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Quote TMH1153
Selected dates in 2026
2 adults and 2 children
Tell us your requirements and we can send you multiple holiday choices using our discounted and exclusive offers
This exciting itinerary blends the vibrant culture of Chicago, the laid-back paradise of Hawaii and the charm of San Francisco. A holiday designed to give you the best of city life, iconic landmarks and tropical island escapes, all in one unforgettable journey.
Begin your adventure in the Windy City with 3 nights at The Conrad, by Hilton Chicago, perfectly located within sight of the Magnificent Mile. Known for its world-class shopping, restaurants and architectural landmarks, Chicago is a city that surprises at every turn.
Whether you love architecture, music, or culture, Chicago provides an unforgettable start to your holiday.
Fly onwards to Oahu and spend 7 nights at the stunning Turtle Bay Resort on the island’s beautiful North Shore. With a fully insured car included, you can explore at your own pace – from hidden coves and lush hiking trails to the vibrant energy of Waikiki Beach.
The North Shore is known as the surfing capital of the world, offering a mix of adventure, natural beauty and true Hawaiian hospitality.
End your journey with 3 nights at the Hyatt Centric Fisherman’s Wharf. With a prime location, you’re close to the city’s most famous attractions, stunning waterfront views and world-class dining.
San Francisco offers the perfect blend of charm, culture and scenic beauty to complete your multi-centre holiday.
Get in touch with our team today to begin planning your Hawaii, Chicago and San Francisco holiday.
All offers and prices are subject to availability at the time of booking and our terms and conditions. Selected travel dates apply. Offers are based on maximum occupancy for accommodation and based on a per person price unless stated otherwise. Resort fees/entrance fees are not included.
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All Tailormade Hawaii holidays are designed and created specifically for you. We have numerous suggestions and great offers to choose from.
Please advise us of your requirements and our specialists will create your unique holiday using our discounted prices.
Book with confidence – we are fully covered by ABTA (F8106), ATOL (4151) and IATA for your complete protection.