GMT -5 hours
Upscale eateries, endless shopping opportunities all in the iconic Windy City
Located on the shores of Lake Michigan, Chicago is known as the ‘Windy City’ and has an instantly recognisable skyline of spectacular skyscrapers. With a great combination of city attractions - stunning modern and traditional architecture, beautiful green parks, a renowned Blues and Jazz scene and fantastic shopping - it is a truly wonderful city to visit, particularly in the summer months.
Route 66 is a bucket-list favourite and this legendary self drive takes you through the heart of America, from Chicago to LA.
- Chicago has its fair share of amazing museums. Spend some time exploring the Art Institute of Chicago or the Field Museum home to Sue, the largest Tyrannosaurus Rex skeleton in the world
- Chicago is renowned for its shopping opportunities and the Magnificent Mile is one of America’s most famous shopping destinations
- When it comes to dining, the city has plenty to offer from high end restaurants to causal eateries. Don’t miss the chance to try Chicago’s famous deep dish pizza
- The city’s setting on the edge of Lake Michigan is one of its real highlights – you can relax on North Beach or wander along Lake Shore Drive or visit the attractions at Navy Pier
- Chicago marks the start of what is possibly America’s, if not the world’s most famous road trip – Route 66. Spend a few days here before heading off on the road
Chicago & Route 66 holiday highlights
The ‘Windy City’ is bursting with culture. Discover eclectic neighbourhoods, diverse cuisine and a vibrant art community. Chicago is famous for its blues and jazz scene, and blend of traditional architecture and modern edifices that are surrounded by pretty green parks.
Downtown is home to Chicago’s biggest sights, theatres, shops and restaurants. The trendy North has plenty of entertainment, especially if you’re looking for bars and clubs, whilst the West is the fashionable district to live in and also offers a great array of shops and bars. Further west you’ll find the Far West Side which is not often frequented by tourists but is home to some beautiful park areas, top blues clubs and some great dining options. If you’re looking for the historic Pullman District you’ll want to head southeast, the Polish village is northwest and the Irish quarter is in the far southwest.
Chicago has its fair share of attractions including some amazing museums. Spend some time exploring the Art Institute of Chicago, the Field Museum which is home to Sue, the largest Tyrannosaurus Rex skeleton in the world, and the Museum of Science and Industry, the largest science centre in the Western hemisphere. Alternatively drop by the Shedd, the world’s largest indoor aquarium and home to whales, sharks, penguins and more, or Adler Planetarium on the edge of Lake Michigan. The lakeside is where you'll also find Navy Pier and a number of shops, eateries, parks, museums and a whole range of fun attractions. There is a large Ferris wheel, IMAX cinema, a funhouse maze and Shakespeare theatre and you can take sightseeing boat tours out onto the lake too.
Shopping in Chicago is located on the famed Magnificent Mile along Michigan Avenue. Along this stretch you’ll find Neiman Marcus, Saks Fifth Avenue and Nordstrom alongside boutiques and speciality shops such as Tiffany & Co., Ralph Lauren, the Disney Store and the Apple Store. If you’re looking for international brands, nearby Oak Street offers chic fashion outlets and trendy cafes. You can also visit the city’s iconic Marshall Field’s State Store (now known as Macy’s) or browse the cool stores and up and coming designers on North Damen Avenue.
Chicago has some great places for eating out and some specifics districts are dedicated to certain flavours. If you’re looking for Greek food, then Devon Avenue is the place to be. Enjoy oriental flavours in Chinatown and soul food and delectable barbecued delights in Chatham. Lincoln Square and Albany Park have a great range of Middle Eastern, German and Korean eateries whilst Uptown offers a whole host of African and Asian delights, with a few Swedish restaurants thrown in for good measure. If haute cuisine and celebrity chefs are your order of the day, Lincoln Park and Wicker Park have some award-winning restaurants to choose from.
However, if you want to taste classic deep-dish pizza, then you have to head to the place they’re said to originate from, Pizzeria Uno. There is also a distinctly Chicago style hot-dog of Vienna beef loaded with relish, mustard, peppers, tomato wedges, a dill pickle spear and celery salt all in a poppy seed bun. But don’t go asking for ketchup as most locals think it destroys the delicate balance of flavours the hotdog is famed for.
Synonymous with kitschy Americana - neon road signs, classic gas stations and motels, and gleaming Mustangs and Chevys - Route 66 is one of the world’s most iconic road trips. Established in 1926 to improve transportation links across the country, it is firmly placed in the American consciousness and has amassed a host of cultural references, from Steinbeck’s classic novel The Grapes of Wrath to the much-covered rhythm and blues song (Get Your Kicks on) Route 66. This legendary road takes you through the heart of America, from Chicago to LA.
While officially Route 66 no longer exists (it was decommissioned in 1985), 85% of the original route remains. You can’t follow a single highway as some parts have been closed but you can plan a route that covers the main areas. This can be done comfortably in two weeks if you drive 100-300 miles a day. Stop off at classic diners such as the Cozy Dog Drive In, roadside attractions and historic gems such as the Abraham Lincoln Presidential Library and Museum. The Route 66 Association Hall of Fame & Museum is an ode to all things Americana, with historic and quirky Route 66 artifacts and memorabilia.