How long is the flight from Waikiki to Chicago?

A quick flight from Waikiki to Chicago can take about 30h 11m. Air Canada provides one of the quickest options available for as low as $1,103. There are 10947 mi between Waikiki and Chicago. This flight may include one or multiple stops.

What is the cheapest day to fly from Waikiki to Chicago?

Travelers seeking maximum savings on their Waikiki to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Tuesday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

How far in advance should I book a flight from Waikiki to Chicago?

Users have found that booking a flight from Waikiki to Chicago at least 20 days early can save you up to 15% on average compared to booking a flight this week. If booking 20 days before your flight isn’t an option for you, users have found flights from Waikiki to Chicago for as little as $1,247 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $1,247 for flights departing within the next 3 days.

What is the cheapest month to fly from Waikiki to Chicago?

May is one of the best times of the year to fly to Chicago from Waikiki. Prices for May average $1,458 per person but you can even find prices for as low as $1,127. The most expensive prices can be found in the month of December. Opting for a May flight can save you 34% on your journey compared to booking in December

What is the cheapest time of day to fly from WK1 to CHI?

When flying from Waikiki to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Can I find deals for flights from Waikiki to Chicago that include hotel bookings?

Yes. In addition to deals on Waikiki to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Waikiki to Chicago?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Waikiki to Chicago.

Can I find deals for business class flights from Waikiki to Chicago?

Yes. Cheapflights offers flight deals from Waikiki to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$726+ Cheap Flights from Waikiki to Chicago

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Cheapflights Tip: The best prices from Waikiki to Chicago are usually found in May or March, booked 21 days in advance, depart on a Wednesday or Tuesday and return on a Monday

Cheap flight deals from Waikiki to Chicago

Round-trip from	$1,038 (Gotogate)
One-way from	$726 (Kiwi.com)
Popular in	December
Cheapest in	May
Average price	$1,558

From Waikiki to Chicago (CHI)

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One-way flight from Waikiki to Chicago (CHI)

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Highest demand for flights based on searches. 11% potential increase in price ($198 potential increase over avg. RT price).

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Cheapest flight prices on average. 3% potential price decrease ($46 potential savings vs. average RT price).

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Average for round-trip flights in September 2025

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Find flight deals from Waikiki to Chicago

Cheapest flights from Waikiki to Chicago
Explore the most affordable flight options available from Waikiki to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

Mon 11/34:45 pmPER - ORD

2 stops35h 56mMultiple Airlines

Tue 11/183:40 pmORD - PER

2 stops36h 35mMultiple Airlines

Deal found 9/15

$1,053

Sat 11/13:15 pmPER - ORD

2 stops37h 26mMultiple Airlines

Tue 11/183:40 pmORD - PER

2 stops36h 35mMultiple Airlines

Deal found 9/13

$1,092

Thu 11/1310:30 pmPER - ORD

2 stops30h 11mAir Canada

Mon 11/173:40 pmORD - PER

2 stops39h 55mAir Canada

Deal found 9/14

$1,103

Wed 10/2910:30 amPER - ORD

2 stops41h 10mJapan Airlines

Wed 11/55:35 pmORD - PER

2 stops40h 20mJapan Airlines

Deal found 9/13

$1,174

Mon 9/2910:30 amPER - ORD

2 stops26h 58mMultiple Airlines

Tue 10/213:14 pmORD - PER

2 stops30h 01mMultiple Airlines

Deal found 9/14

$1,193

Wed 10/297:10 amPER - ORD

2 stops27h 04mQantas Airways

Wed 11/51:23 pmORD - PER

2 stops28h 22mQantas Airways

Deal found 9/13

$1,204

Mon 11/310:55 pmPER - ORD

3 stops52h 06mAir Canada

Tue 11/188:15 pmORD - PER

3 stops53h 15mAir Canada

Deal found 9/15

$1,348

Fri 10/3112:15 amPER - ORD

2 stops27h 25mJapan Airlines

Tue 11/1810:20 amORD - PER

2 stops47h 35mJapan Airlines

Deal found 9/13

$1,424

Best flights from Waikiki to Chicago
Discover carefully curated flight deals from Waikiki to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 15, 2025.

Mon 11/34:45 pmPER - ORD

2 stops35h 56mMultiple Airlines

Tue 11/183:40 pmORD - PER

2 stops36h 35mMultiple Airlines

Deal found 9/15

$1,053

Thu 11/1310:30 pmPER - ORD

2 stops30h 11mAir Canada

Mon 11/173:40 pmORD - PER

2 stops39h 55mAir Canada

Deal found 9/14

$1,103

Wed 10/2910:30 amPER - ORD

2 stops41h 10mJapan Airlines

Wed 11/55:35 pmORD - PER

2 stops40h 20mJapan Airlines

Deal found 9/13

$1,174

Wed 10/297:10 amPER - ORD

2 stops27h 04mQantas Airways

Wed 11/51:23 pmORD - PER

2 stops28h 22mQantas Airways

Deal found 9/13

$1,204

Wed 10/294:45 pmPER - ORD

2 stops50h 17mUnited Airlines

Wed 11/56:25 pmORD - PER

2 stops31h 30mUnited Airlines

Deal found 9/14

$1,493

Mon 11/39:55 pmPER - ORD

2 stops45h 21mANA

Tue 11/184:25 pmORD - PER

1 stop37h 45mANA

Deal found 9/15

$1,548

Sat 11/13:15 pmPER - ORD

2 stops37h 26mMultiple Airlines

Tue 11/183:40 pmORD - PER

2 stops36h 35mMultiple Airlines

Deal found 9/13

$1,092

Mon 9/2910:30 amPER - ORD

2 stops26h 58mMultiple Airlines

Tue 10/213:14 pmORD - PER

2 stops30h 01mMultiple Airlines

Deal found 9/14

$1,193

Fri 10/3112:15 amPER - ORD

2 stops27h 25mJapan Airlines

Tue 11/1810:20 amORD - PER

2 stops47h 35mJapan Airlines

Deal found 9/13

$1,424

Wed 10/295:05 pmPER - ORD

2 stops44h 19mMultiple Airlines

Wed 11/56:45 amORD - PER

3 stops42h 00mMultiple Airlines

Deal found 9/13

$1,510

Last-minute flights from Waikiki to Chicago
Discover last-minute flight deals from Waikiki to Chicago. Data last updated September 15, 2025 and is based on user searches.

Thu 9/1810:30 amPER - ORD

2 stops47h 10mQantas Airways

Sat 10/115:17 pmORD - PER

2 stops49h 33mQantas Airways

Deal found 9/13

$1,480

Mon 9/2910:30 amPER - ORD

2 stops26h 58mMultiple Airlines

Tue 10/213:14 pmORD - PER

2 stops30h 01mMultiple Airlines

Deal found 9/14

$1,193

Mon 9/2912:25 pmPER - ORD

2 stops33h 40mJapan Airlines

Mon 10/201:05 amORD - PER

2 stops34h 35mJapan Airlines

Deal found 9/14

$1,595

Wed 10/2910:30 amPER - ORD

2 stops41h 10mJapan Airlines

Wed 11/55:35 pmORD - PER

2 stops40h 20mJapan Airlines

Deal found 9/13

$1,174

Wed 10/297:10 amPER - ORD

2 stops27h 04mQantas Airways

Wed 11/51:23 pmORD - PER

2 stops28h 22mQantas Airways

Deal found 9/13

$1,204

Wed 10/2910:45 pmPER - ORD

1 stop29h 45mQatar Airways

Wed 11/51:15 pmORD - PER

2 stops32h 45mQatar Airways

Deal found 9/13

$1,445

Wed 10/294:45 pmPER - ORD

2 stops50h 17mUnited Airlines

Wed 11/56:25 pmORD - PER

2 stops31h 30mUnited Airlines

Deal found 9/14

$1,493

Wed 10/295:05 pmPER - ORD

2 stops44h 19mMultiple Airlines

Wed 11/56:45 amORD - PER

3 stops42h 00mMultiple Airlines

Deal found 9/13

$1,510

Fri 10/3112:15 amPER - ORD

2 stops27h 25mJapan Airlines

Tue 11/1810:20 amORD - PER

2 stops47h 35mJapan Airlines

Deal found 9/13

$1,424

One-way flights from Waikiki to Chicago
Search for one-way flight options from Waikiki to Chicago. Find affordable one-way fares based on user searches. Data last updated September 15, 2025.

Mon 11/1711:10 pmPER - ORD

3 stops50h 20mMultiple Airlines

Deal found 9/15

$726

Tue 9/2311:35 pmPER - ORD

3 stops46h 10mMultiple Airlines

Deal found 9/14

$740

Sat 11/154:40 amPER - ORD

3 stops51h 45mMultiple Airlines

Deal found 9/15

$748

Mon 9/2210:15 amPER - ORD

3 stops41h 10mMultiple Airlines

Deal found 9/14

$772

Mon 9/2910:15 amPER - ORD

3 stops59h 30mMultiple Airlines

Deal found 9/14

$804

Sat 9/2710:15 amPER - ORD

2 stops41h 40mMultiple Airlines

Deal found 9/14

$856

Thu 9/256:25 pmPER - ORD

3 stops41h 18mMultiple Airlines

Deal found 9/14

$868

Fly from

Fly to

Route

Depart

Return

Price

PerthChicago

PER - ORD

PERORD

Perth

Mon 11/3

4:45 pm-2:41 pm

2 stops35h 56m

Chicago O'Hare Intl

Tue 11/18

3:40 pm-6:15 pm

2 stops36h 35m

$1,053

PerthChicago

PER - ORD

PERORD

Perth

Sat 11/1

3:15 pm-3:41 pm

2 stops37h 26m

Chicago O'Hare Intl

Tue 11/18

3:40 pm-6:15 pm

2 stops36h 35m

$1,092

PerthChicago

PER - ORD

PERORD

Perth

Thu 11/13

10:30 pm-2:41 pm

2 stops30h 11m

Chicago O'Hare Intl

Mon 11/17

3:40 pm-9:35 pm

2 stops39h 55m

$1,103

PerthChicago

PER - ORD

PERORD

Perth

Wed 10/29

10:30 am-2:40 pm

2 stops41h 10m

Chicago O'Hare Intl

Wed 11/5

5:35 pm-11:55 pm

2 stops40h 20m

$1,174

PerthChicago

PER - ORD

PERORD

Perth

Mon 9/29

10:30 am-12:28 am

2 stops26h 58m

Chicago O'Hare Intl

Tue 10/21

3:14 pm-10:15 am

2 stops30h 01m

$1,193

PerthChicago

PER - ORD

PERORD

Perth

Wed 10/29

7:10 am-9:14 pm

2 stops27h 04m

Chicago O'Hare Intl

Wed 11/5

1:23 pm-7:45 am

2 stops28h 22m

$1,204

PerthChicago

PER - ORD

PERORD

Perth

Fri 10/31

12:15 am-2:40 pm

2 stops27h 25m

Chicago O'Hare Intl

Tue 11/18

10:20 am-11:55 pm

2 stops47h 35m

$1,424

PerthChicago

PER - ORD

PERORD

Perth

Wed 10/29

4:45 pm-6:02 am

2 stops50h 17m

Chicago O'Hare Intl

Wed 11/5

6:25 pm-3:55 pm

2 stops31h 30m

$1,493

PerthChicago

PER - ORD

PERORD

Perth

Wed 10/29

5:05 pm-12:24 am

2 stops44h 19m

Chicago O'Hare Intl

Wed 11/5

6:45 am-2:45 pm

3 stops42h 00m

$1,510

PerthChicago

PER - ORD

PERORD

Perth

Mon 11/3

9:55 pm-5:16 am

2 stops45h 21m

Chicago O'Hare Intl

Tue 11/18

4:25 pm-8:10 pm

1 stop37h 45m

$1,548

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 17 results

Best time to book a flight from Waikiki to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Waikiki with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Waikiki to Chicago

How far ahead should I book a flight from Waikiki to Chicago?

To ensure you get the cheapest price possible for a flight from Waikiki to Chicago, you should look to book at least 19 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Waikiki to Chicago?

Currently, August is the cheapest month in which you can book a flight from Waikiki to Chicago (average of $245). Flying from Waikiki to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

How long is the flight from Waikiki to Chicago?
A quick flight from Waikiki to Chicago can take about 30h 11m. Air Canada provides one of the quickest options available for as low as $1,103. There are 10947 mi between Waikiki and Chicago. This flight may include one or multiple stops.
Can I find deals for flights from Waikiki to Chicago that include hotel bookings?
Yes. In addition to deals on Waikiki to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Waikiki to Chicago?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Waikiki to Chicago.
Can I find deals for business class flights from Waikiki to Chicago?
Yes. Cheapflights offers flight deals from Waikiki to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Waikiki to Chicago?
Currently, August is the cheapest month in which you can book a flight from Waikiki to Chicago (average of $245). Flying from Waikiki to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top airline flying from Waikiki to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Japan Airlines	Cheapest$965	Average$973	FlexibilityNo cancel fee	On-time79%

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$726+ Cheap flights from Waikiki, Australia to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/17. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Waikiki to Chicago with Cheapflights

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2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Waikiki to Chicago are usually found in May or March, booked 21 days in advance, depart on a Wednesday or Tuesday and return on a Monday

Cheap flight deals from Waikiki to Chicago

Keep the following information in mind while searching for Waikiki to Chicago flight deals. Data was last updated September 15, 2025.

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Waikiki to Chicago

Cheapest flights from Waikiki to ChicagoExplore the most affordable flight options available from Waikiki to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

Explore the most affordable flight options available from Waikiki to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Waikiki to Chicago that are best for you.

Best time to book a flight from Waikiki to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Waikiki with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Waikiki to Chicago

How far ahead should I book a flight from Waikiki to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Waikiki to Chicago. Price data was last updated on September 12, 2025.

What is the cheapest month to book a flight from Waikiki to Chicago?

Related info for your journey

Find useful and relevant information for your journey from Waikiki to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

How long is the flight from Waikiki to Chicago?

Can I find deals for flights from Waikiki to Chicago that include hotel bookings?

How can I find direct flights from Waikiki to Chicago?

Can I find deals for business class flights from Waikiki to Chicago?

What is the cheapest month to book a flight from Waikiki to Chicago?

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Alternative routes for Waikiki to Chicago

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Top airline flying from Waikiki to Chicago

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Cheapest flights from Waikiki to Chicago
Explore the most affordable flight options available from Waikiki to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.