Chicago-4-day-itinerary

Day 1: Explore Downtown Chicago

Morning

  • Start at Millennium Park, a iconic urban park featuring famous landmarks like the “Cloud Gate” sculpture (also known as “The Bean”) and the Jay Pritzker Pavilion.
  • Take a stroll through the beautiful Lurie Garden, located just north of Millennium Park.

Afternoon

  • Head to the Art Institute of Chicago, one of the top art museums in the country. Spend a few hours exploring the vast collections, including works by famous American artists like Grant Wood and Thomas Hart Benton.
  • Grab lunch at Portillo’s, a Chicago institution serving up hot dogs, Italian beef sandwiches, and chocolate cake.

Evening

  • Take an architectural river cruise with Chicago’s First Lady Cruises to see the city’s iconic skyline from a different perspective.
  • End the night with dinner at Girl & the Goat, a Mediterranean-inspired restaurant from Top Chef winner Stephanie Izard.

Accommodation

  • Stay at the Kimpton Hotel Monaco Chicago, a stylish boutique hotel located in the heart of downtown.

Transportation

  • Use public transportation: take the ‘L’ train (Red Line) to Harrison Station, or hop on bus #146 to get around the city.
  • Ride-hailing services like Uber and Lyft are also widely available.

Tips & Other Things to Know

  • Be prepared for crowds and long lines at popular attractions.
  • Take advantage of Chicago’s many free museums and attractions on certain days of the week or month.
  • Don’t forget to try some of Chicago’s famous deep-dish pizza!

Day 2: Wicker Park & Bucktown

Morning

  • Start in Wicker Park, a trendy neighborhood filled with independent boutiques, record stores, and coffee shops. Explore the shops along Milwaukee Avenue.
  • Visit the Wicker Park Farmers Market (seasonal) for some fresh produce and artisanal goods.

Afternoon

  • Head to Bucktown, another hip neighborhood just north of Wicker Park. Check out the vibrant street art scene and grab lunch at Big Star, a taco joint with a fun atmosphere.
  • Visit the Polish Museum of America to learn about the history and culture of Poland.

Evening

  • Enjoy dinner at The Polo Cafe, serving up classic American comfort food in a cozy setting.
  • Catch a show or live music performance at The Empty Bottle, a beloved music venue and bar.

Accommodation (same as Day 1)

  • Stay at the Kimpton Hotel Monaco Chicago.

Transportation

  • Take the ‘L’ train (Blue Line) to Damen Station, then transfer to bus #50 to get around Wicker Park and Bucktown.
  • Ride-hailing services like Uber and Lyft are also widely available.

Tips & Other Things to Know

  • Be prepared for a more laid-back atmosphere in these neighborhoods.
  • Don’t miss the beautiful Humboldt Park, just west of Bucktown, featuring a stunning botanical garden and walking trails.

Day 3: Lincoln Park & Lakeview

Morning

  • Spend the morning exploring Lincoln Park, one of Chicago’s largest and most popular parks. Visit the Lincoln Park Zoo (free admission) and stroll through the beautiful gardens.
  • Take a walk along the Lakefront Trail, which runs along Lake Michigan.

Afternoon

  • Head to Lakeview, a vibrant neighborhood known for its nightlife, restaurants, and shopping. Grab lunch at Pequod’s Pizza, famous for its deep-dish pies with a caramelized crust.
  • Visit the Peggy Notebaert Nature Museum to learn about the natural history of the Chicago region.

Evening

  • Enjoy dinner at Alinea, a Michelin three-star restaurant offering avant-garde, experimental cuisine (reservations required).
  • Catch a Cubs game at Wrigley Field, one of baseball’s most iconic stadiums (seasonal).

Accommodation (same as Day 1)

  • Stay at the Kimpton Hotel Monaco Chicago.

Transportation

  • Take the ‘L’ train (Red Line) to Fullerton Station, then transfer to bus #151 to get around Lincoln Park and Lakeview.
  • Ride-hailing services like Uber and Lyft are also widely available.

Tips & Other Things to Know

  • Be prepared for crowds in these popular neighborhoods.
  • Don’t miss the beautiful North Avenue Beach, a popular spot for swimming and sunbathing during the summer months.

Day 4: Hyde Park & Museum Campus

Morning

  • Spend the morning exploring Hyde Park, a charming neighborhood home to the University of Chicago. Visit the Oriental Institute Museum, which features a vast collection of ancient Near Eastern artifacts.
  • Take a stroll through the beautiful Midway Plaisance, a scenic park designed by Frederick Law Olmsted.

Afternoon

  • Head to the Museum Campus, a scenic lakefront area featuring several museums, including the Field Museum and the Shedd Aquarium. Spend a few hours exploring these world-class institutions.
  • Grab lunch at The Berghoff, a historic German restaurant serving up classic dishes like schnitzel and sauerbraten.

Evening

  • Enjoy dinner at A10, a contemporary American bistro with a focus on local, seasonal ingredients.
  • Catch a show or concert at the University of Chicago’s Logan Center for the Arts.

Accommodation (same as Day 1)

  • Stay at the Kimpton Hotel Monaco Chicago.

Transportation

  • Take the ‘L’ train (Red Line) to 51st/53rd Street Station, then transfer to bus #2 or #28 to get around Hyde Park and Museum Campus.
  • Ride-hailing services like Uber and Lyft are also widely available.

Tips & Other Things to Know

  • Be prepared for a more laid-back atmosphere in these neighborhoods.
  • Don’t miss the beautiful Jackson Park, a scenic park designed by Frederick Law Olmsted featuring several lagoons, gardens, and walking trails.