Chicago, Illinois-6-day-itinerary

Chicago 6-Day Itinerary

Day 1: Arrival and Exploring Downtown

Morning

  • Arrive in Chicago and check-in to your hotel:
    • Hotel: The Wit Hotel (downtown location, trendy vibe)
    • Address: 201 N State St, Chicago, IL 60601
  • Start your day at Millennium Park:
    • Willis Tower (Sears Tower): Take in panoramic views of the city from the Skydeck on the 103rd floor
    • Cloud Gate (The Bean): Snap a photo with this iconic mirrored sculpture

Afternoon

  • Grab lunch at:
    • Portillo’s: Try their famous Chicago-style hot dogs and Italian beef sandwiches
    • Address: 520 W Taylor St, Chicago, IL 60607
  • Visit the Art Institute of Chicago:
    • Must-see exhibits: American Gothic, Nighthawks, and A Sunday on La Grande Jatte

Evening

  • Enjoy dinner at:
    • Girl & the Goat: Mediterranean-inspired cuisine from Top Chef winner Stephanie Izard
    • Address: 809 W Randolph St, Chicago, IL 60607
  • Take a stroll along the Magnificent Mile (Michigan Avenue) for upscale shopping and city views

Day 2: Museums and Parks

Morning

  • Visit the Field Museum:
    • Sue the T. Rex: Get up close with the largest and most complete T. Rex skeleton
    • Ancient Egyptian Collection: Explore mummies, sarcophagi, and temple reliefs
  • Take a short walk to:
    • Grant Park: Relax in this sprawling green space

Afternoon

  • Head to the Museum of Science and Industry:
    • Coal Mine: Explore a recreated coal mine from the 1930s
    • German Submarine U-505: Board a World War II submarine

Evening

  • Dine at:
    • Alinea: Avant-garde, experimental cuisine (reservations essential)
    • Address: 1723 N Halsted St, Chicago, IL 60614
  • Catch a show or concert at:
    • The Second City: Legendary comedy troupe and improv hub

Day 3: Wicker Park and Bucktown

Morning

  • Explore the trendy neighborhoods of Wicker Park and Bucktown:
    • Wicker Park Farmers Market (seasonal): Fresh produce, artisanal goods, and street food
    • Bucktown’s boutique shops: Discover unique fashion, home decor, and art galleries

Afternoon

  • Grab lunch at:
    • Big Star: Tacos and craft beer in a retro-tastic setting
    • Address: 1531 N Damen Ave, Chicago, IL 60622
  • Visit the Wicker Park Fountain: A picturesque spot for photos

Evening

  • Enjoy dinner at:
    • The Polo Cafe: Cozy American bistro with a focus on local ingredients
    • Address: 238 W Armitage Ave, Chicago, IL 60614
  • Take in some live music or comedy at:
    • The Vic Theatre: Intimate venue hosting various performances

Day 4: Lincoln Park and Lake Michigan

Morning

  • Visit the Lincoln Park Zoo: Free admission to this charming urban zoo
  • Stroll through the Lincoln Park Conservatory: Explore the beautiful gardens and greenhouses

Afternoon

  • Take a leisurely walk along:
    • Lake Michigan shoreline: Enjoy the city views, beaches, and parks
    • North Avenue Beach: Rent kayaks or paddleboards for some on-water fun

Evening

  • Dine at:
    • Aba: Mediterranean-inspired cuisine with a focus on seafood
    • Address: 302 N Green St, Chicago, IL 60607
  • Catch a sunset cruise or architectural tour on Lake Michigan:

Day 5: Navy Pier and Streeterville

Morning

  • Visit Navy Pier: This lakefront attraction offers boat cruises, an amusement park, and entertainment options
  • Take in the views from:
    • The Crystal Gardens: A six-story, indoor botanical garden

Afternoon

  • Explore the upscale neighborhood of Streeterville:
    • Water Tower Place: Shop and dine at this iconic complex
    • Maggie Daley Park: Innovative playgrounds and green spaces

Evening

  • Enjoy dinner at:
    • The Purple Pig: Global small plates and craft cocktails
    • Address: 500 N Michigan Ave, Chicago, IL 60611
  • Take a romantic horse-drawn carriage ride through the city:

Day 6: Pilsen and Chinatown

Morning

  • Visit the vibrant neighborhood of Pilsen:
    • National Museum of Mexican Art: Explore the largest Latino cultural institution in the US
    • Pilsen Farmers Market (seasonal): Fresh produce, artisanal goods, and street food

Afternoon

  • Head to Chinatown for lunch and exploration:
    • Try Dim Sum at: Fat Rice or MingHin Cuisine
    • Explore Chinatown Square: Authentic shops, restaurants, and cultural attractions

Evening

  • Farewell dinner at:
    • Blackbird: Modern American cuisine with a focus on seasonal ingredients
    • Address: 619 W Randolph St, Chicago, IL 60661
  • End your trip with a scenic helicopter tour of the city:

Transportation

  • ‘L’ Train (Elevated Train): Convenient and affordable way to navigate the city
  • Bus: Comprehensive network covering all neighborhoods
  • Ride-hailing apps: Uber and Lyft operate in Chicago
  • Water Taxi: A fun way to travel along Lake Michigan

Tips and Essentials

  • Weather: Pack layers for unpredictable Midwestern weather
  • Comfortable shoes: Be prepared for extensive walking and exploring
  • Sunscreen and sunglasses: Protect yourself from the sun during outdoor activities
  • Cash and credit cards: Many establishments accept both, but it’s always a good idea to have some cash on hand
  • Chicago CityPASS: Consider purchasing this discount pass for attractions and experiences

Things to Know

  • Tipping culture: 15-20% is standard in Chicago
  • Local customs: Be respectful of the city’s diverse neighborhoods and cultures
  • Safety: As with any major city, be aware of your surroundings, especially at night
  • Events and festivals: Check the city’s event calendar to catch unique experiences during your visit