Perfectly pairing Chicago’s vibrancy with Aruba’s turquoise waters, this 10-night itinerary combines the American Midwest’s most iconic city with a week-long relaxation in the blissful Caribbean.
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Itinerary
3 Nights – Chicago
7 Nights – Aruba
✈ UK – Chicago (3 Nights): You’ll first fly from the UK to the great city of Chicago, where we’ll transfer you to your hotel for 3 nights. Blending fast-paced buzz with Midwestern charm, Chicago stretches along its Great Lakes shoreline for endless culture, shopping, dining and experiences. From the wide downtown boulevards and Magnificent Mile’s shopping to the “home of Soul food” South Side, there isn’t a neighbourhood here that isn’t worth exploring.
Take in 94th-floor panoramas of skyscrapers and lakes from 360 Chicago’s breathtaking deck. Lose yourself in the sculpture-filled Millenium Park. Definitely join the locals for some spirited sports at Wrigley Field. Whether you’re snapping the famous Bean structure and nearby Pritzker Pavilion, taking it easy along the North Pier or digging into some Chicago Deep Dish Pizza, you’ll be in a city that doesn’t disappoint. Browse the Art Institute and Field Museum, sample Chinatown’s dumplings and make the most of Chicago’s endless theatres, bars, clubs and steakhouses.
✈ Chicago – Aruba (7 Nights): Next you’ll be transferred back to the airport for a flight to the stunning Caribbean island of Aruba for 7 nights of well-earned relaxation. With its year-round sunshine, turquoise warm waters and white-sanded shores, Aruba is loved for its tropical climate, lush greenery and quaint Dutch architecture. Sunshine here bounces off pastel-painted buildings, and this island’s colonial heritage is beautifully preserved- both visually, and in the town names. The modern capital of Oranjestad and the quaint Noord village form beautifully laid-out streets and Roman Catholic chapels, plus gleaming designer malls and upscale restaurants.
Sheltered by their location outside the Hurricane Belt, Aruba’s beaches are some of the most beautiful on earth. From powdery-soft alabaster coves and secluded limestone cliffs to long stretches of white sand, over 15 beaches here offer everything from lounging under palms to world-class windsurfing. Escape in the solitude at Baby Beach, snorkel at Boca Catalina and dine overlooking crystal-clear waters at Eagle Beach. With outdoor markets, casino resorts and everything from Aloe factories to bird sanctuaries, Aruba truly is a treasure. The island measures 21 miles tip-to-tip, and we can arrange transfers for whichever part you fancy exploring.
✈ Aruba – UK: We’ll be at your hotel on your departure day to escort you to the airport for your flight back to the UK.
Why choose eShores?
One to One Service
Our experienced personal travel consultants will ensure you find the most suitable holiday, whilst taking care of every last detail. Everything from start to finish will be effortless.
100% Tailor Made
We can use any hotel, in any destination, so we will craft an itinerary to suit your exact needs. Also, as we can provide any itinerary, the only holiday we'll offer, is the one that's right for you.
Fully Protected
Our ATOL bonding provides you with the financial protection you need and as a member of the Travel Trust Association, you'll have 100% financial protection. Covering you for any eventuality.
Competitive Pricing
As a tour operator & travel agent, we'll search the market to ensure that we find you the best price. Also as an online business, we can ensure our prices are as competitive as possible.
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NatalieAnne
I have booked 3 big holidays with eShores and always been looked after very well. Great company who care about their customers. Particular shout out to Emma McDonough and Dave Felton
Posted 20 hours ago -
Michael
Laura has proved efficient, helpful and patient at the research/booking stage of our holiday.
Posted 1 day ago -
DavidPaul
eShores managed our holiday to Skopelos and Skiathos in June 2024. The arrangements went to plan with clear communications from the eShores team. When my wife injured her knee whilst we were on holiday, and we needed to change the return transfer arrangements it was easy to contact eShores, and they made the necessary changes. We have just booked a similar holiday in 2025 with eShores.
Posted 1 day ago -
RobertEdward
Dave Felton smashed it again. I've booked previously with Dave and can't see past him. His customer service and knowledge of the world is mighty impressive. I've passed his name on to others who have booked with him who also sing his praises. I've booked my holiday for 2025 and will continue to use Dave with confidence going forward.
Posted 5 days ago -
Laurence
Emma has done great work again organising Dubai, Phuket and Bangkok for the New Year. Organised excactly what we were looking also taking into account value. Thank you Laurence
Posted 6 days ago -
Anonymous
Thank you Emily, for all your help in planning a special holiday. Your help and advice was greatly appreciated
Posted 1 week ago -
Helen
Excellent customer service from Hannah, recent holiday to Andalucia was excellent, any queries questions dealt with quickly and efficiently. Just booked another holiday to Cairo again Hannah has tailored the holiday exactly 👍
Posted 1 week ago -
Christine
Excellent service. Very professional and patient. Easy to contact and prompt answers to any questions we had. Definitely recommend.
Posted 1 week ago -
Anonymous
No flexibility in what customer is looking for and will not price match with what is on offer. Limited service and need to be fair in choices
Posted 1 week ago -
Anonymous
Michelle was knowledgeable and insightful about my needs as a solo traveller in Australia. She sorted options quickly, consulted and then held prices whilst I conferred with my family over there.
Posted 1 week ago
Talk To The Experts
Your personal travel consultant will get to know your needs, ensuring they find you the most suitable holiday, at the best price!