Chicago 5 days

Explore Chicago's rich architectural history through engaging exhibits and interactive displays. It's the perfect starting point to understand the city's iconic skyline.

• Book tickets online in advance to save time.
• Check their schedule for guided tours, which are highly recommended.

Stroll along the scenic Chicago Riverwalk, offering stunning views of the city's famous architecture from a unique perspective. Numerous cafes and restaurants line the path.

• Consider a boat tour departing from the Riverwalk for a guided architectural experience.
• Great spot for a leisurely lunch with a view.

Experience Chicago's architectural masterpieces from the water on this highly-rated boat tour. Knowledgeable docents explain the history and design of the city's most significant buildings.

• Book tickets well in advance, especially during peak season.
• Sit on the open-air deck for the best views and photo opportunities.

Enjoy craft cocktails and small plates with breathtaking panoramic views of Millennium Park and the city skyline. It's a sophisticated spot for evening drinks.

• Arrive early to secure a spot with a view, as it gets crowded.
• Dress code is smart casual.

Home to one of the nation's finest art collections, featuring Impressionist masterpieces, Thorne Miniature Rooms, and contemporary works. Plan for at least 3-4 hours to explore its vast galleries.

• Purchase tickets online to skip the ticket line.
• Don't miss the Modern Wing for stunning architecture and diverse collections.

Visit iconic public art installations like Cloud Gate (The Bean) and Crown Fountain. The park also features Lurie Garden and the Pritzker Pavilion.

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

A gastropub offering elevated pub fare and a wide selection of craft beers, located conveniently near Millennium Park. It's a great spot for a satisfying lunch.

• Try their signature burgers or the fish and chips.
• Good for people-watching from their outdoor seating.

Step back in time at this historic jazz club, once a hangout for Al Capone. Enjoy live jazz music in an intimate, vintage atmosphere.

• Check their schedule for live music performances and cover charges.
• Cash is preferred for cover charges and sometimes for drinks.

Discover natural history treasures, including Sue the T. rex, ancient Egyptian mummies, and sparkling gems. It's one of the largest natural history museums in the world.

• Consider purchasing a Go Chicago Pass if you plan to visit multiple museums.
• Focus on a few key exhibits to avoid museum fatigue.

Explore diverse aquatic life from oceans, rivers, and lakes around the globe. Highlights include the Caribbean Reef and the Amazon Rising exhibits.

• Book your timed entry tickets online in advance.
• The "Waters of the World" exhibit is particularly impressive.

Savor a classic Chicago deep-dish pizza experience at this popular eatery. Known for its thick, cheesy pies, it's a must-try for any visitor.

• Deep-dish pizzas take about 45 minutes to bake, so order early.
• Consider sharing a pizza as they are very filling.

Experience the cosmos at the Adler Planetarium, offering immersive sky shows and fascinating exhibits on space exploration. The views of the city skyline from here are also spectacular.

• Check the show schedule and book tickets for your preferred showtime.
• The exterior of the planetarium offers iconic photo opportunities.

One of the oldest and last free zoos in the country, featuring a diverse collection of animals in a beautiful setting. Explore the zoo's various exhibits and gardens.

• Visit the Kovler Lion House and the Regenstein Macaque Forest.
• Check for any special events or feeding times.

Wander through the charming streets of Old Town, known for its Victorian architecture, unique boutiques, and lively atmosphere. Explore Wells Street for shops and eateries.

• Look out for the historic Second City comedy club.
• Plenty of cafes for a relaxed lunch break.

Discover a stunning array of plant life in one of the largest and most impressive conservatories in the United States. Its themed rooms offer a tropical escape year-round.

• The Desert House and the Fern Room are particularly noteworthy.
• Great for photography enthusiasts.

Indulge in innovative, globally inspired dishes at this highly acclaimed restaurant by Stephanie Izard. The menu is designed for sharing and offers a vibrant dining experience.

• Reservations are essential and should be made months in advance.
• Be adventurous and try a variety of the small plates.

Experience breathtaking views from the 103rd floor of Willis Tower, including the famous glass Ledge. On a clear day, you can see up to four states.

• Go early in the morning to avoid long queues.
• Step out onto The Ledge for an exhilarating experience.

Explore one of Chicago's premier shopping districts, featuring high-end boutiques, department stores, and flagship retailers. It's also home to architectural gems like the Wrigley Building.

• Window shopping is a great free activity.
• Look for the historic Water Tower as a landmark.

A vibrant food hall offering a curated selection of Chicago's best local eateries under one roof. Perfect for a diverse and delicious lunch.

• Try the tamales or the BBQ from different vendors.
• Offers a great variety for groups with different tastes.

Enjoy sophisticated cocktails and unparalleled city views from the 96th floor of the John Hancock Center. It's a memorable spot for a farewell drink.

• Dress code is smart casual; no athletic wear.
• The views at sunset are particularly stunning.