$184 Cheap flight deals from Chicago (CHI) to Waimanalo (HNL)

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This Weekend's Flight Deals from Chicago to Waimanalo

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, Jan 2 - Wed, Jan 7
ORD
O'Hare Intl.
HNL
Daniel K. Inouye Intl.
$798 Roundtrip, found 14 hours ago
$798
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Fri, Jan 2 from O'Hare Intl. to Daniel K. Inouye Intl., returning Wed, Jan 7, priced at $798 found 14 hours ago
Sun, Jan 4 - Sat, Jan 10
MDW
Midway Intl.
HNL
Daniel K. Inouye Intl.
$873 Roundtrip, found 4 days ago
$873
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Sun, Jan 4 from Midway Intl. to Daniel K. Inouye Intl., returning Sat, Jan 10, priced at $873 found 4 days ago

Airfares from $184 One Way, $370 Round Trip from Chicago to Waimanalo

Prices starting at $370 for return flights and $184 for one-way flights to Waimanalo 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, Feb 3 - Tue, Feb 10
ORD
Chicago
HNL
Oahu
$370 Roundtrip, found 5 days ago
$370
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Tue, Feb 3 from Chicago to Oahu, returning Tue, Feb 10, priced at $370 found 5 days ago
Wed, Feb 4 - Tue, Feb 10
ORD
Chicago
HNL
Oahu
$378 Roundtrip, found 6 days ago
$378
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Wed, Feb 4 from Chicago to Oahu, returning Tue, Feb 10, priced at $378 found 6 days ago
Mon, Feb 2 - Tue, Feb 10
ORD
Chicago
HNL
Oahu
$381 Roundtrip, found 5 days ago
$381
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Mon, Feb 2 from Chicago to Oahu, returning Tue, Feb 10, priced at $381 found 5 days ago
Tue, Feb 3 - Tue, Feb 10
ORD
Chicago
HNL
Oahu
$382 Roundtrip, found 5 days ago
$382
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Feb 3 from Chicago to Oahu, returning Tue, Feb 10, priced at $382 found 5 days ago
Mon, Feb 2 - Fri, Feb 6
ORD
Chicago
HNL
Oahu
$386 Roundtrip, found 5 days ago
$386
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Mon, Feb 2 from Chicago to Oahu, returning Fri, Feb 6, priced at $386 found 5 days ago

Waimanalo 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! (1,002 reviews)

Feb 2 - Feb 6

4 night stay

Chicago (CHI) to Honolulu (HNL)

United • Non-stop roundtrip • Coach
Price was $1,253, price is now $838 per person
$838
per person
found 1 day ago
This is a quiet little gem. Off the tourist path and scenery is spectacular. Enjoyed listening to Uncle Danny kanikapila. Tea, banana bread and coffee were yummy. Driveway, parking and stairs are a bit intimidating but just go slow. It is worth it. Am afraid to tell others about this wonderful place because I don’t want it to change. I will come again.

Reviewed on Nov 2, 2025

Ilikai by Luana Hawaii Vacation Rentals
3.0-star property

Ilikai by Luana Hawaii Vacation Rentals

8.6/10 Excellent! (51 reviews)

Feb 6 - Feb 10

4 night stay

Chicago (CHI) to Honolulu (HNL)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,230, price is now $1,098 per person
$1,098
per person
found 1 day ago
The room was fully furnished with everything we needed. No washing machine but that was minor. Awesome view. Valet parking was great!!! Will book again.

Reviewed on Aug 13, 2025

Ala Moana Hotelcondo by Luana Vacation Rental
3.5-star property

Ala Moana Hotelcondo by Luana Vacation Rental

7.4/10 Good! (256 reviews)

Feb 19 - Feb 23

4 night stay

Chicago (ORD) to Honolulu (HNL)

Alaska Airlines • Non-stop • Coach

Honolulu (HNL) to Chicago (ORD)

Delta • Non-stop • Coach
Price was $2,312, price is now $1,214 per person
$1,214
per person
found 9 hours ago
Room should be cleaned every couple of days

Reviewed on Apr 30, 2022

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Waimanalo packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Waikiki Beach Resort & Spa
4.0-star property

Hyatt Regency Waikiki Beach Resort & Spa

8.8/10 Excellent! (4,606 reviews)

Feb 13 - Feb 16

3 night stay

Chicago (CHI) to Honolulu (HNL)

American Airlines • PremiumEconomy

Honolulu (HNL) to Chicago (CHI)

Delta • PremiumEconomy
Price was $2,132, price is now $1,832 per person
$1,832
per person
found 1 day ago
During check in (waiting in line) front desk clerk was very rude, she calls me to come up then because I was quickly texting she turned me back ???. Our room had rattling knocking noise coming from connecting room door in the other side room, constantly throughout the night..

Reviewed on Dec 15, 2025

OUTRIGGER Waikiki Beachcomber Hotel
4.0-star property

OUTRIGGER Waikiki Beachcomber Hotel

9/10 Wonderful! (2,486 reviews)

Feb 13 - Feb 16

3 night stay

Chicago (CHI) to Honolulu (HNL)

American Airlines • PremiumEconomy

Honolulu (HNL) to Chicago (CHI)

Delta • PremiumEconomy
Price was $2,042, price is now $1,848 per person
$1,848
per person
found 1 day ago
Great beach nearby. Location perfect.

Reviewed on Oct 25, 2025

OUTRIGGER Waikiki Beach Resort
4.0-star property

OUTRIGGER Waikiki Beach Resort

9/10 Wonderful! (3,280 reviews)

Feb 13 - Feb 16

3 night stay

Chicago (CHI) to Honolulu (HNL)

American Airlines • PremiumEconomy

Honolulu (HNL) to Chicago (CHI)

Delta • PremiumEconomy
Price was $2,170, price is now $1,969 per person
$1,969
per person
found 1 day ago
Hotel staff welcoming. Room showing its age but clean and comfortable. The hotel is across from the International Market Place, so certain type of vacationers may like this very busy but convenient location.

Reviewed on Oct 12, 2025

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Waimanalo first class flight packages

Price found within the past 48 hours. Click for updated prices.
Stay Hotel Waikiki
3.0-star property

Stay Hotel Waikiki

7.8/10 Good! (1,357 reviews)

Feb 10 - Feb 16

6 night stay

Chicago (CHI) to Honolulu (HNL)

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,992, price is now $2,553 per person
$2,553
per person
found 1 day ago
Location and price are 5 star worthy. You are getting what you pay for, though. Room is fair. Bathroom is mediocre, except for the shower, which is pretty bad. Hot water takes 5 minutes to come on in the morning. The shower head is too low and puts out very little pressure. I would have still rated the hotel 4/5, but for the mold in the shower. It’s all over the tiles and grout. I was literally able to wipe and scrape it off with my finger. This is inexcusable. Very poorly cleaned. Room 502 if the hotel is interested in fixing these issues.

Reviewed on Nov 23, 2025

Paradise Bay Resort
3.5-star property

Paradise Bay Resort

8.8/10 Excellent! (1,002 reviews)

Feb 10 - Feb 16

6 night stay

Chicago (CHI) to Honolulu (HNL)

American Airlines • Non-stop roundtrip • FirstClass
Price was $3,653, price is now $2,884 per person
$2,884
per person
found 1 day ago
This is a quiet little gem. Off the tourist path and scenery is spectacular. Enjoyed listening to Uncle Danny kanikapila. Tea, banana bread and coffee were yummy. Driveway, parking and stairs are a bit intimidating but just go slow. It is worth it. Am afraid to tell others about this wonderful place because I don’t want it to change. I will come again.

Reviewed on Nov 2, 2025

Hyatt Regency Waikiki Beach Resort & Spa
4.0-star property

Hyatt Regency Waikiki Beach Resort & Spa

8.8/10 Excellent! (4,606 reviews)

Feb 10 - Feb 16

6 night stay

Chicago (CHI) to Honolulu (HNL)

American Airlines • Non-stop roundtrip • FirstClass
Price was $3,656, price is now $2,928 per person
$2,928
per person
found 1 day ago
During check in (waiting in line) front desk clerk was very rude, she calls me to come up then because I was quickly texting she turned me back ???. Our room had rattling knocking noise coming from connecting room door in the other side room, constantly throughout the night..

Reviewed on Dec 15, 2025

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See all available trips from Chicago to Waimanalo
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More About Flying To Waimanalo from Chicago

Route Information for Flights from Chicago to Waimanalo

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

Chicago to Waimanalo

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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.