$184 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.
MDW
Midway Intl.
HNL
Daniel K. Inouye Intl.
$763 Roundtrip, found 6 days ago
$763
Roundtrip
found 6 days ago
ORD
O'Hare Intl.
HNL
Daniel K. Inouye Intl.
$798 Roundtrip, found 2 hours ago
$798
Roundtrip
found 2 hours ago
Airfares from $184 One Way, $370 Round Trip from Chicago to Pearl City
Prices starting at $370 for return flights and $184 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.
ORD
Chicago
HNL
Oahu
$370 Roundtrip, found 4 days ago
$370
Roundtrip
found 4 days ago
ORD
Chicago
HNL
Oahu
$378 Roundtrip, found 6 days ago
$378
Roundtrip
found 6 days ago
ORD
Chicago
HNL
Oahu
$381 Roundtrip, found 4 days ago
$381
Roundtrip
found 4 days ago
ORD
Chicago
HNL
Oahu
$382 Roundtrip, found 4 days ago
$382
Roundtrip
found 4 days ago
ORD
Chicago
HNL
Oahu
$386 Roundtrip, found 4 days ago
$386
Roundtrip
found 4 days ago
Pearl City economy flight packages
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Ala Moana Hotelcondo by Luana Vacation Rental
7.4/10 Good! (256 reviews)
Feb 10 - Feb 17
7 night stay
Chicago (ORD) to Honolulu (HNL)
United • Non-stop roundtrip • Coach
Price was $3,843, price is now $1,669 per person
$1,669
per person
found 1 day ago
Room should be cleaned every couple of days
Reviewed on Apr 30, 2022
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
Pearl City packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
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
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
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
Pearl City first class flight packages
Price found within the past 48 hours. Click for updated prices.
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
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
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
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.