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Chicago makes it easy to fill a weekend or a longer getaway with iconic architecture, vibrant neighborhoods, lakefront attractions, world-class museums, and a food scene all its own. Whether you're visiting for a short trip or an extended stay, there are plenty of ways to experience the city's history, culture, and distinctive character.
Red Roof hotels in the Chicago area offer an affordable home base for exploring the city's top attractions, from its famous landmarks and museums to its diverse neighborhoods and lakefront destinations.
Navy Pier is Chicago's iconic lakefront destination, home to restaurants, shopping, boat cruises, rides, parks, and sweeping views of Lake Michigan. Originally built as a freight port, it has evolved over more than a century into one of the city's most visited attractions. Consider the Explorer Pass for admission to Navy Pier's attractions, along with access to more than 25 additional Chicago experiences.
One of the most memorable things to do in Chicago is to experience the city from the water. Cruises range from relaxing lake tours and architecture river tours to dinner cruises where you can watch the skyline shift from golden sunset to glittering city lights. The Chicago River offers some of the best vantage points for the city's world-famous architecture.
Chicago's food scene is legendary, built around deep-dish pizza, Italian beef sandwiches, Chicago-style hot dogs, and much more. For visitors who want to go beyond the obvious, guided food tours are a great option. The Secret Food Tour takes you to neighborhood spots that often go unnoticed by out-of-towners, while other options include a Chinatown tasting walk, a bike tour covering Polish pierogis and Mexican tortas, and a 2.5-hour walking tour of Chicago's best pizzas, craft beer, and hot dogs.
Chicago is home to a thriving urban art scene, with striking murals spread across neighborhoods throughout the city. Guided urban art tours take you off the main tourist path and into the backstreets, explaining the history and meaning behind the works you encounter. It is one of the most distinctive and rewarding outdoor things to do in Chicago.
Located in Grant Park, the Art Institute of Chicago is one of the oldest and largest art museums in the United States. Founded in 1879, the museum houses a collection of more than 300,000 works spanning thousands of years of human creativity.
Millennium Park sits just one block from Lake Michigan in the heart of downtown Chicago and draws around 25 million visitors every year. The 24.5-acre park is home to world-class art, architecture, and landscape design. Highlights include the Crown Fountain, which combines public art with interactive water features, and Cloud Gate, the iconic mirrored sculpture affectionately known as The Bean, which has become one of the most recognizable symbols of Chicago.
Located on the 94th floor of the John Hancock Center, 360 CHICAGO offers breathtaking views of the city skyline, Lake Michigan, and on clear days all four neighboring states: Illinois, Wisconsin, Indiana, and Michigan. The observation deck's TILT experience allows visitors to lean out over the city on a glass panel from 1,000 feet above street level. A bar on-site makes it a great spot to watch the sunset.
The Shedd Aquarium is one of Chicago's most beloved attractions, home to approximately 32,000 animals across freshwater and marine environments. Interactive exhibits, dolphin presentations, and coral reef dives make it a standout destination for families and nature lovers alike. It is one of the most visited cultural institutions in the United States.
The Willis Tower, still widely known by its former name, the Sears Tower, stands at 1,451 feet and remains Chicago's tallest building. The Skydeck observation deck on the 103rd floor offers panoramic city views, and The Ledge, a glass-floored balcony extending out from the building's side, gives visitors a stomach-dropping look straight down to the streets below.
No visit to Chicago is complete without deep-dish pizza. Lou Malnati's Pizzeria on Wells Street is celebrated for its signature buttery crust, while Pequod's Pizza on North Clybourn Avenue is known for its caramelized cheese crust and late-night hours. Both are essential stops for any first-time visitor.
Chicago's prohibition-era history is as fascinating as it is infamous. Names like Al Capone, Johnny Torrio, and Bugs Moran defined a turbulent era that shaped the city's identity. The 90-minute Mob and Crime Bus Tour explores Chicago's darker past, visiting sites including the location of the St. Valentine's Day Massacre and the Biograph Theatre, where notorious bank robber John Dillinger was shot by FBI agents in 1934.
Founded in 1893, the Field Museum is one of the largest natural history museums in the world, with a collection of more than 24 million objects. Its grand Neoclassical halls house dinosaur fossils, rare gemstones, ancient Egyptian artifacts, and exhibits spanning the cultures of the Americas, Africa, Asia, and the Pacific Islands. The Stanley Field Hall is home to one of the museum's most striking displays - a cast of a massive Titanosaur dinosaur, one of the largest creatures ever to walk the earth.
Located in Lincoln Park, the Chicago History Museum brings the city's past to life through immersive, thematic exhibitions. Facing Freedom traces the city's civil rights struggles from the 1850s through the 1970s, while Crossroads of America lets visitors step inside a historic jazz club or board Chicago's very first L train. The museum's Chicago dioramas chart the city's remarkable growth from a frontier outpost to one of America's great metropolises.
Built in 1875 after its predecessor was destroyed in the Great Chicago Fire of 1871, the Holy Name Cathedral is one of Chicago's most striking examples of Gothic Revival architecture. The cathedral's entrance features massive bronze doors weighing more than 500 kg each, cast to resemble planks of wood. Inside, highlights include the Stations of the Cross rendered in Rocco Alicante marble, bronze sculptures of the Evangelists, and the bishop's throne of the Chicago Diocese.
Stretching along the Lake Michigan shoreline in Lincoln Park, North Avenue Beach is one of Chicago's most popular outdoor destinations. The beach features a beachfront bar, kayak and paddleboard rentals, volleyball courts hosting international competitions, and serves as the viewing area for the annual Chicago Air and Water Show each August.
Ready to explore Chicago? Red Roof® offers affordable, comfortable hotels conveniently located near the city's top attractions. Book your stay at redroof.com or call 800.RED.ROOF (800.733.7663). RediRewards® members earn 10 points per dollar on every stay - join for free at redroof.com.
