Ultimate Chicago bucket list: See the city’s most iconic sights
Experience Chicago’s top attractions, from towering skyscrapers to vibrant neighborhoods and cultural landmarks for every kind of explorer.
Edited by Robin Reetz | October 24, 2025
Chicago is a city that pulses with energy, history, and a bold, unmistakable charm. Whether you're drawn to its iconic skyline, world-class museums, deep-dish pizza, or vibrant neighborhoods, the Windy City offers something for every traveler. From strolling along the lakefront to exploring the architectural wonders of the Loop, a visit to Chicago is a dynamic mix of culture, cuisine, and character. Ready to start planning your next trip? These are some of the best things to do in Chicago.
Marvel at Millennium Park's Cloud Gate
Start your Chicago adventure at Millennium Park, home to one of the city's most photographed landmarks — Cloud Gate, affectionately known as "The Bean." Snap a selfie against its reflective surface, then wander through lush gardens and public art installations in the surrounding park. In summer, catch free concerts at the Jay Pritzker Pavilion or catch some rays while relaxing on the Great Lawn. With the Magnificent Mile just steps away, you're perfectly positioned to explore Chicago's vibrant downtown scene. After a day of urban discovery, unwind at Waldorf Astoria Chicago, an elevated city escape with timeless Parisian design, a rejuvenating spa, and an on-site restaurant, Brass Tack, known for its expertly crafted cocktails and its extensive wine list.
Discover art and history at the Museum Campus
Chicago's Museum Campus brings together three world-class institutions: the Field Museum (home to Sue, the T. rex), the Shedd Aquarium, and the Adler Planetarium. Spend a day exploring natural history, aquatic wonders, and the stars — all within walking distance of Grant Park and the lakefront. The area is ideal for families and curious travelers, offering seasonal festivals and stunning skyline views.
After exploring, settle in at Hilton Chicago, a historic hotel overlooking Grant Park. The hotel features spacious guest rooms, an indoor pool, a fitness center, and on-site dining, blending classic architecture with modern comfort.
Stroll the Chicago Riverwalk
The Chicago Riverwalk is a scenic pedestrian path lined with restaurants, bars, public art, and kayak rentals. Take an architecture boat tour to learn about the city's storied skyline, or simply enjoy a sunset stroll along the water. The Riverwalk connects several neighborhoods and is a lively spot for both residents and visitors, especially during summer evenings. Canopy by Hilton Chicago Central Loop is nearby, offering convenient access to the Riverwalk and other must-visit Chicago spots. Enjoy the property’s vibrant design, craft cocktail bar, and free Canopy Bikes for exploring the city's neighborhoods.
Explore Lincoln Park and its free zoo
Lincoln Park is a green oasis just north of downtown, offering gardens, trails, and the historic Lincoln Park Zoo — making it a favorite for families and outdoor enthusiasts. Plan a picnic by the lake, visit the zoo's wildlife exhibits, or explore the neighborhood's charming boutiques and cafe.
For a stay that puts you near the action, theWit Chicago, a Hilton Hotel features contemporary design, a vibrant rooftop lounge, and easy access to the theater district and Millennium Park.
Catch a seasonal festival or event
Chicago's calendar is packed with can't-miss events, from Restaurant Week in the winter to the Air and Water Show and the Jazz Festival in late summer. Plan your visit around the Chicago Architecture Biennial for an even deeper dive into the city's rich design legacy. For easy access to the festivities, Hilton Garden Inn Chicago Downtown South Loop provides comfortable rooms, on-site dining, and a welcoming home base near Millennium Park and Grant Park.
Disclaimer: We used AI assistance to generate this content. All information was reviewed by Hilton's team to ensure it meets our standards for accuracy and ethics, allowing us to better match your travel needs and connect you with the right stay.
Explore more
A Traveling Insider's Guide to Chicago
Allow us to help you navigate your Chicago vacation using this guide to the Windy City.
The Perfect Getaway: A weekend exploring Chicago's food scene
From lollipop chicken wings to Vienna hot dogs (Chicago-style, of course), the Windy City knows its food — and so do we. So, grab your appetite and let our food-focused itinerary take you through a perfect weekend in Chicago.
The Perfect Getaway: A long weekend in Chicago for Labor Day
The Windy City comes alive in the warmer months, with outdoor fests, sidewalk dining, and a bustling lakefront that's perfect for soaking up late-summer vibes.
Chicago's Magnificent Mile: An ultimate guide to shopping, dining, and attractions
Iconic architecture, storied boutiques and plenty of sights make walking Chicago's main shopping district a treat no matter where you start.
Read more:
Find travel inspiration