How long does it take to fly to Chicago?

Average flight duration from Hawaii to Chicago depends on which airport you fly into and out of. Flying from Kahului to Chicago O'Hare Intl Airport is 7h 50m on average, while flying from Honolulu to Chicago O'Hare Intl Airport is 8h 04m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

How many flights depart from Hawaii to Chicago on average per week?

The number of flights available between Hawaii and Chicago is 2 per week as of August 2026. The most frequent departure day is Mon, with 100% of weekly flights leaving on this day.

What is the cheapest airline that flies from Hawaii to Chicago?

Southwest, Delta, and American Airlines are the most popular carriers operating from Hawaii to Chicago

What airlines fly to Chicago?

United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Chicago from Hawaii according to our data. United Airlines is the first choice among our users, with 50% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Hawaii to Chicago?

Prices for flights from Hawaii to Chicago are updated daily.

How many operators does momondo search for flights from Hawaii to Chicago?

The number of operators available for flights from Hawaii to Chicago is 5 as of August 2026.

How old do you have to be to fly from Hawaii to Chicago?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Hawaii to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$217 Cheap Flights from Hawaii to Chicago in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Hawaii to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:10 pm - 4:05 pmLIH Lihue-ORD Chicago O'Hare Intl

13h 55m1 stop Phoenix Sky Harbor Intl

6:59 am - 3:02 pmORD Chicago O'Hare Intl-LIH Lihue

13h 03m1 stop Phoenix Sky Harbor Intl

$424American Airlines

Thu, Sep 24 - Wed, Sep 30

9:10 pm - 2:20 pmLIH Lihue-ORD Chicago O'Hare Intl

12h 10m1 stop Phoenix Sky Harbor Intl

6:59 am - 3:02 pmORD Chicago O'Hare Intl-LIH Lihue

13h 03m1 stop Phoenix Sky Harbor Intl

$424American Airlines

Tue, Sep 22 - Wed, Sep 30

9:51 pm - 1:29 pmLIH Lihue-ORD Chicago O'Hare Intl

10h 38m1 stop Seattle/Tacoma Intl

6:20 am - 5:36 pmORD Chicago O'Hare Intl-LIH Lihue

16h 16m2 stops Minneapolis St Paul Los Angeles Los Angeles

$430Delta

Tue, Oct 13 - Tue, Oct 20

8:45 pm - 6:04 pmLIH Lihue-ORD Chicago O'Hare Intl

16h 19m2 stops Los Angeles Los Angeles Salt Lake City

12:50 pm - 7:10 pmORD Chicago O'Hare Intl-LIH Lihue

11h 20m1 stop Seattle/Tacoma Intl

$430Delta

Tue, Sep 22 - Wed, Sep 30

7:35 pm - 11:28 amLIH Lihue-ORD Chicago O'Hare Intl

10h 53m1 stop Denver Intl

7:00 am - 3:40 pmORD Chicago O'Hare Intl-LIH Lihue

13h 40m1 stop Denver Intl

$444United Airlines

Tue, Oct 13 - Tue, Oct 20

1:03 pm - 5:42 amLIH Lihue-ORD Chicago O'Hare Intl

11h 39m1 stop Los Angeles Los Angeles

5:00 am - 11:59 amORD Chicago O'Hare Intl-LIH Lihue

11h 59m1 stop San Francisco

$444United Airlines

Fri, Sep 11 - Fri, Sep 18

10:35 am - 1:22 pmKOA Kona Intl-ORD Chicago O'Hare Intl

21h 47m1 stop San Diego

2:18 pm - 2:48 pmORD Chicago O'Hare Intl-KOA Kona Intl

29h 30m1 stop San Diego

$497Alaska Airlines

Sat, Sep 19 - Sat, Sep 26

6:00 am - 11:49 pmKOA Kona Intl-ORD Chicago O'Hare Intl

13h 49m2 stops Honolulu San Diego

9:31 am - 7:32 pmORD Chicago O'Hare Intl-KOA Kona Intl

14h 01m2 stops Seattle/Tacoma Intl Honolulu

$529Multiple Airlines

Fri, Nov 6 - Tue, Nov 10

9:41 pm - 1:26 pmHNL Honolulu-ORD Chicago O'Hare Intl

10h 45m1 stop Portland

6:05 am - 3:55 pmORD Chicago O'Hare Intl-HNL Honolulu

14h 50m1 stop San Diego

$530Multiple Airlines

Thu, Aug 27 - Mon, Aug 31

10:40 pm - 7:21 pmOGG Kahului-ORD Chicago O'Hare Intl

15h 41m1 stop San Diego

8:17 pm - 9:37 pmORD Chicago O'Hare Intl-OGG Kahului

30h 20m1 stop San Diego

$544Alaska Airlines

Thu, Sep 10 - Mon, Sep 14

Cheap last minute flights

Enter your travel dates to find the best prices.

7:30 am - 11:36 pmHNL Honolulu-ORD Chicago O'Hare Intl

11h 06m1 stop San Diego

5:42 pm - 12:12 amORD Chicago O'Hare Intl-HNL Honolulu

11h 30m1 stop Seattle/Tacoma Intl

$660Multiple Airlines

Wed, Aug 12 - Tue, Aug 18

7:30 am - 11:36 pmHNL Honolulu-ORD Chicago O'Hare Intl

11h 06m1 stop San Diego

6:20 am - 7:03 pmORD Chicago O'Hare Intl-HNL Honolulu

17h 43m1 stop San Diego

$660Multiple Airlines

Wed, Aug 12 - Tue, Aug 18

9:55 pm - 6:57 pmHNL Honolulu-ORD Chicago O'Hare Intl

16h 02m1 stop San Diego

6:20 am - 7:03 pmORD Chicago O'Hare Intl-HNL Honolulu

17h 43m1 stop San Diego

$715Alaska Airlines

Wed, Aug 12 - Tue, Aug 18

11:55 am - 5:45 amHNL Honolulu-MDW Chicago Midway

12h 50m1 stop Ontario

2:50 pm - 9:15 pmMDW Chicago Midway-HNL Honolulu

11h 25m1 stop Los Angeles Los Angeles

$780Southwest

Thu, Aug 13 - Sat, Aug 15

8:10 am - 4:30 amHNL Honolulu-MDW Chicago Midway

15h 20m1 stop San Diego

6:15 am - 12:35 pmMDW Chicago Midway-HNL Honolulu

11h 20m1 stop San Diego

$780Southwest

Wed, Aug 12 - Fri, Aug 14

9:30 pm - 4:59 pmHNL Honolulu-ORD Chicago O'Hare Intl

14h 29m2 stops Los Angeles Los Angeles Minneapolis St Paul

8:28 am - 9:20 pmORD Chicago O'Hare Intl-HNL Honolulu

17h 52m2 stops Minneapolis St Paul Los Angeles Los Angeles

$811Delta

Thu, Aug 13 - Sat, Aug 22

9:30 pm - 1:41 pmHNL Honolulu-ORD Chicago O'Hare Intl

11h 11m1 stop Los Angeles Los Angeles

7:29 am - 4:43 pmORD Chicago O'Hare Intl-HNL Honolulu

14h 14m1 stop Los Angeles Los Angeles

$818Delta

Sat, Aug 15 - Mon, Aug 24

9:45 pm - 4:05 pmKOA Kona Intl-ORD Chicago O'Hare Intl

13h 20m1 stop Phoenix Sky Harbor Intl

5:00 am - 1:58 pmORD Chicago O'Hare Intl-KOA Kona Intl

13h 58m1 stop Phoenix Sky Harbor Intl

$826American Airlines

Fri, Aug 14 - Sun, Aug 16

7:00 am - 10:30 pmHNL Honolulu-ORD Chicago O'Hare Intl

10h 30m1 stop San Francisco

9:30 am - 1:28 pmORD Chicago O'Hare Intl-HNL Honolulu

8h 58mnonstop

$1,090United Airlines

Sat, Aug 15 - Sun, Sep 6

7:00 am - 10:59 pmHNL Honolulu-ORD Chicago O'Hare Intl

10h 59m1 stop San Francisco

9:30 am - 1:28 pmORD Chicago O'Hare Intl-HNL Honolulu

8h 58mnonstop

$1,226United Airlines

Sat, Aug 15 - Mon, Aug 24

Cheap direct flights

Enter your travel dates to find the best prices.

7:00 pm - 7:20 amHNL Honolulu-ORD Chicago O'Hare Intl

8h 20mnonstop

10:00 am - 3:25 pmORD Chicago O'Hare Intl-HNL Honolulu

9h 25mnonstop

$691American Airlines

Wed, Dec 2 - Mon, Dec 7

7:00 pm - 7:22 amHNL Honolulu-ORD Chicago O'Hare Intl

8h 22mnonstop

10:00 am - 3:26 pmORD Chicago O'Hare Intl-HNL Honolulu

9h 26mnonstop

$711American Airlines

Thu, Nov 19 - Mon, Nov 23

7:40 pm - 7:48 amHNL Honolulu-ORD Chicago O'Hare Intl

8h 08mnonstop

9:30 am - 2:41 pmORD Chicago O'Hare Intl-HNL Honolulu

9h 11mnonstop

$731United Airlines

Tue, Dec 1 - Mon, Dec 7

4:50 pm - 5:01 amHNL Honolulu-ORD Chicago O'Hare Intl

8h 11mnonstop

9:30 am - 2:58 pmORD Chicago O'Hare Intl-HNL Honolulu

9h 28mnonstop

$740United Airlines

Mon, Dec 21 - Mon, Jan 4

7:00 pm - 7:22 amHNL Honolulu-ORD Chicago O'Hare Intl

8h 22mnonstop

10:00 am - 3:26 pmORD Chicago O'Hare Intl-HNL Honolulu

9h 26mnonstop

$746American Airlines

Thu, Nov 19 - Mon, Nov 23

7:00 pm - 7:10 amHNL Honolulu-ORD Chicago O'Hare Intl

8h 10mnonstop

10:00 am - 3:15 pmORD Chicago O'Hare Intl-HNL Honolulu

9h 15mnonstop

$759American Airlines

Wed, Feb 3 - Sun, Feb 7

7:00 pm - 7:10 amHNL Honolulu-ORD Chicago O'Hare Intl

8h 10mnonstop

10:00 am - 3:15 pmORD Chicago O'Hare Intl-HNL Honolulu

9h 15mnonstop

$759American Airlines

Mon, Feb 1 - Sun, Feb 7

7:00 pm - 7:25 amHNL Honolulu-ORD Chicago O'Hare Intl

8h 25mnonstop

10:00 am - 3:18 pmORD Chicago O'Hare Intl-HNL Honolulu

9h 18mnonstop

$759American Airlines

Thu, Nov 5 - Sat, Nov 14

4:50 pm - 5:01 amHNL Honolulu-ORD Chicago O'Hare Intl

8h 11mnonstop

9:30 am - 2:58 pmORD Chicago O'Hare Intl-HNL Honolulu

9h 28mnonstop

$811United Airlines

Mon, Dec 28 - Tue, Jan 5

4:00 pm - 5:04 amHNL Honolulu-ORD Chicago O'Hare Intl

8h 04mnonstop

9:45 am - 1:57 pmORD Chicago O'Hare Intl-HNL Honolulu

9h 12mnonstop

$848United Airlines

Thu, Oct 22 - Mon, Oct 26

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

American Airlines flights from Hawaii to Chicago

Our best American Airlines deals on Hawaii to Chicago flight tickets

American Airlines

Sep 22

LIH9:10 pmLihue

12h 10m

1 stop

ORD2:20 pmChicago O'Hare Intl

Sep 30

ORD6:59 amChicago O'Hare Intl

13h 03m

1 stop

LIH3:02 pmLihue

$424

American Airlines

Sep 9

KOA9:45 pmKona Intl

13h 20m

1 stop

ORD4:05 pmChicago O'Hare Intl

Sep 13

ORD6:55 amChicago O'Hare Intl

14h 05m

1 stop

KOA4:00 pmKona Intl

$438

American Airlines

Sep 9

KOA9:45 pmKona Intl

13h 20m

1 stop

ORD4:05 pmChicago O'Hare Intl

Sep 13

ORD6:00 amChicago O'Hare Intl

15h 00m

2 stops

KOA4:00 pmKona Intl

$444

Delta flights from Hawaii to Chicago

Our best Delta deals on Hawaii to Chicago flight tickets

Delta

Sep 22

LIH8:45 pmLihue

16h 19m

2 stops

ORD6:04 pmChicago O'Hare Intl

Sep 30

ORD12:50 pmChicago O'Hare Intl

11h 20m

1 stop

LIH7:10 pmLihue

$430

Delta

Sep 21

LIH9:54 pmLihue

15h 07m

1 stop

ORD6:01 pmChicago O'Hare Intl

Sep 29

ORD12:50 pmChicago O'Hare Intl

11h 20m

1 stop

LIH7:10 pmLihue

$434

Delta

Oct 13

LIH9:51 pmLihue

15h 19m

2 stops

ORD6:10 pmChicago O'Hare Intl

Oct 20

ORD7:35 amChicago O'Hare Intl

15h 01m

2 stops

LIH5:36 pmLihue

$435

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

LihueChicago

LIH Lihue - ORD Chicago O'Hare Intl

LIHORD

Lihue

Thu 9/24

9:10 pm-4:05 pm

1 stop13h 55m

Chicago O'Hare Intl

Wed 9/30

6:59 am-3:02 pm

1 stop13h 03m

$424

LihueChicago

LIH Lihue - ORD Chicago O'Hare Intl

LIHORD

Lihue

Tue 9/22

9:10 pm-2:20 pm

1 stop12h 10m

Chicago O'Hare Intl

Wed 9/30

6:59 am-3:02 pm

1 stop13h 03m

$424

LihueChicago

LIH Lihue - ORD Chicago O'Hare Intl

LIHORD

Lihue

Tue 10/13

9:51 pm-1:29 pm

1 stop10h 38m

Chicago O'Hare Intl

Tue 10/20

6:20 am-5:36 pm

2 stops16h 16m

$430

LihueChicago

LIH Lihue - ORD Chicago O'Hare Intl

LIHORD

Lihue

Tue 9/22

8:45 pm-6:04 pm

2 stops16h 19m

Chicago O'Hare Intl

Wed 9/30

12:50 pm-7:10 pm

1 stop11h 20m

$430

LihueChicago

LIH Lihue - ORD Chicago O'Hare Intl

LIHORD

Lihue

Tue 10/13

7:35 pm-11:28 am

1 stop10h 53m

Chicago O'Hare Intl

Tue 10/20

7:00 am-3:40 pm

1 stop13h 40m

$444

Quickest round-trip

LihueChicago

LIH Lihue - ORD Chicago O'Hare Intl

LIHORD

Lihue

Fri 9/11

1:03 pm-5:42 am

1 stop11h 39m

Chicago O'Hare Intl

Fri 9/18

5:00 am-11:59 am

1 stop11h 59m

$444

Kailua-KonaChicago

KOA Kona Intl - ORD Chicago O'Hare Intl

KOAORD

Kona Intl

Sat 9/19

10:35 am-1:22 pm

1 stop21h 47m

Chicago O'Hare Intl

Sat 9/26

2:18 pm-2:48 pm

1 stop29h 30m

$497

Kailua-KonaChicago

KOA Kona Intl - ORD Chicago O'Hare Intl

KOAORD

Kona Intl

Fri 11/6

6:00 am-11:49 pm

2 stops13h 49m

Chicago O'Hare Intl

Tue 11/10

9:31 am-7:32 pm

2 stops14h 01m

$529

HonoluluChicago

HNL Honolulu - ORD Chicago O'Hare Intl

HNLORD

Honolulu

Thu 8/27

9:41 pm-1:26 pm

1 stop10h 45m

Chicago O'Hare Intl

Mon 8/31

6:05 am-3:55 pm

1 stop14h 50m

$530

KahuluiChicago

OGG Kahului - ORD Chicago O'Hare Intl

OGGORD

Kahului

Thu 9/10

10:40 pm-7:21 pm

1 stop15h 41m

Chicago O'Hare Intl

Mon 9/14

8:17 pm-9:37 pm

1 stop30h 20m

$544

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Hawaii to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Hawaii, with most prices found around $527. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from Hawaii to Chicago during February average around $561.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $757. This is often the case because there is less demand to fly during this day of the week. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Hawaii to Chicago for around $1,065.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Hawaii to Chicago during this time can be as low as $817. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $825.

What is the cheapest Hawaii to Chicago flight route?

Fly from Kahului to Chicago O'Hare Intl for the best Hawaii - Chicago flight prices

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

You are more likely to see cheaper flights to Chicago from Hawaii when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $828 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Hawaii for as low as $590 on momondo.

What cabin class options are available on Hawaii to Chicago flights?

There are 4 cabin classes available to choose from on Hawaii to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Hawaii to Chicago flights?

You could potentially save up to 58% on your flight if you consider stops on a Hawaii to Chicago flight.

Cheap Hawaii to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Hawaii to Chicago

Best Price Found	$385
Fastest flight time	7h 50m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Hawaii in the past 72 hours is $385. The best round-trip flight deal from Hawaii to Chicago found on momondo in the last 72 hours is $750.

The fastest flight from Hawaii to Chicago takes 7h 50m

Direct flights go from Hawaii to Chicago every day.

There are 3 airports in Chicago. From Hawaii there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

Frequently asked questions about flying from Hawaii to Chicago

When did momondo last update prices for flights from Hawaii to Chicago?
Prices for flights from Hawaii to Chicago are updated daily.
How many operators does momondo search for flights from Hawaii to Chicago?
The number of operators available for flights from Hawaii to Chicago is 5 as of August 2026.
How old do you have to be to fly from Hawaii to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Hawaii to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Hawaii to Chicago?
Based on momondo bookings for flights between Hawaii and Chicago, the leading plane model is Boeing 787-10 Dreamliner, making up 50.52% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 24.74%, Airbus A330-200 with 4.12%, and Airbus A330 with 3.09%.

Best airlines flying from Hawaii to Chicago

Compare and see reviews for airlines that fly from Hawaii to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $230	Free Cancellation	Rating 7.8 8,505 reviews	Search Delta flights
American Airlines	PriceFrom $422	Free Cancellation	Rating 7.1 11,903 reviews	Search American Airlines flights
United Airlines	PriceFrom $447	Free Cancellation	Rating 7.4 10,104 reviews	Search United Airlines flights
Alaska Airlines	PriceFrom $473	Free Cancellation	Rating 7.9 12,796 reviews	Search Alaska Airlines flights
Southwest	PriceFrom $580	Free Cancellation	Rating 8.0 4,221 reviews	Search Southwest flights

Merrillville

New Buffalo

Hammond

Portage

Benton Harbor

Lansing

Saint Joseph

Valparaiso

Schererville

Munster

Chesterton

Monticello

Crown Point

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Hawaii to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Hawaii to Chicago for you.

Can I find flights from Hawaii to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Hawaii with this policy.

How can momondo help me find flights from Hawaii to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Hawaii.

I’m not ready to book a flight from Hawaii to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Hawaii. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Thu 9/10

Thu 9/17

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Nearby airports

Airlines

Cabin classes

Other United States destinations

Other flights from Hawaii

Complete your trip

Feeling lucky

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Cheap flights from Hawaii to Chicago from $217

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Hawaii to Chicago departing on 2/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find the cheapest flights from Hawaii to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

American Airlines flights from Hawaii to Chicago

Our best American Airlines deals on Hawaii to Chicago flight tickets

Delta flights from Hawaii to Chicago

Our best Delta deals on Hawaii to Chicago flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Hawaii to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Hawaii to Chicago

What is the cheapest month to fly to Chicago?

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

What is the cheapest Hawaii to Chicago flight route?

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

What cabin class options are available on Hawaii to Chicago flights?

Can stopping save me money on Hawaii to Chicago flights?

What is the cheapest airline that flies from Hawaii to Chicago?

What airlines fly to Chicago?

How many flights depart from Hawaii to Chicago on average per week?

How long does it take to fly to Chicago?

Cheap Hawaii to Chicago flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying from Hawaii to Chicago

Best airlines flying from Hawaii to Chicago

Compare and see reviews for airlines that fly from Hawaii to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

Popular cities in the United States

Popular flights according to clicks in the last 7 days on momondo

Fly to other destinations from Hawaii

According to popular flight searches on momondo this year

Complete your trip to Chicago

Explore popular destinations other users love

According to popular flight searches on momondo this year