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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 37 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 37 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 $177, or $177 for flights within the next 24 hours.

Cheap flights from Hawaii to Chicago in September, October 2020

The best prices found for Hawaii to CHI flights for September, October
28 Oct - 2 Nov
$363pp
HNL
Honolulu
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
HNL
Honolulu
27 Oct - 3 Nov
$364pp
OGG
Kahului
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
OGG
Kahului
26 Oct - 2 Nov
$373pp
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 2020 flight deals

Cheap flights to Chicago from Hawaii found for this year
28 Oct - 2 Nov
$363pp
HNL
Honolulu
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
HNL
Honolulu
27 Oct - 3 Nov
$364pp
OGG
Kahului
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
OGG
Kahului
26 Oct - 2 Nov
$373pp
OGG
Kahului
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
OGG
Kahului

Non-stop flights to Chicago from Hawaii

Save time with Hawaii to Chicago direct flight deals
14 Jan - 15 Jan
$720pp
HNL
Honolulu
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
HNL
Honolulu
23 Dec - 30 Dec
$745pp
HNL
Honolulu
Multiple 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
4 Oct - 18 Oct
$646pp
OGG
Kahului
Delta
   
2 STOPS
MDW
Chicago Midway
MDW
Chicago Midway
Delta
   
2 STOPS
OGG
Kahului
4 Oct - 18 Oct
$646pp
OGG
Kahului
Delta
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
OGG
Kahului
1 Oct - 5 Oct
$704pp
HNL
Honolulu
Delta
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
HNL
Honolulu

One-way flights to Chicago from Hawaii

The cheapest one-way flights from Hawaii to Chicago
8:40 am - 12:15 pm
Multiple Airlines
1 Stop
22h 35m
OGG - ORD
Multiple Airlines
$156
Kiwi.com
8:40 am - 12:15 pm
Multiple Airlines
1 Stop
22h 35m
OGG - ORD
Multiple Airlines
$157
Kiwi.com
11:20 am - 2:00 pm
Multiple Airlines
1 Stop
22h 40m
OGG - ORD
Multiple Airlines
$169
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.

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 $363, but on average you can expect to pay $411.

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

Cheapflights has at least 2 direct flights from Hawaii to Chicago under $800. A good price for a nonstop flight from Hawaii to Chicago is less than $732.

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

There are currently 11+ open flights from Hawaii to Chicago within the next 7 days for less than $700.

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 Kona Intl - 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 $467, our data indicates the cheapest price to be $265. The most popular route (Honolulu - Chicago O'Hare Intl), is priced around $354.

How long is the flight from Hawaii to Chicago?

There are many flights that can get you from Hawaii to Chicago in 11h 27m. Fly via Delta to get the fastest option.

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 September in Chicago
77.0 °F
Avg rainfall for September in Chicago
2.4 ″

Airports servicing

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

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)
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