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Cheap flights from Chicago to Hawaii from $183

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 4/18. 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

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:00 am - 1:40 pm
ORD
-
HNL
11h 40m
1 stop
Multiple Airlines Logo
7:50 am - 11:59 pm
HNL
-
ORD
11h 09m
1 stop
$407Multiple Airlines
Wed, Aug 19 - Fri, Aug 28
Multiple Airlines Logo
8:00 am - 5:00 pm
ORD
-
HNL
14h 00m
1 stop
Multiple Airlines Logo
10:20 pm - 1:54 pm
HNL
-
ORD
10h 34m
1 stop
$412Multiple Airlines
Wed, Sep 2 - Tue, Sep 8
American Airlines Logo
6:00 am - 12:22 pm
ORD
-
LIH
11h 22m
1 stop
American Airlines Logo
2:12 pm - 5:47 am
LIH
-
ORD
10h 35m
1 stop
$422American Airlines
Sun, May 3 - Thu, May 7
American Airlines Logo
6:00 am - 12:22 pm
ORD
-
LIH
11h 22m
1 stop
American Airlines Logo
2:12 pm - 7:18 am
LIH
-
ORD
12h 06m
1 stop
$424American Airlines
Thu, Apr 16 - Tue, Apr 21
Delta Logo
7:00 am - 2:40 pm
ORD
-
HNL
12h 40m
1 stop
Delta Logo
3:40 pm - 12:26 pm
HNL
-
ORD
15h 46m
1 stop
$424Delta
Mon, Apr 20 - Wed, Apr 29
Southwest Logo
10:20 am - 9:10 pm
MDW
-
HNL
15h 50m
1 stop
Southwest Logo
8:10 am - 4:30 am
HNL
-
MDW
15h 20m
1 stop
$428Southwest
Wed, Aug 19 - Wed, Aug 26
Delta Logo
7:00 am - 4:05 pm
ORD
-
HNL
14h 05m
1 stop
Delta Logo
1:30 pm - 8:34 am
HNL
-
ORD
14h 04m
2 stops
$430Delta
Tue, Sep 1 - Wed, Sep 9
Southwest Logo
10:40 am - 9:00 pm
MDW
-
HNL
15h 20m
2 stops
Southwest Logo
8:00 am - 5:25 am
HNL
-
MDW
16h 25m
1 stop
$434Southwest
Tue, Apr 14 - Tue, Apr 21
Alaska Airlines Logo
8:00 am - 7:52 pm
ORD
-
KOA
16h 52m
1 stop
Alaska Airlines Logo
1:16 pm - 1:13 pm
KOA
-
ORD
18h 57m
1 stop
$442Alaska Airlines
Tue, Apr 28 - Thu, May 7
Alaska Airlines Logo
8:00 am - 7:52 pm
ORD
-
KOA
16h 52m
1 stop
Alaska Airlines Logo
1:16 pm - 1:13 pm
KOA
-
ORD
18h 57m
1 stop
$498Alaska Airlines
Wed, Apr 22 - Fri, May 1

Delta flights from Chicago to Hawaii

Our best Delta deals on Chicago to Hawaii flight tickets
Delta
Apr 20
ORD7:00 amChicago O'Hare Intl
12h 40m
1 stop
HNL2:40 pmHonolulu
Apr 29
HNL3:40 pmHonolulu
15h 46m
1 stop
ORD12:26 pmChicago O'Hare Intl
$424
Delta
Apr 23
ORD7:15 amChicago O'Hare Intl
15h 25m
1 stop
LIH5:40 pmLihue
May 5
LIH8:20 pmLihue
12h 03m
1 stop
ORD1:23 pmChicago O'Hare Intl
$425
Delta
Apr 20
MDW9:29 amChicago Midway
16h 51m
2 stops
HNL9:20 pmHonolulu
Apr 29
HNL3:15 pmHonolulu
12h 32m
1 stop
MDW8:47 amChicago Midway
$430

Southwest flights from Chicago to Hawaii

Our best Southwest deals on Chicago to Hawaii flight tickets
Southwest
Aug 19
MDW10:20 amChicago Midway
15h 50m
1 stop
HNL9:10 pmHonolulu
Aug 26
HNL8:10 amHonolulu
15h 20m
1 stop
MDW4:30 amChicago Midway
$428
Southwest
Apr 14
MDW10:40 amChicago Midway
15h 20m
2 stops
HNL9:00 pmHonolulu
Apr 21
HNL8:00 amHonolulu
16h 25m
1 stop
MDW5:25 amChicago Midway
$434
Southwest
Apr 15
MDW7:30 amChicago Midway
18h 30m
2 stops
HNL9:00 pmHonolulu
Apr 22
HNL9:05 pmHonolulu
15h 50m
2 stops
MDW5:55 pmChicago Midway
$439

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 March 23, 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

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Wed 8/19

7:00 am-1:40 pm

1 stop11h 40m

Honolulu

Fri 8/28

7:50 am-11:59 pm

1 stop11h 09m

$407

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Wed 9/2

8:00 am-5:00 pm

1 stop14h 00m

Honolulu

Tue 9/8

10:20 pm-1:54 pm

1 stop10h 34m

$412
Quickest round-trip

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Sun 5/3

6:00 am-12:22 pm

1 stop11h 22m

Lihue

Thu 5/7

2:12 pm-5:47 am

1 stop10h 35m

$422

ChicagoLihue

ORD - LIH

ORDLIH

Chicago O'Hare Intl

Thu 4/16

6:00 am-12:22 pm

1 stop11h 22m

Lihue

Tue 4/21

2:12 pm-7:18 am

1 stop12h 06m

$424

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Mon 4/20

7:00 am-2:40 pm

1 stop12h 40m

Honolulu

Wed 4/29

3:40 pm-12:26 pm

1 stop15h 46m

$424

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 8/19

10:20 am-9:10 pm

1 stop15h 50m

Honolulu

Wed 8/26

8:10 am-4:30 am

1 stop15h 20m

$428

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Tue 9/1

7:00 am-4:05 pm

1 stop14h 05m

Honolulu

Wed 9/9

1:30 pm-8:34 am

2 stops14h 04m

$430

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 4/14

10:40 am-9:00 pm

2 stops15h 20m

Honolulu

Tue 4/21

8:00 am-5:25 am

1 stop16h 25m

$434

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Tue 4/28

8:00 am-7:52 pm

1 stop16h 52m

Kona Intl

Thu 5/7

1:16 pm-1:13 pm

1 stop18h 57m

$442

ChicagoKailua-Kona

ORD - KOA

ORDKOA

Chicago O'Hare Intl

Wed 4/22

8:00 am-7:52 pm

1 stop16h 52m

Kona Intl

Fri 5/1

1:16 pm-1:13 pm

1 stop18h 57m

$498

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 January, then you should wait until February to fly from Chicago, when ticket prices are also cheap, with an average price of $631.

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 $779. 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 $1,093. 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 $929. Flights at noon are often more expensive with an average ticket price of $1,248.

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 $794 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 $697 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 21% 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

$386

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 $386. The best round-trip flight deal from Chicago to Hawaii found on momondo in the last 72 hours is $652.
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

  • 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 $242Free CancellationRating
7.9
8,318 reviews
Search Delta flights
Hawaiian AirlinesPriceFrom $316Free CancellationRating
7.8
2,840 reviews
Search Hawaiian Airlines flights
Alaska AirlinesPriceFrom $363Free CancellationRating
7.9
12,101 reviews
Search Alaska Airlines flights
United AirlinesPriceFrom $401Free CancellationRating
7.4
9,463 reviews
Search United Airlines flights
American AirlinesPriceFrom $423Free CancellationRating
7.1
11,486 reviews
Search American Airlines flights
SouthwestPriceFrom $442Free CancellationRating
8.0
4,324 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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