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Cheap flights from Chicago to Hawaii from $212

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 8/23. 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 - 12:15 pm
ORD
-
LIH
11h 15m
1 stop
American Airlines Logo
1:45 pm - 6:01 am
LIH
-
ORD
11h 16m
1 stop
$424American Airlines
Tue, Oct 20 - Mon, Oct 26
Delta Logo
7:35 am - 5:20 pm
ORD
-
LIH
14h 45m
1 stop
Delta Logo
9:45 pm - 7:34 pm
LIH
-
ORD
16h 49m
2 stops
$430Delta
Tue, Oct 20 - Mon, Oct 26
United Airlines Logo
12:45 pm - 7:42 pm
ORD
-
LIH
11h 57m
1 stop
United Airlines Logo
2:31 pm - 5:53 am
LIH
-
ORD
10h 22m
1 stop
$463United Airlines
Wed, Jun 3 - Tue, Jun 9
Southwest Logo
6:40 am - 2:10 pm
MDW
-
LIH
12h 30m
2 stops
Southwest Logo
8:25 pm - 12:05 pm
LIH
-
MDW
10h 40m
1 stop
$491Southwest
Mon, Aug 24 - Thu, Aug 27
Alaska Airlines Logo
2:18 pm - 2:51 pm
ORD
-
KOA
29h 33m
1 stop
Alaska Airlines Logo
10:35 am - 1:22 pm
KOA
-
ORD
21h 47m
1 stop
$494Alaska Airlines
Tue, Aug 25 - Thu, Aug 27
Southwest Logo
6:40 am - 2:10 pm
MDW
-
LIH
12h 30m
2 stops
Southwest Logo
6:15 am - 11:45 pm
LIH
-
MDW
12h 30m
2 stops
$496Southwest
Mon, Aug 24 - Thu, Aug 27
Multiple Airlines Logo
2:18 pm - 2:51 pm
ORD
-
KOA
29h 33m
1 stop
Multiple Airlines Logo
6:00 am - 11:57 pm
KOA
-
ORD
12h 57m
2 stops
$499Multiple Airlines
Sat, Sep 19 - Fri, Sep 25
Multiple Airlines Logo
6:00 am - 1:26 pm
ORD
-
OGG
12h 26m
1 stop
Multiple Airlines Logo
10:30 pm - 6:50 pm
OGG
-
ORD
15h 20m
1 stop
$509Multiple Airlines
Thu, May 28 - Thu, Jun 4
United Airlines Logo
6:03 am - 11:46 am
ORD
-
KOA
10h 43m
1 stop
United Airlines Logo
8:00 pm - 12:19 pm
KOA
-
ORD
11h 19m
1 stop
$524United Airlines
Wed, Sep 2 - Wed, Sep 2
Alaska Airlines Logo
3:28 pm - 10:14 pm
ORD
-
KOA
11h 46m
1 stop
Alaska Airlines Logo
8:00 am - 11:59 pm
KOA
-
ORD
10h 59m
1 stop
$540Alaska Airlines
Mon, Jun 1 - Mon, Jun 8

Southwest flights from Chicago to Hawaii

Our best Southwest deals on Chicago to Hawaii flight tickets
Southwest
Aug 24
MDW6:40 amChicago Midway
12h 30m
2 stops
LIH2:10 pmLihue
Aug 27
LIH8:25 pmLihue
10h 40m
1 stop
MDW12:05 pmChicago Midway
$491
Southwest
Aug 24
MDW6:40 amChicago Midway
12h 30m
2 stops
LIH2:10 pmLihue
Aug 27
LIH6:15 amLihue
12h 30m
2 stops
MDW11:45 pmChicago Midway
$496
Southwest
Sep 24
MDW10:15 amChicago Midway
10h 55m
1 stop
LIH4:10 pmLihue
Oct 2
LIH6:15 amLihue
12h 30m
2 stops
MDW11:45 pmChicago Midway
$520

Alaska Airlines flights from Chicago to Hawaii

Our best Alaska Airlines deals on Chicago to Hawaii flight tickets
Alaska Airlines
Aug 24
ORD7:59 pmChicago O'Hare Intl
20h 45m
1 stop
LIH11:44 amLihue
Aug 27
LIH10:42 amLihue
21h 40m
1 stop
ORD1:22 pmChicago O'Hare Intl
$478
Alaska Airlines
Jun 1
ORD3:28 pmChicago O'Hare Intl
11h 46m
1 stop
KOA10:14 pmKona Intl
Jun 8
KOA8:00 amKona Intl
10h 59m
1 stop
ORD11:59 pmChicago O'Hare Intl
$540
Alaska Airlines
May 24
ORD7:59 pmChicago O'Hare Intl
20h 31m
1 stop
LIH11:30 amLihue
Jun 7
LIH12:30 pmLihue
12h 50m
1 stop
ORD6:20 amChicago O'Hare Intl
$554

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 May 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 - LIH

ORDLIH

Chicago O'Hare Intl

Tue 10/20

6:00 am-12:15 pm

1 stop11h 15m

Lihue

Mon 10/26

1:45 pm-6:01 am

1 stop11h 16m

$424

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Tue 10/20

7:35 am-5:20 pm

1 stop14h 45m

Lihue

Mon 10/26

9:45 pm-7:34 pm

2 stops16h 49m

$430

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Wed 6/3

12:45 pm-7:42 pm

1 stop11h 57m

Lihue

Tue 6/9

2:31 pm-5:53 am

1 stop10h 22m

$463

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Mon 8/24

6:40 am-2:10 pm

2 stops12h 30m

Lihue

Thu 8/27

8:25 pm-12:05 pm

1 stop10h 40m

$491

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 8/25

2:18 pm-2:51 pm

1 stop29h 33m

Kona Intl

Thu 8/27

10:35 am-1:22 pm

1 stop21h 47m

$494

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Mon 8/24

6:40 am-2:10 pm

2 stops12h 30m

Lihue

Thu 8/27

6:15 am-11:45 pm

2 stops12h 30m

$496

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sat 9/19

2:18 pm-2:51 pm

1 stop29h 33m

Kona Intl

Fri 9/25

6:00 am-11:57 pm

2 stops12h 57m

$499

ChicagoKahului

ORD - OGG

ORDOGG

Chicago O'Hare Intl

Thu 5/28

6:00 am-1:26 pm

1 stop12h 26m

Kahului

Thu 6/4

10:30 pm-6:50 pm

1 stop15h 20m

$509
Quickest round-trip

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 9/2

6:03 am-11:46 am

1 stop10h 43m

Kona Intl

Wed 9/2

8:00 pm-12:19 pm

1 stop11h 19m

$524

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 6/1

3:28 pm-10:14 pm

1 stop11h 46m

Kona Intl

Mon 6/8

8:00 am-11:59 pm

1 stop10h 59m

$540

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 $547.

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 $760. 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 $1,069. 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 $800 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 $657 on momondo.

Can stopping save me money on Chicago to Hawaii flights?

You could potentially save up to 43% 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

$312

Fastest flight time

8h 56m

Direct flights

Mon, Tue, Wed, Fri, Sat and Sun

Airports in Hawaii

40 airports
The best one-way flight to Hawaii from Chicago in the past 72 hours is $312. The best round-trip flight deal from Chicago to Hawaii found on momondo in the last 72 hours is $890.
The fastest flight from Chicago to Hawaii takes 8h 56m
Direct flights go from Chicago to Hawaii on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
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
7.9
8,455 reviews
Search Delta flights
Hawaiian AirlinesPriceFrom $295Free CancellationRating
7.8
2,837 reviews
Search Hawaiian Airlines flights
Alaska AirlinesPriceFrom $363Free CancellationRating
7.9
12,348 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $394Free CancellationRating
7.4
9,694 reviews
Search United Airlines flights
American AirlinesPriceFrom $422Free CancellationRating
7.1
11,667 reviews
Search American Airlines flights
SouthwestPriceFrom $442Free CancellationRating
8.0
4,306 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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