A magical blend of architectural grandeur, cultural richness and lakeside charm

welcome to the windy city

Embark on a journey to the vibrant city of Chicago, where iconic landmarks, cultural treasures, and rich history await.
From the towering silhouette of Willis Tower to the shimmering spectacle of Cloud Gate, also known as "The Bean," Chicago's skyline is a showcase of architectural innovation. Explore Navy Pier, a beloved waterfront destination offering entertainment, dining, and views of Lake Michigan and lose yourself in the rhythm of the blues at legendary clubs like Buddy Guy's Legends or catch a live jazz performance at the historic Green Mill.

Take a shopping spree along the Magnificent Mile, home to upscale boutiques, department stores, and luxury retailers and marvel at architectural wonders as you walk along Chicago's famed Riverwalk.  Sports lovers can experience iconic venues such as Wrigley Field and the United Center and witness the fierce rivalry between the Cubs and the Chicago White Sox, a testament to the city's passion for baseball. Dive into Chicago's vibrant cultural scene, from world-class museums like the Art Institute of Chicago to the immersive exhibits at the Museum of Science and Industry. And meet SUE, the largest and most complete Tyrannosaurus rex skeleton ever discovered standing tall at the Field Museum.

Famous for its gangster tales in the roaring 1920s and 1930s Chicago's got style, swagger, and a slice of history - contact us today to start planning your adventure!
Chicago River & City at sunset

Things to see & do

Browse through our recommended selection of things to see and do in Chicago. Many of these are included in our suggested itineraries, however, if there is
anything you see that particularly takes your interest, please let us know and we will include it in your holiday package or put you in touch with the right people.

Millennium Park

Wander through the inner city oasis of Millennium Park boasting the mesmerising Cloud Gate sculpture, affectionately known as ‘The Bean’ - a reflective masterpiece that captivates visitors with its unique, seamless form. The Bean's reflective exterior, inspired by liquid mercury, captures the dynamic life of Millennium Park, reflecting people, lights, skyline, and greenery. Its polished surface invites touch and self-reflection, enhancing the interactive experience. The curved underside, mirroring the sky and park entrance, inspired the name "Cloud Gate."


Take your Chicago experience to a whole new level at TILT, nestled on the 94th floor of the John Hancock Building. Brace yourself for jaw-dropping panoramic views of the skyline and Lake Michigan through floor-to-ceiling windows. And here's the real kicker – TILT, the thrill-packed attraction where those windows actually tilt you outward. It's not just a view; it's a view that'll have you screaming for more!

Navy Pier

Step onto the vibrant world of Navy Pier, Chicago's hotspot for entertainment stretching over 1,000 meters across Lake Michigan. It's the go-to place for events, intriguing attractions, cultural vibes, delectable dining, and shopping galore. And you can’t miss the iconic Centennial Wheel – the dazzling gem on this lakeside treasure!

Live Music at Kingston Mines

Check out who’s playing at Kingston Mines where their slogan says it all - ‘Hear Blues - Drink Booze - Talk Loud - You’re Among Friends’! Legendary blues club founded in 1968 known for its electric atmosphere and live blues performances. Come on down, get comfortable, enjoy a meal, and sit back and soak in the best of Chicago’s music scene. Check with Travel USA to see who’s playing whilst you’re in town.

Try Deep Dish Pizza

Indulge in the Chicago deep dish pizza experience – a local legend renowned for its buttery, thick crust embracing layers of cheese, toppings, and tomato sauce, all baked to perfection in a deep pan. It's not pizza as we know it - it's a culinary experience that'll redefine your pizza standards. 

Chicago Riverwalk

Discover the vibrant Chicago Riverwalk, an award-winning, pedestrian-friendly scenic walkway stretching two kilometres along Chicago River’s south bank from Lake Michigan to Lake Street. Eat, drink, play and explore as you stroll along the river, enjoying waterfront cafes, boat tours, and captivating views of iconic architecture along the way.

Museum of Science & Industry

Be wowed by the Museum of Science & Industry, one of the largest science museums in the world housed in the historic Palace of Fine Arts.  Step back in time aboard a World War II-era U-505 submarine, stroll through a coal mine replica, hop on the Pioneer Zephyr, and explore modern aviation on a groovy 1960s-style fully restored 727. A must-see adventure!

Wrigley Field Tour

Step up to the plate at Wrigley Field. Embark on a pilgrimage to the heartbeat of baseball and proud home to the Chicago Cubs. Whether you're catching a game during the season or exploring the ground on a guided tour, immerse yourself in history. Wander the dugouts, set foot on the field, and soak in the charm of ivy-covered walls and iconic architecture.

Chicago Riverboat Tour

Take a leisurely cruise along the scenic river and witness the city's architectural marvels from a unique perspective. Cruising through the heart of downtown, the tour captures the essence of Chicago as it unveils iconic skyscrapers, historic bridges, and local landmarks.

Fashion Outlets of Chicago

Discover style at Chicago’s premier shopping destination with over 130 designer stores offering discounted shopping options. Located minutes from downtown, it boasts iconic brands, luxury boutiques, and trendy outlets, ensuring a diverse and fashionable shopping experience. Enjoy savings, exclusive deals, and a chic atmosphere that makes every visit a fashion-forward delight.

Lake Michigan

This breathtaking freshwater jewel that borders Chicago, plays a central role in the city's identity offering a stunning contrast to the city’s skyline. Its expansive shores offer recreational havens, from sandy beaches and waterfront parks to sailing and kayaking and its renowned Lakefront Trail, stretching some 30 km around the lake. With its scenic beauty, outdoor activities, and cooling breezes, Lake Michigan serves as a cherished natural escape and a vibrant source of inspiration for residents and visitors alike.

Experience Live Sport

Experience live sport - the American way! Catch the adrenaline, the cheers, and the thrill of a live game - because experiencing sports the American way is an absolute must! In Chicago, there are 6 pro teams across all sports including MLB’s legendary rivalry between the Cubs and the Whitesox. Chat with Travel USA to score your tickets and we'll look to lock in your seats before you even pack your bags!

Adler Planetarium

Reach for the stars at Adler Planetarium, America’s pioneering celestial haven dedicated to astronomy, astrophysics, and space exploration. Perched on the shores of Lake Michigan, it unveils breathtaking celestial wonders and events through immersive exhibits, interactive displays, and a cutting-edge sky theatre.

The Magnificent Mile

Walk the Magnificent Mile, an upscale stretch of Michigan Avenue showcasing the city's vibrant energy and cosmopolitan charm. Renowned for its upscale shopping, dining, and entertainment, it stands as a premier destination for visitors seeking a taste of the city's sophisticated allure. 

Art Institute of Chicago

Marvel at the impressive collection housed in the Art Institute of Chicago, one of the oldest and largest art museums in the world and a must-visit destination for art enthusiasts. It’s collection spans centuries, showcasing masterpieces from classical to contemporary, creating an unmissable destination for anyone with an appreciation for the artistic journey through time.

Live music at the Green Mill

Take in some live Jazz at the Green Mill, a historic jazz club that transports visitors to a bygone era of Chicago's musical legacy. Revel in the timeless charm, complete with no-frills rules - no meals, no reservations, no tickets, and definitely no credit cards. Just great music and a rich dose of nostalgia! 

Shedd Aquarium

Explore the wonders of the deep at the Shedd Aquarium, one of the largest indoor aquariums in the world where visitors get to explore the world’s oceans, lakes, rivers and reefs - all in the heart of Chicago! Meet beluga whales, sharks, sea otters, turtles, rockhopper penguins and so much more. Secure your tickets early to avoid disappointment.

Willis Tower

Stand tall at the Willis Tower, the iconic skyscraper, formerly known as the Sears Tower. Renowned for its architectural significance and sweeping panoramas of the city, visitors can elevate their Chicago experience at the Skydeck, where glass-floored ledges invite you to look down to take in the breathtaking views, literally right under your nose! 

Field Museum

Globally acclaimed museum weaving together the tapestry of the natural world and human history.  Home to an extensive collection of artifacts, fossils, and specimens, from Egyptian mummies to the man-eating lions of Tsavo and the star of the show - SUE, the largest T-Rex skeleton ever unearthed.

Woodfield Mall

Shop ‘till you drop at Woodfield Mall as you go searching for bargains at Illinois' largest shopping mall. Boasting over 2 million square feet of retail paradise and with 275 stores, featuring high-end fashion brands and popular retailers, it is a shopping mecca for locals and tourists located just 40 minutes from downtown Chicago.

Chicago with Go City Pass

With Travel USA and Go City, sightseeing couldn’t be easier. One pass, one price, all the sights. See more, spend less - save up to 50% on the best attractions, tours, and activities. From skyline sunsets to must-visit museums, we’ve got you covered.

N.B. The all-inclusive pass is included in Travel USA’s Chicago and selected Illinois packages giving you unlimited access to more than 30 attractions, tours, and activities during your stay.


Aerial view of Millennium Park & stadium in Chicago

interested in finding out more?

Contact us today for expert travel advice and personalised trip planning assistance.
Chicago River showing all the bridges

Not quite what you're looking for?

Our packages and featured 'things to see and do' have been created to excite, inspire and inform Kiwi travellers about what we recommend they do when travelling to the USA. All of these can be personalised to your individual needs and preferences. Contact us to discuss your requirements so we can work together to create the perfect adventure for you.