Luxury Holidays in Chicago

Chicago, the Windy City, exudes a dynamic energy that pulses through its towering skyline and diverse neighbourhoods. Nestled on the shores of Lake Michigan, it's a metropolis of architectural marvels, from the iconic Willis Tower to the historic Wrigley Building. Renowned for its blues and jazz heritage, Chicago's music scene thrives in legendary venues like the Chicago Theatre and the Green Mill Cocktail Lounge. Culinary delights await in its bustling food scene, showcasing everything from deep-dish pizza to gourmet cuisine. With world-class museums, vibrant festivals, and a rich cultural tapestry, Chicago beckons visitors to immerse themselves in its boundless charm and vitality.

Chicago has an excellent range of properties in and around its vibrant downtown area, featuring spectacular views over this picturesque city’s skyline, from the stone-carved facades to its famous canals, or the endless expanse of Lake Michigan. With so many hotels and the Chicago milieux made famous by so many movies, you cannot help but feel a little glam wherever you go.

Great reasons to holiday in Chicago

• The Skydeck at Willis Tower (aka Sears Tower)
• More fine dining restaurants than any other US city
• Home of the famous Chicago deep-dish pizza and the classic Chicago hot dog
• Cool blues and jazz bars
• Boardwalk fun on Navy Pier
• Incredible museums and galleries
• Boat and hovercraft rides on deep blue Lake Michigan
• Shop til' you drop on the famous Magnificent Mile
• St Patrick’s Day – One of the largest parades, complete with honorary ‘dyed green river’ – Annual, 15th March
• Wine Lover’s Weekend – Tours and a Grand Tasting. March, check for dates
• Taste of Chicago – The nation’s number one outdoor food festival
• Chicago Jazz Festival – Global superstars and local talents come together at this free lakefront festival

Things to do on holiday in Chicago

A holiday in Chicago is a feast for the eyes at every turn, and the best way to take it all in is simply to walk. The downtown area is actually pretty easy to negotiate.

Head towards beautiful Lincoln Park or Grant Park, both found on a neat strip between Chicago’s famous Lake Shore Drive and the lake itself. On your way, you’ll encounter stunning architecture unlike any other in the US. And once you reach the parks you’ll see why the so-called Second City is also one of America’s greenest cities. Open spaces, grand fountains and modern sculpture give way to the super-clean lakeshore beach, and the expanse of Lake Michigan.

Head up to the 103rd floor of the Willis Tower (formerly known as, and still often referred to as Sears Tower). Don’t worry, there is a lift – incidentally one of the fastest in the world at 488 metres per minute. Up until 1998, this was the tallest building in the world, to be succeeded by Kuala Lumpur’s Petronas Towers. From the Skydeck, peer down onto other skyscrapers. The Skydeck features glass-bottomed skyboxes that protrude from its mirror façade as you look down on passing helicopters. Come here on a sunny evening and watch as the purple sky gives way to an elegant web of streetlights that emanates from beneath you. A limitless view takes in the states of Indiana on the other side of Lake Michigan, Illinois, and Wisconsin to the west.

Chicago is a hotbed of exhibits, from a quiet wander through the Chicago Art Institute or Museum of Contemporary Art, to marvelling at the summer fireworks spectacular blasting annually from Navy Pier. Alternatively, take a trip of scientific discovery at the Field Museum of Natural History, or one of the world’s largest indoor aquariums – the John G Shedd Aquarium.

Food and Chicago go hand in hand. The city features a host of dining options from fine dining and a la carte cuisine to signature fast food that the locals here do best.

A highlight of Chicago’s fine dining elite has to be the exquisite Signature Room on the 95th floor of the John Hancock Center. Chicago’s second tallest tower is a design masterpiece with the food, and view, to match. Alternatively, why not visit 360 Chicago at the John Hancock Observatory for wrap-around views and great cuisine at the 94th Floor Cafe.

But do make sure you try Chicago’s world-renowned deep-dish pizza and the Chicago hot dog. Both were more or less invented here, and every establishment will tell you that theirs is best. The original deep-dish pizza – essentially a pizza pie made upside down – was from Pizzeria Uno, which still stands today on East Ohio Street. The hot dogs you’ll find on practically every street corner with all the relish and trimmings, but note: true Chicagoans never put ketchup on their dogs.

And as well as its Italian connection, Chicago stays true to its Irish roots. It’s the greatest city in America in which to celebrate St Patrick’s Day, when it famously dyes the Chicago River green. Lastly, Chicago has an esteemed sporting legacy that should be experienced at least once. Check out the local baseball team the Cubs at world-famous Wrigley Field, basketball legends the Chicago Bulls at United Center, or the multi-NFL-championship-winning Bears at Soldier Field.

Chicago Facts

• State - Illinois
• Area - 591 square kilometres
• Population - 2.7 million

Chicago Weather

With four defined seasons to look forward to each year, Chicago falls under what’s known as the humid continental zone. Average summer temperatures, when humidity is also high, are in the mid-20s (Celsius) but can often hit 32. Conversely, winters can be snowy and cold while Autumn and Spring are mild seasons in comparison and produce little in the way of humidity.

Twin Centre & Multi Centre

Chicago’s position acts as a gateway from west to east, and as such is the perfect place to start your American adventure. From here Boston, NYC and Washington DC are easily reached, each involving a short domestic flight. This allows you to add to your US holiday experience by witnessing some of its most famous and culturally inspirational cities all in the same holiday.

Chicago Holidays 2025 / 2026

Book now for your 2025 / 2026 American holidays! At Kenwood Travel we provide tailored luxury holiday packages. With over 45 years' experience as a direct sell tour operator, our experts are on hand now to help you plan a breezy adventure in the Windy City, so give us a call.