What is the cheapest airline that flies from O'ahu to Chicago?

Delta, Alaska Airlines, and United Airlines are the most popular carriers operating from O'ahu to Chicago

How many flights depart from O'ahu to Chicago on average per week?

46 flights are operational weekly from O'ahu to Chicago as of December 2025. The most popular departure day for this route is Tue, with 15% of flights per week taking off on this day.

What airlines fly to Chicago?

United Airlines, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Chicago from O'ahu according to our data. United Airlines is the first choice among our users, with 38% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How many flights depart from O'ahu to Chicago on average per day?

As of December 2025, 6 flights take off from O'ahu and land in Chicago each day. The most common flight departure time for this route is 7:00PM, with 100% of daily flights taking off in the evening.

When did momondo last update prices for flights from O'ahu to Chicago?

Prices for flights from O'ahu to Chicago refresh daily.

How many operators does momondo search for flights from O'ahu to Chicago?

The number of operators available for flights from O'ahu to Chicago is 6 as of December 2025.

How old do you have to be to fly from O'ahu to Chicago?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from O'ahu to Chicago.

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

The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$263 Cheap Flights from O'ahu to Chicago in 2025/26

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Find the cheapest flights from O'ahu to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:17 am - 11:37 pm

HNL

ORD

11h 20m1 stop

9:00 am - 6:53 pm

ORD

HNL

13h 53m1 stop

$366Multiple Airlines

Tue, Feb 3 - Tue, Feb 10

11:16 pm - 2:29 pm

HNL

ORD

11h 13m1 stop

9:00 am - 6:53 pm

ORD

HNL

13h 53m1 stop

$370Alaska Airlines

Wed, Jan 28 - Wed, Feb 4

11:16 pm - 2:29 pm

HNL

ORD

11h 13m1 stop

8:00 am - 10:08 pm

ORD

HNL

18h 08m1 stop

$371Hawaiian Airlines

Thu, Jan 22 - Thu, Jan 29

5:00 pm - 9:43 am

HNL

ORD

12h 43m1 stop

7:00 am - 4:43 pm

ORD

HNL

13h 43m1 stop

$375United Airlines

Thu, Jan 15 - Thu, Jan 22

11:16 pm - 2:29 pm

HNL

ORD

11h 13m1 stop

3:44 pm - 12:48 pm

ORD

HNL

25h 04m1 stop

$381Multiple Airlines

Thu, Jan 22 - Tue, Jan 27

11:16 pm - 2:29 pm

HNL

ORD

11h 13m1 stop

6:06 pm - 11:11 am

ORD

HNL

21h 05m1 stop

$389Multiple Airlines

Wed, Jan 21 - Sun, Jan 25

8:11 am - 11:59 pm

HNL

ORD

11h 48m1 stop

8:20 am - 12:49 pm

ORD

HNL

32h 29m1 stop

$392Hawaiian Airlines

Fri, Feb 13 - Sun, Feb 22

10:50 pm - 1:15 pm

HNL

ORD

10h 25m1 stop

5:40 am - 2:32 pm

ORD

HNL

12h 52m1 stop

$406United Airlines

Sun, Jan 18 - Wed, Jan 21

5:15 pm - 9:08 am

HNL

MDW

11h 53m1 stop

6:00 am - 3:10 pm

MDW

HNL

13h 10m1 stop

$427Delta

Thu, Jan 22 - Thu, Jan 29

4:50 pm - 9:53 am

HNL

MDW

13h 03m1 stop

9:32 am - 9:28 pm

MDW

HNL

15h 56m2 stops

$429Delta

Wed, Jan 28 - Wed, Feb 4

Alaska Airlines flights from O'ahu to Chicago

Our best Alaska Airlines deals on O'ahu to Chicago flight tickets

Alaska Airlines

Jan 28

HNL11:16 pmHonolulu

11h 13m

1 stop

ORD2:29 pmChicago O'Hare Intl

Feb 4

ORD9:00 amChicago O'Hare Intl

13h 53m

1 stop

HNL6:53 pmHonolulu

$370

Find similar

Alaska Airlines

Feb 20

HNL11:35 pmHonolulu

11h 23m

1 stop

ORD2:58 pmChicago O'Hare Intl

Mar 3

ORD8:20 amChicago O'Hare Intl

15h 29m

1 stop

HNL7:49 pmHonolulu

$478

Find similar

Hawaiian Airlines flights from O'ahu to Chicago

Our best Hawaiian Airlines deals on O'ahu to Chicago flight tickets

Hawaiian Airlines

Jan 22

HNL11:16 pmHonolulu

11h 13m

1 stop

ORD2:29 pmChicago O'Hare Intl

Jan 29

ORD8:00 amChicago O'Hare Intl

18h 08m

1 stop

HNL10:08 pmHonolulu

$371

Find similar

Hawaiian Airlines

Feb 13

HNL8:11 amHonolulu

11h 48m

1 stop

ORD11:59 pmChicago O'Hare Intl

Feb 22

ORD8:20 amChicago O'Hare Intl

32h 29m

1 stop

HNL12:49 pmHonolulu

$392

Find similar

Hawaiian Airlines

Feb 16

HNL11:35 pmHonolulu

11h 23m

1 stop

ORD2:58 pmChicago O'Hare Intl

Feb 20

ORD2:07 pmChicago O'Hare Intl

11h 33m

1 stop

HNL9:40 pmHonolulu

$543

Find similar

Fly from

Fly to

Route

Depart

Return

Price

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Tue 2/3

8:17 am-11:37 pm

1 stop11h 20m

Chicago O'Hare Intl

Tue 2/10

9:00 am-6:53 pm

1 stop13h 53m

$366

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 1/28

11:16 pm-2:29 pm

1 stop11h 13m

Chicago O'Hare Intl

Wed 2/4

9:00 am-6:53 pm

1 stop13h 53m

$370

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 1/22

11:16 pm-2:29 pm

1 stop11h 13m

Chicago O'Hare Intl

Thu 1/29

8:00 am-10:08 pm

1 stop18h 08m

$371

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 1/15

5:00 pm-9:43 am

1 stop12h 43m

Chicago O'Hare Intl

Thu 1/22

7:00 am-4:43 pm

1 stop13h 43m

$375

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Thu 1/22

11:16 pm-2:29 pm

1 stop11h 13m

Chicago O'Hare Intl

Tue 1/27

3:44 pm-12:48 pm

1 stop25h 04m

$381

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Wed 1/21

11:16 pm-2:29 pm

1 stop11h 13m

Chicago O'Hare Intl

Sun 1/25

6:06 pm-11:11 am

1 stop21h 05m

$389

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Fri 2/13

8:11 am-11:59 pm

1 stop11h 48m

Chicago O'Hare Intl

Sun 2/22

8:20 am-12:49 pm

1 stop32h 29m

$392

HonoluluChicago

HNL - ORD

HNLORD

Honolulu

Sun 1/18

10:50 pm-1:15 pm

1 stop10h 25m

Chicago O'Hare Intl

Wed 1/21

5:40 am-2:32 pm

1 stop12h 52m

$406

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Thu 1/22

5:15 pm-9:08 am

1 stop11h 53m

Chicago Midway

Thu 1/29

6:00 am-3:10 pm

1 stop13h 10m

$427

HonoluluChicago

HNL - MDW

HNLMDW

Honolulu

Wed 1/28

4:50 pm-9:53 am

1 stop13h 03m

Chicago Midway

Wed 2/4

9:32 am-9:28 pm

2 stops15h 56m

$429

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 O'ahu 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 September is, on average, the cheapest month to fly to Chicago from O'ahu, with most prices found around $558. If you’re not able to fly to Chicago in September, then May is your next best option. Flight prices from O'ahu to Chicago during May average around $598.

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 Monday when prices can be found for as low as $809. 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 O'ahu to Chicago for around $1,129.

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 at noon. Flights from O'ahu to Chicago during this time can be as low as $618. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $881.

What is the cheapest O'ahu to Chicago flight route?

Fly from Honolulu to Chicago O'Hare Intl for the best O'ahu - Chicago flight prices

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

You are more likely to see cheaper flights to Chicago from O'ahu when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $807 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from O'ahu for as low as $563 on momondo.

What cabin class options are available on O'ahu to Chicago flights?

There are 4 cabin classes available to choose from on O'ahu 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 O'ahu to Chicago flights?

No. A direct flight is the cheapest option for a flight between O'ahu to Chicago.

Cheap O'ahu to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from O'ahu to Chicago

Best Price Found	$366
Fastest flight time	8h 09m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from O'ahu in the past 72 hours is $366. The best round-trip flight deal from O'ahu to Chicago found on momondo in the last 72 hours is $677.

The fastest flight from O'ahu to Chicago takes 8h 09m

Direct flights go from O'ahu to Chicago every day.

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

Search flight deals

When did momondo last update prices for flights from O'ahu to Chicago?
Prices for flights from O'ahu to Chicago refresh daily.
How many operators does momondo search for flights from O'ahu to Chicago?
The number of operators available for flights from O'ahu to Chicago is 6 as of December 2025.
How old do you have to be to fly from O'ahu to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from O'ahu to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from O'ahu to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from O'ahu to Chicago is Boeing 737-800 (19.31% of total bookings). The next most popular plane models are Airbus A321neo (12.32%), Boeing 737-900 (8.74%), and Boeing 737 MAX 8 (8.66%).

Best airlines flying from O'ahu to Chicago

Compare and see reviews for airlines that fly from O'ahu to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $305	Free Cancellation	Rating 7.9 8,014 reviews	Search Delta flights
Hawaiian Airlines	PriceFrom $335	Free Cancellation	Rating 7.8 2,821 reviews	Search Hawaiian Airlines flights
American Airlines	PriceFrom $467	Free Cancellation	Rating 7.2 11,053 reviews	Search American Airlines flights
Alaska Airlines	PriceFrom $512	Free Cancellation	Rating 8.0 11,502 reviews	Search Alaska Airlines flights
Southwest	PriceFrom $581	Free Cancellation	Rating 8.0 4,252 reviews	Search Southwest flights
United Airlines	PriceFrom $717	Free Cancellation	Rating 7.4 9,102 reviews	Search United Airlines flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from O'ahu to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from O'ahu to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from O'ahu to Chicago with flexible booking policies on momondo?

All flight searches from O'ahu to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from O'ahu to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from O'ahu. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Of course. momondo tracks the price of O'ahu to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Popular cities in the United States

Flights to New Yorkfrom $45

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Flights to Orlandofrom $29

Flights to San Franciscofrom $49

Flights to Las Vegasfrom $39

Flights to Washington, D.C.from $58

Flights to Bostonfrom $50

Flights to Atlantafrom $46

Flights to Dallasfrom $51

Flights to Seattlefrom $62

Flights to Denverfrom $38

Cheap flights from O'ahu to Chicago from $263

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from O'ahu to Chicago departing on 1/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names and deals

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Filter for what you want

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Find the cheapest flights from O'ahu to Chicago

Cheap round-trip flights

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Alaska Airlines flights from O'ahu to Chicago

Our best Alaska Airlines deals on O'ahu to Chicago flight tickets

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Our best Hawaiian Airlines deals on O'ahu to Chicago flight tickets

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

See travel insights to Chicago from

How to get the cheapest flight ticket from O'ahu to Chicago

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from O'ahu, with most prices found around $558. If you’re not able to fly to Chicago in September, then May is your next best option. Flight prices from O'ahu to Chicago during May average around $598.

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?

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from O'ahu to Chicago during this time can be as low as $618. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $881.

What is the cheapest O'ahu to Chicago flight route?

Fly from Honolulu to Chicago O'Hare Intl for the best O'ahu - Chicago flight prices

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

What cabin class options are available on O'ahu to Chicago flights?

There are 4 cabin classes available to choose from on O'ahu 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 O'ahu to Chicago flights?

No. A direct flight is the cheapest option for a flight between O'ahu to Chicago.

What is the cheapest airline that flies from O'ahu to Chicago?

Delta, Alaska Airlines, and United Airlines are the most popular carriers operating from O'ahu to Chicago

What airlines fly to Chicago?

How many flights depart from O'ahu to Chicago on average per day?

As of December 2025, 6 flights take off from O'ahu and land in Chicago each day. The most common flight departure time for this route is 7:00PM, with 100% of daily flights taking off in the evening.

How many flights depart from O'ahu to Chicago on average per week?

46 flights are operational weekly from O'ahu to Chicago as of December 2025. The most popular departure day for this route is Tue, with 15% of flights per week taking off on this day.

Cheap O'ahu to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from O'ahu to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

When did momondo last update prices for flights from O'ahu to Chicago?

How many operators does momondo search for flights from O'ahu to Chicago?

How old do you have to be to fly from O'ahu to Chicago?

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

What is the most popular plane model from O'ahu to Chicago?

Best airlines flying from O'ahu to Chicago

Compare and see reviews for airlines that fly from O'ahu to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from O'ahu to Chicago?

Can I find flights from O'ahu to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from O'ahu to Chicago?

I’m not ready to book a flight from O'ahu to Chicago right now. Can momondo alert me if 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.

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