$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 2 hours ago
$596
Roundtrip
found 2 hours 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 2 hours ago
Sat, Oct 17 - Sun, Oct 18
ORD
O'Hare Intl.
HNL
Daniel K. Inouye Intl.
$681 Roundtrip, found 17 hours ago
$681
Roundtrip
found 17 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 17 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 19 - Tue, Jan 26
ORD
Chicago
HNL
Oahu
$410 Roundtrip, just found
$410
Roundtrip
just found
Select Alaska Airlines flight, departing Tue, Jan 19 from Chicago to Oahu, returning Tue, Jan 26, priced at $410 just found
Tue, Jan 19 - Tue, Jan 26
ORD
Chicago
HNL
Oahu
$410 Roundtrip, just found
$410
Roundtrip
just found
Select Alaska Airlines flight, departing Tue, Jan 19 from Chicago to Oahu, returning Tue, Jan 26, priced at $410 just found
Wed, Nov 11 - Tue, Nov 17
ORD
Chicago
HNL
Oahu
$418 Roundtrip, just found
$418
Roundtrip
just found
Select Alaska Airlines flight, departing Wed, Nov 11 from Chicago to Oahu, returning Tue, Nov 17, priced at $418 just found
Tue, Feb 2 - Wed, Feb 3
ORD
Chicago
HNL
Oahu
$424 Roundtrip, found 2 days ago
$424
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Tue, Feb 2 from Chicago to Oahu, returning Wed, Feb 3, priced at $424 found 2 days ago
Thu, Jan 28 - Wed, Feb 3
ORD
Chicago
HNL
Oahu
$437 Roundtrip, found 10 hours ago
$437
Roundtrip
found 10 hours ago
Select Bargain Flight flight, departing Thu, Jan 28 from Chicago to Oahu, returning Wed, Feb 3, priced at $437 found 10 hours ago

Pearl City 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)

Southwest Airlines • Non-stop • Coach

Honolulu (HNL) to Chicago (CHI)

Alaska Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,569, price is now $972 per person
$972
per person
found 3 hours 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

Ilikai by Luana Hawaii Vacation Rentals
3.0-star property

Ilikai by Luana Hawaii Vacation Rentals

8.8/10 Excellent! (61 reviews)

Nov 26 - Dec 1

5 night stay

Chicago (CHI) to Honolulu (HNL)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,684, price is now $1,305 per person
$1,305
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

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 23 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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Pearl City 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! (628 reviews)

Nov 13 - Nov 20

7 night stay

Chicago (CHI) to Honolulu (HNL)

Delta • Non-stop roundtrip • FirstClass
Price was $3,193, price is now $2,737 per person
$2,737
per person
just found
Very clean, close to shops and the beach. Staff is friendly. We love that parking is included. Would definitely go back to same resort and will recommend to others.

Reviewed on Oct 5, 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 13 - Nov 20

7 night stay

Chicago (CHI) to Honolulu (HNL)

Delta • Non-stop roundtrip • FirstClass
Price was $9,008, price is now $4,570 per person
$4,570
per person
just found

OUTRIGGER Reef Waikiki Beach Resort
4.5-star property

OUTRIGGER Reef Waikiki Beach Resort

9.4/10 Exceptional! (3,152 reviews)

Nov 13 - Nov 20

7 night stay

Chicago (CHI) to Honolulu (HNL)

Delta • Non-stop roundtrip • FirstClass
Price was $3,384, price is now $2,931 per person
$2,931
per person
just found
.

Reviewed on Oct 11, 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.