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Cheap flights from Waikiki to Chicago (HNL - CHI)

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The best prices from Waikiki to Chicago are usually found in August or February, booked 60 days in advance, depart on a Monday or Tuesday and return on a Tuesday

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

HNL - CHI
Price
$546 - $749
CHI
Temperature
33.8 - 84.2 °F
CHI
Rainfall
0.7 - 4.3 inches

Popular in

December

High demand for flights, 15% potential price rise

Cheapest in

August

Best time to find cheap flights, 14% potential price drop

Round-trip from

$546

From Waikiki to Chicago

One-way from

$165

One-way flight from Waikiki to Chicago

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

It’s generally more expensive to depart on a Sunday, if you have to leave on this day you can still search on Cheapflights to find great options that meet your needs.

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

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 20 days in advance, which can save you up to 10% on flights from Waikiki to Chicago compared to booking the week you need them. Waiting 20 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $137. For sooner than that we have options available in the next 3 days from $157.

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

Flights from Waikiki to Chicago lean towards being more expensive in December. Prices are generally better when you fly from Waikiki to Chicago in April, with the cheapest ticket starting at $33.

When is the cheapest time to fly from Waikiki to Chicago (HNL - CHI)?

When flying from Waikiki to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 33% versus a flight in the afternoon.

Cheap flights from Waikiki to Chicago in January, February 2021

The best prices found for HNL to CHI flights for January, February
16 Feb - 23 Feb
$315pp
HNL
Honolulu
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
HNL
Honolulu
17 Feb - 24 Feb
$326pp
HNL
Honolulu
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
HNL
Honolulu
16 Feb - 23 Feb
$338pp
HNL
Honolulu
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
HNL
Honolulu

Waikiki to Chicago 2021 flight deals

Cheap flights to Chicago from Waikiki found for this year
16 Feb - 23 Feb
$315pp
HNL
Honolulu
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
HNL
Honolulu
1 Mar - 10 Mar
$319pp
HNL
Honolulu
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
HNL
Honolulu
1 Mar - 10 Mar
$320pp
HNL
Honolulu
Multiple Airlines
     
3 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
HNL
Honolulu

Non-stop flights to Chicago from Waikiki

Save time with Waikiki to Chicago direct flight deals
13 May - 18 May
$760pp
HNL
Honolulu
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
HNL
Honolulu
11 May - 18 May
$761pp
HNL
Honolulu
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
HNL
Honolulu
1 Mar - 10 Mar
$762pp
HNL
Honolulu
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
HNL
Honolulu

Last minute flights from Waikiki to Chicago

Late deals on round-trip flights to Chicago from Waikiki, departing today and this week
28 Jan - 3 Mar
$411pp
HNL
Honolulu
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
HNL
Honolulu
28 Jan - 3 Mar
$428pp
HNL
Honolulu
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
HNL
Honolulu
28 Jan - 3 Mar
$435pp
HNL
Honolulu
United Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
   
2 STOPS
HNL
Honolulu

One-way flights to Chicago from Waikiki

The cheapest one-way flights from Waikiki to Chicago
10:20 am - 3:27 pm
Multiple Airlines
1 Stop
25h 07m
HNL - ORD
Multiple Airlines
$165
Kiwi.com
9:20 am - 3:46 pm
Multiple Airlines
1 Stop
25h 26m
HNL - ORD
Multiple Airlines
$171
Kiwi.com
11:40 am - 1:28 pm
Alaska Airlines
1 Stop
20h 48m
HNL - ORD
Alaska Airlines

Related info for your journey

Useful info, stats and facts about Waikiki to Chicago flights.

Flight FAQs

From Waikiki to Chicago

Are flight prices decreasing from Honolulu to Chicago 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 Honolulu and Chicago 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.

What safety measures are being taken by airlines flying from Honolulu to Chicago to control the spread of COVID-19?

Alaska Airlines and Delta are some of the many airlines that have implemented additional safety measures to control the spread of COVID-19. New policies for travelers booking flights from Honolulu to Chicago include masks being provided and required on board, daily cleaning and sanitization, use of HEPA filters, pre-flight testing for antibodies and symptoms, and socially distanced seating (for a limited time). Keep in mind that policies will vary by airline.

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

Due to the rapidly changing circumstances due to COVID-19, airlines like American Airlines, United Airlines, and Delta flying from Honolulu to Chicago have implemented new flexible cancellation policies.

Can I find flights from Waikiki to Chicago for under $400 on Cheapflights?

Yes, there are multiple flights from Waikiki to Chicago for under $400. The cheapest flight booked recently is on Multiple Airlines for just $315, but on average you can expect to pay $347.

Are there nonstop flights from Waikiki to Chicago for under $800 on Cheapflights?

Cheapflights has at least 20 direct flights from Waikiki to Chicago under $800. A good price for a nonstop flight from Waikiki to Chicago is less than $815.

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

There are currently 15+ open flights from Waikiki to Chicago within the next 7 days for less than $500.

Is Honolulu weather warmer or cooler than Chicago?

Expect the weather to be around 90 °F on average in August. As the temperature peaks, try to get your plans done early, as flight price and availability will have an impact on your travels. The climate in Chicago is generally colder than in Honolulu.

How long is the flight from Waikiki to Chicago?

A quick flight from Waikiki to Chicago can take about 10h 05m. United Airlines provides one of the quickest options available for as low as $367. Both multi-stop and nonstop flights can be found to your destination and back.

What are the cheapest airlines flying from Waikiki to Chicago round-trip?

Our cheapest airline available from Waikiki to Chicago is Alaska Airlines. Our recent data shows that you can find tickets from as low as $354 on this airline. Additional options worth looking into are United Airlines and American Airlines, starting at $356 and $386 round-trip. Alaska Airlines is 44% cheaper than the average price of flights available within the next 90 days to this destination.

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

The cheapest airline for a one-way flight from Waikiki to Chicago is Alaska Airlines ($172).

Destination information for Chicago

Things to know before you go. Useful info for your trip from Waikiki to Chicago
Average temperature for January in Chicago
33.8 °F
Avg rainfall for January in Chicago
0.7 ″

Airports servicing Honolulu

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 4 airlines flying from Waikiki to Chicago

The chart below displays the airlines Cheapflights users traveling from Waikiki to Chicago 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
$270 $570 No cancel fee 75%
American Airlines
$269 $605 No cancel fee 71%
Delta
$305 $680 No cancel fee N/A
United Airlines
$331 $806 No cancel fee 69%

Hourly flight availability from Waikiki to Chicago

Evening 6 PM to midnight 100% of HNL to CHI departures
Early morning Midnight to 6 AM 0% of HNL to CHI departures
Morning 6 AM to noon 0% of HNL to CHI departures
Afternoon Noon to 6 PM 0% of HNL to CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Waikiki to Chicago
Sunday
2 daily flights
Monday
0 flights
Tuesday
2 daily flights
Wednesday
0 flights
Thursday
2 daily flights
Friday
2 daily flights
Saturday
2 daily flights
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