Day 1: Arrival and Downtown Exploration

Morning:

• Arrive in Chicago and check into your hotel.
• Start your trip with a walk through Millennium Park: visit The Bean (Cloud Gate) and enjoy the Crown Fountain.
• Grab a quick coffee at Wildberry Pancakes and Café near the park.

Afternoon:

• Visit the Art Institute of Chicago, one of the top art museums in the world. Explore famous works like American Gothic and Nighthawks.
• Stroll along the Chicago Cultural Center nearby for free exhibitions.
• Have a late lunch at Revival Food Hall, a trendy food court offering local bites.

Night:

• Enjoy an Architectural Boat Tour on the Chicago River—perfect for stunning views of Chicago’s skyline. (Book the evening slot for twilight views.)
• Dine at Gibsons Bar & Steakhouse or Lou Malnati’s Pizzeria for a classic deep-dish pizza experience.
• End the night with drinks at a rooftop bar like Cindy’s Rooftop or LondonHouse for panoramic skyline views.

Day 2: Museums and Navy Pier

• Morning:

  • Have breakfast at The Bongo Room in the South Loop.
  • Spend your morning exploring Museum Campus:
    • Visit the Field Museum to see Sue the T. rex.
    • Explore the Shedd Aquarium, home to incredible marine life.

  Afternoon:

  • Grab lunch at Portillo's for a Chicago-style hot dog or Italian beef sandwich.
  • Head to Navy Pier:
    • Walk along the pier, ride the Centennial Wheel for great lake views, and explore shops.
    • Check out the Chicago Children’s Museum if traveling with kids.

  Night:

  • Take an evening stroll or relax at Ohio Street Beach (near Navy Pier) for a quieter lakefront experience.
  • Enjoy dinner at RPM Italian or a lakeside spot like Shore Club.
  • Watch the fireworks at Navy Pier if it’s summer (Wednesdays and Saturdays).

Day 3: Chicago’s Neighborhoods & History

• Morning:

  • Have a hearty breakfast at Manny’s Cafeteria & Delicatessen, a historic deli.
  • Explore the West Loop: Visit Fulton Market and its industrial-chic vibe with street art, coffee shops, and boutiques.

  Afternoon:

  • Discover Chicago’s history at the Chicago History Museum in Lincoln Park.
  • Stroll through Lincoln Park Zoo (free entry) and enjoy the lush green spaces of Lincoln Park Conservatory.
  • Lunch at Cafe Ba-Ba-Reeba! for tapas in Lincoln Park.

  Night:

  • Visit Wrigleyville:
    • If it’s baseball season, catch a Cubs game at Wrigley Field.
    • Explore local sports bars like Murphy's Bleachers for a lively atmosphere.
  • End the night with live music at Kingston Mines for a classic Chicago blues experience.

Day 4: Magnificent Mile and Views

• Morning:

  • Breakfast at Eataly, a bustling Italian marketplace on the Magnificent Mile.
  • Shop and explore the Magnificent Mile: High-end stores, iconic buildings, and department stores like Nordstrom and Water Tower Place.

  Afternoon:

  • Visit the 360 Chicago Observation Deck at the John Hancock Building. Try The Tilt for a thrilling view of the city!
  • Grab lunch at The Purple Pig, known for Mediterranean small plates.
  • Stroll along the Chicago Riverwalk for photo spots and a relaxing vibe.

  Night:

  • Book dinner at Alinea (for a Michelin-starred experience; reservations required) or Girl & The Goat.
  • Head to the Chicago Theatre to see a show, or catch a performance at Second City, famous for improv comedy.
  • Late-night cocktails at The Aviary for a unique mixology experience.

Day 5: Science, Parks, and Views

• Morning:

  • Breakfast at Do-Rite Donuts & Chicken.
  • Visit the Museum of Science and Industry—a family-friendly space with interactive exhibits, a U-505 submarine, and more.

  Afternoon:

  • Explore Hyde Park: Walk through Jackson Park and visit the University of Chicago campus with its Gothic architecture.
  • Grab lunch at Medici on 57th, a beloved Hyde Park institution.
  • Head back to the city center and walk along Grant Park and Buckingham Fountain for serene lakefront views.

  Night:

  • Dine at The Gage for upscale American comfort food near Millennium Park.
  • End the night with a Chicago Speakeasy Tour: Visit hidden bars like The Violet Hour or The Office for a 1920s-inspired experience.