Cheap flights from Hawaii (HI) to Chicago (CHI)

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

All the information you need to plan the best null to CHI flight in 2022: compare Hawaii to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
What is the cheapest month to fly from Hawaii to Chicago?

Due to multiple factors, expect to potentially pay more when booking in June. For low rates, January can be a great choice for travel to Chicago. Flights to Chicago from Hawaii in January are about $734 on average during January, but can be found for as low as $390.

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

To save up to 8% on this flight, we recommend booking at least 41 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Hawaii to Chicago from $802 1-2 weeks out and tickets from $802 for flights departing within the next 72 hours.

When is the cheapest time to fly from Hawaii to Chicago (HI - CHI)?

When flying from Hawaii 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.

Cheap flights from Hawaii to Chicago in August, September 2022

The best prices found for Hawaii to CHI flights for August, September
22 Sep - 27 Sep
$389pp
OGG
Kahului
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
OGG
Kahului
22 Sep - 27 Sep
$413pp
OGG
Kahului
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
OGG
Kahului
22 Sep - 27 Sep
$447pp
OGG
Kahului
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
OGG
Kahului

Hawaii to Chicago 2022 flight deals

Cheap flights to Chicago from Hawaii found for this year
22 Sep - 27 Sep
$389pp
OGG
Kahului
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
OGG
Kahului
10 Nov - 14 Nov
$399pp
OGG
Kahului
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
OGG
Kahului
10 Nov - 14 Nov
$411pp
OGG
Kahului
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
OGG
Kahului

Cheap American Airlines flights from Hawaii to Chicago

12 Oct - 14 Oct
$510pp
HNL
Honolulu
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
HNL
Honolulu
6 Sep - 13 Sep
$527pp
LIH
Lihue
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
LIH
Lihue
9 Nov - 15 Nov
$532pp
HNL
Honolulu
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
   
2 STOPS
HNL
Honolulu

Cheap Alaska Airlines flights from Hawaii to Chicago

10 Nov - 14 Nov
$536pp
OGG
Kahului
Alaska Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
   
2 STOPS
OGG
Kahului
22 Sep - 27 Sep
$599pp
OGG
Kahului
Alaska Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
   
2 STOPS
OGG
Kahului
22 Sep - 27 Sep
$619pp
OGG
Kahului
Alaska Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
   
2 STOPS
OGG
Kahului

Non-stop flights to Chicago from Hawaii

Save time with Hawaii to Chicago direct flight deals
6 Oct - 13 Oct
$831pp
OGG
Kahului
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
OGG
Kahului
13 Oct - 31 Oct
$851pp
HNL
Honolulu
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
HNL
Honolulu
15 Sep - 19 Sep
$853pp
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 Hawaii to Chicago

Late deals on round-trip flights to Chicago from Hawaii, departing today and this week
11 Aug - 25 Aug
$602pp
HNL
Honolulu
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
HNL
Honolulu
9 Aug - 17 Aug
$620pp
OGG
Kahului
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
   
2 STOPS
OGG
Kahului
10 Aug - 18 Aug
$627pp
OGG
Kahului
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
OGG
Kahului

One-way flights to Chicago from Hawaii

The cheapest one-way flights from Hawaii to Chicago
11:24 am - 3:06 pm
Multiple Airlines
1 Stop
22h 42m
OGG - ORD
Multiple Airlines
$195
Kiwi.com
10:55 am - 11:28 am
Multiple Airlines
1 Stop
19h 33m
OGG - ORD
Multiple Airlines
$209
Kiwi.com
10:55 am - 12:13 pm
Multiple Airlines
1 Stop
20h 18m
OGG - ORD
Multiple Airlines
$210
Kiwi.com

Related info for your journey

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

Flight FAQs

From Hawaii to Chicago

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

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

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

Yes, there are multiple flights from Hawaii to Chicago for under $400. The cheapest flight booked recently is on Multiple Airlines for just $389, but on average you can expect to pay $470.

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

Cheapflights has at least 20 direct flights from Hawaii to Chicago under $900. A good price for a nonstop flight from Hawaii to Chicago is less than $896.

Are there last-minute flights available from Hawaii to Chicago for under $700?

There are currently 20+ open flights from Hawaii to Chicago within the next 7 days for less than $700.

What are the cheapest flights from Hawaii to Chicago?

While on average a flight from Hawaii to Chicago is generally $1,450, our data shows the cheapest flight currently is $250. When looking at the most popular route, (Honolulu - Chicago O'Hare Intl), you can expect to pay $460 for that flight.

What are the most popular routes from Hawaii to Chicago?

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

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

American Airlines, Alaska Airlines and Delta are the most popular airlines when flying from Hawaii to Chicago.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

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

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

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

COVID-19 testing requirements
Visitors from Hawaii are not required to present a negative COVID-19 PCR test or antigen result upon entering Chicago.

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

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

Returning to Hawaii from Chicago

COVID-19 testing requirements
Visitors from Chicago are not required to present a negative COVID-19 PCR test or antigen result upon entering Hawaii.

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

Hide COVID Travel Restrictions for Chicago, IL

Departure points for flights from Hawaii to Chicago

Select to see more specific information for flights to Chicago from all departure points in Hawaii.

Top 5 airlines flying from Hawaii to Chicago

The chart below displays the airlines Cheapflights users traveling from Hawaii 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
Juneyao Airlines
$12 $20 No cancel fee 66%

We couldn't confirm the COVID-19 safety measures taken by Juneyao Airlines. Please check directly on their website for additional information.

Alaska Airlines
$272 $626 No cancel fee 75%
American Airlines
$346 $661 No cancel fee 71%
United Airlines
$366 $837 No cancel fee 69%
Delta
$366 $1,038 No cancel fee N/A