Chicago 5 days

Experience Chicago's legendary architecture from the best vantage point: the Chicago River. This highly-rated tour covers over 50 significant buildings, narrated by knowledgeable docents.

• Book tickets in advance, especially for popular times.
• Arrive 15-20 minutes early for good seating.

A gastropub with a sophisticated yet comfortable atmosphere, offering elevated pub fare and a wide selection of beers. It's conveniently located near Millennium Park.

Home to iconic public art, including Cloud Gate ('The Bean'), Crown Fountain, and the Pritzker Pavilion. It's a vibrant urban oasis perfect for a stroll and people-watching.

• Visit Cloud Gate early in the morning or late evening to avoid crowds.
• Check the schedule for free concerts or events at the Pritzker Pavilion.

Located atop the Chicago Athletic Association Hotel, this popular rooftop bar offers stunning panoramic views of Millennium Park and the city skyline. Enjoy craft cocktails and small bites.

• Expect a line, especially on weekends.
• Dress code is smart casual.

One of the oldest and largest art museums in the United States, renowned for its Impressionist and Post-Impressionist collections, as well as American art. Allow ample time to explore its vast galleries.

• Purchase tickets online to save time.
• Focus on specific wings if time is limited.

A vibrant food hall featuring a curated selection of Chicago's best local chefs and restaurants, offering diverse culinary options from tacos to BBQ. Perfect for a quick and varied lunch.

A famous stretch of Michigan Avenue known for its upscale boutiques, department stores, restaurants, and historic architecture. Enjoy window shopping or indulge in some retail therapy.

• Look for the historic Water Tower and Pumping Station.
• Explore side streets for unique boutiques.

A wildly popular West Loop eatery from celebrity chef Stephanie Izard, known for its creative, globally-inspired small plates meant for sharing. Reservations are essential.

• Book reservations months in advance.
• Be adventurous and try a variety of dishes.

Ascend to the 103rd floor of the Willis Tower for breathtaking 360-degree views of Chicago and up to four states. Step out onto 'The Ledge,' a glass balcony extending from the building.

• Visit on a clear day for the best visibility.
• Consider the 'Fast Pass' option to skip lines during peak times.

A public plaza featuring Picasso's iconic sculpture, 'Chicago Peace'. It's a great spot to admire modern art and the surrounding modernist architecture.

Explore this hip neighborhood known for its independent boutiques, vintage shops, record stores, vibrant street art, and diverse culinary scene. It offers a more local and bohemian vibe.

• Wander along Milwaukee Avenue and Damen Avenue for shopping.
• Check out the murals and street art, particularly around the Damen, Milwaukee, and North intersection.

A renowned Chicago pizzeria specializing in New Haven-style 'apizza' (thin crust, coal-fired pies) and craft beers brewed on-site. It's a casual and lively spot.

• The Margherita pizza is a classic.
• Try one of their seasonal brews.

Discover natural history's wonders, from the towering skeleton of SUE the T. rex to ancient Egyptian mummies and sparkling gems. It's one of the largest natural history museums globally.

• Book tickets online to save time.
• Prioritize exhibits that interest you most, as it's impossible to see everything.

Conveniently located within the Museum Campus, this cafe offers a variety of sandwiches, salads, and hot dishes for a quick and easy lunch amidst your museum explorations.

Explore diverse aquatic life from around the world, featuring habitats like the Caribbean Reef, Amazon Rising, and the Oceanarium. It's a fantastic experience for all ages.

• Purchase tickets in advance, especially for timed entry exhibits.
• Check the schedule for animal feeding and training demonstrations.

Indulge in Chicago's famous deep-dish pizza at this iconic establishment. Known for its thick, buttery crust filled with cheese and sauce, it's a quintessential Chicago dining experience.

• Deep-dish pizzas take about 45-60 minutes to bake, so order early.
• Consider sharing a pizza to try different toppings.

One of the oldest zoos in the United States, offering free admission and a diverse collection of animals in a beautiful park setting. It's a charming place for a leisurely morning walk.

• Check the zoo map for animal feeding times.
• The zoo is always open, but exhibits have specific hours.

A stunning Victorian glass conservatory housing a variety of plant collections, including palms, ferns, and seasonal flower shows. It's a beautiful and tranquil escape.

Wander through the charming streets of Old Town, known for its well-preserved Victorian architecture, unique boutiques, and lively atmosphere. It's a delightful area for a relaxed afternoon stroll.

• Explore Wells Street for shops and restaurants.
• Admire the historic rowhouses on quieter side streets.

A dimly lit, speakeasy-style steakhouse offering exceptional dry-aged steaks, classic cocktails, and a sophisticated ambiance. It's perfect for a romantic and memorable final dinner.

• Reservations are highly recommended and can be difficult to secure.
• The French-inspired menu has excellent seafood and side options as well.