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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.
Reviews: Rated Excellent
Linda
Fabulous service. I rang to ask about our short break to Istanbul and it was booked for us within the hour. You can’t get better service than that. Thank you Dave Felton
Posted 9 hours agoStephen
Kelly arranged my recently booked multi centre holiday, having used eShores on a couple of occasions previous the usual high standards remain! They get an understanding of you requirements, pull together a proposed itinerary, and then happily amend/ provide alternative costings for different hotels/ flights as required once you get in to the detail of what you want (easier to do with their proposed itinerary!). Great service, and at a good cost!
Posted 17 hours agoTina Smyth
Just returned from a trip to Singapore and Bali arranged by Andy had a brilliant time, couldn’t fault the service I had he arranged everything from flights accommodation and transfers. I would highly recommend eShores and would definitely use them again. ThankYou Andy
Posted 1 day agoStephen
Kelly from eshores listened and understood what we wanted from our holiday of which she was fantastic,very patient and set the whole holiday up. Very professional. Thank you.. Ste Leather
Posted 3 days agoSarah C
Used eShores to book a multi destination holiday for 4 days in Miami then 10 days Jamaica. Really pleased with the hotels chosen especially Shelbourne in Miami and the service received especially follow up call to check everything was ok. Whole trip when smoothly
Posted 6 days agoStephen
We are looking forward to our 3 centre holiday in November to the USA, everything has been set up for us Chris was excellent in giving us all the details. We changed a few things after the first quote like you do but sorted it straight away. Excellent service, reasonable price and quick response just looking forward to the trip
Posted 1 week agoANDREW and Caroline McKie
We recently travelled to Bali much delayed by covid restrictions but found eshores very good with excellent communication keeping us up to date with advice on travell restrictions as circumstances changed. Our holiday when we were able to travel was fantastic exceeding our expectations ,and we feel certain that we will be using eShores for our next trip .
Posted 1 week agoTom & Gloria
We have just returned from a fantastic holiday at the Habtoor Grand Resort in Dubai - all organised by Kadie. The location of this hotel is at the end of the beach, near to the Sky Diving school, and the new Marina. It's also close to The Walk which has many shops and restaurants. Staff and service at the hotel were 5* and we would reccommend the upgrade to Club Rooms. We have travelled several times with eShores to different regions all of which were organised by Kadie. From our initial enquiry we are always given options on where to stay, activities and excursions and any potential offers that are available. The service provided by Kadie and eShores is exemplary and we have never had an issue using them. Looking forward to our next adventure to Australia - organised by Kadie of course.
Posted 1 week agoPatricia
I can’t rate eShores enough and Andy in particular. Not only did he find us the best package for the best value but he was also very supportive and reassuring when I needed to contact him before and even during the trip with a couple of questions. Everything was organised like clockwork and took all the stress out. Next time I won’t bother shopping around and will go directly to eShores.
Posted 1 week agoLiz
Matthew has looked after our holidays for several years and is very efficient and friendly. I always feel we have got the best deal and have never had any cause for complaint with E Shores
Posted 1 week ago
Other Holidays you may like
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Miami & Bahamas
New York & St Lucia
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.
Linda
Fabulous service. I rang to ask about our short break to Istanbul and it was booked for us within the hour. You can’t get better service than that. Thank you Dave Felton
Posted 9 hours agoStephen
Kelly arranged my recently booked multi centre holiday, having used eShores on a couple of occasions previous the usual high standards remain! They get an understanding of you requirements, pull together a proposed itinerary, and then happily amend/ provide alternative costings for different hotels/ flights as required once you get in to the detail of what you want (easier to do with their proposed itinerary!). Great service, and at a good cost!
Posted 17 hours agoTinaSmyth
Just returned from a trip to Singapore and Bali arranged by Andy had a brilliant time, couldn’t fault the service I had he arranged everything from flights accommodation and transfers. I would highly recommend eShores and would definitely use them again. ThankYou Andy
Posted 1 day agoStephen
Kelly from eshores listened and understood what we wanted from our holiday of which she was fantastic,very patient and set the whole holiday up. Very professional. Thank you.. Ste Leather
Posted 3 days agoSarahC
Used eShores to book a multi destination holiday for 4 days in Miami then 10 days Jamaica. Really pleased with the hotels chosen especially Shelbourne in Miami and the service received especially follow up call to check everything was ok. Whole trip when smoothly
Posted 6 days agoStephen
We are looking forward to our 3 centre holiday in November to the USA, everything has been set up for us Chris was excellent in giving us all the details. We changed a few things after the first quote like you do but sorted it straight away. Excellent service, reasonable price and quick response just looking forward to the trip
Posted 1 week agoANDREWand Caroline McKie
We recently travelled to Bali much delayed by covid restrictions but found eshores very good with excellent communication keeping us up to date with advice on travell restrictions as circumstances changed. Our holiday when we were able to travel was fantastic exceeding our expectations ,and we feel certain that we will be using eShores for our next trip .
Posted 1 week agoTom& Gloria
We have just returned from a fantastic holiday at the Habtoor Grand Resort in Dubai - all organised by Kadie. The location of this hotel is at the end of the beach, near to the Sky Diving school, and the new Marina. It's also close to The Walk which has many shops and restaurants. Staff and service at the hotel were 5* and we would reccommend the upgrade to Club Rooms. We have travelled several times with eShores to different regions all of which were organised by Kadie. From our initial enquiry we are always given options on where to stay, activities and excursions and any potential offers that are available. The service provided by Kadie and eShores is exemplary and we have never had an issue using them. Looking forward to our next adventure to Australia - organised by Kadie of course.
Posted 1 week agoPatricia
I can’t rate eShores enough and Andy in particular. Not only did he find us the best package for the best value but he was also very supportive and reassuring when I needed to contact him before and even during the trip with a couple of questions. Everything was organised like clockwork and took all the stress out. Next time I won’t bother shopping around and will go directly to eShores.
Posted 1 week agoLiz
Matthew has looked after our holidays for several years and is very efficient and friendly. I always feel we have got the best deal and have never had any cause for complaint with E Shores
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!