$196 Cheap flight deals from Chicago (CHI) to Haleiwa (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 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.
ORD
O'Hare Intl.
HNL
Daniel K. Inouye Intl.
$479 Roundtrip, found 10 hours ago
$479
Roundtrip
found 10 hours ago
MDW
Midway Intl.
HNL
Daniel K. Inouye Intl.
$592 Roundtrip, found 5 days ago
$592
Roundtrip
found 5 days ago
RFD
Greater Rockford
HNL
Daniel K. Inouye Intl.
$1,194 Roundtrip, found 20 hours ago
$1,194
Roundtrip
found 20 hours ago
Airfares from $196 One Way, $360 Round Trip from Chicago to Haleiwa
Prices starting at $360 for return flights and $196 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.
ORD
Chicago
HNL
Oahu
$360 Roundtrip, found 5 hours ago
$360
Roundtrip
found 5 hours ago
ORD
Chicago
HNL
Oahu
$369 Roundtrip, found 8 hours ago
$369
Roundtrip
found 8 hours ago
ORD
Chicago
HNL
Oahu
$370 Roundtrip, found 2 hours ago
$370
Roundtrip
found 2 hours ago
ORD
Chicago
HNL
Oahu
$374 Roundtrip, found 13 hours ago
$374
Roundtrip
found 13 hours ago
ORD
Chicago
HNL
Oahu
$379 Roundtrip, found 2 days ago
$379
Roundtrip
found 2 days ago
Haleiwa economy flight packages
Price found within the past 48 hours. Click for updated prices.
4.5-star property
Sheraton Waikiki Beach Resort
9.2/10 Wonderful! (2,732 reviews)
Feb 6 - Feb 9
3 night stay
Chicago (CHI) to Honolulu (HNL)
Alaska Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,457, price is now $937 per person
$937
per person
found 1 day ago
When we got into our family room, and I crawled into my bed it was wet. The sheets were wet with urine from a previous guest before us. The urine had even soaked into the mattress there was so much. I called housekeeping and after 20 minutes I called again because nobody responded.
What was most upsetting was that the general manger on duty the next day was not apologizing and saying sorry, he offered to give us a 200.00 food credit.
Our family has never been to Hawaii and we paid a lot of money to stay at this beautiful hotel.
I expected more from the management and was extremely disappointed in how they tried to compensate for a gross error in preparing our room.
If the manager would have said, he was very sorry and offered to upgrade our room or even offer to cover one of our four nights that would have been respectable service.
He did end up giving us a food credit equal to one night, but I had to almost beg and plead with him.
Reviewed on Dec 6, 2025
3.5-star property
Ala Moana Hotelcondo by Luana Vacation Rental
7.4/10 Good! (256 reviews)
Feb 13 - Feb 17
4 night stay
Chicago (CHI) to Honolulu (HNL)
United • Roundtrip • Coach
Save 100% on your flight
Price was $2,645, price is now $1,394 per person
$1,394
per person
found 1 day ago
Room should be cleaned every couple of days
Reviewed on Apr 30, 2022
3.5-star property
Paradise Bay Resort
8.8/10 Excellent! (1,002 reviews)
Feb 25 - Mar 2
5 night stay
Chicago (CHI) to Honolulu (HNL)
United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,648, price is now $990 per person
$990
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
Haleiwa 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 24 - Mar 1
5 night stay
Chicago (CHI) to Honolulu (HNL)
Alaska Airlines • Non-stop roundtrip • FirstClass
Price was $2,954, price is now $2,170 per person
$2,170
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
Waikiki Resort Hotel
8.6/10 Excellent! (2,635 reviews)
Feb 24 - Mar 1
5 night stay
Chicago (CHI) to Honolulu (HNL)
Alaska Airlines • Non-stop roundtrip • FirstClass
Price was $3,285, price is now $2,227 per person
$2,227
per person
found 1 day ago
It was a great place to stay
Reviewed on Nov 21, 2025
3.5-star property
Paradise Bay Resort
8.8/10 Excellent! (1,002 reviews)
Feb 24 - Mar 1
5 night stay
Chicago (CHI) to Honolulu (HNL)
Alaska Airlines • Non-stop roundtrip • FirstClass
Price was $3,540, price is now $2,443 per person
$2,443
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 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
Need bargain Chicago to Haleiwa flights in an instant? Find discount air tickets at Orbitz! At Orbitz, we don’t need to run sales to provide you with low prices on flights.
Find Guaranteed Low Prices wWth Cutting-Edge Mobile Tools
When you’re searching for Chicago to Haleiwa flights in a hurry, just use our mobile app. Once you’ve booked your air ticket, you can rely on our app to provide you with further details on your trip and to help you to find exclusive offers on hotels we know you’ll love to stay in.
Accumulate Miles and Enjoy Greater Discounts
If you are part of a frequent flyer program, you can also earn miles and points with the qualifying flights you book with Orbitz. Enjoy great deals on your Chicago to Haleiwa flights and get points and miles in return.
Stay Informed With Personalized Flight Alerts
Orbitz is the top source for low cost flights from Chicago to Haleiwa. We pride ourselves on not only offering you value for money but providing you with personal travel care. This is why we send you flight alerts about your travel plans at no added cost when you provide us with your email address or phone number.
See Significant Savings That Fit Your Schedule
We make it as easy as possible for you to book great deals on flights from Chicago to Haleiwa. You won’t be forced to compromise on your schedule—you can pick Chicago to Haleiwa flights that suit your needs.
Flights from Chicago
- Chicago to Orlando
- Chicago to Houston
- Chicago to New York
- Chicago to Phoenix
- Chicago to Dallas
- Chicago to London
- Chicago to Los Angeles
- Chicago to New Orleans
- Chicago to Rome
- Chicago to Paris
- Chicago to Washington
- Chicago to Toronto
- Chicago to San Francisco
- Chicago to Cleveland
- Chicago to Detroit
- Chicago to Montreal
- Chicago to Sacramento
- Chicago to Kansas City
- Chicago to Hartford
- Chicago to Atlantic City
Haleiwa Airports
More Destinations
- Flights from Al-Aqiq (ABT) to Kapolei (JRF)
- Flights from Ancona (AOI) to Kapolei (JRF)
- Flights from Napa (APC) to Kapolei (JRF)
- Flights from Alpena (APN) to Kapolei (JRF)
- Flights from Ashgabat (ASB) to Kapolei (JRF)
- Flights from St. George's (BDA) to Kapolei (JRF)
- Flights from Dnepropetrovsk (DNK) to Kapolei (JRF)
- Flights from Edinburgh (EDI) to Kapolei (JRF)
- Flights from Guangyuan (GYS) to Kapolei (JRF)
- Flights from Hurghada (HRG) to Kapolei (JRF)
- Flights from Chandigarh (IXC) to Kapolei (JRF)
- Flights from Leh (IXL) to Kapolei (JRF)
- Flights from Kaben (KBT) to Kapolei (JRF)
- Flights from Kahramanmaras (KCM) to Kapolei (JRF)
- Flights from Kumamoto (KMJ) to Kapolei (JRF)
- Flights from Pohang (KPO) to Kapolei (JRF)
- Flights from Lampedusa (LMP) to Kapolei (JRF)
- Flights from Moorea (MOZ) to Kapolei (JRF)
- Flights from Nuqui (NQU) to Kapolei (JRF)
- Flights from Nyaung-U (NYU) to Kapolei (JRF)
- Flights from Plovdiv (PDV) to Kapolei (JRF)
- Flights from Parkersburg (PKB) to Kapolei (JRF)
- Flights from Pondicherry (PNY) to Kapolei (JRF)
- Flights from Poznan (POZ) to Kapolei (JRF)
- Flights from Pikeville (PVL) to Kapolei (JRF)
- Flights from Taichung (RMQ) to Kapolei (JRF)
- Flights from Corn Island (RNI) to Kapolei (JRF)
- Flights from Savannah (SAV) to Kapolei (JRF)
- Flights from Shannon (SNN) to Kapolei (JRF)
- Flights from Szczecin (SZZ) to Kapolei (JRF)
- Flights from Toulouse (TLS) to Kapolei (JRF)
- Flights from Tainan (TNN) to Kapolei (JRF)
- Flights from Mayne Island (YAV) to Kapolei (JRF)
- Flights from Yantai (YNT) to Kapolei (JRF)
- Flights from Sudbury (YSB) to Kapolei (JRF)
- Flights from St. John's (YYT) to Kapolei (JRF)
- Flights from San Francisco to Honolulu
- Flights from Austin to Oahu
- Flights from Boston to Oahu
- Flights from Chicago to Oahu
- Flights from Denver to Oahu
- Flights from Detroit to Oahu
- Flights from Ho Chi Minh City to Oahu
- Flights from Houston to Oahu
- Flights from Los Angeles to Oahu
- Flights from Miami to Oahu
- Flights from Minneapolis - St. Paul to Oahu
- Flights from New York to Oahu
- Flights from Phoenix to Oahu
- Flights from Portland to Oahu
- Flights from Salt Lake City to Oahu
- Flights from San Antonio to Oahu
- Flights from Seattle to Oahu
- Flights from Vancouver to Oahu
- Flights from Washington to Oahu
- Flights from Newark to Oahu
- Flights from Tivat to Kapolei
- Flights from South Lake Tahoe to Kapolei
- Flights from Kenai to Kapolei
- Flights from Excursion Inlet to Kapolei
- Flights from Key West to Kapolei
- Flights from Winston-Salem to Kapolei
- Flights from Hailey to Kapolei
- Flights from Kwajalein to Kapolei
- Flights from McAllen to Kapolei
- Flights from Mili to Kapolei
- Flights from Marathon to Kapolei
- Flights from Athens to Kapolei
- Flights from Sleetmute to Kapolei
- Flights from Comox to Kapolei
- Flights from Birmingham to Kapolei
- Flights from Halifax to Kapolei
- Flights from Savannah to Kapolei
- Flights from Incheon to Kapolei
- Flights from Itajai to Kapolei
- Flights from Riga to Kapolei
- Flights from San Javier to Kapolei
- Flights from Ji'an to Kapolei
- Flights from Grande Prairie to Kapolei
- Flights from Zhengzhou to Kapolei
- Flights from Karmoy to Kapolei
- Flights from Belgrade to Kapolei
- Flights from Ballasalla to Kapolei
- Flights from Dharavandhoo to Kapolei
- Flights from Baños del Inca to Kapolei
- Flights from West Chicago to Kapolei
- Flights from Kapolei to Kapolei
- Flights from Swansea to Kapolei
- Flights from Boston to Waialua
- Flights from Chicago to Waialua
- Flights from Denver to Waialua
- Flights from Kansas City to Waialua
- Flights from Los Angeles to Waialua
- Flights from Miami to Waialua
- Flights from New York to Waialua
- Flights from Salt Lake City to Waialua
- Flights from Washington to Waialua
- Flights from Osaka to Waialua
- Flights from Newark to Waialua
- Flights from Houghton to Waialua
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.