Chicago, Illinois 4 Day Itinerary

Day 1: Downtown Exploration

• Morning: Start your day with breakfast at Amy’s Café & Bookstore, a charming café with a large selection of books.

• Afternoon: Visit the Navy Pier. Enjoy the views, visit the Centennial Wheel, and explore the Chicago Children’s Museum or the Shakespeare Theater. Lunch at Nalo Kitchen located on the pier.

• Evening: Take a River Architecture Tour with Shoreline Sightseeing. Have dinner at Girl & The Goat or Alinea, both are renowned Chicago eateries.

Day 2: Museums and Parks

• Morning: Visit the Field Museum and explore the natural history exhibits. Have brunch at Café Brauer.

• Afternoon: Head to Millennium Park, visit the iconic Cloud Gate (aka The Bean) and Grant Park. Lunch can be grabbed at Park Grill. In the afternoon, you might want to visit the Art Institute of Chicago.

• Evening: Dinner at Avec or Blackbird, both offering farm-to-table dishes. After dinner, take a stroll in the vibrant neighborhood of Wicker Park or Lincoln Park.

Day 3: Architecture and Neighborhoods

• Morning: Visit the Shedd Aquarium and have lunch at Gio’s Chicken Amalfitano.

• Afternoon: Take a walking tour of Frank Lloyd Wright buildings or join a guided tour of the Robie House in Oak Park, a suburban neighborhood west of downtown Chicago.

• Evening: Dinner at Alinea (if you didn’t go on Day 1). Alternatively, try Au Cheval, a popular burger spot. Spend the evening exploring the bars and nightlife in Wicker Park or Lincoln Park.

Day 4: Foodie Adventure

• Morning: Visit the Chicago French Market for breakfast and explore local vendors offering a variety of international foods.

• Afternoon: Take a food tour with Fooditor, or visit the Green City Market on Saturdays. Have lunch at Birrieria Zaragoza for some delicious goat birria.

• Evening: Farewell dinner at The Purple Pig, known for its Mediterranean cuisine. After dinner, enjoy a nightcap at The Signature Room with stunning views of the city skyline.

Things to Know:

• Chicago’s public transportation system is operated by the Chicago Transit Authority (CTA), with trains and buses serving the city and suburbs. You can use a Ventra card for easy travel.

• The best time to visit Chicago is from May to October when the weather is most pleasant.

Tips:

• Book tickets in advance for popular attractions like museums, tours, and restaurants to secure your spot.

• Chicago’s summers can be hot and humid, so pack appropriate clothing. In winter, temperatures drop significantly, so warm layers are a must.

• Embrace the local culture by trying deep-dish pizza (Lou Malnati’s or Giordano’s) and Chicago-style hot dogs (Superdawg or Portillo’s).