Chicago, USA-5-day-itinerary

Chicago Itinerary: 5 Days of Exploration

Day 1: Millennium Park and Downtown Chicago

Morning

  • 9:00 AM: Start your day with breakfast at Lou Mitchell’s, a classic American diner serving up pancakes, waffles, and omelets.
  • 10:00 AM: Head to Millennium Park and take in the stunning views of the city from the Cloud Gate (The Bean) sculpture. Snap some photos and explore the park’s beautiful gardens.

Afternoon

  • 1:00 PM: Grab lunch at Portillo’s, a Chicago institution famous for their hot dogs, Italian beef sandwiches, and chocolate cake.
  • 2:30 PM: Visit the Art Institute of Chicago (open until 5:00 PM). With over 300,000 works of art on display, you could easily spend hours here.

Evening

  • 7:00 PM: Enjoy dinner at Girl & the Goat, a Mediterranean-inspired restaurant from Top Chef winner Stephanie Izard.
  • 9:00 PM: Catch some live music or comedy at one of Chicago’s many venues, like Second City or The Green Mill Jazz Club.

Day 2: Navy Pier and Lakefront

Morning

  • 9:00 AM: Start your day with a scenic walk along the Lake Michigan shoreline, taking in the views of the city from the water.
  • 10:30 AM: Visit Navy Pier, a lakefront attraction featuring boat cruises, an amusement park (open seasonally), and entertainment options.

Afternoon

  • 1:00 PM: Grab lunch at Billy Goat Tavern, famous for its cheeseburgers and location on the pier.
  • 2:30 PM: Explore the Peggy Notebaert Nature Museum (open until 5:00 PM). Learn about the natural world through interactive exhibits.

Evening

  • 6:00 PM: Enjoy dinner at The Purple Pig, a Mediterranean small-plates restaurant from James Beard Award winners.
  • 8:00 PM: Take in a show on Broadway or Off-Broadway, with options like Hamilton or The Book of Mormon.

Day 3: Wrigley Field and North Side

Morning

  • 9:00 AM: Start your day with breakfast at Wildberry Cafe, a cozy spot serving up pancakes and omelets.
  • 10:30 AM: Visit Wrigley Field, the historic home of the Chicago Cubs. Take a guided tour (open until 5:00 PM).

Afternoon

  • 1:00 PM: Grab lunch at The Berghoff, an old-school German restaurant serving up sausages and schnitzel.
  • 2:30 PM: Explore the Lincoln Park Conservatory (open until 7:00 PM). Stroll through the beautiful gardens and greenhouses.

Evening

  • 6:00 PM: Enjoy dinner at Blackbird, a contemporary American restaurant from Paul Kahan and Donnie Madia.
  • 8:00 PM: Catch some live music or comedy at one of Chicago’s many venues, like The Vic Theatre or Zanies Comedy Club.

Day 4: The Loop and Willis Tower

Morning

  • 9:00 AM: Start your day with breakfast at The Polo Cafe, a cozy spot serving up omelets and pancakes.
  • 10:30 AM: Visit the Willis Tower (formerly Sears Tower), one of the tallest buildings in the world. Take in panoramic views from the Skydeck on the 103rd floor.

Afternoon

  • 1:00 PM: Grab lunch at The Gage, a modern American restaurant serving up sandwiches and salads.
  • 2:30 PM: Explore the Chicago History Museum (open until 5:00 PM). Learn about the city’s rich history through interactive exhibits.

Evening

  • 6:00 PM: Enjoy dinner at Au Cheval, a trendy diner serving up burgers and sandwiches.
  • 8:00 PM: Catch some live music or comedy at one of Chicago’s many venues, like The Riviera Theatre or The Arcada Theatre.

Day 5: West Loop and Pilsen

Morning

  • 9:00 AM: Start your day with breakfast at Makro, a trendy cafe serving up sandwiches and pastries.
  • 10:30 AM: Visit the National Museum of Mexican Art (open until 5:00 PM). Explore the beautiful gardens and exhibits.

Afternoon

  • 1:00 PM: Grab lunch at Big Star, a vintage-inspired diner serving up burgers and hot dogs.
  • 2:30 PM: Explore the Pilsen neighborhood, known for its vibrant street art, shops, and restaurants.

Transportation

  • The ‘L’ (elevated train) is an easy way to get around Chicago. Use the Ventra app or purchase a Visitor Pass for convenient travel.
  • Buses are also widely available throughout the city.
  • Uber/Lyft and taxis are readily available, but be aware that traffic in Chicago can be heavy.

Tips

  • Weather: Be prepared for changing weather conditions. Bring layers, especially during spring and fall.
  • Safety: Be mindful of your surroundings, especially at night or in crowded areas.
  • Tipping: Tip servers 15-20% for good service.
  • Free attractions: Many museums and galleries offer free admission on certain days of the week or month.

Accommodations

  • The Robey, a boutique hotel with rooftop views
  • The Langham Chicago, a luxurious hotel in the Gold Coast area
  • Airbnb options are also available throughout the city.