Chicago & Hawaii

3/5
10 Nights
  • 3 Nights The Drake Hotel, Chicago
  • Great Location on Miracle Mile
  • 7 Nights Aqua Aloha Surf, Waikiki
  • Located Close to Waikiki Beach
Or call us on 0203 542 8888 our travelplanners are waiting to assist you
SAVE £245 per person

3 Nights The Drake Hotel, Chicago

  • Located in the Heart of Downtown Chicago
  • Close to Lake Michigan

7 Nights Aqua Aloha Surf, Waikiki

  • Value-For-Money Boutique Hotel
  • Located in a Quiet Spot Close to Waikiki Beach, Premium Shopping & Restaurants

Prices

YearDatesPrices From
202408th September - 27th September£2129 per person
3 nights Chicago - 7 nights Hawaii

Add:

  • Applicable resort fee per day to be paid locally
  • Flights from London
  • Regional flights available on request
Based on 2 Adults Sharing
Prices subject to availability at the time of booking

About Chicago & Hawaii

Chicago & Hawaii Twin Centre

Make magical memories on this fantastic a twin centre holiday to Chicago and Hawaii. From the hustle and bustle of the vibrant  “Windy City” to the world famous surfing beaches of Waikiki, Hawaii.   Two iconic destinations all wrapped up into one amazing holiday.

Chicago

World-famous for its friendly hospitality, Chicago is a vast city of fine architecture, relaxing beaches, tranquil parks and a wealth of neighbourhoods to explore. The home of the Blues, Chicago has numerous music venues, lively or relaxed bars and an unrivalled selection of restaurants. Tour the Chicago River by boat or stroll along the 29 miles of lakeside paths taking in the scenery at your leisure. Ride the subway to the many different neighbourhoods each offering sights and sounds unique to its history and modern day culture.

Opened on New Year’s Eve in 1920 and regarded as one of Chicago’s most iconic places to stay the Drake Hotel’s traditional charm and classic décor has given it movie star billing with scenes from “Risky Business”, “What Women Want” and “My Best Friend’s Wedding” on its credit list.

The hotel’s elegant guestrooms and varied dining venues along with a prestigious setting in Chicago’s Gold Coast neighbourhood on the Magnificent Mile close to Lake Michigan’s Oak Street Beach makes the Drake Hotel the perfect jumping off point for exploring all that this vibrant city has to offer.

Hawaii

Breeze into the Aqua Aloha Surf Waikiki open air lobby and feel instantly welcome and relaxed, ready for an amazing Waikiki holiday. The vintage, art-deco surfer ambience of this boutique hotel provides a true holiday feel in a quiet location and only a couple of blocks from the world-famous Waikiki Beach. With all the modern amenities you could want packaged perfectly in a small, intimate setting, the Aqua Aloha Surf Waikiki is a perfect choice for a getaway-from-it-all holiday. Begin your day with a complimentary Hawaiian-style breakfast with a delicious range of island fruits, pastries and rich Kona coffee. Slip into your beachwear and take the short stroll to one of the world’s most famous beaches with miles of sandy shores to enjoy, lay back and watch the world go by or try some of the exciting water sports on the beachfront. With dozens of tempting restaurants and premium shopping nearby there’s plenty to keep you occupied. The Honolulu Zoo, Royal Hawaiian Centre and USS Arizona Memorial are just some of the nearby attractions worth visiting during this spectacular Hawaiian beach break.Tuesday nights at the Aqua Aloha Surf Waikiki Hotel begin with the weekly Manager’s Reception including complimentary signature drink, “The Wipeout”, a great way to begin a night of tropical entertainment. Guest rooms are styled with surf-inspired furnishings and include modern convenient amenities. Complimentary wi-fi, flat-screen TV, microwave, refrigerator and bath amenities provide a comfortable stay or upgrade to a spacious suite or one-bedroom suite with views of the Koolau Mountains from a private lanai.For complete luxury upgrade to the award-winning Hyatt Regency Waikiki Beach Resort & Spa. An idyllic Hawaiian paradise nestled between the world renowned Waikiki Beach and the vibrant city centre. Enjoy superb personalized service, spacious guest rooms where luxury is first and foremost and evening entertainment including Aloha Friday, perfect for limbering up with live music, fire-knife hula dancing and a fabulous Polynesian show. The Na Ho’ola Spa recharges the body and mind or for the more daring surfing lessons are taken on Waikiki Beach.
Call travelplanners on 020 3542 8888 today to book or for more details.

Our Customers Love Us!

Multi centre holiday to Hawaii

Booked a multi centre holiday with Paula, who offered good advice and put a suitable package together for us.
Communication was excellent and the price was very competitive. Thanks Paula!

Hawaiian Dream Trip

From start to finish Tyler was very supportive and flexible with our requests. It took over three weeks for me to finally define my requirements but Tyler was patient throughout and provides us with price updates and changes every step of the way. He explored all the options with us and provided guidance and detailed information. We never felt under pressure to “sign up”, but he was available at all stages.

Top Notch

Ashlee top notch

Excellent Service

Excellent service from chris on booking our holiday. Very professional and informative. Nothing was a problem to him. Highly recommend

Great Service & Knowlege

Sean was excellent, he was extremely patient with us while we decided on hotels for a multi centre USA trip and gave us valuable advice to help us decide. He got us a great deal and we are very excited for our trip now! Thanks again Sean!

Fantastic Company

What can I say other than Travelplanners are the best for organising and booking your holiday. I have used Travelplanners for several years now and would honestly not use anybody else. Travelplanners provide a fantastic, friendly service and will not be beaten on price…..

Excellent service.

Shirin was excellent throughout and got us all of our flights and car hire. She was super helpful and knowledgeable about meeting all of our needs. I’ve recommended her service already and some friends have booked via her as well!

Effortless planning of our road trip

The planning and booking process has been Great Steve Taylor helped us find the right holiday for our 30th Wedding anniversary, looking forward to the holiday!

Booking with travelplanners

We found Paul ( C ) very helpful and understanding when looking into our request for our fly drive holiday to the USA. We have used Paul over numerous years for booking our flights too the United States..

Highly recommend Travelplanners!

Stephen helped us to book our 2 week holiday to Orlando, and the whole process was seamless from start to finish! Stephen was extremely knowledgeable and was more than happy to give us some “top tips” along the way…he stayed in contact via email, answering my countless questions (sorry!!) and managed to find us the very best possible deal……

A journey of thousands of miles begins with TravelPlanners.…

This travel company was recommended to me by a work colleague over a discussion about road trips in California. I had tried for months comparing prices with quite a few travel operators for travel to California in 2025. I was advised to try TravelPlanners for their competitive prices, and personal customer services…..

I have used travelplanners before

I have used travelplanners before without any problems but the service given by Adam was above and beyond. He answered all my questions, made multiple changes without any problem and found us a very very good price. I would not hesitate to use again. Thank you.

Fantastic

Tyler is your man! After having tried the high street and ‘main stream’ travel agents and tried to have a go at building our own holiday with little success I decided to email TravelPlanners late one night with a rough outline of our hopes for a multi destination trip to America…..

We had a great experience booking our….

We had a great experience booking our family holiday to Orlando with your agent Stephen Metcalfe. He went above and beyond with recommendations and trying to get the price right for us – thank you!

Great company, organised our holiday perfectly.

Paula was wonderful and arranged all aspects of our trip for us, apart from our flight home as we were using our points. She made sure our flights connect without too much hanging around and booked us two great hotels for when we get off QM2 and travel further. Great service.

Excellent service by Chris Kelly

I used travel planners to help me with my booking to Dubai and Mauritius for new year. His knowledge and expertise was very valuable and will definitely be using travel planners again in the future

Great holiday and itinerary

Our holiday was tailored to the needs of all in our party, the itinerary was just right and the advice that came with it from Adam was perfect!
We will be using them again once we have saved up again!

California holiday

David from Travel Planners was excellent in planning an itinerary for my friend and I on our holiday to California. He asked us where we wanted to stay and found good, reasonably priced hotels which were central to where we needed to be….

Multi centre holiday

Have just booked a multi centre holiday to the USA a year in advance, Paul Corderoy has gone out of his way to make sure we are happy with all details, changing little things to accommodate all our wishes. Very knowledgeable, will definitely use Travelplanners again.

Great

Again Travel planners came up trumps! We have used travel planners for all our visits to the states to visit family, they always beat my best quotes (You have to look around when you are on a budget!) And I always know we are in safe hands…So much so we are already looking at going back next year, the time we had just wasn’t enough this year after not seeing the family for nearly 7! Would highly recommend Travel planners and their team!

Excellent

Chris was excellent, always on hand to give me a call, answer all my questions and provide me with multiple quotes so we could decide on the best deals. Thanks Chris!