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 2021: compare Hawaii to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
How far in advance should I book a flight from Hawaii to Chicago?

Travelers have found it’s best to book a flight 20 days in advance to save up to 10% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 20 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Hawaii to Chicago 1-2 weeks in advance for as low as $137, or $157 for flights within the next 24 hours.

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

Our data shows that April tends to be the cheapest month to fly to Chicago from Hawaii. Users have commonly found prices around $135 for the month, but tickets can be as low as $33. Due to multiple factors, prepare for potentially higher prices in December.

Cheap flights from Hawaii to Chicago in May, June 2021

The best prices found for Hawaii to CHI flights for May, June
11 May - 18 May
$556pp
HNL
Honolulu
Alaska Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
 
1 STOP
HNL
Honolulu
2 Jun - 5 Jun
$558pp
HNL
Honolulu
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
HNL
Honolulu
13 Jun - 24 Jun
$559pp
HNL
Honolulu
Multiple Airlines
     
3 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
HNL
Honolulu

Hawaii to Chicago 2021 flight deals

Cheap flights to Chicago from Hawaii found for this year
17 Aug - 22 Aug
$469pp
HNL
Honolulu
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
HNL
Honolulu
27 Sep - 5 Oct
$475pp
HNL
Honolulu
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
HNL
Honolulu
22 Sep - 5 Oct
$477pp
HNL
Honolulu
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
HNL
Honolulu

Non-stop flights to Chicago from Hawaii

Save time with Hawaii to Chicago direct flight deals
21 Sep - 30 Sep
$820pp
HNL
Honolulu
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
HNL
Honolulu
31 May - 9 Jun
$826pp
HNL
Honolulu
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
HNL
Honolulu
27 Aug - 7 Sep
$826pp
OGG
Kahului
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
OGG
Kahului

Last minute flights from Hawaii to Chicago

Late deals on round-trip flights to Chicago from Hawaii, departing today and this week
18 May - 25 May
$572pp
HNL
Honolulu
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
HNL
Honolulu
18 May - 25 May
$577pp
HNL
Honolulu
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
HNL
Honolulu
18 May - 25 May
$590pp
HNL
Honolulu
Alaska Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
 
1 STOP
HNL
Honolulu

One-way flights to Chicago from Hawaii

The cheapest one-way flights from Hawaii to Chicago
6:25 pm - 2:23 pm
Alaska Airlines
2 Stops
38h 58m
KOA - ORD
Alaska Airlines
10:55 am - 8:29 am
American Airlines
1 Stop
16h 34m
OGG - ORD
American Airlines
7:19 am - 7:55 pm
Multiple Airlines
2 Stops
31h 36m
HNL - ORD
Multiple Airlines
$264
Gotogate

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

Are flight prices decreasing from Hawaii 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 Hawaii 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 Hawaii to Chicago to control the spread of COVID-19?

Airlines globally have implemented additional safety measures to accommodate you. Alaska Airlines is one of them. Airline carriers are regularly disinfecting and sanitizing their aircraft. Masks are provided and are mandatory while on board. Pre-flight testing for symptoms and antibodies, alongside socially distanced seating (for a limited time) will work towards keeping travelers safer while flying from Hawaii to Chicago. Policies will vary by airline.

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 American Airlines, United Airlines, and Delta flying from Hawaii to Chicago have implemented new flexible cancellation policies.

Can I find flights from Hawaii to Chicago for under $500 on Cheapflights?

Yes, there are multiple flights from Hawaii to Chicago for under $500. The cheapest flight booked recently is on Alaska Airlines for just $450, but on average you can expect to pay $487.

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 $863.

Are there last-minute flights available from Hawaii to Chicago for under $600?

There are currently 20+ open flights from Hawaii to Chicago within the next 7 days for less than $600.

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

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

What are the most popular routes from Hawaii to Chicago?

The most popular flight routes from Hawaii to Chicago are Honolulu - Chicago O'Hare Intl, Honolulu - Chicago Midway and Kahului - Chicago O'Hare Intl.

What are the cheapest Flights from Hawaii to Chicago?

Looking for the cheapest flight from Hawaii to Chicago? While on average our users pay $1,159, our data indicates the cheapest price to be $272. The most popular route (Honolulu - Chicago O'Hare Intl), is priced around $493.

What are the most reliable airlines from Hawaii to Chicago?

No one likes to see their flight delayed. When booking a flight from Hawaii to Chicago consider choosing United Airlines (97%), Air New Zealand (97%) or American Airlines (93%) as they are the most reliable in getting you off to your destination on time.

How long is the flight from Hawaii to Chicago?

There are many flights that can get you from Hawaii to Chicago in 10h 46m. Fly via United Airlines, Delta, or American Airlines to get the fastest option. Both multi-stop and nonstop flights can be found to your destination and back.

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

Our cheapest airline available from Hawaii to Chicago is Alaska Airlines. Our recent data shows that you can find tickets from as low as $450 on this airline. An additional option worth looking into is United Airlines, starting at $516.

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

The cheapest airline one-way is Alaska Airlines, with whom users have recently found tickets for as low as $233. Check flights for American Airlines, as they currently have the next best price.

Departure points for flights from Hawaii to Chicago

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

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Hawaii to Chicago.
Average temperature for May in Chicago
71.6 °F
Avg rainfall for May in Chicago
4.3 ″

Airports servicing

Hana (HNM)
Honolulu (HNL)
Hilo (ITO)
Kapalua West Maui (JHM)
Kapolei Kalaeloa (JRF)
Kona Intl (KOA)

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 4 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
Alaska Airlines
$270 $566 No cancel fee 75%
Delta
$301 $612 No cancel fee N/A
American Airlines
$269 $617 No cancel fee 71%
United Airlines
$304 $754 No cancel fee 69%
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