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Cheap flights from Chicago to Hawaii from $218

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 8/18. 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.
United Airlines Logo
1:00 pm - 8:14 pm
ORD
-
LIH
12h 14m
1 stop
United Airlines Logo
1:00 pm - 4:45 am
LIH
-
ORD
10h 45m
1 stop
$424United Airlines
Sat, Aug 22 - Thu, Aug 27
Delta Logo
7:48 am - 7:16 pm
ORD
-
LIH
16h 28m
2 stops
Delta Logo
9:55 pm - 4:58 pm
LIH
-
ORD
14h 03m
1 stop
$430Delta
Tue, Aug 18 - Thu, Aug 27
Delta Logo
7:48 am - 7:16 pm
ORD
-
LIH
16h 28m
2 stops
Delta Logo
8:41 pm - 6:19 pm
LIH
-
ORD
16h 38m
2 stops
$435Delta
Tue, Aug 18 - Thu, Aug 27
American Airlines Logo
11:49 am - 8:09 pm
ORD
-
LIH
13h 20m
1 stop
American Airlines Logo
9:00 pm - 12:44 pm
LIH
-
ORD
10h 44m
1 stop
$452American Airlines
Sun, Aug 23 - Mon, Aug 31
Alaska Airlines Logo
8:20 pm - 2:35 pm
ORD
-
KOA
23h 15m
1 stop
Alaska Airlines Logo
10:35 am - 1:22 pm
KOA
-
ORD
21h 47m
1 stop
$493Alaska Airlines
Tue, Aug 11 - Wed, Aug 26
Southwest Logo
10:15 am - 4:10 pm
MDW
-
LIH
10h 55m
1 stop
Southwest Logo
8:25 pm - 12:05 pm
LIH
-
MDW
10h 40m
1 stop
$494Southwest
Wed, Aug 19 - Wed, Aug 26
Multiple Airlines Logo
8:20 pm - 2:35 pm
ORD
-
KOA
23h 15m
1 stop
Multiple Airlines Logo
6:30 pm - 7:21 pm
KOA
-
ORD
19h 51m
2 stops
$499Multiple Airlines
Tue, Aug 11 - Wed, Aug 26
Southwest Logo
6:40 am - 4:10 pm
MDW
-
LIH
14h 30m
2 stops
Southwest Logo
8:25 pm - 12:05 pm
LIH
-
MDW
10h 40m
1 stop
$500Southwest
Wed, Aug 19 - Wed, Aug 26
Multiple Airlines Logo
2:22 pm - 11:06 am
ORD
-
KOA
25h 44m
1 stop
Multiple Airlines Logo
10:35 am - 1:22 pm
KOA
-
ORD
21h 47m
1 stop
$503Multiple Airlines
Sat, Sep 19 - Fri, Sep 25
Alaska Airlines Logo
6:01 am - 2:48 pm
ORD
-
KOA
13h 47m
1 stop
Alaska Airlines Logo
10:35 am - 1:22 pm
KOA
-
ORD
21h 47m
1 stop
$504Alaska Airlines
Mon, Sep 7 - Thu, Sep 17

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Southwest flights from Chicago to Hawaii

Our best Southwest deals on Chicago to Hawaii flight tickets
Southwest
Aug 19
MDW10:15 amChicago Midway
10h 55m
1 stop
LIH4:10 pmLihue
Aug 26
LIH8:25 pmLihue
10h 40m
1 stop
MDW12:05 pmChicago Midway
$494
Southwest
Aug 19
MDW6:40 amChicago Midway
14h 30m
2 stops
LIH4:10 pmLihue
Aug 26
LIH8:25 pmLihue
10h 40m
1 stop
MDW12:05 pmChicago Midway
$500
Southwest
Aug 21
MDW6:40 amChicago Midway
10h 55m
1 stop
LIH12:35 pmLihue
Aug 26
LIH8:25 pmLihue
10h 40m
1 stop
MDW12:05 pmChicago Midway
$523

Alaska Airlines flights from Chicago to Hawaii

Our best Alaska Airlines deals on Chicago to Hawaii flight tickets
Alaska Airlines
Sep 15
ORD1:03 pmChicago O'Hare Intl
12h 11m
1 stop
LIH8:14 pmLihue
Sep 29
LIH10:45 amLihue
21h 37m
1 stop
ORD1:22 pmChicago O'Hare Intl
$492
Alaska Airlines
Aug 11
ORD8:20 pmChicago O'Hare Intl
23h 15m
1 stop
KOA2:35 pmKona Intl
Aug 26
KOA10:35 amKona Intl
21h 47m
1 stop
ORD1:22 pmChicago O'Hare Intl
$493
Alaska Airlines
Sep 15
ORD1:03 pmChicago O'Hare Intl
12h 11m
1 stop
LIH8:14 pmLihue
Sep 29
LIH10:45 amLihue
21h 37m
1 stop
ORD1:22 pmChicago O'Hare Intl
$497

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 June 26, 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

Sat 8/22

1:00 pm-8:14 pm

1 stop12h 14m

Lihue

Thu 8/27

1:00 pm-4:45 am

1 stop10h 45m

$424

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Tue 8/18

7:48 am-7:16 pm

2 stops16h 28m

Lihue

Thu 8/27

9:55 pm-4:58 pm

1 stop14h 03m

$430

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Tue 8/18

7:48 am-7:16 pm

2 stops16h 28m

Lihue

Thu 8/27

8:41 pm-6:19 pm

2 stops16h 38m

$435

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Sun 8/23

11:49 am-8:09 pm

1 stop13h 20m

Lihue

Mon 8/31

9:00 pm-12:44 pm

1 stop10h 44m

$452

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 8/11

8:20 pm-2:35 pm

1 stop23h 15m

Kona Intl

Wed 8/26

10:35 am-1:22 pm

1 stop21h 47m

$493
Quickest round-trip

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Wed 8/19

10:15 am-4:10 pm

1 stop10h 55m

Lihue

Wed 8/26

8:25 pm-12:05 pm

1 stop10h 40m

$494

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 8/11

8:20 pm-2:35 pm

1 stop23h 15m

Kona Intl

Wed 8/26

6:30 pm-7:21 pm

2 stops19h 51m

$499

ChicagoLihue

MDW - LIH

MDWLIH

Chicago Midway

Wed 8/19

6:40 am-4:10 pm

2 stops14h 30m

Lihue

Wed 8/26

8:25 pm-12:05 pm

1 stop10h 40m

$500

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Sat 9/19

2:22 pm-11:06 am

1 stop25h 44m

Kona Intl

Fri 9/25

10:35 am-1:22 pm

1 stop21h 47m

$503

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Mon 9/7

6:01 am-2:48 pm

1 stop13h 47m

Kona Intl

Thu 9/17

10:35 am-1:22 pm

1 stop21h 47m

$504

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 $545.

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 $757. 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 $1,086. 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 $822 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 $656 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

$464

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 $464. The best round-trip flight deal from Chicago to Hawaii found on momondo in the last 72 hours is $954.
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), Kona Intl (KOA), 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
8,440 reviews
Search Delta flights
Hawaiian AirlinesPriceFrom $316Free CancellationRating
7.8
2,826 reviews
Search Hawaiian Airlines flights
Alaska AirlinesPriceFrom $361Free CancellationRating
7.9
12,574 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $399Free CancellationRating
7.4
9,889 reviews
Search United Airlines flights
American AirlinesPriceFrom $422Free CancellationRating
7.1
11,757 reviews
Search American Airlines flights
SouthwestPriceFrom $470Free CancellationRating
7.9
4,243 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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