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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Anonymous
We were looking for a two island holiday at Rhodes and Kos. Emily provided us with a number of options and recommendations for flights and hotels which enabled us to make a final choice. She was extremely helpful in dealing with our requests and room preferences and the whole process was handled very efficiently.
Posted 1 hour ago -
Julia
So impressed with Eshores. Chris Eaves handles our arrangements and we have just booked our fifth holiday with him. Nothing is too much trouble and as we are two mature ladies his patience is much appreciated. We always feel confident in his advice and suggestions. Over the years he has arranged some complex itineraries for us including a three stop holiday with all flights, hotels and transfers organised - bliss. This time were off to Turkey and Chris has organised everything for us. Another worry free holiday sorted in 2026! Thanks Chris to you and everyone at Eshores.
Posted 14 hours ago -
LukeRoger
Rob was very helpful and attentive and responded to my emails quickly and I was very impressed with the service provided. I have no hesitation in recommending eShores and I will certainly be using them again for future holidays.
Posted 16 hours ago -
Keith
Excellent service
Posted 1 day ago -
Kaye
Leanne was a delight to work with, proactively suggesting options, whilst remembering they had to be practical. What I appreciated most was how responsive and efficient Leanne was. Everything was handled promptly. Even though we haven’t taken the trip yet, I already feel confident that things will run smoothly thanks to the excellent groundwork that Leanne put in place.
Posted 2 days ago -
Sally
I’ve now lost count of the trips I’ve booked with Gavin at e-shores and how he always manages to know exactly what we like and gets a great price - always the same or less than I research myself. Our latest was Greek island hopping to Mykonos, Paros, Naxos and Santorini and the hotels Gavin booked were all outstanding and the typically small, boutique hotels with less crowds. We went out of season (1st - 13th Sept) and everything went smoothly from the airport transfers, the welcome we had at each hotel and the beauty of each island having its own magic. Looking forward to the next trip already booked through Gavin in November! Thank you everyone-shores - the Napiers!
Posted 3 days ago -
Anonymous
I found your representative very informatative. She listened carefully to our requests and completed every thing we asked for, including changing flight times that were better suited to us.Many thanks. I have already recommended the company already.
Posted 4 days ago -
Alaine
Great care is given to assist with what your looking for in a holiday.
Posted 5 days ago -
Robert
Always get great service from EShores (thank you, Emma). Nothing is ever too much trouble no matter how many times I change my mind! Would not consider using anyone else
Posted 5 days ago -
Christopher
Laura was fanastic, knew just what we needed and found it hassle fre when other agents had struggled :-)
Posted 6 days 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!