$205 Cheap flight deals from Chicago (CHI) to Haleiwa (HNL)

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This Weekend's Flight Deals from Chicago to Haleiwa

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.

Sun, Oct 25 - Mon, Oct 26
MDW
Midway Intl.
HNL
Daniel K. Inouye Intl.
$596 Roundtrip, found 23 hours ago
$596
Roundtrip
found 23 hours ago
Select Southwest Airlines flight, departing Sun, Oct 25 from Midway Intl. to Daniel K. Inouye Intl., returning Mon, Oct 26, priced at $596 found 23 hours ago
Sun, Oct 25 - Mon, Oct 26
ORD
O'Hare Intl.
HNL
Daniel K. Inouye Intl.
$659 Roundtrip, found 23 hours ago
$659
Roundtrip
found 23 hours ago
Select Alaska Airlines flight, departing Sun, Oct 25 from O'Hare Intl. to Daniel K. Inouye Intl., returning Mon, Oct 26, priced at $659 found 23 hours ago

Airfares from $205 One Way, $410 Round Trip from Chicago to Haleiwa

Prices starting at $410 for return flights and $205 for one-way flights to Haleiwa 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 2 - Tue, Feb 9
ORD
Chicago
HNL
Oahu
$410 Roundtrip, found 2 days ago
$410
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Tue, Feb 2 from Chicago to Oahu, returning Tue, Feb 9, priced at $410 found 2 days ago
Tue, Feb 2 - Tue, Feb 9
ORD
Chicago
HNL
Oahu
$410 Roundtrip, found 2 days ago
$410
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Tue, Feb 2 from Chicago to Oahu, returning Tue, Feb 9, priced at $410 found 2 days ago
Mon, Nov 9 - Thu, Nov 12
ORD
Chicago
HNL
Oahu
$418 Roundtrip, found 2 days ago
$418
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Mon, Nov 9 from Chicago to Oahu, returning Thu, Nov 12, priced at $418 found 2 days ago
Tue, Feb 2 - Wed, Feb 3
ORD
Chicago
HNL
Oahu
$424 Roundtrip, found 16 hours ago
$424
Roundtrip
found 16 hours ago
Select Alaska Airlines flight, departing Tue, Feb 2 from Chicago to Oahu, returning Wed, Feb 3, priced at $424 found 16 hours ago
Thu, Jan 28 - Wed, Feb 3
ORD
Chicago
HNL
Oahu
$437 Roundtrip, found 6 days ago
$437
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Thu, Jan 28 from Chicago to Oahu, returning Wed, Feb 3, priced at $437 found 6 days ago

Haleiwa 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! (1,007 reviews)

Dec 3 - Dec 8

5 night stay

Chicago (CHI) to Honolulu (HNL)

Alaska Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,577, price is now $926 per person
$926
per person
found 1 day ago
Great location, very peaceful and great views

Reviewed on Oct 17, 2026

Oceanfront Vacation Villas at Turtle Bay
4.5-star property

Oceanfront Vacation Villas at Turtle Bay

9.4/10 Exceptional! (118 reviews)

Dec 7 - Dec 11

4 night stay

Chicago (ORD) to Honolulu (HNL)

American Airlines • Coach

Honolulu (HNL) to Chicago (ORD)

Alaska Airlines • Coach
Price was $3,235, price is now $2,032 per person
$2,032
per person
found 1 day ago
No beach or umbrella chairs, you beed to pay $60 for 2 hrs and $80 for 4 hrs, The Ritz employees treat you like you very dismissive as you are in turtle bay village but not associated with the ritz. I give this listing a 0.

Reviewed on Aug 27, 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)

Nov 30 - Dec 6

6 night stay

Chicago (CHI) to Honolulu (HNL)

Southwest Airlines • Roundtrip • Coach
Price was $8,108, price is now $3,073 per person
$3,073
per person
found 1 day ago

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Haleiwa packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Ilikai by Luana Hawaii Vacation Rentals
3.0-star property

Ilikai by Luana Hawaii Vacation Rentals

8.8/10 Excellent! (61 reviews)

Nov 29 - Dec 6

7 night stay

Chicago (CHI) to Honolulu (HNL)

United • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $4,752, price is now $2,825 per person
$2,825
per person
found 1 day ago
We had 3 adults staying there. It was advertised for 3 adults, however, the futon foldout was only big enough for a kid. We took pictures of our adult kids and their heads went over the futon. However. After complaining, the owners dropped off a double/queen blow up mattress, about the 3 day into the stay, meanwhile one of the kids had to move into our room. So, bad news, the room was not set up for 3 adults, but good news after days of complaining, the bed was corrected.

Reviewed on Aug 27, 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)

Nov 29 - Dec 6

7 night stay

Chicago (CHI) to Honolulu (HNL)

United • Roundtrip • PremiumEconomy
Price was $11,089, price is now $4,629 per person
$4,629
per person
found 1 day ago

Panoramic Oceanview Resort
4.0-star property

Panoramic Oceanview Resort

9/10 Wonderful! (30 reviews)

Nov 29 - Dec 6

7 night stay

Chicago (CHI) to Honolulu (HNL)

United • Roundtrip • PremiumEconomy
Price was $4,328, price is now $3,251 per person
$3,251
per person
found 1 day ago

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Haleiwa first class flight packages

Price found within the past 48 hours. Click for updated prices.
'Alohilani Resort Waikiki Beach
5.0-star property

'Alohilani Resort Waikiki Beach

8.6/10 Excellent! (4,251 reviews)

Dec 6 - Dec 12

6 night stay

Chicago (CHI) to Honolulu (HNL)

Delta • Non-stop • FirstClass

Honolulu (HNL) to Chicago (CHI)

United • Non-stop • FirstClass
Price was $2,977, price is now $2,604 per person
$2,604
per person
found 20 hours ago
Helen was excellent! She was very attentive to our every need. Thank you!

Reviewed on Oct 16, 2026

Paradise Bay Resort
3.5-star property

Paradise Bay Resort

8.8/10 Excellent! (1,007 reviews)

Dec 6 - Dec 12

6 night stay

Chicago (CHI) to Honolulu (HNL)

Delta • Non-stop • FirstClass

Honolulu (HNL) to Chicago (CHI)

United • Non-stop • FirstClass
Price was $3,469, price is now $2,710 per person
$2,710
per person
found 20 hours ago
Great location, very peaceful and great views

Reviewed on Oct 17, 2026

OUTRIGGER Reef Waikiki Beach Resort
4.5-star property

OUTRIGGER Reef Waikiki Beach Resort

9.4/10 Exceptional! (3,152 reviews)

Dec 6 - Dec 12

6 night stay

Chicago (CHI) to Honolulu (HNL)

Delta • Non-stop • FirstClass

Honolulu (HNL) to Chicago (CHI)

United • Non-stop • FirstClass
Price was $3,540, price is now $3,044 per person
$3,044
per person
found 20 hours ago

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More About Flying To Haleiwa from Chicago

Route Information for Flights from Chicago to Haleiwa

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

Chicago to Haleiwa

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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.