Chicago 5 days

Dive into Chicago's rich architectural history with interactive exhibits and model displays. Learn about the city's pioneering skyscrapers and urban planning.

• Book tickets online in advance.
• Consider joining one of their guided tours for deeper insights.

Stroll along the scenic Chicago Riverwalk, offering stunning views of the city's iconic architecture from water level. Enjoy the vibrant atmosphere with cafes and public art.

• Perfect for photography, especially during golden hour.
• Grab a coffee or a drink at one of the riverside cafes.

Experience Chicago's legendary architecture from the Chicago River on this highly-rated boat tour. Knowledgeable docents explain the history and design of the city's most famous buildings.

• Book tickets well in advance, especially for popular times.
• Sit on the open-air upper deck for unobstructed views.

A Chicago institution since 1898, The Berghoff offers classic German-American cuisine in a historic setting. Enjoy hearty meals and a wide selection of beers in their main dining room or bar.

• Try their famous Wiener Schnitzel or Corned Beef.
• The bar area is great for a more casual experience.

Home to one of the most extensive and impressive art collections in the world, including masterpieces by Monet, Renoir, and Van Gogh. Explore diverse galleries spanning centuries and cultures.

• Focus on specific wings if time is limited; the Impressionist collection is a must-see.
• Check for special exhibitions which may require separate tickets.

A vibrant urban oasis featuring iconic public art, including Cloud Gate (The Bean) and Crown Fountain. Enjoy the Pritzker Pavilion and Lurie Garden.

• Take photos with your reflection in Cloud Gate.
• The park is a great spot for a leisurely lunch if you pack your own.

Chicago's premier shopping district, offering a mix of luxury boutiques, department stores, and popular retailers. Enjoy window shopping or indulge in some retail therapy along Michigan Avenue.

• Look for the historic Water Tower and Pumping Station.
• Many flagship stores offer unique architectural designs.

A lively Italian trattoria serving delicious small plates (cicchetti) perfect for sharing. Enjoy a wide selection of wines and a convivial atmosphere in this River North favorite.

• Order a variety of dishes to sample different flavors.
• Reservations are highly recommended, especially on weekends.

Experience breathtaking panoramic views of Chicago and up to four states from the 103rd floor of Willis Tower. Step out onto The Ledge, a glass balcony extending 4.3 feet out from the building.

• Visit early in the morning to avoid the longest queues.
• On a clear day, the views are unparalleled.

Explore Chicago's historic Little Italy, a vibrant neighborhood known for its authentic Italian restaurants and bakeries. Enjoy the lively atmosphere and rich culinary heritage.

• Consider stopping at a bakery for some cannoli or biscotti.
• This neighborhood is also home to the University of Illinois Chicago (UIC).

A beloved Chicago summer tradition, Mario's serves authentic, fresh-squeezed Italian lemonades in a variety of flavors. It's a perfect sweet treat on a warm day.

• Try the classic lemon or a mixed fruit flavor.
• Often has a line, but it moves quickly.

Chef Stephanie Izard's acclaimed West Loop restaurant offers a globally-inspired menu with bold flavors and creative dishes. The energetic atmosphere and communal tables make for a memorable dining experience.

• Reservations are extremely difficult to secure; book months in advance.
• The 'Goat' dishes are signature and highly recommended.

Explore natural history with world-class exhibits, including Sue the T. rex, ancient Egyptian artifacts, and dazzling gems and minerals. It's a journey through time and across continents.

• Prioritize the exhibits that interest you most, as it's vast.
• Check the museum's website for any timed entry requirements.

Discover aquatic life from around the globe, featuring diverse habitats like the Caribbean Reef, Amazon Rising, and the Oceanarium. It's an immersive experience for all ages.

• Consider purchasing a CityPASS if you plan to visit multiple attractions.
• The dolphin show in the Oceanarium is a popular (and often crowded) highlight.

The first planetarium in the Western Hemisphere, offering fascinating exhibits on space exploration, astronomy, and our universe. Enjoy immersive sky shows in its state-of-the-art theaters.

• The sky shows are a major draw; book tickets for your preferred showtime.
• The exterior offers fantastic skyline views, especially at sunset.

A local favorite for authentic Chicago-style deep-dish and thin-crust pizza. Enjoy delicious pies and classic Italian dishes in a casual, friendly setting.

• The deep-dish pizza takes about 45 minutes to bake, so order early.
• They have multiple locations; this one is convenient to the South Loop.

One of the oldest and last free zoological gardens in the United States. Explore diverse animal collections in a beautiful park setting, with views of the city skyline.

• The zoo is free, making it a great budget-friendly activity.
• Check feeding times for certain animals for more active viewing.

A stunning Victorian-era glass conservatory housing a diverse collection of plants and flowers, including tropical, subtropical, and desert species. It's a lush escape year-round.

• Free admission, though donations are appreciated.
• Especially beautiful during spring flower shows.

Enjoy the vibrant atmosphere of one of Chicago's most popular lakefront beaches. Walk along the shore, rent bikes, or simply relax with views of the city skyline and Lake Michigan.

• Rent a Divvy bike for a scenic ride along the Lakefront Trail.
• The iconic beach house is a great spot for photos.

Famous for its exceptionally rich and decadent 'single cheeseburger,' Au Cheval is a popular diner-style spot. Expect a wait, but many find it worth it for the culinary experience.

• The wait can be very long, especially during peak hours; consider going during off-hours or on a weekday.
• The burger is the star, but other diner classics are also available.