Chicago 5 days

Explore Chicago's rich architectural history through engaging exhibits and models. It's a great starting point to understand the city's iconic skyline and design principles.

• Book tickets online in advance.
• Check their schedule for guided walking tours.

A beautifully landscaped pedestrian promenade along the south bank of the Chicago River, offering stunning views of the city's architecture from water level.

• Consider a boat tour for a different perspective.
• Many restaurants and bars line the Riverwalk.

Experience a 90-minute narrated cruise offering an unparalleled look at Chicago's legendary architecture from the Chicago River. Expert docents provide fascinating insights into the buildings and their history.

• Highly recommended, book well in advance.
• Arrive early for the best seating.

A popular spot known for its sophisticated ambiance and contemporary American cuisine. It offers a cozy setting perfect for a romantic dinner.

• Reservations are essential, especially on weekends.
• Try their signature cocktails.

One of the oldest and largest art museums in the United States, housing a world-class collection spanning centuries and cultures. Don't miss the Impressionist and Post-Impressionist works.

• Allocate at least 3 hours.
• Consider a guided tour to see highlights.

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. It's adjacent to the Art Institute.

Connected to Millennium Park, this expansive park offers unique recreational opportunities, including an adventurous climbing wall, a ribbon skating/rolling path, and a whimsical children's play garden.

Located atop the Chicago Athletic Association Hotel, this popular rooftop bar offers breathtaking panoramic views of Millennium Park and Lake Michigan. Enjoy creative cocktails and small plates.

• Expect a wait, especially during peak hours.
• Go just before sunset for the best light.

A renowned stretch of Michigan Avenue known for its upscale boutiques, department stores, and diverse dining options. It's perfect for window shopping or finding unique souvenirs.

A Chicago institution famous for its delicious Garrett Mix, a combination of caramel and cheese popcorn. It's a must-try snack experience.

• Try the Garrett Mix!

One of the oldest continuously operating zoos in North America, offering free admission. It's a beautiful green space with a variety of animals and historic architecture.

• Combine with a visit to the Lincoln Park Conservatory nearby.

A highly acclaimed restaurant by Chef Stephanie Izard, offering a creative menu of globally inspired small plates meant for sharing. The atmosphere is lively and energetic.

• Reservations are notoriously difficult to get; book months in advance.
• The menu changes seasonally, so explore new dishes.

A natural history museum renowned for its extensive collections, including Sue the T. Rex, ancient Egyptian artifacts, and Halls of Gems and Jades. It's a fascinating journey through Earth's history.

• Purchase tickets online to save time.
• Focus on a few key exhibits if time is limited.

Home to a diverse array of aquatic life from around the globe, including beluga whales, dolphins, sharks, and colorful coral reefs. The Caribbean Reef and Amazon Rising exhibits are highlights.

• Book timed entry tickets in advance.
• Check the schedule for animal encounters and shows.

America's first planetarium, offering immersive sky shows and fascinating exhibits on space exploration and astronomy. The views of the city skyline from its location are spectacular.

• Consider the Sky Pass for access to all shows.
• The historical Atwood Sphere is a unique attraction.

A classic Chicago deep-dish pizza experience. This popular spot offers delicious, authentic pies in a casual setting, perfect for a hearty meal after a day of exploring.

• Deep-dish pizzas take time to bake, so order early.
• They also have excellent thin-crust options.

A vibrant and eclectic neighborhood known for its independent boutiques, vintage shops, art galleries, and lively music scene. It offers a more local and bohemian vibe.

• Explore the many murals and street art.
• Great area for unique finds.

A popular taco joint in Wicker Park with a lively atmosphere, extensive whiskey selection, and delicious, creative tacos. It's a great spot for a casual and fun lunch.

• Can get very busy; expect a wait.
• Try the variety of tacos and queso.

A speakeasy-style French steakhouse with a dimly lit, intimate ambiance. Known for its exceptional steaks, classic cocktails, and decadent desserts.

• Reservations are highly recommended.
• Dress code is smart casual.

A legendary jazz club with a rich history, once frequented by Al Capone. Experience live jazz music in an authentic, vintage setting.

• Check their schedule for live music performances.
• Cash only for cover charge and some drinks.