Cheap flights from Chicago (CHI) to Waikiki

Know your dates, get live prices in seconds:

From
To
Depart
Return
Any month
Compare vs. Cheapflights |
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime

We work with more than 300 partners to bring you better travel deals

The best prices from Chicago to Waikiki are usually found in August or May, booked 12 days in advance, depart on a Tuesday or Wednesday and return on a Monday

How to find the cheapest flight from
Chicago (CHI) to Waikiki

All the information you need to plan the best CHI to HNL flight in 2021: compare Chicago to Waikiki flight prices with the expected peak season, weather and rainfall in Waikiki.
CHI - W1K
Price
$617 - $864

Popular in

December

High demand for flights, 21% potential price rise

Cheapest in

August

Best time to find cheap flights, 9% potential price drop

Round-trip from

$617

From Chicago to Waikiki

One-way from

$220

One-way flight from Chicago to Waikiki

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest month to fly from Chicago to Waikiki?

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, March can be a great choice for travel to Waikiki. Flights to Waikiki from Chicago in March are about $456 on average during March, but can be found for as low as $229.

Cheap flights from Chicago to Waikiki in August, September 2021

The best prices found for CHI to Waikiki flights for August, September
28 Sep - 4 Oct
$270pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
HNL
Honolulu
HNL
Honolulu
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
21 Sep - 27 Sep
$276pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
HNL
Honolulu
HNL
Honolulu
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
28 Sep - 4 Oct
$280pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
HNL
Honolulu
HNL
Honolulu
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Chicago to Waikiki 2021 flight deals

Cheap flights to Waikiki from Chicago found for this year
28 Sep - 4 Oct
$270pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
HNL
Honolulu
HNL
Honolulu
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
21 Sep - 27 Sep
$276pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
HNL
Honolulu
HNL
Honolulu
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
28 Sep - 4 Oct
$280pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
HNL
Honolulu
HNL
Honolulu
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Non-stop flights to Waikiki from Chicago

Save time with Chicago to Waikiki direct flight deals
7 Oct - 7 Oct
$463pp
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
HNL
Honolulu
HNL
Honolulu
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
2 Sep - 5 Sep
$468pp
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
HNL
Honolulu
HNL
Honolulu
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
11 Sep - 14 Sep
$498pp
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
HNL
Honolulu
HNL
Honolulu
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to Waikiki

Late deals on round-trip flights to Waikiki from Chicago, departing today and this week
14 Aug - 28 Aug
$486pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
HNL
Honolulu
HNL
Honolulu
Sun Country Air
   
2 STOPS
ORD
Chicago O'Hare Intl
12 Aug - 16 Aug
$491pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
HNL
Honolulu
HNL
Honolulu
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
13 Aug - 1 Dec
$498pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
HNL
Honolulu
HNL
Honolulu
Alaska Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

One-way flights to Waikiki from Chicago

The cheapest one-way flights from Chicago to Waikiki
1:35 pm - 8:39 am
Sun Country Air
2 Stops
24h 04m
ORD - HNL
Sun Country Air
1:45 pm - 6:25 am
Alaska Airlines
2 Stops
21h 40m
ORD - HNL
Alaska Airlines
2:10 am - 4:40 pm
Multiple Airlines
2 Stops
19h 30m
ORD - HNL
Multiple Airlines
$232
Kiwi.com

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Chicago</span> to <span class="emphasized">Waikiki</span> flights.

Flight FAQs

From Chicago to Waikiki

Are flight prices decreasing from Chicago to Waikiki due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Chicago and Waikiki for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

Which airlines flying from Chicago to Waikiki have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Chicago to Waikiki that may be offering flexible cancellation policies are American Airlines, United Airlines, and Delta. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

Can I find flights from Chicago to Waikiki for under $300 on Cheapflights?

Yes, there are multiple flights from Chicago to Waikiki for under $300. The cheapest flight booked recently is on Multiple Airlines for just $270, but on average you can expect to pay $318.

Are there nonstop flights from Chicago to Waikiki for under $500 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Waikiki under $500. A good price for a nonstop flight from Chicago to Waikiki is less than $603.

Are there last-minute flights available from Chicago to Waikiki for under $500?

There are currently 20+ open flights from Chicago to Waikiki within the next 7 days for less than $500.

What are the most popular airlines that fly from Chicago to Waikiki?

Major Airline, American Airlines and Alaska Airlines are the most popular airlines when flying from Chicago to Waikiki.

What are the cheapest Flights from Chicago to Waikiki?

While on average a flight from Chicago to Waikiki is generally $1,404, our data shows the cheapest flight currently is $275. When looking at the most popular route, (Chicago O'Hare Intl - Honolulu), you can expect to pay $266 for that flight.

What are the most reliable airlines from Chicago to Waikiki?

Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Waikiki on time: American Airlines(87%), Qantas Airways(87%), United Airlines(86%.)

How long is the flight from Chicago to Waikiki?

Departing from Chicago to Waikiki will take you 12h 55m.

What are the cheapest airlines to fly from Chicago to Waikiki one-way?

The cheapest airline one-way is Alaska Airlines, with whom users have recently found tickets for as low as $196. However, be on the lookout for offers from Sun Country Air and United Airlines, as they are both options that can get you from Chicago to Waikiki for a low price.

COVID Restrictions

View COVID Travel Restrictions for Waikiki

Do I need a COVID test to fly to Waikiki from Chicago?

Information is based on travel restrictions for travel to Waikiki within the United States

Most visitors from Chicago need to provide a negative COVID-19 test result and/or quarantine to enter Waikiki.

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Waikiki.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Waikiki.

Do I need a test to fly back to Chicago from Waikiki?

Returning to Chicago from Waikiki

COVID-19 testing requirements
Visitors from Waikiki must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from Waikiki are not required to quarantine after entering Chicago.

Hide COVID Travel Restrictions for Waikiki

Alternative routes for Chicago to Waikiki

See prices for flight routes from nearby airports that may be better suited for you.

Destination information for Waikiki

Things to know before you go - useful duration and weather info for your trip from Chicago to Waikiki.

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Airports servicing Aiea

Top 5 airlines flying from Chicago to Waikiki

The chart below displays the airlines Cheapflights users traveling from Chicago to Waikiki choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Alaska Airlines
$272 $533 No cancel fee 75%
American Airlines
$264 $651 No cancel fee 71%
Sun Country Air
$415 $659 No cancel fee 83%
Delta
$280 $785 No cancel fee N/A
United Airlines
$336 $823 No cancel fee 69%

Hourly flight availability from Chicago to Waikiki

See what time of day planes typically take off from Chicago towards Waikiki.
Morning 6 AM to noon 100% of CHI to Waikiki departures
Early morning Midnight to 6 AM 0% of CHI to Waikiki departures
Afternoon Noon to 6 PM 0% of CHI to Waikiki departures
Evening 6 PM to midnight 0% of CHI to Waikiki departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Chicago to Waikiki
See how many times per day planes take to the skies headed from Chicago to Waikiki.
Sunday
5 daily flights
Monday
5 daily flights
Tuesday
5 daily flights
Wednesday
5 daily flights
Thursday
5 daily flights
Friday
5 daily flights
Saturday
5 daily flights
Home North America USA Hawaii Waikiki Cheap flights from Chicago to Waikiki