Chicago Illinois 2 Day Itinerary

Day 1: Exploring the City

Morning:

  • Start your day with a hearty breakfast at Amy’s Breakfast Club, known for its innovative twists on classic dishes.
  • Visit The Art Institute of Chicago, one of the oldest and largest art museums in the United States, featuring works from all periods and cultures. (Admission: $25 for adults, free for children under 14 and members.)

Afternoon:

  • Head to Millennium Park to see The Bean (Cloud Gate), an iconic sculpture, and the Lurie Garden.
  • Take a stroll along Navy Pier, where you can enjoy lakefront views, visit the Chicago Children’s Museum, or ride the Ferris wheel.
  • For lunch, grab some deep-dish pizza at Lou Malnati’s Pizzeria.

Evening:

  • Explore The Magnificent Mile, Chicago’s premier commercial district with numerous shops, restaurants, and architecture.
  • Dine at Girl & The Goat, a popular restaurant by Chef Stephanie Izard offering innovative small plates. (Reservations recommended.)
  • End your day with a visit to Cocktail Cabinet or The Violet Hour, renowned cocktail bars in Chicago.

Transportation:

  • The Chicago Transit Authority (CTA) operates an extensive network of buses and trains throughout the city, making it easy to get around. Consider getting a Ventra card for touchless travel.

Day 2: Discovering History and Nature

Morning:

  • Visit the Field Museum, one of the largest natural history museums in the world, home to Sue, the T. rex skeleton. (Admission: $24 for adults, free for children under 3.)
  • Stroll along Lake Shore Path and enjoy the lakefront views.
  • Grab lunch at The Purple Pig, an Italian eatery with a focus on charcuterie.

Afternoon:

  • Explore Lincoln Park Zoo, one of the oldest zoos in North America, free of charge.
  • Visit Frank Lloyd Wright’s Robie House, a National Historic Landmark designed by the famous architect. (Admission: $20 for adults, $15 for students and seniors.)
  • For dinner, head to Alinea, one of the world’s best restaurants offering a unique tasting menu experience. (Reservations extremely limited and require booking months in advance.)

Evening:

  • Take a sunset cruise on Lake Michigan with Shoreline Sightseeing, or enjoy a leisurely stroll through Lincoln Park.
  • Cap off your evening at The Signature Room in the John Hancock Center, offering stunning views of the city and a fine dining experience.

Things to Know:

  • Chicago is known as “The Windy City,” but it’s not because of its weather; it’s due to the city’s political leaders’ reputations for loquaciousness!
  • Tipping in Chicago is customary: 18-20% for dining, $1-2 per bag for hotel porters.
  • Chicago summers can be quite humid and hot, while winters can be cold with significant snowfall. Always check the weather forecast before your visit.