Inspiration for your own tailor-made trip
Chicago - Saugatuck
100% customisable for you
Your holiday begins today. After whizzing through airport security and enjoying some nibbles and refreshments in the airport lounge, board your direct flight to Chicago. The journey takes around nine hours so make sure to have your entertainment lined up – you can download our carefully-curated ‘Sounds of North America’ Spotify playlist beforehand to get in the mood. After touching down, you’ll be privately transferred to a trendy hotel in the heart of the West Loop, one of Chicago’s most vibrant neighbourhoods.
After a bright and early start (jet lag will give you a helping hand here) with a classic American breakfast, it’s time to hit the streets of the city. Nestled on the shores of Lake Michigan, Chicago is a vibrant cosmopolitan hub in a superb natural setting. On the streets, architects like Sullivan, Burnham and Frank Lloyd Wright have left their creative mark on the city, while on the shores of Lake Michigan lies Millennium Park, a sweeping green oasis filled with points of interest. Today you’ll be armed with the Go Chicago Card, a valuable pass that gives you access to all the main sites, including the Art Institute of Chicago, Frank Lloyd Wright's house and studio, and the Skydeck Ledge, a glass observation cabin located on the 103rd floor of the Willis Tower. We can also organise for you to head out on a guided walk with a local architecture-obsessed resident to admire some of the city’s finest architectural gems.
For a change of pace after yesterday’s sightseeing extravaganza, the next two days are dedicated to getting under the skin of Chicago and discovering some of its more intimate corners. The food scene here is exceptionally vibrant, varied and best experienced with one of our knowledgable guides on the ground. First up: the warehouses of Fulton Market. At the end of the 19th century, the warehouses were the main meat packing houses for the meat produced in Chicago (nearly 80% of American consumption). This neighbourhood now hosts a mixture of businesses, bars and trendy restaurants. You’ll have the opportunity to check out the bustling French Market, which serves everything from Italian and Belgian food to Vietnamese and Ethiopian, before finishing up at a classic Irish-American ice cream parlour. Besides plenty of foodie indulgence, there is plenty more to keep you busy in Chicago. Enjoy long strolls through lakeside Millennium Park, visit some of Chicago's many museums, see a stand-up show on Broadway, catch a sports game or relax in a small blues or jazz bar. We can also arrange for one of your evenings to be spent at Andy's Jazz Club, where you can enjoy a delicious dinner and a classic jazz show.
Today you’ll be swapping the big city for tranquil Saugatuck, a small lakeside town that has become a popular resort for city-dwellers looking for fresh air and peace and quiet. After fuelling up on breakfast at your hotel, pick up your rental car and drive two-and-a-half hours round the southern tip of Lake Michigan to an elegant hotel in the heart of town. The rest of today is yours to play with. You can meander through town, poking your head into one of the many art galleries and boutique shops (Saugatuck is a popular refuge for artists), or find a cosy lakeside bar to enjoy an evening drink.
The last two days of your getaway to Lake Michigan are all about enjoying the small things in life and getting into nature. Mornings can be spent enjoying a spot of lakeside yoga before tucking into a fresh pastry at a local cafe. You can also work on your drive at one of the nearby golf courses, enjoy a leisurely bike ride in Saugatuck Dunes State Park or head out onto the water for a spot of kayaking, boating or fishing. As for the evenings, we can help you plan your itinerary to include a wine tasting at a local winery, a concert or theatre performance at the Saugatuck Centre for the Arts or find a downtown pub to enjoy some local beers and ciders. We have also arranged for you to spend one of the two days discovering Kalamazoo River on a vintage boat. The boat ride is slow and relaxed, giving you plenty of time to admire the beautiful houses that line the river.
Sadly the time has come to embark on the journey back to the UK. It will be hard to peel yourself away from the Saugatuck, but at least you’ll be heading back fresh and rejuvenated after a week of lakeside fun. Drive two-and-a-half hours back to the airport in Chicago to drop off your car and then hop on your nine-hour flight back to the UK.
Everything in this itinerary is entirely customisable, down to the smallest details. Here are some more suggestions of what could be included
Each of our trips is entirely tailor-made with originality, quality and cultural immersion in mind. Our team of destination specialists will craft itineraries based on your tastes, using their first-hand knowledge and the help of our in-country team of Concierges and guides. All trips are accompanied by a wide range of additional services, including a 24-hour helpline, the Original Travel app, fast-track airport services and much more.
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Our team of destination experts will get to know you and your unique requirements for your holiday
We work with you to build an ultra-personalised holiday itinerary with your choice of accommodation, experiences and activities
All of our holidays include little extras designed to make a big difference to your trip, from fast-tracking you through airport check-in and security to our network of local Concierges
