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

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

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 January, February 2021

The best prices found for Hawaii 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
1 Feb - 31 Mar
$334pp
HNL
Honolulu
Multiple Airlines
 
1 STOP
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

Hawaii to Chicago 2021 flight deals

Cheap flights to Chicago from Hawaii 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 Hawaii

Save time with Hawaii to Chicago direct flight deals
12 May - 17 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 Hawaii to Chicago

Late deals on round-trip flights to Chicago from Hawaii, 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 Hawaii

The cheapest one-way flights from Hawaii to Chicago
5:10 pm - 4:23 pm
United Airlines
2 Stops
18h 13m
HNL - ORD
United Airlines
$166
United
11:40 am - 1:28 pm
Alaska Airlines
1 Stop
20h 48m
HNL - ORD
Alaska Airlines
2:20 pm - 3:46 pm
Multiple Airlines
2 Stops
20h 26m
KOA - ORD
Multiple Airlines
$177
Kiwi.com

Related info for your journey

Useful info, stats and facts about Hawaii to Chicago 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 and Delta are some airlines that have done so. 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 $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 $315, but on average you can expect to pay $346.

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

Cheapflights has at least 20 direct flights from Hawaii to Chicago under $800. A good price for a nonstop flight from Hawaii to Chicago is less than $808.

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

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

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 $1,139, our data indicates the cheapest price to be $274. The most popular route (Honolulu - Chicago O'Hare Intl), is priced around $315.

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 (94%), Air New Zealand (94%) or American Airlines (51%) 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 7h 50m. Fly via United Airlines, Delta, or Alaska 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 $354 on this airline. An additional option worth looking into is United Airlines, starting at $356.

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

The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as $166. Check flights for Alaska Airlines, as they currently have the next best price.

Arrival points for flights from Hawaii to Chicago

Destination information for Chicago

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

Airports servicing

Honolulu (HNL)
Hilo (ITO)
Kapalua (JHM)
Kapolei Kalaeloa (JRF)
Keahole-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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