Chicago 2 Day Itinerary

Day 1: Exploring Downtown Chicago

Morning:

  • Start your day with breakfast at The Original Pancake House (1735 North Lake Shore Drive), famous for its giant pancakes.
  • Head to Navy Pier (600 East Grand Avenue) and enjoy the beautiful lakefront views. Don’t forget to visit the Centennial Wheel or the Chicago Children’s Museum.
  • Take a Architecture River Cruise from Navy Pier or Michigan Ave Dock (112 East Wacker Drive). This 90-minute tour will give you an insight into the city’s iconic architecture.

Afternoon:

  • Have lunch at Lou Malnati’s Pizzeria (439 N Michigan Ave), known for its famous Chicago-style deep dish pizza.
  • Visit Millennium Park (201 E Randolph St) and take a picture with The Bean (Cloud Gate). Also, check out the Frank Gehry-designed Jay Pritzker Pavilion.
  • Explore The Art Institute of Chicago (111 S Michigan Ave), one of the oldest and largest art museums in the United States.

Evening:

  • Have dinner at Girl & The Goat (809 West Randolph Street), a popular restaurant offering innovative small plates.
  • End your day with a visit to Willis Tower Skydeck (233 S Wacker Dr) for breathtaking views of the city from 1,353 feet above ground.

Day 2: Discovering Chicago’s Neighborhoods

Morning:

  • Have breakfast at Ann Sather’s Bakery & Cafe (Multiple locations), a local favorite known for its cinnamon rolls and omelets.
  • Visit the vibrant neighborhood of Wicker Park and explore shops on North Damen Avenue. Don’t miss The Vintage Bazaar for unique finds.
  • Head to Lincoln Park Zoo (2001 North Clark Street), one of the oldest zoos in North America, with free admission all year round.

Afternoon:

  • Have lunch at Avec (615 West Randolph Street), offering Mediterranean small plates in a cozy setting.
  • Take a stroll around Lake Michigan and enjoy the beauty of Lincoln Park. Visit the Alfred Caldwell Lily Pool, a hidden gem within the park.
  • Spend your afternoon exploring Chicago’s Music Box Theatre (2116 South Stockton Drive) in the Andersonville neighborhood. Check out their schedule for live performances.

Evening:

  • Have dinner at Alinea (178 West Huron Street), one of the world’s top restaurants, offering a unique dining experience. Reservations are recommended and expensive. For more budget-friendly options in the area, try Big Star (1531 North Damen Avenue) or Girl & The Goat (2427 W North Ave).
  • End your day with a comedy show at Second City (1616 North Wells Street), known for launching the careers of many famous comedians like Tina Fey, Steve Carell, and Bill Murray.

Things to Know:

  • Chicago’s public transportation system is easy to navigate. The ‘L’ train (elevated rail) and buses are operated by the CTA.
  • Chicago summers can be hot and humid, while winters are cold with snowfall. Dress accordingly and check the weather forecast before you go.
  • Tips are expected in restaurants, bars, and for taxis or ride-shares. A common practice is to tip around 20% of the bill.
  • For more information about events, attractions, and deals, visit the Choose Chicago website (https://www.choosechicago.com/).