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Cheap flights from Chicago to Hawaii from $216

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 9/6. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Hawaii

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
9:30 am - 5:41 pmORD  Chicago O'Hare Intl-LIH Lihue
13h 11m1 stop Los Angeles Los Angeles
Delta Logo
9:55 pm - 5:00 pmLIH  Lihue-ORD Chicago O'Hare Intl
14h 05m1 stop Seattle/Tacoma Intl
$432Delta
Tue, Sep 1 - Thu, Sep 3
Delta Logo
7:00 am - 5:31 pmORD  Chicago O'Hare Intl-KOA Kona Intl
15h 31m1 stop Seattle/Tacoma Intl
Delta Logo
10:02 pm - 1:38 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
10h 36m1 stop Los Angeles Los Angeles
$438Delta
Wed, Sep 9 - Wed, Oct 28
American Airlines Logo
6:55 am - 4:00 pmORD  Chicago O'Hare Intl-KOA Kona Intl
14h 05m1 stop Los Angeles Los Angeles
American Airlines Logo
9:45 pm - 4:05 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
13h 20m1 stop Phoenix Sky Harbor Intl
$438American Airlines
Fri, Sep 11 - Mon, Sep 14
American Airlines Logo
5:00 am - 3:02 pmORD  Chicago O'Hare Intl-KOA Kona Intl
14h 02m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
10:21 pm - 1:40 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
11h 19m1 stop Phoenix Sky Harbor Intl
$438American Airlines
Sun, Nov 1 - Sun, Nov 8
United Airlines Logo
12:55 pm - 9:05 pmORD  Chicago O'Hare Intl-LIH Lihue
12h 10m1 stop Los Angeles Los Angeles
United Airlines Logo
8:30 pm - 11:09 amLIH  Lihue-ORD Chicago O'Hare Intl
10h 39m1 stop Denver Intl
$444United Airlines
Fri, Jan 1 - Mon, Jan 11
United Airlines Logo
2:30 pm - 10:35 pmORD  Chicago O'Hare Intl-LIH Lihue
12h 05m1 stop San Francisco
United Airlines Logo
8:30 pm - 11:42 amLIH  Lihue-ORD Chicago O'Hare Intl
11h 12m1 stop Denver Intl
$444United Airlines
Sat, Jan 23 - Sun, Jan 31
Southwest Logo
5:45 am - 1:15 pmMDW  Chicago Midway-LIH Lihue
11h 30m1 stop Las Vegas Harry Reid Intl
Southwest Logo
4:05 pm - 11:35 amLIH  Lihue-MDW Chicago Midway
15h 30m1 stop Oakland
$444Southwest
Sun, Nov 8 - Thu, Nov 12
Southwest Logo
5:45 am - 1:15 pmMDW  Chicago Midway-LIH Lihue
11h 30m1 stop Las Vegas Harry Reid Intl
Southwest Logo
11:50 am - 5:55 amLIH  Lihue-MDW Chicago Midway
14h 05m2 stops Honolulu Oakland
$445Southwest
Sun, Nov 8 - Thu, Nov 12
Multiple Airlines Logo
7:55 pm - 4:09 pmORD  Chicago O'Hare Intl-LIH Lihue
24h 14m1 stop San Diego
Multiple Airlines Logo
6:31 pm - 1:54 pmLIH  Lihue-ORD Chicago O'Hare Intl
15h 23m2 stops Honolulu San Diego
$469Multiple Airlines
Tue, Feb 2 - Tue, Feb 9
Multiple Airlines Logo
6:00 am - 2:42 pmORD  Chicago O'Hare Intl-LIH Lihue
13h 42m1 stop Seattle/Tacoma Intl
Multiple Airlines Logo
6:00 am - 11:59 pmLIH  Lihue-ORD Chicago O'Hare Intl
12h 59m2 stops Honolulu Seattle/Tacoma Intl
$470Multiple Airlines
Wed, Sep 9 - Wed, Sep 16

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Southwest flights from Chicago to Hawaii

Our best Southwest deals on Chicago to Hawaii flight tickets
Southwest
Nov 9
MDW5:45 amChicago Midway
11h 35m
1 stop
ITO1:20 pmHilo Intl
Nov 12
ITO9:25 pmHilo Intl
10h 25m
1 stop
MDW11:50 amChicago Midway
$434
Southwest
Nov 9
MDW5:45 amChicago Midway
11h 35m
1 stop
ITO1:20 pmHilo Intl
Nov 12
ITO11:35 amHilo Intl
14h 20m
2 stops
MDW5:55 amChicago Midway
$440
Southwest
Nov 8
MDW5:45 amChicago Midway
11h 30m
1 stop
LIH1:15 pmLihue
Nov 12
LIH4:05 pmLihue
15h 30m
1 stop
MDW11:35 amChicago Midway
$444

Alaska Airlines flights from Chicago to Hawaii

Our best Alaska Airlines deals on Chicago to Hawaii flight tickets
Alaska Airlines
Aug 28
ORD8:17 pmChicago O'Hare Intl
23h 31m
1 stop
KOA2:48 pmKona Intl
Aug 31
KOA10:35 amKona Intl
21h 47m
1 stop
ORD1:22 pmChicago O'Hare Intl
$497
Alaska Airlines
Sep 1
ORD2:18 pmChicago O'Hare Intl
12h 19m
1 stop
OGG9:37 pmKahului
Sep 8
OGG12:59 pmKahului
25h 22m
1 stop
ORD7:21 pmChicago O'Hare Intl
$614
Alaska Airlines
Jan 30
ORD7:55 pmChicago O'Hare Intl
22h 41m
1 stop
OGG2:36 pmKahului
Feb 5
OGG11:34 pmKahului
13h 27m
1 stop
ORD5:01 pmChicago O'Hare Intl
$635

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 August 10, 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

Cheapest round-trip

ChicagoLihue

ORD Chicago O'Hare Intl - LIH Lihue

ORDLIH

Chicago O'Hare Intl

Tue 9/1

9:30 am-5:41 pm

1 stop13h 11m

Lihue

Thu 9/3

9:55 pm-5:00 pm

1 stop14h 05m

$432

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Wed 9/9

7:00 am-5:31 pm

1 stop15h 31m

Kona Intl

Wed 10/28

10:02 pm-1:38 pm

1 stop10h 36m

$438

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Fri 9/11

6:55 am-4:00 pm

1 stop14h 05m

Kona Intl

Mon 9/14

9:45 pm-4:05 pm

1 stop13h 20m

$438

ChicagoKailua-Kona

ORD Chicago O'Hare Intl - KOA Kona Intl

ORDKOA

Chicago O'Hare Intl

Sun 11/1

5:00 am-3:02 pm

1 stop14h 02m

Kona Intl

Sun 11/8

10:21 pm-1:40 pm

1 stop11h 19m

$438
Quickest round-trip

ChicagoLihue

ORD Chicago O'Hare Intl - LIH Lihue

ORDLIH

Chicago O'Hare Intl

Fri 1/1

12:55 pm-9:05 pm

1 stop12h 10m

Lihue

Mon 1/11

8:30 pm-11:09 am

1 stop10h 39m

$444

ChicagoLihue

ORD Chicago O'Hare Intl - LIH Lihue

ORDLIH

Chicago O'Hare Intl

Sat 1/23

2:30 pm-10:35 pm

1 stop12h 05m

Lihue

Sun 1/31

8:30 pm-11:42 am

1 stop11h 12m

$444

ChicagoLihue

MDW Chicago Midway - LIH Lihue

MDWLIH

Chicago Midway

Sun 11/8

5:45 am-1:15 pm

1 stop11h 30m

Lihue

Thu 11/12

4:05 pm-11:35 am

1 stop15h 30m

$444

ChicagoLihue

MDW Chicago Midway - LIH Lihue

MDWLIH

Chicago Midway

Sun 11/8

5:45 am-1:15 pm

1 stop11h 30m

Lihue

Thu 11/12

11:50 am-5:55 am

2 stops14h 05m

$445

ChicagoLihue

ORD Chicago O'Hare Intl - LIH Lihue

ORDLIH

Chicago O'Hare Intl

Tue 2/2

7:55 pm-4:09 pm

1 stop24h 14m

Lihue

Tue 2/9

6:31 pm-1:54 pm

2 stops15h 23m

$469

ChicagoLihue

ORD Chicago O'Hare Intl - LIH Lihue

ORDLIH

Chicago O'Hare Intl

Wed 9/9

6:00 am-2:42 pm

1 stop13h 42m

Lihue

Wed 9/16

6:00 am-11:59 pm

2 stops12h 59m

$470

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 $613.

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 $747. 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 $1,087. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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 from Chicago 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 $834 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 $650 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 44% 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

$423

Fastest flight time

8h 56m

Direct flights

Every day

Airports in Hawaii

40 airports
The best one-way flight to Hawaii from Chicago in the past 72 hours is $423. The best round-trip flight deal from Chicago to Hawaii found on momondo in the last 72 hours is $827.
The fastest flight from Chicago to Hawaii takes 8h 56m
Direct flights go from Chicago to Hawaii every day.
There are 40 airports in Hawaii. From Chicago there are direct flights to Honolulu (HNL), Kahului (OGG).
Search flight deals

Frequently asked questions about flying from Chicago to Hawaii

  • 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
DeltaPriceFrom $241Free CancellationRating
7.8
8,497 reviews
Search Delta flights
Alaska AirlinesPriceFrom $361Free CancellationRating
7.9
12,790 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $398Free CancellationRating
7.4
10,098 reviews
Search United Airlines flights
American AirlinesPriceFrom $423Free CancellationRating
7.1
11,896 reviews
Search American Airlines flights
Hawaiian AirlinesPriceFrom $423Free CancellationRating
7.8
2,818 reviews
Search Hawaiian Airlines flights
SouthwestPriceFrom $439Free CancellationRating
8.0
4,214 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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