Chicago Usa 7 Day Itinerary

Day 1: Arrival and Exploring Downtown

Morning

  • Arrive at O’Hare International Airport (ORD) or Midway International Airport (MDW)
  • Take a taxi, Uber, or Lyft to your accommodation in downtown Chicago
  • Check-in to your hotel:
    • Recommended hotels: The Langham Chicago, The Wit Hotel, or Kimpton Hotel Monaco Chicago

Afternoon

  • Start at Millennium Park and take a stroll through the beautiful Lurie Garden
  • Visit the famous “Cloud Gate” sculpture (also known as “The Bean”)
  • Walk to the nearby Art Institute of Chicago, one of the top art museums in the country

Evening

  • Head to The Loop for dinner:
    • Try Portillo’s for classic Chicago-style hot dogs and Italian beef sandwiches
    • Or visit Girl & the Goat, a Mediterranean-inspired restaurant from Top Chef winner Stephanie Izard
  • Catch a show at the historic Auditorium Theatre or take a stroll along the Chicago Riverwalk

Day 2: Museums and Parks

Morning

  • Visit the Field Museum, home to Sue, the largest T. rex skeleton ever found
  • Explore the nearby Shedd Aquarium, featuring dolphins, beluga whales, and more

Afternoon

  • Spend time in Grant Park, which hosts many festivals throughout the year (including Lollapalooza)
  • Relax in Maggie Daley Park, a unique urban park with a playground, climbing wall, and suspension bridges

Evening

  • Enjoy dinner at:
    • Alinea, a Michelin three-star restaurant known for avant-garde cuisine
    • Or try Blackbird, a modern American bistro with a focus on local ingredients
  • Take a sunset cruise on Lake Michigan or stroll along the Navy Pier

Day 3: Architecture and Culture

Morning

  • Take an architecture river cruise to learn about Chicago’s rich history of building design
  • Visit the Frank Lloyd Wright Home and Studio in Oak Park (optional)

Afternoon

  • Explore the vibrant Pilsen neighborhood, known for its street art, Mexican cuisine, and cultural attractions
  • Stop by the National Museum of Mexican Art, showcasing a diverse collection of Mexican art

Evening

  • Dine at:
    • Carnitas Uruapan, serving authentic Michoacan-style Mexican cuisine
    • Or try The Polo Cafe, offering classic American comfort food
  • Catch a live music or comedy show at the iconic Buddy Guy’s Legends or Second City

Day 4: Wicker Park and Bucktown

Morning

  • Take the ‘L’ train (Blue Line) to Damen Avenue in Wicker Park
  • Explore the trendy boutiques, record stores, and art galleries along Milwaukee Avenue

Afternoon

  • Visit the Wicker Park Farmers Market (seasonal)
  • Stop by the iconic Six Corners intersection, featuring a unique shopping experience

Evening

  • Enjoy dinner at:
    • Big Star, serving tacos and whiskey in a retro-themed setting
    • Or try The Bongo Room, offering Southern-inspired comfort food
  • Catch a live music performance at the Double Door or Subterranean

Day 5: Lincoln Park and Lakeview

Morning

  • Take a stroll through the beautiful Lincoln Park Zoo (free admission)
  • Visit the Peggy Notebaert Nature Museum, featuring interactive exhibits on nature and conservation

Afternoon

  • Explore the charming shops and restaurants along Armitage Avenue in Lincoln Park
  • Stop by the historic Music Box Theatre, hosting independent films and live performances

Evening

  • Dine at:
    • Alinea’s sister restaurant, Next, offering innovative, theme-based cuisine
    • Or try The Purple Pig, serving Mediterranean-inspired small plates
  • Take a walk along the Lake Michigan shoreline in Lincoln Park or catch a show at the Vic Theatre

Day 6: Hyde Park and Kenwood

Morning

  • Visit the University of Chicago campus, featuring stunning Gothic architecture and scenic quadrangles
  • Stop by the Oriental Institute Museum, showcasing ancient Middle Eastern and Mediterranean artifacts

Afternoon

  • Explore the charming boutiques and eateries along 53rd Street in Hyde Park
  • Visit the Frederick Law Olmsted-designed Jackson Park, featuring beautiful gardens and a tranquil atmosphere

Evening

  • Enjoy dinner at:
    • The Promontory, serving upscale American cuisine with a focus on local ingredients
    • Or try Medici on 57th, offering Italian-inspired dishes in a cozy setting
  • Catch a live music performance at the University of Chicago’s Mandel Hall or the Promontory

Day 7: Departure

Morning

  • Spend some time shopping for souvenirs or exploring a new neighborhood
  • Depart for O’Hare International Airport (ORD) or Midway International Airport (MDW)

Additional Tips and Information

  • Transportation: Chicago has an extensive public transportation system, including the ‘L’ train and buses. You can also hail a taxi, use Uber or Lyft, or rent a car.
  • Weather: Chicago is known for its unpredictable weather. Pack layers and waterproof gear to be prepared for any conditions.
  • Safety: As with any major city, take necessary precautions to stay safe. Avoid walking alone in dimly lit areas at night and keep valuables secure.
  • Tipping: A standard 15-20% tip is expected at restaurants and bars.
  • Festivals and Events: Chicago hosts many festivals throughout the year, including Lollapalooza, Pitchfork Music Festival, and the Taste of Chicago. Check local event calendars to catch something during your visit.

Other Recommendations

  • Take a stroll along the 606 elevated trail, offering scenic views of the city
  • Visit the historic Robie House, a National Historic Landmark designed by Frank Lloyd Wright
  • Explore the vibrant street art scene in the Wicker Park and Bucktown neighborhoods