hawaii every day.
There are 3 airports near Hawaii: Honolulu (HNL), Kona Intl (KOA), Kahului (OGG)
Search flight deals

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

    Prices for flights from Chicago to Hawaii were last updated today.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Hawaii.

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

    The travel and health documents required for your trip to Hawaii 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 Hawaii. 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 Chicago to Hawaii?

Best airlines flying from Chicago to Hawaii

Compare and see reviews for airlines that fly from Chicago to Hawaii with momondo
Airline
Rating
Free Cancellation
Price
Hawaiian AirlinesPriceFrom $231Free CancellationRating
7.8
2,817 reviews
Search Hawaiian Airlines flights
DeltaPriceFrom $311Free CancellationRating
7.9
8,010 reviews
Search Delta flights
American AirlinesPriceFrom $381Free CancellationRating
7.2
11,047 reviews
Search American Airlines flights
Alaska AirlinesPriceFrom $398Free CancellationRating
8.0
11,402 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $443Free CancellationRating
7.4
9,065 reviews
Search United Airlines flights
SouthwestPriceFrom $568Free CancellationRating
8.0
4,250 reviews
Search Southwest flights

Why use momondo?

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

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 Chicago to Hawaii for you.

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

Yes. All flights to Hawaii from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once all potential Chicago to Hawaii flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Yes. momondo can track prices for Chicago to Hawaii flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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