Chicago, USA 2 Day Itinerary

Day 1: Exploring Downtown Chicago

Morning:

  • Start your day with a hearty breakfast at Amy’s Café & Bookstore in Wicker Park. This charming café offers delicious meals and a cozy atmosphere perfect for an early start.

  • Head downtown by using the Chicago Transit Authority (CTA), which provides affordable and convenient public transportation. The ‘L’ train is especially popular.

  • Arrive at Millennium Park and visit the iconic Cloud Gate (also known as “The Bean”). Take some stunning photos of your reflection!

  • Next, walk over to The Art Institute of Chicago (artic.edu), one of the oldest and largest art museums in the United States.

Afternoon:

  • Grab lunch at Girl & The Goat, a renowned restaurant offering innovative small plates with global influences. Reservations are highly recommended!

  • After lunch, take a stroll along the famous Magnificent Mile (Michigan Avenue) and enjoy shopping at various high-end stores or explore historic buildings like the Wrigley Building.

  • Visit Navy Pier, where you can enjoy views of Lake Michigan, ride the Centennial Wheel, or attend a show at the Chicago Shakespeare Theater.

Evening:

  • For dinner, try Gibsons Bar & Steakhouse, known for its classic ambiance and delicious steaks.

  • End your day by taking in a comedy show at Second City – Chicago’s famous improv theatre that has launched the careers of numerous comedians, including Tina Fey, Stephen Colbert, and Steve Carell!

Day 2: Discovering Chicago’s Neighborhoods

Morning:

  • Begin your day with breakfast at Ann Sather’s Bakery, offering a variety of delicious breakfast dishes and pastries in Lakeview.

  • Hop on the CTA Red Line to head to Hyde Park, home to the University of Chicago and the Museum of Science and Industry. Spend the morning exploring this vast museum that offers interactive exhibits for all ages.

Afternoon:

  • For lunch, grab a bite at The Promontory, a restaurant, music venue, and community gathering space in Hyde Park.

  • Take the Green Line back to downtown and explore the vibrant neighborhood of Wicker Park. Check out the independent boutiques on Milwaukee Avenue or visit the Chop Shop, a bike shop, coffee bar, and eatery all in one!

Evening:

Things to Know:

  • The weather in Chicago can be unpredictable, so pack layers and always check the forecast before heading out.

  • Be aware that some attractions may require advance tickets or reservations.

  • Chicago is a foodie’s paradise! Don’t hesitate to try new restaurants or dishes during your visit.

Transportation:

  • The CTA provides extensive coverage throughout the city, with trains and buses running 24/7. Taxis and ride-sharing services like Uber and Lyft are also widely available.

Tips:

  • Consider purchasing a Go Chicago Card for access to attractions, tours, and restaurants at a discounted rate.

  • Take some time to explore the city’s diverse neighborhoods – each one offers a unique vibe and experiences that reflect Chicago’s rich cultural tapestry.