Chicago, IL

What to do in Chicago, IL

Millennium Park

Millennium Park is a must-visit destination in Chicago, offering a blend of breathtaking architecture, landscape design, and art. The park is famous for its iconic Cloud Gate, also known as “The Bean,” a massive reflective sculpture that has become a symbol of the city. Visitors can explore the Lurie Garden, an urban oasis featuring a variety of flowers and plants, or take a leisurely stroll along the winding paths. Throughout the year, the park hosts numerous events and festivals, including outdoor concerts and art installations. The Jay Pritzker Pavilion, an outdoor amphitheater within the park, is the perfect spot to catch a live performance during the summer months.

Art Institute of Chicago

As one of the oldest and largest art museums in the United States, the Art Institute of Chicago is a cultural gem that attracts art enthusiasts from around the world. Housing a remarkable collection of artworks spanning centuries and continents, the museum features renowned pieces such as Grant Wood’s “American Gothic” and Georges Seurat’s “A Sunday on La Grande Jatte.” Visitors can explore galleries dedicated to Impressionist, Post-Impressionist, and American art, among others. The iconic lion statues guarding the entrance have become a symbol of the city and offer a perfect photo opportunity for tourists.

Navy Pier

A beloved landmark and entertainment destination, Navy Pier offers a diverse array of attractions for visitors of all ages. From iconic ferris wheel rides that provide stunning views of the city skyline to the Chicago Children’s Museum, there’s plenty to see and do. The pier’s lineup of restaurants, shops, and outdoor promenades make it an ideal spot for leisurely walks and waterfront dining. In addition, Navy Pier frequently hosts special events, including fireworks displays, cultural festivals, and live performances, ensuring there’s always something new to experience.

The Magnificent Mile

Stretching along Michigan Avenue, the Magnificent Mile is a shopper’s paradise, featuring a mix of luxury boutiques, department stores, and specialty shops. Beyond its world-class shopping, this bustling thoroughfare is also home to architectural marvels, upscale hotels, and a vibrant dining scene. Visitors can admire the striking architecture of the Wrigley Building and the Tribune Tower or take a leisurely stroll through the picturesque Riverwalk. The area comes alive during the holiday season with dazzling lights and festive decorations, making it a magical destination for seasonal celebrations.

Chicago River Architecture Tour

Exploring Chicago’s architectural marvels from the vantage point of the Chicago River is a captivating experience that shouldn’t be missed. Architectural boat tours offer an informative and scenic journey through the city’s iconic skyscrapers and historic buildings. Visitors can learn about the renowned architects and engineers who shaped the city’s skyline while gliding along the river. The tour provides an opportunity to appreciate landmarks such as the Wrigley Building, Willis Tower, and the iconic Marina City complex. Whether during the day or illuminated by the city lights at night, this tour offers a unique perspective on Chicago’s rich architectural heritage.

Example Two-Day Itinerary

Day 1

Morning

Start your day at Millennium Park, where you can see the iconic Cloud Gate sculpture, also known as “The Bean.” Take a stroll through the Lurie Garden and enjoy the picturesque views of the city skyline.

Late Morning

Walk over to the Art Institute of Chicago and explore its extensive collection of art, including famous pieces like Grant Wood’s “American Gothic” and Georges Seurat’s “A Sunday on La Grande Jatte.”

Afternoon

Head to the Navy Pier for a mix of entertainment, dining, and sightseeing. Take a ride on the Navy Pier Ferris Wheel for stunning views of Lake Michigan and the city.

Evening

Enjoy an evening performance at the Chicago Shakespeare Theater, located on Navy Pier. The theater offers a range of classical and contemporary plays and musicals.

Day 2

Morning

Begin your day by visiting the Chicago Riverwalk. Take a relaxing walk along the river and admire the architectural landmarks nearby.

Late Morning

Make your way to the Chicago Architecture Center for an informative and visually stunning tour that delves into the city’s renowned architecture.

Afternoon

Head to the Magnificent Mile for some world-class shopping and dining. Explore the upscale boutiques, department stores, and diverse culinary options along this renowned stretch.

Evening

Spend your evening at the Chicago Riverwalk once again, this time taking an architecture boat tour. The tour provides a unique perspective of the city’s signature buildings and their history.

This two-day itinerary offers a blend of culture, art, architecture, and scenic views, allowing you to experience the best of Chicago’s diverse offerings.