$250 Cheap flight deals from Chicago (CHI) to Waialua (HNL)

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This Weekend's Flight Deals from Chicago to Waialua

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Jun 5 - Sun, Jun 14
ORD
O'Hare Intl.
HNL
Daniel K. Inouye Intl.
$700 Roundtrip, found 2 days ago
$700
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Fri, Jun 5 from O'Hare Intl. to Daniel K. Inouye Intl., returning Sun, Jun 14, priced at $700 found 2 days ago
Sun, Jun 7 - Thu, Jun 11
MDW
Midway Intl.
HNL
Daniel K. Inouye Intl.
$814 Roundtrip, found 2 days ago
$814
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sun, Jun 7 from Midway Intl. to Daniel K. Inouye Intl., returning Thu, Jun 11, priced at $814 found 2 days ago

Airfares from $250 One Way, $458 Round Trip from Chicago to Waialua

Prices starting at $458 for return flights and $250 for one-way flights to Waialua were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Sep 1 - Wed, Sep 9
ORD
Chicago
HNL
Oahu
$458 Roundtrip, found 8 hours ago
$458
Roundtrip
found 8 hours ago
Select Alaska Airlines flight, departing Tue, Sep 1 from Chicago to Oahu, returning Wed, Sep 9, priced at $458 found 8 hours ago
Thu, Sep 10 - Wed, Sep 16
ORD
Chicago
HNL
Oahu
$470 Roundtrip, just found
$470
Roundtrip
just found
Select Delta flight, departing Thu, Sep 10 from Chicago to Oahu, returning Wed, Sep 16, priced at $470 just found
Thu, Sep 10 - Wed, Sep 16
ORD
Chicago
HNL
Oahu
$501 Roundtrip, just found
$501
Roundtrip
just found
Select Alaska Airlines flight, departing Thu, Sep 10 from Chicago to Oahu, returning Wed, Sep 16, priced at $501 just found
Mon, Sep 21 - Tue, Sep 29
ORD
Chicago
HNL
Oahu
$509 Roundtrip, found 2 hours ago
$509
Roundtrip
found 2 hours ago
Select Alaska Airlines flight, departing Mon, Sep 21 from Chicago to Oahu, returning Tue, Sep 29, priced at $509 found 2 hours ago
Thu, Sep 10 - Wed, Sep 16
ORD
Chicago
HNL
Oahu
$516 Roundtrip, just found
$516
Roundtrip
just found
Select Delta flight, departing Thu, Sep 10 from Chicago to Oahu, returning Wed, Sep 16, priced at $516 just found

Waialua economy flight packages

Price found within the past 48 hours. Click for updated prices.
Paradise Bay Resort
3.5-star property

Paradise Bay Resort

8.8/10 Excellent! (1,004 reviews)

Jul 6 - Jul 10

4 night stay

Chicago (CHI) to Honolulu (HNL)

Delta • Non-stop • Coach

Honolulu (HNL) to Chicago (CHI)

Alaska Airlines • Non-stop • Coach
Price was $1,961, price is now $1,308 per person
$1,308
per person
found 1 day ago
Although the weather was disappointing for a couple of days (rain) during our stay, the resort was still great with helpful staff. It was peaceful and quiet. We especially loved the floating deck where we were able to relax and have some drinks while watching the tide roll in and out in the evenings. Definitely a 10 all the way around!! We can't wait to stay there on our next visit. Mahalo!

Reviewed on May 30, 2026

Ala Moana Hotelcondo by Luana Vacation Rental
3.5-star property

Ala Moana Hotelcondo by Luana Vacation Rental

7.6/10 Good! (258 reviews)

Jul 21 - Jul 27

6 night stay

Chicago (CHI) to Honolulu (HNL)

Alaska Airlines • Non-stop • Coach

Honolulu (HNL) to Chicago (CHI)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,888, price is now $1,464 per person
$1,464
per person
found 1 day ago
Room should be cleaned every couple of days

Reviewed on Apr 30, 2022

Waikiki Shore by OUTRIGGER
3.0-star property

Waikiki Shore by OUTRIGGER

8.4/10 Very Good! (576 reviews)

Jul 17 - Jul 21

4 night stay

Chicago (CHI) to Honolulu (HNL)

Southwest Airlines • Non-stop • Coach

Honolulu (HNL) to Chicago (CHI)

Alaska Airlines • Non-stop • Coach
Price was $2,254, price is now $1,685 per person
$1,685
per person
found 1 day ago
This place would be 5 stars if the seating area and table on the porch were the ones pictured in the listing. The owner clearly invested a lot of time decorating their place and appointing the kitchen with lots of dishes and cooking utensils. However, most, ironically, there is absolutely nowhere to sit and enjoy a meal, unless you want to stare at a wall and sit on a barstool. The outside table and chairs are not the one picture, and seem to be available only to drink cocktails, not to eat a meal. We found ourselves, unable to prepare a lot of food and needing to go out to restaurants because there was no seating area.

Reviewed on Feb 23, 2025

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Waialua first class flight packages

Price found within the past 48 hours. Click for updated prices.
Royal Kuhio
3.5-star property

Royal Kuhio

8.6/10 Excellent! (579 reviews)

Jul 11 - Jul 15

4 night stay

Chicago (MDW) to Honolulu (HNL)

Delta • Roundtrip • FirstClass
Price was $3,078, price is now $2,671 per person
$2,671
per person
found 10 hours ago
Good size room with all the kitchen amenities. Hotel parking was not an issue. Staff was courteous.

Reviewed on Feb 16, 2026

Ala Moana Hotelcondo by Luana Vacation Rental
3.5-star property

Ala Moana Hotelcondo by Luana Vacation Rental

7.6/10 Good! (258 reviews)

Jul 11 - Jul 15

4 night stay

Chicago (MDW) to Honolulu (HNL)

Delta • Roundtrip • FirstClass
Price was $3,544, price is now $2,708 per person
$2,708
per person
found 10 hours ago
Room should be cleaned every couple of days

Reviewed on Apr 30, 2022

OUTRIGGER Reef Waikiki Beach Resort
4.5-star property

OUTRIGGER Reef Waikiki Beach Resort

9.4/10 Exceptional! (3,102 reviews)

Jul 11 - Jul 15

4 night stay

Chicago (MDW) to Honolulu (HNL)

Delta • Roundtrip • FirstClass
Price was $3,313, price is now $2,898 per person
$2,898
per person
found 10 hours ago
This is my second time in Hawaii and both times I stayed at an outrigger resort. However, this outrigger reef resort was not impressive at all. We kept having plumbing issues with the toilet from the day we checked in… There were a couple of stains on the carpet… The lining in the ceiling inside of the shower was either dirty or moldy. The direct beach access was very small to the point where we had to walk further down past our hotel to get full access to the beach. My mom and I ate breakfast at the Monkeypod restaurant located inside of the resort and for the most part the staff was nice and helpful. However we did come across one rude waiter, who had an attitude when he brought me my change from my bill, but didn’t bring me my coins…Neither did he mention that they were out of coins, and when I asked about it, he had an attitude as if i had no right to ask about a shortage of my own money. Also, I think it’s a total scam that not only do we pay a $250 deposit but we also pay a $56 a day resort fee… Which includes nothing! Beach access can’t be included in that because beaches are accessible to anybody and everybody all throughout Hawaii for no additional cost so the resort fee is really pointless. On a more positive note the staff was friendly.

Reviewed on May 30, 2026

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More About Flying To Waialua from Chicago

Route Information for Flights from Chicago to Waialua

Origin Airport IATA Code
CHI
Destination Airport IATA Code
HNL
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Waialua

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.