10 Best Attractions in Chicago

Chicago is not just a city Frank Sinatra sang about; it’s a place that offers something for everyone. With its towering skyscrapers, lively streets filled with Midwestern charm, and plenty of green spaces, this city blends big-city energy with a welcoming atmosphere. It’s the third-largest city in the U.S., home to roughly 2.7 million people.

Known as the “Birthplace of the Modern Skyscraper,” Chicago has much more to offer beyond its skyline. From world-class museums and unbeatable food to legendary sports teams and unforgettable waterfront views, the city truly has it all.

This guide highlights some of the top Chicago attractions to help you make the most of your trip.

Navy Pier is one of Chicago’s most iconic spots—and it truly offers something for every age group. Think local eateries, indoor gardens, free outdoor music, public art, and classic lake cruises. The Centennial Wheel, a 200-foot Ferris wheel with temperature-controlled cabins, is the star attraction, offering incredible skyline and lake views. If you’re visiting during the summer, you’ll also catch the seasonal fireworks every Wednesday and Saturday night.

This scenic lakefront campus is home to three major institutions: the Shedd Aquarium, the Field Museum, and the Adler Planetarium. Surrounded by peaceful parks, gardens, and walking paths, it’s the perfect place to explore everything from ancient history and marine life to stars and galaxies—plus enjoy beautiful views of Lake Michigan.

The Chicago Riverwalk is a waterfront promenade perfect for a peaceful stroll. You can enjoy outdoor dining, take a sunset boat ride, rent a kayak to paddle between skyscrapers, or simply relax under the twinkling evening lights. Don’t miss Art on theMART, the world’s largest permanent digital art projection. You can also explore a historic bridgehouse museum or hop on a fun tiki-themed boat.

Chicago’s theatre community is one of the country’s most impressive, boasting over 200 theatres. From Broadway tours to intimate local productions, there’s always something worth seeing. For great deals, check Hot Tix for discounted tickets, and try visiting during Chicago Theatre Week in February for additional specials.

Millennium Park Campus is a year-round hub of excitement. In winter, you can go ice skating, and in summer, there’s outdoor dining near Cloud Gate (the famous “Bean”). Enjoy free concerts and movies at the Jay Pritzker Pavilion, splash around the Crown Fountain, or stroll through the serene Lurie Garden, home to butterflies and migratory birds.

Chicago has two thrilling observation decks:

• 360 CHICAGOat the former John Hancock Center, home to TILT, where the platform gently leans you outward 1,000 feet above the city for unbelievable views of The Magnificent Mile and Lake Michigan.
• Skydeck Chicagoin Willis Tower, where you can step into The Ledge—glass boxes extending 4 feet outside the skyscraper at 1,353 feet above ground.

Both offer unforgettable, high-flying perspectives.

With 26 miles of lakefront and 25 beaches, Chicago is absolutely a beach city.
North Avenue Beach is the go-to spot for activities like volleyball, paddleboarding, or yoga with skyline views.
Another great pick is Oak Street Beach, the closest beach to downtown and perfect for relaxing between sightseeing stops.

What makes Chicago’s beaches extra special? They’re free and staffed with lifeguards daily from 11 a.m. to 7 p.m. in the summer.

Opened in 1907, the Green Mill Cocktail Lounge is a legendary jazz club with a rich past. It was famously frequented by gangster Al Capone, and his preferred booth remains a popular feature today. The venue also appeared in films like High Fidelity, Soul Food, and Prelude to a Kiss. Rumors of secret underground tunnels add to their mysterious charm.

Located on the Gold Coast, Oak Street is Chicago’s most luxurious shopping stretch. This chic neighborhood features designer boutiques such as Jimmy Choo, Tory Burch, and Giorgio Armani, alongside jewelers like Harry Winston and elegant bridal salons like Vera Wang. If you’re in the mood to splurge, this is your spot.

Lincoln Park is a vibrant neighborhood perfect for boutique shopping and café-hopping. You’ll find everything from fashion and home goods to gifts and specialty stores. Popular stops include Art Effect, Alice & Wonder, and Enzo Custom. Between shops, stroll through the area’s leafy streets or visit nearby Lincoln Park Zoo or the Conservatory.

Imagine soaking up panoramic views from iconic skyscrapers, exploring world-famous museums, and taking peaceful walks along the lakefront. Whatever brings you here, Chicago greets you with warm Midwestern charm and endless surprises.

Ready to explore Chicago? Secure your stay at Skylark Motel Chicago and enjoy convenient access to the city’s best sights. Reserve your room today.