Cheap flights from Waikiki to Chicago (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 to Chicago (CHI)

All the information you need to plan the best null to CHI flight in 2022: compare Waikiki to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
W1K - CHI
Price
$546 - $749
CHI
Temperature
23 - 73.4 °F
CHI
Precipitation
1.7 - 4.9 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 (CHI)

One-way from

$214

One-way flight from Waikiki to Chicago (CHI)

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
How far in advance should I book a flight from Waikiki to Chicago?

To save up to 12% on this flight, we recommend booking at least 61 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Waikiki to Chicago from $683 1-2 weeks out and tickets from $687 for flights departing within the next 72 hours.

When is the cheapest time to fly from Waikiki to Chicago (W1K - 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.

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

August is one of the best times of the year to fly to Chicago from Waikiki. Prices for August average $633 per person but you can even find prices for as low as $364. The most expensive prices can be found in the month of December. Opting for a August flight can save you 18% on your journey compared to booking in August

Cheap flights from Waikiki to Chicago in January, February 2022

The best prices found for Waikiki to CHI flights for January, February
19 Feb - 26 Feb
$302pp
HNL
Honolulu
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
HNL
Honolulu
19 Feb - 23 Feb
$326pp
HNL
Honolulu
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
HNL
Honolulu
2 Feb - 7 Feb
$333pp
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 2022 flight deals

Cheap flights to Chicago from Waikiki found for this year
19 Feb - 26 Feb
$302pp
HNL
Honolulu
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
HNL
Honolulu
19 Feb - 23 Feb
$326pp
HNL
Honolulu
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
HNL
Honolulu
2 Feb - 7 Feb
$333pp
HNL
Honolulu
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
HNL
Honolulu

Non-stop flights to Chicago from Waikiki

Save time with Waikiki to Chicago direct flight deals
12 May - 16 May
$821pp
HNL
Honolulu
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
HNL
Honolulu
15 Feb - 1 Mar
$827pp
HNL
Honolulu
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
HNL
Honolulu
9 Feb - 16 Feb
$831pp
HNL
Honolulu
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United 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
27 Jan - 30 Jan
$335pp
HNL
Honolulu
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
HNL
Honolulu
29 Jan - 2 Feb
$346pp
HNL
Honolulu
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
HNL
Honolulu
29 Jan - 2 Feb
$361pp
HNL
Honolulu
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
HNL
Honolulu

One-way flights to Chicago from Waikiki

The cheapest one-way flights from Waikiki to Chicago
3:15 am - 12:51 am
United Airlines
2 Stops
17h 36m
HNL - ORD
United Airlines
$214
United
3:05 am - 3:21 am
Delta
2 Stops
20h 16m
HNL - ORD
Delta
$216
Delta
11:30 am - 12:19 pm
Alaska Airlines
2 Stops
20h 49m
HNL - ORD
Alaska Airlines

Related info for your journey

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

Flight FAQs

From Waikiki to Chicago

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

Some of the carriers operating flights from Waikiki to Chicago 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 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 $302, but on average you can expect to pay $352.

Are there nonstop flights from Waikiki to Chicago for under $900 on Cheapflights?

Cheapflights has at least 20 direct flights from Waikiki to Chicago under $900. A good price for a nonstop flight from Waikiki to Chicago is less than $890.

Are there last-minute flights available from Waikiki to Chicago for under $400?

There are currently 20+ open flights from Waikiki to Chicago within the next 7 days for less than $400.

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

To fly one-way, consider booking your trip with Alaska Airlines, which is currently one of the cheapest options available, starting at $198. United Airlines flights start at $204 while deals on Delta start at $216 one-way.

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

Before booking your flight from Waikiki to Chicago check out the most popular airlines for this route: American Airlines, Alaska Airlines or Delta.

What are the most popular routes from Waikiki to Chicago?

When deciding which route to take from Waikiki to Chicago consider Honolulu - Chicago O'Hare Intl, Honolulu - Chicago Midway or Honolulu - Chicago Greater Rockford as they are the most popular.

What are the cheapest flights from Waikiki to Chicago?

Looking at all options, your cheapest flight can be booked for $196. While the most popular route (Honolulu - Chicago O'Hare Intl) can be booked for $326 on average our data indicates $1,092 when flying from Waikiki to Chicago.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

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

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

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

COVID-19 testing requirements
Visitors from Waikiki must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Chicago.

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

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

Returning to Waikiki from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Waikiki.

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

Hide COVID Travel Restrictions for Chicago, IL

Destination information for Chicago

Things to know before you go - useful duration and weather 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 Aiea

Airports servicing 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
American Airlines
$269 $605 No cancel fee 71%
Alaska Airlines
$270 $570 No cancel fee 75%
Delta
$305 $680 No cancel fee N/A
United Airlines
$331 $806 No cancel fee 69%

Hourly flight availability from Waikiki to Chicago

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