Itinerary Highlights
    • Experience two sides of Chicago: its iconic sites followed by its burgeoning music and food scene
    • Swap hip and trendy Chicago for some lakeside leisure in tranquil Saugatuck
    • Sail down the Kalamazoo River on a vintage boat to admire the town’s glamorous waterfront houses

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Lake Michigan, the largest body of fresh water in the country, is so vast it looks and feels more like an ocean than a lake. Your first waterside destination is Chicago, a city crammed with architectural feats, pristine parks and glamorous jazz bars. After an action-packed few days in the big city, the second part of your holiday on Lake Michigan is all about relaxing. You will spend two days in Saugatuck, a pocket-sized resort town offering elegant waterfront eateries and welcoming art galleries, as well as plenty of opportunities for fun activities on the lake.


Everything is 100% tailored to 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.

DAYS 3 & 4


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.

DAYS 6 & 7


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.

DAYS 8 & 9


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.

A la carte


Head out with a local guide to discover Chicago’s singular and fascinating architecture. The walk starts at Pioneer Court, which is near architectural masterpieces like the Tribune Tower, the Wrigley Building and the Magnificent Mile. From here, continue onwards to the Loop, with your eyes fixed to the buildings at all times. Other sites you’ll see include the Carbide & Carbon Building, the Cloud Gate (nicknamed "The Bean"), the Chicago Cultural Center and City Hall, as well as public art by Picasso, Miro, Chagall and Calder.


Most of the legendary clubs on the South and West Sides of Chicago, where glorious old-timers like Howling Wolf, Muddy Waters, Elmore James and Hound Dog Taylor performed, have unfortunately disappeared. Nevertheless, Chicago remains a linchpin in the nation’s blues and jazz scene and there are still plenty of clubs that charm with their timeless feel. Andy's Jazz Club is one of our absolute favourites. You can enjoy a delicious dinner before settling in for a jazz show.

A Rough Idea of Price

Dependent on season, accommodation and activities
The estimated cost for this trip starts from £2,780 to £3,475 per person. The final cost of the trip depends on the way we tailor it especially for you. The final cost varies according to several factors, which include the level of service, length of trip and advance booking time. The exact price will be provided on your personalised quote. The average starting price for this trip is £2,955 per person.
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