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

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This Weekend's Flight Deals from Chicago to Pearl City

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 18 - Sat, Oct 24
MDW
Midway Intl.
HNL
Daniel K. Inouye Intl.
$596 Roundtrip, found 1 day ago
$596
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sun, Oct 18 from Midway Intl. to Daniel K. Inouye Intl., returning Sat, Oct 24, priced at $596 found 1 day ago
Sat, Oct 17 - Sun, Oct 18
ORD
O'Hare Intl.
HNL
Daniel K. Inouye Intl.
$681 Roundtrip, found 10 hours ago
$681
Roundtrip
found 10 hours ago
Select Delta flight, departing Sat, Oct 17 from O'Hare Intl. to Daniel K. Inouye Intl., returning Sun, Oct 18, priced at $681 found 10 hours ago

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

Prices starting at $410 for return flights and $205 for one-way flights to Pearl City 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, Jan 26 - Tue, Feb 2
ORD
Chicago
HNL
Oahu
$410 Roundtrip, found 1 hour ago
$410
Roundtrip
found 1 hour ago
Select Alaska Airlines flight, departing Tue, Jan 26 from Chicago to Oahu, returning Tue, Feb 2, priced at $410 found 1 hour ago
Tue, Jan 26 - Tue, Feb 2
ORD
Chicago
HNL
Oahu
$410 Roundtrip, found 1 hour ago
$410
Roundtrip
found 1 hour ago
Select Alaska Airlines flight, departing Tue, Jan 26 from Chicago to Oahu, returning Tue, Feb 2, priced at $410 found 1 hour ago
Tue, Feb 2 - Wed, Feb 3
ORD
Chicago
HNL
Oahu
$424 Roundtrip, found 1 day ago
$424
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Feb 2 from Chicago to Oahu, returning Wed, Feb 3, priced at $424 found 1 day ago
Thu, Jan 28 - Wed, Feb 3
ORD
Chicago
HNL
Oahu
$437 Roundtrip, found 3 hours ago
$437
Roundtrip
found 3 hours ago
Select Bargain Flight flight, departing Thu, Jan 28 from Chicago to Oahu, returning Wed, Feb 3, priced at $437 found 3 hours ago
Tue, Jan 26 - Tue, Feb 2
ORD
Chicago
HNL
Oahu
$448 Roundtrip, found 2 days ago
$448
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Tue, Jan 26 from Chicago to Oahu, returning Tue, Feb 2, priced at $448 found 2 days ago

Pearl City economy flight packages

Price found within the past 48 hours. Click for updated prices.
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 13 - Nov 17

4 night stay

Chicago (CHI) to Honolulu (HNL)

Alaska Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,533, price is now $978 per person
$978
per person
found 1 day ago

Paradise Bay Resort
3.5-star property

Paradise Bay Resort

8.8/10 Excellent! (1,007 reviews)

Nov 30 - Dec 5

5 night stay

Chicago (ORD) to Honolulu (HNL)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,847, price is now $1,120 per person
$1,120
per person
found 1 day ago
We booked a mountain view studio with a kitchenette for three nights. The photos on the website make the rooms look so much nicer than in person. The rooms are dated and, with just a little bit of investment, could be so much nicer... and could possibly live up to the 4 star rating. The view from the harbor view rooms is truly lovely. Our mountain view room had minimal mountain, but when I sat on the balcony with my morning coffee, I could see a bit of the bay. And the view from the lobby and reception area was great. Each morning, there was coffee, fruit, and banana bread, and one can sit there and look at the bay, the mountains, and the chickens! Or bring your coffee to the floating dock and enjoy the bay from there. The service was good, requests for a couple of things were quickly met, while a request for towels took a bit of time. The kitchenette was simply, but adequately, stocked. We were on the go during our stay on Oahu, so did not use the amenities, but would have loved to kayak on the calm waters. I would recommend this hotel, for the location and the views. Our expectations on a 'resort room' were higher than they should have been, but as long as you know, then you will not be disappointed. Aloha and mahalo.

Reviewed on Oct 11, 2026

Oceanfront Vacation Villas at Turtle Bay
4.5-star property

Oceanfront Vacation Villas at Turtle Bay

9.4/10 Exceptional! (118 reviews)

Nov 12 - Nov 16

4 night stay

Chicago (CHI) to Honolulu (HNL)

Southwest Airlines • Non-stop • Coach

Honolulu (HNL) to Chicago (CHI)

Alaska Airlines • Non-stop • Coach
Save 100% on your flight
Price was $4,055, price is now $2,462 per person
$2,462
per person
found 17 hours 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

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More About Flying To Pearl City from Chicago

Route Information for Flights from Chicago to Pearl City

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

Chicago to Pearl City

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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.