$176 Cheap flight deals from Chicago (CHI) to Pearl City (HNL)
Earn rewards on top of your airline miles with Orbitz Rewards
Many airlines offer flexible change policies
Sign up to receive text alerts about your trip
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.
ORD
O'Hare Intl.
HNL
Daniel K. Inouye Intl.
$747 Roundtrip, found 10 hours ago
$747
Roundtrip
found 10 hours ago
MDW
Midway Intl.
HNL
Daniel K. Inouye Intl.
$761 Roundtrip, found 4 days ago
$761
Roundtrip
found 4 days ago
RFD
Greater Rockford
HNL
Daniel K. Inouye Intl.
$964 Roundtrip, found 5 days ago
$964
Roundtrip
found 5 days ago
Airfares from $176 One Way, $355 Round Trip from Chicago to Pearl City
Prices starting at $355 for return flights and $176 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.
MDW
Chicago
HNL
Oahu
$355 Roundtrip, found 18 hours ago
$355
Roundtrip
found 18 hours ago
MDW
Chicago
HNL
Oahu
$360 Roundtrip, found 18 hours ago
$360
Roundtrip
found 18 hours ago
ORD
Chicago
HNL
Oahu
$361 Roundtrip, found 4 days ago
$361
Roundtrip
found 4 days ago
MDW
Chicago
HNL
Oahu
$364 Roundtrip, found 1 day ago
$364
Roundtrip
found 1 day ago
ORD
Chicago
HNL
Oahu
$366 Roundtrip, found 18 hours ago
$366
Roundtrip
found 18 hours ago
Pearl City economy 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)
Mar 19 - Mar 25
6 night stay
Chicago (CHI) to Honolulu (HNL)
Southwest Airlines • Non-stop • Coach
Honolulu (HNL) to Chicago (CHI)
Delta • Non-stop • Coach
Price was $1,324, price is now $849 per person
$849
per person
found 1 day ago
One block away from Kalākaua behind the Hyatt. It ’ll get a tad bit noisy depending on where your room faces but bring some ear plugs and you’ll be fine. The staff were seriously one of the nicest I’ve ever experienced in a hotel. The free coffee and laundry made the entire stay well worth it.
Reviewed on Jan 19, 2026
3.5-star property
Ala Moana Hotelcondo by Luana Vacation Rental
7.4/10 Good! (256 reviews)
Apr 5 - Apr 11
6 night stay
Chicago (CHI) to Honolulu (HNL)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $3,113, price is now $1,709 per person
$1,709
per person
found 1 day ago
Room should be cleaned every couple of days
Reviewed on Apr 30, 2022
3.5-star property
Waikiki Resort Hotel
8.6/10 Excellent! (2,635 reviews)
Mar 19 - Mar 25
6 night stay
Chicago (CHI) to Honolulu (HNL)
Southwest Airlines • Non-stop • Coach
Honolulu (HNL) to Chicago (CHI)
Delta • Non-stop • Coach
Save 100% on your flight
Price was $1,972, price is now $1,091 per person
$1,091
per person
found 1 day ago
It was a great place to stay
Reviewed on Nov 21, 2025
Pearl City packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Waikiki Circle Hotel
8.4/10 Very Good! (1,079 reviews)
Mar 22 - Mar 27
5 night stay
Chicago (ORD) to Honolulu (HNL)
United • PremiumEconomy
Honolulu (HNL) to Chicago (ORD)
Delta • PremiumEconomy
Price was $2,554, price is now $2,142 per person
$2,142
per person
found 1 day ago
Rooms were very small for the rate.
Reviewed on Jan 14, 2026
3.0-star property
Ilikai by Luana Hawaii Vacation Rentals
8.6/10 Excellent! (51 reviews)
Mar 22 - Mar 27
5 night stay
Chicago (ORD) to Honolulu (HNL)
United • PremiumEconomy
Honolulu (HNL) to Chicago (ORD)
Delta • PremiumEconomy
Price was $12,464, price is now $4,947 per person
$4,947
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
3.5-star property
Paradise Bay Resort
8.8/10 Excellent! (1,002 reviews)
Mar 22 - Mar 27
5 night stay
Chicago (ORD) to Honolulu (HNL)
United • PremiumEconomy
Honolulu (HNL) to Chicago (ORD)
Delta • PremiumEconomy
Price was $2,995, price is now $2,352 per person
$2,352
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
Pearl City first class flight packages
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Waikiki Shore by OUTRIGGER
8.4/10 Very Good! (542 reviews)
Mar 21 - Mar 27
6 night stay
Chicago (ORD) to Honolulu (HNL)
American Airlines • Non-stop roundtrip • FirstClass
Price was $3,830, price is now $3,290 per person
$3,290
per person
found 9 hours ago
This place would be 5 stars if the seating area and table on the porch were the ones pictured in the listing. The owner clearly invested a lot of time decorating their place and appointing the kitchen with lots of dishes and cooking utensils. However, most, ironically, there is absolutely nowhere to sit and enjoy a meal, unless you want to stare at a wall and sit on a barstool.
The outside table and chairs are not the one picture, and seem to be available only to drink cocktails, not to eat a meal. We found ourselves, unable to prepare a lot of food and needing to go out to restaurants because there was no seating area.
Reviewed on Feb 23, 2025
3.0-star property
Ilikai by Luana Hawaii Vacation Rentals
8.6/10 Excellent! (51 reviews)
Mar 21 - Mar 27
6 night stay
Chicago (ORD) to Honolulu (HNL)
United • Roundtrip • FirstClass
Price was $16,600, price is now $7,261 per person
$7,261
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
3.5-star property
Paradise Bay Resort
8.8/10 Excellent! (1,002 reviews)
Mar 21 - Mar 27
6 night stay
Chicago (ORD) to Honolulu (HNL)
United • Roundtrip • FirstClass
Price was $4,952, price is now $4,116 per person
$4,116
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
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
Orbitz has your best deals on Chicago to Pearl City flights. From guaranteed low prices to cutting-edge mobile tools, the perfect trip begins on Orbitz.
Get Orbitz On the Go for Flights from Chicago to Pearl City
Use our mobile apps for Android and iPhone to find the best price on flights from Chicago to Pearl City. Check your flight status, gate and baggage claim details, and book exclusive mobile deals on hotels — even on the same day.
Rack Up Miles While Flying for Cheaper
Earn miles or points toward your frequent flyer program on select Chicago to Pearl City flights. When you book your flight on Orbitz, simply add your qualifying frequent flyer number where prompted. You can also store your airline frequent flyer or loyalty program numbers in your Orbitz account profile to automatically add them to your future reservations.
Worry Less With Flight Alerts
Orbitz is the best source for booking flights from Chicago to Pearl City. But we also keep you updated about flight delays, booking changes, or service disruptions with free alerts. Get alerts on Chicago to Pearl City flights sent to your email or via voice or text to your mobile phone. We can also send the alerts to up to 6 other email addresses or phone numbers, which is helpful if you are being picked up at the airport.
Budget Travel Planning Made Easy
It's easy to find discount air tickets for flights from Chicago to Pearl City on Orbitz. Mix and match airlines for your departing and your returning flights to find the lowest fares and the best schedule.
Flights from Chicago
- Chicago to Los Angeles
- Chicago to New York
- Chicago to Orlando
- Chicago to Toronto
- Chicago to Houston
- Chicago to London
- Chicago to Detroit
- Chicago to Phoenix
- Chicago to Rome
- Chicago to Cleveland
- Chicago to Dallas
- Chicago to New Orleans
- Chicago to San Francisco
- Chicago to Washington
- Chicago to Paris
- Chicago to Sao Paulo
- Chicago to Sacramento
- Chicago to Killeen
- Chicago to Kansas City
- Chicago to Montreal
Pearl City Airports
More Destinations
- Flights from Beijing to Mililani
- Flights from Atlanta to Waipahu
- Flights from Boston to Waipahu
- Flights from Los Angeles to Waipahu
- Flights from Miami to Waipahu
- Flights from Minneapolis - St. Paul to Waipahu
- Flights from New York to Waipahu
- Flights from Phoenix to Waipahu
- Flights from Washington to Waipahu
- Flights from Jacksonville to Waipahu
- Flights from Newark to Waipahu
- Flights from Los Angeles to Oahu
- Flights from Abilene (ABI) to Honolulu (HNL)
- Flights from Auckland (AKL) to Honolulu (HNL)
- Flights from Atlanta (ATL) to Honolulu (HNL)
- Flights from Austin (AUS) to Honolulu (HNL)
- Flights from Mesa (AZA) to Honolulu (HNL)
- Flights from Birmingham (BHM) to Honolulu (HNL)
- Flights from Nashville (BNA) to Honolulu (HNL)
- Flights from Boise (BOI) to Honolulu (HNL)
- Flights from Boston (BOS) to Honolulu (HNL)
- Flights from Baltimore (BWI) to Honolulu (HNL)
- Flights from Cleveland (CLE) to Honolulu (HNL)
- Flights from Columbus (CMH) to Honolulu (HNL)
- Flights from Colorado Springs (COS) to Honolulu (HNL)
- Flights from Angeles City (CRK) to Honolulu (HNL)
- Flights from Cincinnati (CVG) to Honolulu (HNL)
- Flights from Da Nang (DAD) to Honolulu (HNL)
- Flights from Denver (DEN) to Honolulu (HNL)
- Flights from Detroit (DTW) to Honolulu (HNL)
- Flights from Dubai (DXB) to Honolulu (HNL)
- Flights from Wenatchee (EAT) to Honolulu (HNL)
- Flights from New Bern (EWN) to Honolulu (HNL)
- Flights from Newark Liberty Intl. Airport (EWR) to Honolulu (HNL)
- Flights from Buenos Aires (EZE) to Honolulu (HNL)
- Flights from Fresno (FAT) to Honolulu (HNL)
- Flights from Kalispell (FCA) to Honolulu (HNL)
- Flights from Fort Lauderdale (FLL) to Honolulu (HNL)
- Flights from Rio de Janeiro (GIG) to Honolulu (HNL)
- Flights from Washington (IAD) to Honolulu (HNL)
- Flights from Seoul (ICN) to Honolulu (HNL)
- Flights from Idaho Falls (IDA) to Honolulu (HNL)
- Flights from El Centro (IPL) to Honolulu (HNL)
- Flights from Leh (IXL) to Honolulu (HNL)
- Flights from Jacksonville (JAX) to Honolulu (HNL)
- Flights from New York (JFK) to Honolulu (HNL)
- Flights from Kailua-Kona (KOA) to Honolulu (HNL)
- Flights from Lihue (LIH) to Honolulu (HNL)
- Flights from Chennai (MAA) to Honolulu (HNL)
- Flights from Merced (MCE) to Honolulu (HNL)
- Flights from Kansas City (MCI) to Honolulu (HNL)
- Flights from Harrisburg (MDT) to Honolulu (HNL)
- Flights from Memphis (MEM) to Honolulu (HNL)
- Flights from Milwaukee (MKE) to Honolulu (HNL)
- Flights from Minneapolis (MSP) to Honolulu (HNL)
- Flights from New Orleans (MSY) to Honolulu (HNL)
- Flights from Oakland (OAK) to Honolulu (HNL)
- Flights from Oklahoma City (OKC) to Honolulu (HNL)
- Flights from Omaha (OMA) to Honolulu (HNL)
- Flights from Portland (PDX) to Honolulu (HNL)
- Flights from Pensacola (PNS) to Honolulu (HNL)
- Flights from Prescott (PRC) to Honolulu (HNL)
- Flights from Pasco (PSC) to Honolulu (HNL)
- Flights from Raleigh (RDU) to Honolulu (HNL)
- Flights from Renton (RNT) to Honolulu (HNL)
- Flights from San Bernardino (SBD) to Honolulu (HNL)
- Flights from Scottsdale (SCF) to Honolulu (HNL)
- Flights from Seattle (SEA) to Honolulu (HNL)
- Flights from St. George (SGU) to Honolulu (HNL)
- Flights from Salt Lake City (SLC) to Honolulu (HNL)
- Flights from Sacramento (SMF) to Honolulu (HNL)
- Flights from Stella Maris (SML) to Honolulu (HNL)
- Flights from Sofia (SOF) to Honolulu (HNL)
- Flights from St. Louis (STL) to Honolulu (HNL)
- Flights from Sydney (SYD) to Honolulu (HNL)
- Flights from Tartu (TAY) to Honolulu (HNL)
- Flights from Nuku'alofa (TBU) to Honolulu (HNL)
- Flights from Tuxtla Gutierrez (TGZ) to Honolulu (HNL)
- Flights from Tirana (TIA) to Honolulu (HNL)
- Flights from Tampa (TPA) to Honolulu (HNL)
- Flights from Taipei (TSA) to Honolulu (HNL)
- Flights from Tulsa (TUL) to Honolulu (HNL)
- Flights from Vancouver (YVR) to Honolulu (HNL)
- Flights from London (YXU) to Honolulu (HNL)
- Flights from Atlanta to Honolulu
- Flights from Boston to Honolulu
- Flights from Chicago to Honolulu
- Flights from Dallas to Honolulu
- Flights from Denver to Honolulu
- Flights from Houston to Honolulu
- Flights from Las Vegas to Honolulu
- Flights from Los Angeles to Honolulu
- Flights from Minneapolis - St. Paul to Honolulu
- Flights from New York to Honolulu
- Flights from Phoenix to Honolulu
- Flights from Portland to Honolulu
- Flights from San Francisco to Honolulu
- Flights from Seattle to Honolulu
- Flights from Sacramento to Honolulu
- Flights from Maui to Honolulu
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.