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$171+ Cheap flights from Hawaii to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
HNL — CHI
Mar 10 — Mar 171
Tue 3/10
Tue 3/17
1 adult, Economy
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Cheap flight deals from Hawaii to Chicago

Cheapest flights from Hawaii to Chicago
Explore the most affordable flight options available from Hawaii to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 8, 2026.

This United Airlines deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/46:05 pm
HNL
-
ORD
Nonstop8h 09m
United Airlines
Wed 3/1112:50 pm
ORD
-
HNL
1 stop12h 26m
United Airlines
Deal found 2/7$372
This Southwest deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/28:05 am
HNL
-
MDW
1 stop12h 20m
Southwest
Mon 3/99:30 pm
MDW
-
HNL
1 stop17h 30m
Southwest
Deal found 2/5$391
This Alaska Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3010:00 pm
HNL
-
ORD
1 stop16h 03m
Multiple Airlines
Wed 5/68:50 am
ORD
-
HNL
1 stop16h 36m
Multiple Airlines
Deal found 2/6$394
This Alaska Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/231:16 pm
KOA
-
ORD
1 stop24h 47m
Multiple Airlines
Tue 4/288:50 am
ORD
-
KOA
2 stops18h 26m
Multiple Airlines
Deal found 2/8$395
This Expedia deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/231:16 pm
KOA
-
ORD
1 stop24h 47m
Alaska Airlines
Tue 4/288:00 am
ORD
-
KOA
1 stop16h 52m
Alaska Airlines
Deal found 2/7$399
This Alaska Airlines deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3010:00 pm
HNL
-
ORD
1 stop16h 03m
Alaska Airlines
Wed 5/68:50 am
ORD
-
HNL
2 stops17h 13m
Alaska Airlines
Deal found 2/7$399
This Southwest deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:00 pm
HNL
-
MDW
1 stop11h 50m
Southwest
Sun 5/102:40 pm
MDW
-
HNL
1 stop11h 25m
Southwest
Deal found 2/6$413
This Delta deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/158:50 pm
KOA
-
ORD
1 stop14h 49m
Delta
Mon 4/207:15 am
ORD
-
KOA
1 stop16h 48m
Delta
Deal found 2/7$424
This Alaska Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:42 pm
OGG
-
ORD
1 stop19h 59m
Alaska Airlines
Wed 5/209:00 am
ORD
-
OGG
1 stop17h 30m
Alaska Airlines
Deal found 2/6$424
This Orbitz deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/281:16 pm
KOA
-
ORD
1 stop18h 57m
Alaska Airlines
Thu 4/308:00 am
ORD
-
KOA
1 stop16h 52m
Alaska Airlines
Deal found 2/5$426
This Delta deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/169:09 pm
OGG
-
ORD
1 stop11h 16m
Delta
Tue 3/317:10 am
ORD
-
OGG
1 stop13h 03m
Delta
Deal found 2/5$428
This Southwest deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/158:25 pm
KOA
-
ORD
1 stop12h 30m
Southwest
Mon 4/206:15 am
ORD
-
KOA
2 stops13h 15m
Southwest
Deal found 2/7$429

Find flight deals from Hawaii to Chicago

Keep the following information in mind while searching for Hawaii to Chicago flight deals. Data was last updated February 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$372
(United Airlines)

One-way from

$171
(Southwest)

Popular in

July

Cheapest in

February

Average price

$471

Good round-trip deal

$464 or less

Good one-way deal

$305 or less
Provider with most accurate pricing for Honolulu-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Honolulu-Chicago (CHI) flights.
Search Deals
From Hawaii to Chicago (CHI)
Search Deals
One-way flight from Hawaii to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($129 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a round-trip flight from Hawaii to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Hawaii to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hawaii to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 8, 2026.
Use the filters below to find and compare flights from Hawaii to Chicago that are best for you.

Fly from

Hawaii

Fly to

Chicago

Route

Depart

Return

Price

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Mon 3/2

8:05 am-12:25 am

1 stop12h 20m

Chicago Midway

Mon 3/9

9:30 pm-10:00 am

1 stop17h 30m

$391

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 4/23

1:16 pm-7:03 pm

1 stop24h 47m

Chicago O'Hare Intl

Tue 4/28

8:50 am-10:16 pm

2 stops18h 26m

$395

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Thu 4/23

1:16 pm-7:03 pm

1 stop24h 47m

Chicago O'Hare Intl

Tue 4/28

8:00 am-7:52 pm

1 stop16h 52m

$399

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 4/30

10:00 pm-7:03 pm

1 stop16h 03m

Chicago O'Hare Intl

Wed 5/6

8:50 am-9:03 pm

2 stops17h 13m

$399

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 4/30

7:23 am-11:43 pm

1 stop11h 20m

Chicago O'Hare Intl

Wed 5/6

3:52 pm-8:26 pm

1 stop33h 34m

$412

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 4/15

8:50 pm-4:39 pm

1 stop14h 49m

Chicago O'Hare Intl

Mon 4/20

7:15 am-7:03 pm

1 stop16h 48m

$424

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Wed 5/13

10:42 pm-11:41 pm

1 stop19h 59m

Chicago O'Hare Intl

Wed 5/20

9:00 am-9:30 pm

1 stop17h 30m

$424

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Tue 4/28

1:16 pm-1:13 pm

1 stop18h 57m

Chicago O'Hare Intl

Thu 4/30

8:00 am-7:52 pm

1 stop16h 52m

$426

KahuluiChicago

OGG - ORD

OGGORD

Kahului

Mon 3/16

9:09 pm-1:25 pm

1 stop11h 16m

Chicago O'Hare Intl

Tue 3/31

7:10 am-3:13 pm

1 stop13h 03m

$428

Kailua-KonaChicago

KOA - ORD

KOAORD

Kona Intl

Wed 4/15

8:25 pm-1:55 pm

1 stop12h 30m

Chicago O'Hare Intl

Mon 4/20

6:15 am-2:30 pm

2 stops13h 15m

$429

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/6

Showing 1-10 of 60 results
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Best time to book a flight from Hawaii to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Hawaii with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Hawaii to Chicago

What is the cheapest month to book a flight from Hawaii to Chicago?

Currently, November is the cheapest month in which you can book a flight from Hawaii to Chicago (average of $222). Flying from Hawaii to Chicago in July is currently the most expensive (average of $689). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from HI to CHI?

Find hourly flight availability from Hawaii to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 8, 2026.

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.

How much does it cost to fly round-trip from Hawaii to Chicago?

Related info for your journey

Find useful and relevant information for your journey from Hawaii to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Hawaii to Chicago?

    Southwest, Alaska Airlines, and Delta can get you from Hawaii to Chicago in just under 12h 20m. Your travel time can differ by up to 12h 27m. Airlines will cover a distance of 4243 mi. This flight may include one or multiple stops.

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

    The cheapest airlines for a one-way flight from Hawaii to Chicago are Southwest ($210), American Airlines ($211), and Delta ($211).

  • 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 Lihue - Chicago O'Hare Intl as they are the most popular.

  • What are the most reliable airlines from Hawaii to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Hawaii to Chicago on time: Avianca (90%), United Airlines (88%), Air New Zealand (88%).

  • What are the cheapest flights from Hawaii to Chicago?

    While on average a flight from Hawaii to Chicago is generally $1,125, our data shows the cheapest flight currently is $219. When looking at the most popular route, (Honolulu - Chicago O'Hare Intl), you can expect to pay $394 for that flight.

  • Can I find deals for flights from Hawaii to Chicago that include hotel bookings?

    Yes. In addition to deals on Hawaii to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Hawaii to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hawaii to Chicago.

  • Can I find deals for business class flights from Hawaii to Chicago?

    Yes. Cheapflights offers flight deals from Hawaii to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Hawaii to Chicago?

    Currently, November is the cheapest month in which you can book a flight from Hawaii to Chicago (average of $222). Flying from Hawaii to Chicago in July is currently the most expensive (average of $689). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Hawaii to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Salt Lake City to O'Hare Intl flights
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Reagan-National to Midway flights
Denver to Midway flights
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Seattle to Midway flights

Top 6 airlines flying from Hawaii to Chicago

Discover the top 6 airlines that operate flights from Hawaii to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$282Average$579FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$322Average$734FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$410Average$812FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$447Average$715FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$467Average$812FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$581Average$776FlexibilityNo cancel feeOn-time63%

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