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O'ahu

Cheap flights from Chicago (CHI) to O'ahu

CHI — HNL
Oct 25 — Nov 11
Sun 10/25
Sun 11/1
1 adult, Economy
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1. Tell us where you want to go

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Find flight deals from Chicago to O'ahu

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

June

Cheapest in

February

Average price

$800

Good round-trip deal

$759 or less

Good one-way deal

$359 or less
Provider with most accurate pricing for Chicago (CHI)-Honolulu flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Honolulu flights.
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Highest demand for flights based on searches. 13% potential increase in price ($128 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in September 2026
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Price to beat on a round-trip flight from Chicago (CHI) to O'ahu.
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Price to beat on a one-way flight from Chicago (CHI) to O'ahu.
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Cheapflights Insights

Everything you need to know about your flight from Chicago to O'ahu

How far ahead should I book a flight from Chicago to O'ahu?

Booking 33 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to O'ahu. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago to O'ahu?

Currently, February is the cheapest month in which you can book a flight from Chicago to O'ahu (average of $612). Flying from Chicago to O'ahu in June is currently the most expensive (average of $1,016). 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 CHI to FUW?

When flying from Chicago to O'ahu, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing O'ahu

Read through reviews of airlines operating flights from Chicago to O'ahu, such as Southwest,Alaska Airlines, andDelta. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,200 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
4.0
Okay

Steven,Sep 2026

OGG - HNL

It was a red eye overnight which I prefer. But this time the seat was SOOOO uncomfortable that sleeping was difficult and painful
Southwest
8.0
Very good
4,200 reviews
Southwest
8.0
Very good
4,200 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
4.0
Okay

Steven,Sep 2026

OGG - HNL

It was a red eye overnight which I prefer. But this time the seat was SOOOO uncomfortable that sleeping was difficult and painful
Alaska Airlines
7.9
Good
12,966 reviews
Southwest
8.0
Very good
4,200 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
4.0
Okay

Steven,Sep 2026

OGG - HNL

It was a red eye overnight which I prefer. But this time the seat was SOOOO uncomfortable that sleeping was difficult and painful
Delta
7.8
Good
8,598 reviews
Southwest
8.0
Very good
4,200 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
4.0
Okay

Steven,Sep 2026

OGG - HNL

It was a red eye overnight which I prefer. But this time the seat was SOOOO uncomfortable that sleeping was difficult and painful
United Airlines
7.4
Good
10,236 reviews
Southwest
8.0
Very good
4,200 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
4.0
Okay

Steven,Sep 2026

OGG - HNL

It was a red eye overnight which I prefer. But this time the seat was SOOOO uncomfortable that sleeping was difficult and painful
American Airlines
7.0
Good
12,085 reviews
Southwest
8.0
Very good
4,200 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
4.0
Okay

Steven,Sep 2026

OGG - HNL

It was a red eye overnight which I prefer. But this time the seat was SOOOO uncomfortable that sleeping was difficult and painful

Related info for your journey

  • What are the cheapest airlines to fly from Chicago to O'ahu one-way?

    To fly one-way, consider booking your trip with Alaska Airlines, which is currently one of the cheapest options available, starting at $193. Delta flights start at $212 while deals on American Airlines start at $266 one-way.

  • What are the cheapest flights from Chicago to O'ahu?

    Looking for the cheapest flight from Chicago to O'ahu? While on average our users pay $1,976, our data indicates the cheapest price to be $273. The most popular route (Chicago O'Hare Intl - Honolulu), is priced around $424.

  • Can I find deals for flights from Chicago to O'ahu that include hotel bookings?

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

  • How can I find direct flights from Chicago to O'ahu?

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

  • Can I find deals for business class flights from Chicago to O'ahu?

    Yes. Cheapflights offers flight deals from Chicago to O'ahu 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 Chicago to O'ahu?

    Currently, February is the cheapest month in which you can book a flight from Chicago to O'ahu (average of $612). Flying from Chicago to O'ahu in June is currently the most expensive (average of $1,016). 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

Browse thousands of different options on Cheapflights for your next trip

Top 5 airlines flying from Chicago to O'ahu

AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$363Average$653FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$394Average$886FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$425Average$669FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$439Average$784FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$477Average$818FlexibilityNo cancel feeOn-time71%

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