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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Dennison
Emma's knowledge of destinations and hotels was outstanding. She went above and beyond to find us the perfect itinerary, nothing was too much trouble. Have already recommended both Emma & eShores to everyone I know and will definitely be booking more holidays with Emma in the future.
Posted 4 minutes ago -
Anonymous
Very organised. Understood our needs and made good suggestions and alternatives to meet our budget
Posted 27 minutes ago -
Simm
Booked a multi centre holiday with eshores for next year , really good customer service I spoke to Matthew he was fantastic looking forward to this get a way next year ,very helpful and take the stress out of it for you .
Posted 55 minutes ago -
Anonymous
Very personal approach. Matt who sorted my honeymoon was extremely responsive via email and appeared to get I touch out of conventional office hours too. Highly recommended service!
Posted 1 day ago -
LouiseGarland
We have just returned from a multi centre Vietnam trip. What can I say, absolutely fantastic holiday from start to finish. Dave helped us all the way. We had a plan in our head and Dave took time to plan our perfect trip. Communication was great, letting us know promptly of any changes. We would definitely book again and highly recommend to others.
Posted 5 days ago -
Hazel
We have recently returned from a multi centre holiday in Thailand. Everything went smoothly as planned, the hotels were all lovely. We would definitely recommend eShores and would book through them in the future. Thanks to Laura who organised the trip for us.
Posted 1 month ago -
Heath
Been using eshore for several years,always come up with requirements we need.Always happy to rearrange. Staff are very knowledgeable and we always use Leanne as our point of contact. Experts for multi centre holidays.
Posted 1 month ago -
DavidHurst
I booked two holidays in 4 months with Dave at eshores. First one a 16 day trip around Vietnam north to south which included numerous flights and taxis. My second holiday was in October traveling around Vietnam again and Cambodia. Every hotel in both countries was spot on, every transfer went smooth with no problems. I'll Definitely use eshores again and thanks to Dave who arranged everything, a fantastic experience 👍👍
Posted 1 month ago -
Parr
Recently booked a four centre holiday to Asia. The process was straightforward and seamless. Rob, the agent who dealt with our requirements was extremely helpful and not pushy. He was very easy to talk with and seemed genuinely interested in our plans. He managed to put together exactly what we wanted and at a great price.
Posted 1 month ago -
Horan
Andy at eshores has been great, he worked hard to meet all our needs and went the extra mile for us! We're looking forward to a great Honeymoon!
Posted 1 month 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!