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Cheap flights from Chicago to Hawaii from $192

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 2/25. 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.
American Airlines Logo
6:00 am - 4:37 pm
ORD
-
LIH
14h 37m
1 stop
American Airlines Logo
10:10 pm - 12:35 pm
LIH
-
ORD
10h 25m
1 stop
$331American Airlines
Tue, Feb 3 - Tue, Feb 3
American Airlines Logo
9:25 am - 5:14 pm
ORD
-
LIH
11h 49m
1 stop
American Airlines Logo
10:30 pm - 1:33 pm
LIH
-
ORD
11h 03m
1 stop
$336American Airlines
Tue, Feb 24 - Tue, Mar 3
Delta Logo
7:25 am - 6:37 pm
ORD
-
KOA
16h 12m
1 stop
Delta Logo
8:55 pm - 1:25 pm
KOA
-
ORD
11h 30m
1 stop
$364Delta
Mon, Mar 9 - Wed, Mar 18
Delta Logo
7:40 am - 7:49 pm
ORD
-
LIH
16h 09m
2 stops
Delta Logo
8:21 pm - 1:24 pm
LIH
-
ORD
12h 03m
1 stop
$370Delta
Tue, Feb 24 - Tue, Mar 10
Alaska Airlines Logo
3:07 pm - 11:46 pm
ORD
-
OGG
12h 39m
1 stop
Alaska Airlines Logo
10:54 pm - 11:59 pm
OGG
-
ORD
20h 05m
1 stop
$402Alaska Airlines
Tue, Mar 3 - Mon, Mar 9
Alaska Airlines Logo
3:52 pm - 9:30 pm
ORD
-
OGG
34h 38m
1 stop
Alaska Airlines Logo
10:42 pm - 6:46 pm
OGG
-
ORD
15h 04m
1 stop
$403Alaska Airlines
Tue, May 12 - Mon, May 18
Southwest Logo
8:10 am - 4:25 pm
MDW
-
LIH
12h 15m
1 stop
Southwest Logo
9:20 pm - 11:45 am
LIH
-
MDW
10h 25m
1 stop
$405Southwest
Mon, Mar 2 - Thu, Mar 5
United Airlines Logo
12:55 pm - 9:21 pm
ORD
-
HNL
12h 26m
1 stop
United Airlines Logo
6:05 pm - 6:14 am
HNL
-
ORD
8h 09mnonstop
$411United Airlines
Sun, Feb 22 - Sun, Mar 1
United Airlines Logo
1:00 pm - 9:08 pm
ORD
-
HNL
12h 08m
1 stop
United Airlines Logo
12:35 pm - 5:01 am
HNL
-
ORD
12h 26m
1 stop
$415United Airlines
Tue, Feb 10 - Fri, Feb 13
Southwest Logo
7:55 am - 4:30 pm
MDW
-
HNL
12h 35m
1 stop
Southwest Logo
9:15 am - 5:00 am
HNL
-
MDW
15h 45m
1 stop
$421Southwest
Mon, Mar 2 - Sat, Mar 7

Southwest flights from Chicago to Hawaii

Our best Southwest deals on Chicago to Hawaii flight tickets
Southwest
Mar 2
MDW8:10 amChicago Midway
12h 15m
1 stop
LIH4:25 pmLihue
Mar 5
LIH9:20 pmLihue
10h 25m
1 stop
MDW11:45 amChicago Midway
$405
Southwest
Mar 2
MDW7:55 amChicago Midway
12h 35m
1 stop
HNL4:30 pmHonolulu
Mar 7
HNL9:15 amHonolulu
15h 45m
1 stop
MDW5:00 amChicago Midway
$421
Southwest
Feb 16
MDW10:15 pmChicago Midway
17h 00m
1 stop
HNL11:15 amHonolulu
Mar 3
HNL9:55 pmHonolulu
14h 40m
1 stop
MDW4:35 pmChicago Midway
$422

United Airlines flights from Chicago to Hawaii

Our best United Airlines deals on Chicago to Hawaii flight tickets
United Airlines
Feb 23
ORD2:35 pmChicago O'Hare Intl
12h 09m
1 stop
LIH10:44 pmLihue
Feb 27
LIH8:40 pmLihue
12h 34m
1 stop
ORD1:14 pmChicago O'Hare Intl
$392
United Airlines
Feb 11
ORD7:00 amChicago O'Hare Intl
14h 04m
1 stop
LIH5:04 pmLihue
Feb 18
LIH8:40 pmLihue
10h 39m
1 stop
ORD11:19 amChicago O'Hare Intl
$393
United Airlines
Feb 22
ORD12:55 pmChicago O'Hare Intl
12h 26m
1 stop
HNL9:21 pmHonolulu
Mar 1
HNL6:05 pmHonolulu
8h 09m
ORD6:14 amChicago O'Hare Intl
$411

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 January 21, 2026.
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 2/3

6:00 am-4:37 pm

1 stop14h 37m

Lihue

Tue 2/3

10:10 pm-12:35 pm

1 stop10h 25m

$331

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Tue 2/24

9:25 am-5:14 pm

1 stop11h 49m

Lihue

Tue 3/3

10:30 pm-1:33 pm

1 stop11h 03m

$336

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 3/9

7:25 am-6:37 pm

1 stop16h 12m

Kona Intl

Wed 3/18

8:55 pm-1:25 pm

1 stop11h 30m

$364

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Tue 2/24

7:40 am-7:49 pm

2 stops16h 09m

Lihue

Tue 3/10

8:21 pm-1:24 pm

1 stop12h 03m

$370

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 3/3

3:07 pm-11:46 pm

1 stop12h 39m

Kahului

Mon 3/9

10:54 pm-11:59 pm

1 stop20h 05m

$402

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Tue 5/12

3:52 pm-9:30 pm

1 stop34h 38m

Kahului

Mon 5/18

10:42 pm-6:46 pm

1 stop15h 04m

$403

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Mon 3/2

8:10 am-4:25 pm

1 stop12h 15m

Lihue

Thu 3/5

9:20 pm-11:45 am

1 stop10h 25m

$405

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Sun 2/22

12:55 pm-9:21 pm

1 stop12h 26m

Honolulu

Sun 3/1

6:05 pm-6:14 am

Nonstop8h 09m

$411

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Tue 2/10

1:00 pm-9:08 pm

1 stop12h 08m

Honolulu

Fri 2/13

12:35 pm-5:01 am

1 stop12h 26m

$415

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 3/2

7:55 am-4:30 pm

1 stop12h 35m

Honolulu

Sat 3/7

9:15 am-5:00 am

1 stop15h 45m

$421

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 $642.

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 Monday. momondo users have found tickets for Monday departures for as low as $921. 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 $1,110. 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 morning. Our users have found flights to Hawaii in the morning for as low as $1,003. Flights at noon are often more expensive with an average ticket price of $1,256.

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 $818 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 $713 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 20% 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

$341

Fastest flight time

9h 04m

Direct flights

Every day

Airports in Hawaii

40 airports
The best one-way flight to Hawaii from Chicago in the past 72 hours is $341. The best round-trip flight deal from Chicago to Hawaii found on momondo in the last 72 hours is $537.
The fastest flight from Chicago to Hawaii takes 9h 04m
Direct flights go from Chicago to Hawaii every day.
There are 40 airports in Hawaii. From Chicago there are direct flights to 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 $210Free CancellationRating
7.8
2,829 reviews
Search Hawaiian Airlines flights
DeltaPriceFrom $250Free CancellationRating
7.9
8,087 reviews
Search Delta flights
Alaska AirlinesPriceFrom $373Free CancellationRating
8.0
11,772 reviews
Search Alaska Airlines flights
American AirlinesPriceFrom $422Free CancellationRating
7.2
11,173 reviews
Search American Airlines flights
United AirlinesPriceFrom $443Free CancellationRating
7.4
9,190 reviews
Search United Airlines flights
SouthwestPriceFrom $468Free CancellationRating
8.0
4,266 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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