Best Things to Do Downtown Chicago

Downtown Chicago, also known as The Loop, is one of the city’s most popular areas to visit. The city is known for its tall skyscrapers, famous landmarks, museums, parks, restaurants, and lively streets, offering several things to do in downtown Chicago. Visitors can enjoy beautiful city views from observation decks, visit museums, see the famous Cloud Gate sculpture, walk along the Chicago River, explore public art, or relax in public parks. Also, there are plenty of places to enjoy local food, including the city’s famous deep-dish pizza. 

Things to Do Downtown Chicago 

With a mix of history, culture, architecture, entertainment, and dining, downtown Chicago has something special for every traveler, family, and adventurer.

1. Visit Millennium Park 

Spanning around 24.5 acres, Millennium Park is a good starting point for exploring downtown. It is known for Cloud Gate, commonly called The Bean, which is one of the city's most recognizable landmarks. Walk through Lurie Garden, see Crown Fountain, take photos at Cloud Gate, and enjoy concerts, festivals, and other events.

Note: Crowds are usually highest between 11:00 a.m. and 3:00 p.m., so visiting Cloud Gate before 9:00 a.m. can mean about 70% fewer people. 

2. Walk Along Chicago Riverwalk 

Another of the best things to do in Chicago Downtown is to explore the Chicago Riverwalk. This 1.25-mile waterfront path runs along the south bank of the Chicago River, from Lake Michigan and Lake Shore Drive to Lake Street. Enjoy a relaxing walk, admire the city skyline, have a meal at a waterfront restaurant like Beat Kitchen, have a local beer at Chicago Brewhouse, or go kayaking or boating. The McCormick Bridgehouse and Chicago River Museum is another interesting stop where visitors can learn about Chicago’s movable bridges.

3. See the City From Skydeck Chicago 

Visiting Skydeck at Willis Tower is one of the most exciting things to do downtown chicago. This former Sears Tower offers amazing views from the 103rd floor, about 1,353 feet above the ground. For a more thrilling experience, step onto The Ledge, a glass balcony that extends from the 103rd floor of the tower. The 360-degree views make Skydeck a popular downtown attraction.

Note: Average wait times on The Ledge range from 45 to 90 minutes during peak afternoon hours.

4. Explore the Art Institute of Chicago 

Exploring the museum is one of the most interesting things to do in downtown Chicago, Illinois, for visitors who want to enjoy local art, history, and culture. The museum has a collection of about 300,000 works of art across 12 collections by famous artists such as Vincent van Gogh, Claude Monet, and Pablo Picasso. Another interesting attraction is the Thorne Miniature Rooms on the lower level, which have 68 small rooms designed to show historical interiors.

5. Magnificent Mile 

Whether shopping, dining, sightseeing, or enjoying local entertainment along North Michigan Avenue, the Magnificent Mile is a lively place with plenty of things to do in Downtown Chicago. It is known for its wide range of stores, from well-known brands to high-end shops. Additionally, it features unique attractions, including the Harry Potter Shop, which offers an immersive experience for fans of the popular series. 

6. Visit Grant Park

Often called Chicago’s Front Yard, this large urban park is located near the city center and is close to several famous attractions. It hosts many festivals, concerts, and outdoor events throughout the year. Visitors can relax, enjoy the outdoors, and experience the lively atmosphere of Chicago in open green spaces. 

Fun Things to Do Downtown Chicago 

Besides sightseeing, Downtown Chicago offers plenty of fun things to do. Common fun things to do in the downtown area include:

1. Ride the Centennial Wheel at Navy Pier 

The enclosed, climate-controlled gondolas at the giant 200-foot Ferris wheel offer beautiful views of Lake Michigan and the Chicago skyline. The ride is one of the best downtown Chicago fun things to do for families, couples, and first-time visitors.

2.  Take an Architecture River Cruise 

Enjoy sightseeing, history, and beautiful skyline views on a Chicago River cruise. It is especially enjoyable on a pleasant afternoon or around sunset. During the relaxing 90-minute cruise, knowledgeable guides share interesting stories about Chicago’s famous buildings.

3. Explore Maggie Daley Park 

Located next to Millennium Park, it offers several things to do in downtown chicago, including rock climbing, mini golf, and seasonal activities. During winter, visitors can enjoy the Skating Ribbon, which winds through the park and provides a unique skating experience.

4. Visit 360 CHICAGO Observation Deck 

Located at 875 N Michigan Ave in the former John Hancock Center, 360 CHICAGO offers beautiful views of the city from about 1,000 feet above the ground. Enjoying the city view is one of the most fun things to do in downtown Chicago.

5. Take a Nighttime Walk 

Downtown Chicago can look completely different at night. A nighttime walk along the Riverwalk, Michigan Avenue, or around Millennium Park offers brightly lit buildings and skyline views.

Free Things to Do Downtown Chicago 

A trip to downtown Chicago is not always expensive. Several attractions and outdoor spaces can be enjoyed without a fee. The free things to do include: 

1. Chicago Cultural Center: The Chicago Cultural Center’s Tiffany dome features a 38-foot diameter containing around 30,000 individual glass pieces. Visitors can also enjoy art exhibits, films, and live performances, many of which are free. 

2. City Gallery in the Historic Water Tower: Visit this historic 19th-century Water Tower to view rotating local art, historic architecture, and work of local photographers.

3. Harold Washington Library Center: Explore the Thomas Hughes Children’s Library. Visitors can attend events, see art exhibits, and relax in the impressive glass-covered Winter Garden. 

4. Daley Plaza: See the famous 50-foot steel Picasso Sculpture, admire the fountain and modern architecture, enjoy free cultural performances and music, browse seasonal farmers and holiday markets, or watch the lively activity of downtown Chicago. 

5. Buckingham Fountain: It is one of the world’s largest fountains in Grant Park. Visitors can sit nearby, relax, and enjoy views of this well-known Chicago landmark. 

Tips for Exploring Downtown Chicago 

The following tips can help visitors enjoy things to do in Downtown Chicago:

• Millennium Park, the Art Institute, Chicago Cultural Center, and Riverwalk can be combined into one sightseeing route. 

• Wear comfortable shoes to explore the walkable areas.

• Check the forecast and carry suitable clothing or rain protection depending on the season. 

• Book a car rental in Downtown Chicago to spend more time at photogenic places and shopping.

• Check if free concerts, festivals, performances, and seasonal activities are available during the visit.

• Observation decks and boat cruises can have timed entry or sell out during busy periods. Therefore, reserve tickets in advance.

Wrapping Up!

Famous landmarks, architecture, museums, parks, shopping, food, entertainment, and waterfront activities make it easy to find things to do in downtown Chicago. Visitors can start at Millennium Park, walk along the Chicago Riverwalk, explore the Art Institute of Chicago, enjoy Navy Pier, or see the skyline from a high observation deck. Hiring a rental car makes it easy to explore all these destinations without waiting for scheduled public transit.