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Luxury Chicago Getaway - 7 Day Itinerary

Viewed by 89 travelers

Sunday December 24: Arrival and Skydeck Experience

Arrive in Chicago and check into your luxurious hotel. Start the day with a visit to the iconic Skydeck Chicago for breathtaking views of the city from the Willis Tower. In the afternoon, indulge in a gourmet lunch at the acclaimed Alinea restaurant. In the evening, take a leisurely stroll along the Chicago Riverwalk and admire the city lights.

  • Skydeck Chicago: Cost - $30 per person, Time - 1-2 hours
  • Alinea: Cost - $300 per person, Time - 2-3 hours
  • Chicago Riverwalk: Free, Time - Evening

Monday December 25: Magnificent Mile and Navy Pier

Start the day with shopping along the Magnificent Mile, Chicago's premier shopping district. Enjoy a luxurious lunch at The Signature Room at the 95th, offering stunning views of the city. In the afternoon, visit the Navy Pier and take a ride on the Centennial Wheel. In the evening, indulge in a gourmet dinner at Spiaggia, known for its exquisite Italian cuisine.

  • Magnificent Mile: Cost - Varies, Time - Morning
  • The Signature Room at the 95th: Cost - $50 per person, Time - 1-2 hours
  • Navy Pier: Cost - Free, Time - Afternoon
  • Spiaggia: Cost - $150 per person, Time - 2-3 hours

Tuesday December 26: Art and Culture

Start the day with a visit to the Art Institute of Chicago, featuring an impressive collection of artworks. Enjoy a gourmet lunch at The Gage, known for its upscale comfort food. In the afternoon, explore the Museum of Contemporary Art and admire contemporary art exhibits. In the evening, catch a performance at the prestigious Chicago Symphony Orchestra.

  • Art Institute of Chicago: Cost - $25 per person, Time - 2-3 hours
  • The Gage: Cost - $50 per person, Time - 1-2 hours
  • Museum of Contemporary Art: Cost - $15 per person, Time - 2-3 hours
  • Chicago Symphony Orchestra: Cost - Varies, Time - Evening

Wednesday December 27: Architectural Marvels

Embark on a luxury architectural boat tour along the Chicago River, showcasing the city's stunning skyline. Enjoy lunch at the elegant Cindy's rooftop restaurant with panoramic views. In the afternoon, visit the Frank Lloyd Wright Home and Studio for an insight into the celebrated architect's work. End the day with a delicious dinner at the world-renowned Alinea.

  • Architectural boat tour: Cost - $50 per person, Time - 2-3 hours
  • Cindy's: Cost - $75 per person, Time - 1-2 hours
  • Frank Lloyd Wright Home and Studio: Cost - $20 per person, Time - 2-3 hours
  • Alinea: Cost - $300 per person, Time - 2-3 hours

Thursday December 28: Shopping and Fine Dining

Explore Chicago's upscale shopping at Oak Street and experience luxury fashion and designer boutiques. Indulge in a gourmet lunch at the award-winning Everest restaurant, offering French cuisine with a modern twist. In the afternoon, visit the Museum of Contemporary Photography to admire captivating photographic artworks. End the day with an exquisite dinner at the Michelin-starred Grace.

  • Oak Street: Cost - Varies, Time - Morning
  • Everest: Cost - $100 per person, Time - 1-2 hours
  • Museum of Contemporary Photography: Cost - Free, Time - 1-2 hours
  • Grace: Cost - $250 per person, Time - 2-3 hours

Friday December 29: Nature and Relaxation

Escape the city and spend the day at the luxurious Lincoln Park Conservatory, surrounded by beautiful gardens and exotic plants. Enjoy a leisurely lunch at the charming North Pond restaurant, set in a picturesque location within the park. In the afternoon, pamper yourself with a spa treatment at the iconic Peninsula Chicago. In the evening, savor a delicious dinner at Blackbird, known for its contemporary American cuisine.

  • Lincoln Park Conservatory: Cost - Free, Time - 1-2 hours
  • North Pond: Cost - $75 per person, Time - 1-2 hours
  • The Peninsula Spa: Cost - Varies, Time - Afternoon
  • Blackbird: Cost - $100 per person, Time - 2-3 hours

Saturday December 30: Hidden Gems and Local Favorites

Discover the hidden gem of Garfield Park Conservatory, a stunning greenhouse with a wide variety of plant species. Afterward, indulge in a delightful brunch at The Publican, known for its farm-to-table cuisine. In the afternoon, explore the trendy Wicker Park neighborhood and browse through unique boutiques and galleries. End the day with a luxurious dinner at Oriole, offering a memorable dining experience.

  • Garfield Park Conservatory: Cost - Free, Time - 1-2 hours
  • The Publican: Cost - $50 per person, Time - 1-2 hours
  • Wicker Park: Cost - Varies, Time - Afternoon
  • Oriole: Cost - $200 per person, Time - 2-3 hours

Hidden Gems and Local Favorites

While exploring Chicago, be sure to visit the hidden gems and local favorites for an authentic experience. Try the lavish afternoon tea at The Drake Hotel, known for its elegant ambiance. Explore the lively Fulton Market District, filled with upscale restaurants and trendy bars. Don't miss the luxurious shopping experience at The 900 Shops on Michigan Avenue, offering high-end brands and boutiques.

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