Package Deals from Chicago to Kailua-Kona from $2592

Kalani Oceanside Retreat features sea views, free WiFi and free private parking, located in Pahoa, 1.4 miles from Kehena Black Sand Beach. A fridge and microwave are also featured, as well as an electric tea pot. Guests at the lodge can enjoy hiking nearby, or make the most of the garden. Lava Tree State Park is 14 miles from Kalani Oceanside Retreat, while Lava Tree State Monument is 17 miles from the property. Hilo International Airport is 34 miles away, and the property offers a paid airport shuttle service.

Located within a 8-minute walk of Onekahakaha Beach and 3.3 miles of The Pacific Tsunami Museum, Aaron’s cottage provides rooms in Hilo. With a garden, the 3-star hotel has air-conditioned rooms with free WiFi, each with a private bathroom. Each room comes with a patio. At the hotel, each room includes a closetand a balcony with a garden view. Selected rooms contain a kitchen with a fridge and a microwave. Guest rooms in Aaron’s cottage are equipped with a flat-screen TV and free toiletries. Lyman Museum & Mission House is 3.6 miles from the accommodation, while University of Hawaii, Hilo is 3.9 miles away. Hilo International Airport is 1.2 miles from the property.

Positioned on the Big Island of Hawaii's Kohala Coast, minutes from Hapuna Beach Park, the Paniolo Greens Resort offers fully furnished villas, an outdoor pool with a children's wading area, and a fitness center. Free WiFi is available throughout the property. The villas include fully equipped kitchens, private balconies, a seating area, a washing machine and dryer, a TV with cable channels, a DVD player, and a CD player. The private bathroom includes a hairdryer and ironing facilities. The Paniolo Greens Resort offers a tranquil location with easy access to many restaurants and popular sites, including a number of top-rated golf courses. Volcano National Park, Waipio Valley and the North Shore are also a short distance away. Guests can enjoy a variety of on-site recreational activities, including Hula lessons and lei making.

Located in Hilo, a 7-minute walk from Onekahakaha Beach and 3.3 miles from The Pacific Tsunami Museum, Arnott's Lodge & Hiking Adventures has accommodations with free WiFi, air conditioning, a terrace and barbecue facilities. All units come with a fridge, microwave, a coffee machine, a stovetop and electric tea pot. There's a private bathroom with shower in all units, along with free toiletries and a hairdryer. After a day of hiking or cycling, guests can relax in the garden or in the shared lounge area. Lyman Museum & Mission House is 3.6 miles from the lodge, while University of Hawaii, Hilo is 3.9 miles from the property. Hilo International Airport is 1.2 miles away.

Offering free WiFi in public spaces, Hilo Reeds Bay Hotel is set in Hilo. Free private parking is available on site. The property is located in a 3-story building with rooms only accessible via stairs. All of the nonsmoking rooms at Hilo Reeds Bay Hotel are equipped with a flat-screen TV and feature a microwave, a refrigerator and coffee making facilities. Kitchenware, an electric skillet and a toaster are also provided. All rooms have a private bathroom and housekeeping is included. Laundry facilities are available on-site at Hilo Reeds Bay Hotel. A number of activities is offered in the area, such as golfing, snorkeling and windsurfing. The Pacific Tsunami Museum is 1.5 mi from Hilo Reeds Bay Hotel, while East Hawaii Cultural Center is 1.6 mi away. The nearest airport is Hilo Airport, 1.2 mi from the property.

A good location for a hassle-free holiday in Hilo, Hilo Vacation Rental is a guest house surrounded by views of the mountain. The property features a garden, barbecue facilities, and parking on-site among other facilities. The property is around 1.3 miles from Rainbow Falls, 2 miles from Lyman Museum & Mission House, and 2.3 miles from The Pacific Tsunami Museum. Guests can enjoy garden views. Featuring free Wifi, the units have a washing machine and a flat-screen TV with cable channels. At the guest house, units have bed linen and towels. Guests can also relax in the shared lounge area. University of Hawaii, Hilo is 2.9 miles from the guest house, while Pana'ewa Rainforest Zoo is 7.3 miles from the property. Hilo International Airport is 3.7 miles away.

Offering a garden, Hawaiian Sanctuary Eco Retreat Center provides accommodations in Pahoa. This farm stay offers free private parking and a 24-hour front desk. Guests can use the spa and wellness center with a sauna, hot tub, and wellness packages, as well as an outdoor swimming pool. Some accommodations include a terrace with garden views, a fully equipped kitchenette, and a private bathroom with walk-in shower. At the farm stay, units come with bed linen and towels. À la carte and continental breakfast options with local specialities, fruit, and juice are available. There is an on-site coffee shop. Yoga classes and fitness classes are provided at the fitness room in house. Guests at the farm stay will be able to enjoy activities in and around Pahoa, like hiking and walking tours. The farm stay has a picnic area where you can spend the day outdoors. Lava Tree State Park is 1.2 miles from Hawaiian Sanctuary Eco Retreat Center, while Lava Tree State Monument is 3.3 miles from the property. Hilo International Airport is 21 miles away.

Located on Kona Coast in Hawaii, this tropical garden resort is less than one mile from Kahaluu Beach. It features a restaurant, tennis court and villas with a fully-equipped kitchen. The resort has 2 outdoor pools, 3 hot tubs. Kona Coast Resort offers spacious, air-conditioned villas furnished with a dining room and a living room with sofa bed and cable TV. Each villa includes a washer/dryer and private patio. Kona Coast Resort Front Desk is open from 6:00am to 11:00pm. The Island Activities desk, open 7 days a week during business hours, is happy to arrange activities including hula dancing lessons and diving excursions. Guests have access to the volleyball courts and tennis courts as well. American and Hawaiian cuisine is served at Sunset Terrace Kona Coast. Guests can work out in the fitness center and use the barbecue facilities. Guests with children can take advantage of the playground. Kona Country Club, a 18-hole golf course, is adjacent to the Kona Coast. Kona International Airport is 13.7 miles from the resort.

Providing garden views, Aloha Junction Bed and Breakfast -Minutes away from Hawaii Volcanoes National Park in Volcano provides accommodations and a shared lounge. There's a private entrance at the vacation home for the convenience of those who stay. There's a sun terrace and guests can access free Wifi and free private parking. All units include a seating area, a flat-screen TV with streaming services, a fully equipped kitchenette, a dining area, and a private bathroom equipped with a hair dryer, while some rooms feature a balcony or a patio. A microwave, a fridge, and kitchenware are also provided, as well as a coffee machine. At the vacation home, all units are equipped with bed linen and towels. Guests at the vacation home can enjoy cycling and hiking nearby, or make the most of the garden. Kilauea is 10 miles from Aloha Junction Bed and Breakfast -Minutes away from Hawaii Volcanoes National Park, while Pana'ewa Rainforest Zoo is 24 miles away. Hilo International Airport is 27 miles from the property.

A good location for a hassle-free getaway in Hilo, Hilltop Legacy Vacation Rental is a vacation home surrounded by views of the garden. The property features a garden, barbecue facilities, and parking on-site among other facilities. Housed in a building dating back to 1934, this vacation home is 2.8 miles from University of Hawaii, Hilo and 7.2 miles from Pana'ewa Rainforest Zoo. Every room includes a flat-screen TV with streaming services. At the vacation home, every unit includes a desk. Every room is fitted with a coffee machine, a private bathroom, and free Wifi, while certain rooms are fitted with a balcony and some have sea views. At the vacation home, every unit is fitted with bed linen and towels. You can play billiards and tennis at this 3-star vacation home, and the area is popular for snorkeling and diving. Guests at the vacation home can enjoy fishing and hiking nearby, or make the most of the sun terrace. Popular points of interest near Hilltop Legacy Vacation Rental include Lyman Museum & Mission House, The Pacific Tsunami Museum, and Rainbow Falls. Hilo International Airport is 3.1 miles from the property.

Mango Sunset Bed and Breakfast enjoys a location in Kailua-Kona, 6.9 miles from Kaloko-Honokohau National Historic Park and 19 miles from Kealakekua Bay. This property offers access to a terrace, free private parking, and free Wifi. Guests can access the bed and breakfast via private entrance. At the bed and breakfast, every unit is fitted with a wardrobe. There's a private bathroom with walk-in shower and a hair dryer in each unit, along with free toiletries. At the bed and breakfast, each unit includes bed linen and towels. Guests at the bed and breakfast can enjoy hiking nearby, or make the most of the garden. Kealakekua Bay State Historical Park is 22 miles from Mango Sunset Bed and Breakfast, while Pu'uhonua o Honaunau National Historical Park is 28 miles from the property. Ellison Onizuka Kona International at Keāhole Airport is 5 miles away.

Offering free WiFi, Holiday Inn Express & Suites Kailua-Kona is located in Kailua-Kona. Featuring a 24-hour front desk, this property also provides guests with an outdoor pool. The hotel has a fitness center and a concierge service. Guest rooms comes with air conditioning, a flat-screen TV with satellite channels, a microwave, a coffee machine, a bath or shower, free toiletries and a desk. The rooms have a private bathroom with a hair dryer. All guest rooms include bed linen. A continental breakfast is served at the property. Kaloko-Honokohau National Historic Park is 3.5 miles from the hotel.

Hilo Bay Oceanfront Bed and Breakfast offers accommodations in Hilo, a 8-minute walk from The Pacific Tsunami Museum and 0.9 miles from Lyman Museum & Mission House. This bed and breakfast features free private parking and free shuttle service. The accommodation offers a shared kitchen, full-day security, and luggage storage for guests. At the bed and breakfast, the units are equipped with a wardrobe. Each room is fitted with a coffee machine, a private bathroom, and free Wifi, while some rooms have a balcony and some have sea views. At the bed and breakfast, each unit is fitted with bed linen and towels. À la carte and continental breakfast options with warm dishes, pancakes, and fruit are available. There is an on-site snack bar, and during warmer months you can make use of the barbecue facilities. Guests at the bed and breakfast can enjoy snorkeling nearby, or make the most of the garden. Rainbow Falls is 2 miles from Hilo Bay Oceanfront Bed and Breakfast, while University of Hawaii, Hilo is 2.5 miles from the property. Hilo International Airport is 2.5 miles away.

Club Wyndham Kona is an authentic resort designed in the style of an 1880's Hawaiian village. Palm thatched roofs, rustic bungalows and paths lie amid flower and fruit bearing trees, palms and tropical vegetation. It is an easy walk or drive to Kailua-Kona Village, ocean activities and exciting night life. The units offer a living room with a flat-screen TV, a dining area with chairs and a table, as well as a fully equipped kitchen. In-unit laundry facilities are also available. The resort offers two outdoor swimming pools with a children's pool, a picnic area with BBQ facilities, two outdoor hot tubs, and a fitness area with exercise equipment. Keauhou Shopping Center is 1 mi from Hotel Kona Hawaiian Hotel, while Hulihee Palace is 1.1 mi away. Kona International Airport is 8.7 mi from the property.

A short distance from breathtaking waterfalls and within driving distance of Hawaii National Volcanoes Park, SCP Hilo Hotel offers comfortable accommodations and a swimming pool. WiFi and guest parking are available throughout the property. Guests can also enjoy locally sourced food and drink from Provisions Market. Some rooms feature a balcony, all rooms includes a refrigerator, air conditioning and a ceiling fan, ironing facilities, and an private bathroom complete with a hairdryer. An outdoor swimming pool is available to guests, as well as on-site laundry facilities, fitness room with Peloton bikes, complimentary bicycles and standup paddle boards. Guests at the SCP Hilo Hotel can enjoy on-site dining at the Coconut Grill. The SCP Hilo Hotel is located only a short distance from the Rainbow and Akaka Falls. The Hilo International Airport is 2.3 mi away from the property.

Located within 2.3 miles of The Original King Kamehameha Statue and 5.6 miles of Kohala Historical Sites State Monument, Kohala Village INN has rooms with air conditioning and a private bathroom in Hawi. The property is around 13 miles from Pu'Ukohola Heiau National Historical Park, 21 miles from Hapuna Golf Course and 2.3 miles from Kamehameha Park. The property provides room service and free WiFi. At the inn, the rooms come with a closet. The private bathroom is equipped with a shower and a hairdryer. All rooms at Kohala Village INN come with a flat-screen TV with cable channels. Big Island Eco Adventures Biea is 4.8 miles from the accommodation, while Mookini Heiau is 5.6 miles from the property. Waimea-Kohala Airport is 24 miles away.

Located on an 18-acre oceanfront property, these Kona apartments boast 3 swimming pools and 2 tennis courts on site. They offer fully equipped kitchens. Kahaluu Beach Park is 1 mile away. A cable TV and a washer and tumble dryer are included in each spacious apartment at Castle Kanaloa at Kona. All of the comfortable apartments feature ceiling fans and balconies with views. Ironing facilities, an in-room safe and a hairdryer are provided in each unit. Guests of Kanaloa can relax in the recreation area and BBQ facilities are featured throughout the property. A tour desk is available to assist guests with day trips in the local area. Keauhou Shopping Village is 15 minutes' drive from Castle Kanaloa at Kona. Kohanaiki Golf & Ocean Club is 12 miles away. Kona International Airport is 30 minutes’ drive away.

Offering massage services, Waikoloa Beach Villas G2 offers accommodations in Waikoloa. The air-conditioned accommodation is a 14-minute walk from Anaeho'omalu Beach, and guests can benefit from on-site private parking and complimentary Wifi. The villa features an outdoor swimming pool and an elevator. Featuring a balcony with mountain views, this villa also comes with a satellite TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 2 bathrooms with a bath and a hair dryer. For added privacy, the accommodation features a private entrance. Sightseeing tours are available in the area. Guests can relax in the garden at the property. Kaloko-Honokohau National Historic Park is 22 miles from the villa, while Kohala Historical Sites State Monument is 30 miles from the property. Ellison Onizuka Kona International at Keāhole Airport is 18 miles away.

Featuring 2 onsite restaurants, Courtyard by Marriott King Kamehameha's Kona Beach Hotel offers rooms with a flat-screen TV and a balcony. The Kona Beach Hotel is within 5 minutes' walk of the Hulihe`e Palace Museum and has seasonal Luaus. The rooms include a refrigerator and a coffee machine with Kona coffee, as well as air conditioning and an in-room safe. The King Kamehameha’s Kona Beach Hotel rooms are modern with island and nature inspired décor. Honu's on the Beach Restaurant is open daily for breakfast and dinner. The Billfish Bar is located near the pool and features refreshments and a light menu. Guests can shop in the air conditioned mall on the ground floor of the hotel. The King Kamehameha’s Kona also has a tour desk and activities desk with information on activities and events in and around the hotel. King Kamehameha’s Kona Beach is within 1 minutes' walk of Atlantis Adventures Kona, an underwater tour. The Old Kona Airport State Park is within 15 minutes' walk of the Courtyard by Marriott King Kamehameha's Kona Beach Hotel.

Located on the coastline of Hilo Bay, the Grand Naniloa Hilo, a DoubleTree by Hilton is 30 mi from Hawaii Volcanoes National Park. All rooms have free WiFi. Guest rooms offer garden, ocean, or harbor views of Hilo Bay, Hamakua Coast, or Hilo Harbor. Each room is equipped with a flat-screen TV and a refrigerator, and bathrooms are finished with German limestone. Suites boast a kitchenette. The Grand Naniloa Hilo, a DoubleTree by Hilton features an outdoor swimming pool and sundeck. The Naniloa Golf Course, located within the hotel grounds and adjacent to the Grand Naniloa Hotel, offers a free round of golf daily to guests. An on-site restaurant is open for breakfast and dinner, and a lobby bar and lounge is open nightly. The 24-hour front desk offers fresh coffee and tea and is run by a multilingual staff. The Ka Lihikai restaurant is open for breakfast, lunch, and dinner. The restaurant sources fresh local seafood catches daily and embodies local-Hawaiian cuisine. The Hilo International Airport and Hilo town center are 2 mi from the Grand Naniloa Hilo, a DoubleTree by Hilton. The hotel is less than 0.9 mi from Coconut Island Park.

This resort offers a multi-level fantasy pool with a 200-foot water slide, manta-ray viewing, and sweeping views of the Pacific Ocean. Guest activities include yoga, lei making, hula lessons, ukulele lessons, and cultural tours of the historic fishing village on property. All occurrences on this site. Spa is temporarily closed for renovations.

Located on The Big Island of Hawaii, this accommodations is less than 5 minutes’ drive to Volcanoes National Park and Volcano Art Center Gallery. Free Wi-Fi is provided in all rooms. Offering a fireplace, each room also includes a refrigerator, tea and coffee-making facilities and an private bathroom at Volcano Village Estates. Select rooms features a bar area or a bay window. Guests can enjoy a stroll through the garden at Cottage Hale Ohia. Hilo International Airport and Black Sand Beach are 30 miles away.

Providing a garden, At the Craters Edge provides accommodations in Volcano. This property offers access to a terrace, free private parking, and free Wifi. The guest house has an outdoor fireplace and a hot tub. All units come with a seating area, a flat-screen TV with streaming services, and a private bathroom with bathrobes, walk-in shower, hot tub, and bidet. A balcony with an outdoor dining area and garden views is offered in all units. At the guest house, each unit is equipped with bed linen and towels. There is an on-site snack bar. Kilauea is 12 miles from the guest house, while Pana'ewa Rainforest Zoo is 24 miles away. Hilo International Airport is 26 miles from the property.

A 18-minute walk from Mauna Lani Beach in Waikoloa, Mauna Lani Point features accommodations with access to a sauna, hot tub, and spa facilities. Both free Wifi and parking on-site are accessible at the vacation home free of charge. The Original King Kamehameha Statue is 31 miles from the vacation home, and Hapuna Golf Course is 8.5 miles away. Each room is fitted with a private bathroom, while some rooms have a fully equipped kitchen with a dishwasher. Guests at Mauna Lani Point will be able to enjoy activities in and around Waikoloa, like cycling. Kaloko-Honokohau National Historic Park is 26 miles from the accommodation, while Kohala Historical Sites State Monument is 29 miles from the property. Ellison Onizuka Kona International at Keāhole Airport is 21 miles away.

Located on the Kohala Coast, Waikoloa Beach Marriott Resort & Spa overlooks the Anaeho’omalu Bay on the Big Island. The hotel offers an on-site spa, nature walks, and lei-making. The rooms include an in-room safe, a TV with cable channels, a refrigerator and a coffee machine. The rooms feature floor-to-ceiling windows and a seating area. The Waikoloa Beach Marriott Resort & Spa offers an outdoor infinity pool, water sports rental, and a tour desk for guest convenience. The hotel features an outdoor pool, a children’s pool and a hot tub. Guests can work out in the gym or work in the business center. Guests at the Waikoloa Beach Marriott Resort & Spa can dine at the Hawaii Calls Restaurant, which features tropical drinks and Pacific Rim cuisine, or the Sunset Luau, offering an authentic Polynesian show every Monday and Wednesday. The Kona Coffee Shop offers coffee and a quick breakfast.

The Hilton Waikoloa Village is located on 62 oceanfront acres in the Waikoloa Beach Resort. The hotel offers a museum walkway, tennis, golf, luau dinner show, and a full-service spa. Guest rooms at the Waikoloa Village Hilton offers views of the tropical gardens, Pacific Ocean and Waiulua Bay. Flat-screen TVs and coffee makers are also included in each room. Hilton Waikoloa Village features 3 swimming pools, including one with a 174 foot water slide. A saltwater lagoon and dolphin encounter are also offered. The hotel also includes on-site stores, several gourmet restaurants, trams that transport guests from the lobby to the towers, and a museum walkway with art from around the Pacific.

Offering a year-round outdoor pool and hot tub, Holualoa Inn is located in Holualoa in the The Big Island Region. Offering free WiFi, this accommodations is 2.7 mi from Kailua-Kona. Select units at this accommodations have a hot tub, while other units provide guest bathrobes and slippers. Each unit features a balcony or a patio with garden, ocean or pool views. For your comfort, each private bathroom includes free toiletries and a hairdryer. BBQ facilities are available to guests of Holualoa Inn. You will find a gift shop at the property. Free guest parking is provided. The nearest airport is Kona International Airport, 9.9 mi from the property.

Providing an oceanfront location directly on Hapuna Beach, The Westin Hapuna Beach Resort offers easy access to a variety of recreational activities, including an 18-hole golf course, along with a family-friendly atmosphere. All rooms feature a private lanai with an ocean view, air conditioning, a seating area, internet access, a refrigerator, a coffee machine, and a flat screen TV with cable channels. The private bathroom includes free toiletries, a hairdryer, bathrobes, and slippers. Guests can also enjoy dinner at the sister property, Mauna Kea Beach Hotel. A complimentary dining shuttle operates in the evening. Additional amenities at The Westin Hapuna Beach Resort include a children's activity program, a full-service spa treatments and modern fitness facilities. Popular attractions and activities, including snorkeling, scuba diving and sailing are easily accessible from the Hapuna Beach Hotel.

Featuring beachfront location and a top-rated golf course, the Mauna Kea Beach Hotel, Autograph Collection offers a fresh flower lei greeting upon arrival, as well access to the array of water activities, on-site bars and restaurants, and private beach services. All guest rooms offer a private lanai with views of the ocean or the golf course. All guest rooms also include nightly turn-down service, a built-in entertainment center with a flat screen TV and an electronics charging station, a refrigerator, and a coffee machine. The private bathrooms provide free toiletries, a hairdryer, bathrobes, and slippers. The Art of Mauna Kea, a beautiful coffee-table book about Mr. Rockefeller's art collection, is also available for the guest's enjoyment. The Mauna Kea Beach Hotel's on-site restaurant, Manta, offers a daily breakfast buffet and dinner made with locally sourced food. There is also Copper Bar, which hosts the cocktail and happy hour, as well as dinner. Guests have access to the restaurants at the Westin Hapuna Beach Resort, the sister property. A complimentary dining shuttle operates in the evening. Guests can enjoy supervised children's activities, Hawaiian culture experiences and a number of spa services. Guests can also take advantage of the 11 on-site tennis courts. The on-site tour desk at the Mauna Kea Beach Hotel, Autograph Collection can also help arrange area tours and excursions.

Offering massage services, Waikoloa Beach Villas M2 offers accommodations in Waikoloa. The air-conditioned accommodation is a 14-minute walk from Anaeho'omalu Beach, and guests can benefit from on-site private parking and complimentary Wifi. The accommodation provides an elevator, an ATM, and organizing tours for guests. Providing mountain views, this vacation home also provides guests with a satellite TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 2 bathrooms with a bath and a hair dryer. The accommodation is non-smoking. Guests can spend time in the water park or enjoy the outdoor swimming pool and garden at the vacation home. Kaloko-Honokohau National Historic Park is 22 miles from Waikoloa Beach Villas M2, while Kohala Historical Sites State Monument is 30 miles away. Ellison Onizuka Kona International at Keāhole Airport is 18 miles from the property.