Chicago 4 days

Dive deep into Chicago's legendary architecture with exhibits, models, and tours. It's the best starting point to understand the city's design heritage.

• Book the Chicago River Cruise tour in advance; it's highly recommended.
• Check for free walking tours offered daily.

Stroll along the scenic Chicago Riverwalk, offering stunning views of the city's iconic skyscrapers and bridges. Numerous cafes and bars line the path.

• Consider a light lunch or drink at one of the riverside eateries.
• Best experienced on a clear day for optimal photo opportunities.

Experience Chicago's architectural masterpieces from the water on this award-winning boat tour. Knowledgeable docents provide fascinating insights into the history and design of each building.

• Book tickets online well in advance, especially during peak season.
• Sit on the left side of the boat for unobstructed views of the Merchandise Mart.
• Dress in layers, as it can be breezy on the river.

A highly acclaimed West Loop restaurant by Stephanie Izard, known for its creative, globally-inspired small plates and vibrant atmosphere. Reservations are essential.

• Book reservations weeks, if not months, in advance.
• Don't miss the famous 'Goat Tagliatelle' and 'Grilled Broccoli'.

One of the oldest and largest art museums in the United States, housing an impressive collection spanning centuries and cultures, including world-renowned Impressionist and Post-Impressionist works.

• Focus on specific wings to avoid museum fatigue; the Impressionist wing is a must-see.
• Download the museum's app for a self-guided tour.

Home to iconic public art installations like Cloud Gate ('The Bean') and Crown Fountain, this urban park is a vibrant hub for locals and visitors alike.

• Take photos with Cloud Gate, especially early or late to avoid crowds.
• Visit the interactive Crown Fountain, a hit with all ages.

An outdoor sculpture by British artist Anish Kapoor, its highly polished, reflective surface allows visitors to see the city skyline and their own distorted reflections.

Located atop the Chicago Athletic Association Hotel, this chic rooftop bar offers spectacular panoramic views of Millennium Park and Lake Michigan, along with craft cocktails.

• Arrive early to secure a good spot with a view.
• They offer small bites if you're feeling peckish.

Explore natural history with world-class exhibits, including Sue the T. Rex, ancient Egyptian mummies, and the Hall of Gems and Jades. It's a journey through time and across continents.

• Prioritize exhibits of interest as it's a large museum.
• Check for special exhibitions that might require separate tickets.

Discover aquatic life from around the globe, featuring diverse habitats from coral reefs to the Great Lakes. Interactive exhibits and animal encounters make it engaging for all.

• Book timed-entry tickets online in advance.
• The Oceanarium is a highlight, showcasing beluga whales and dolphins.

The first planetarium in the Western Hemisphere, offering fascinating exhibits on space exploration, astronomy, and the universe, with engaging sky shows.

• The sky shows are a major draw; check the schedule and book tickets.
• Enjoy the stunning views of the Chicago skyline from the Planetarium's grounds.

Experience the birthplace of Chicago's famous deep-dish pizza. A casual and historic spot offering authentic, hearty pies that are a must-try for any visitor.

• Be prepared for a wait, especially during peak hours.
• The original deep-dish is a classic, but they offer other styles too.

One of the oldest continuously operating zoos in North America, offering free admission and a diverse collection of animals in a beautiful urban park setting.

• Combine your visit with a stroll through Lincoln Park Conservatory.
• Check feeding times for a more engaging animal viewing experience.

A stunning Victorian glass conservatory housing exotic plants from around the world, including tropical flowers and ancient ferns, offering a lush escape.

• The Fern Room and Orchid Room are particularly beautiful.
• A great place to visit regardless of the weather outside.

Explore the charming, historic streets of Old Town, known for its Victorian architecture, unique boutiques, and lively atmosphere. It offers a more intimate Chicago experience.

• Browse the shops along North Avenue and Wells Street.
• Look for the historic Second City comedy club, a Chicago institution.

A Mediterranean-inspired restaurant with a communal dining ethos, known for its inventive small plates, excellent wine list, and energetic ambiance. It's a popular spot for sharing dishes.

• Reservations are highly recommended.
• The chorizo-stuffed dates and whole roasted chicken are signature dishes.