Chicago, Illinois 5 Day Itinerary

Day 1: Downtown Chicago Exploration

  • Morning: Start your day with breakfast at Amy's Café & Bookstore (5800 N Broadway St), a charming spot with delicious food and an extensive book collection.

  • Afternoon: Visit the iconic Navy Pier (600 E Grand Ave) for stunning lakefront views. Don’t miss the Centennial Wheel and the Chicago Children’s Museum.

  • Evening: Head to The Magnificent Mile (N Michigan Ave) for shopping and dining. Have dinner at Gibson's Steakhouse (1028 N Rush St), a classic Chicago spot known for its steaks.

  • Transportation: Chicago Transit Authority (CTA) provides an extensive network of buses and trains. A one-day pass costs $10.

Day 2: Architecture & Museums

  • Morning: Grab breakfast at Ann Sather's Café (multiple locations) and then embark on a Chicago Architecture River Cruise. Book your tickets here.

  • Afternoon: Visit the Art Institute of Chicago (111 S Michigan Ave). Spend hours exploring its extensive collection, including American, European, and contemporary art.

  • Evening: Dine at Alinea (1723 N Halsted St), a 3-Michelin-star restaurant offering an unforgettable dining experience. For a more casual option, try Lou Malnati's Pizzeria (multiple locations) for Chicago-style deep dish pizza.

Day 3: Millennium Park & The Loop

  • Morning: Begin your day with breakfast at Pastriel Bakery (4927 N Kedzie Ave), a popular spot for Latin American pastries and coffee.

  • Afternoon: Head to Millennium Park (201 E Randolph St) to see the iconic Cloud Gate sculpture (known as “The Bean”) and the Crown Fountain. Explore nearby attractions like the Art Gallery of Chicago’s Modern Wing, Frank Gehry’s Pritzker Pavilion, and the Harris Theater for Music and Dance.

  • Evening: Dine at Girl & The Goat (809 W Randolph St), a renowned restaurant offering innovative small plates. After dinner, stroll around The Loop and take in the city lights.

Day 4: Lincoln Park & Lakeshore

  • Morning: Start your day with breakfast at Pastoral Artisan Cheese, Bread & Wine (4719 N Lincoln Ave) and then explore Lincoln Park Zoo. It’s free to enter!

  • Afternoon: Visit the nearby Adler Planetarium (1300 S Lake Shore Dr). Spend time exploring its exhibits, including the Universearium, the Grainger Sky Theater, and the Adler After Dark events.

  • Evening: Dine at Gordon Restaurant & Bar (950 N Clark St), a modern American spot with stunning lake views.

Day 5: Neighborhood Exploration

  • Morning: Head to Wicker Park/Bucktown neighborhoods and grab breakfast at Waffle Love (1723 W Division St).

  • Afternoon: Explore unique shops, galleries, and street art. Don’t miss the Flat Iron Arts Building (1579 N Milwaukee Ave) and the Wicker Park Bucktown Chamber of Commerce Mural.

  • Evening: Dine at Avec (615 West Randolph St), a Mediterranean small plates restaurant in the Fulton Market District. End your evening with a drink at The Violet Hour (1520 N Damen Ave) – Chicago’s famous cocktail bar.

Things to Know:

  • Chi-town locals are friendly, but don’t expect them to strike up conversations easily.
  • Tipping in Chicago is customary and typically 20% of the bill at restaurants.
  • Weather can be unpredictable, so pack layers!
  • The city offers a wide variety of cultural events year-round – check out Chicago Cultural Center for free events.