Indulge in luxury on your 6-day trip to Chicago. From exquisite dining to upscale shopping and world-class attractions, this itinerary will ensure a memorable experience. Check out KAYAK to find the best hotel and flight prices for your trip.
Sunday, November 5: Arrival and The Magnificent Mile
Upon arrival in Chicago, settle into your luxurious hotel and relax before starting your adventure. In the morning, explore the world-renowned Magnificent Mile - a stretch of Michigan Avenue filled with high-end shops, boutiques, and flagship stores. Immerse yourself in luxury brands and indulge in shopping sprees. For the afternoon, visit the Art Institute of Chicago, home to an impressive collection of masterpieces. In the evening, dine at one of the Michelin-starred restaurants in the area.
The Magnificent Mile: Cost estimate varies | Time spent: 3-4 hours
Art Institute of Chicago: Cost estimate $25 (general admission) | Time spent: 2-3 hours
Michelin-starred restaurant: Cost estimate varies | Time spent: 2-3 hours
Restaurants
Start your morning with a delightful breakfast at Ann Sather, a local favorite known for its famous cinnamon rolls and hearty Swedish dishes. Average cost for a meal is about $10 per person.
For lunch, head over to GT Fish & Oyster, a trendy seafood eatery offering a variety of fresh and delicious seafood dishes in a stylish setting. Average cost for a meal is about $20-30 per person.
In the evening, dine at RPM Italian, where you can savor an exquisite Italian meal paired with an extensive selection of wines. The modern and classy atmosphere adds to the enjoyable dining experience. Average cost for a meal is about $30-40 per person.
Restaurants
For breakfast, try The Bongo Room in Wicker Park. Indulge in their creative and decadent brunch options like their signature Chocolate Tower French Toast. Average cost for a meal is about $15 per person.
For lunch, head to Summer House Santa Monica in Lincoln Park. Enjoy their California-inspired menu featuring fresh ingredients and seasonal flavors. Average cost for a meal is about $20 per person.
For dinner, treat yourself to an exquisite dining experience at Alinea in the Grant Park area. Delight in their innovative and artistic tasting menu that showcases culinary craftsmanship. Average cost for a meal is about $300 per person.
Restaurants
Start your day with a delicious breakfast at The Bongo Room, known for their creative and indulgent brunch dishes like their signature chocolate tower french toast. Average cost for a meal is about $15 per person.
For lunch, head to Kuma's Corner and indulge in their epic burgers with unique toppings like mac n' cheese and bacon. Average cost for a meal is about $12 per person.
For a memorable dinner, dine at Alinea, a three-Michelin-starred restaurant known for its innovative, multi-course tasting menu. Average cost for a meal is about $350 per person.
Restaurants
For breakfast, try Pierrot Gourmet, a charming European-style café located near Navy Pier. Indulge in delicious pastries and freshly brewed coffee. Average cost for a meal is about $15 per person.
For lunch, visit The Purple Pig, a popular spot offering a unique menu of Mediterranean-inspired small plates. Try their famous charcuterie and cheese boards. Average cost for a meal is about $25 per person.
For dinner, enjoy a sophisticated dining experience at Spiaggia, an upscale Italian restaurant overlooking Lake Michigan. Sample their exquisite handmade pasta dishes and seafood creations. Average cost for a meal is about $75 per person.
Restaurants
Start your day with a delicious breakfast at Wildberry Pancakes and Cafe. This popular spot offers a variety of pancake flavors and other breakfast favorites. Average cost for a meal is about $15 per person.
For lunch, head to Lou Malnati's Pizzeria. Enjoy their famous deep-dish pizza, along with a variety of other Italian dishes. Average cost for a meal is about $20 per person.
Indulge in a memorable dinner experience at Girl & the Goat. This trendy restaurant offers a menu featuring creative and flavorful dishes made with locally sourced ingredients. Average cost for a meal is about $50 per person.
Restaurants
Start your day with a delightful breakfast at Eggsperience Pancakes & Cafe, which offers a wide variety of pancakes, omelettes, and breakfast skillets. Average cost for a meal is about $12 per person.
For lunch, head to Giordano's, a famous Chicago-style deep dish pizza restaurant. Enjoy their delicious deep-dish pizza with a variety of toppings. Average cost for a meal is about $20 per person.
Indulge in a memorable dinner at Alinea, a renowned Michelin 3-star restaurant known for its innovative and artistic approach to modern cuisine. Average cost for a meal is about $350 per person (excluding beverages).
Restaurants
Start your day with a delightful breakfast at The Purple Pig, known for its innovative and indulgent dishes. Average cost for a meal is about $20 per person.
For a luxurious lunch experience, head to Quartino Ristorante, offering a wide range of Italian tapas and handcrafted cocktails. Average cost for a meal is about $30 per person.
For a memorable dinner affair, visit The Signature Room at the 95th, offering fine dining with panoramic views of Chicago's skyline. Average cost for a meal is about $70 per person.
Monday, November 6: Architectural Wonders and River Cruise
Begin your day with an architectural tour of Chicago's iconic buildings. Take a guided tour or opt for a private yacht tour along the Chicago River. Explore the breathtaking skyline, learn about the city's rich architectural history, and capture stunning photos. In the afternoon, enjoy a luxurious lunch at one of the top-rated restaurants overlooking the river. For the evening, consider a sophisticated cocktail experience at a rooftop bar with panoramic city views.
Architectural tour: Cost estimate $50-80 | Time spent: 2-3 hours
Luxurious lunch: Cost estimate varies | Time spent: 1-2 hours
Rooftop bar: Cost estimate varies | Time spent: 2-3 hours
Tuesday, November 7: Museum and Cultural Exploration
Spend the morning exploring the Museum Campus - a park that houses several renowned museums. Start with a visit to the Field Museum, where you can explore ancient artifacts and learn about natural history. In the afternoon, head to the Museum of Science and Industry to delve into interactive exhibits. As the evening approaches, enjoy a high-end dinner at a chic restaurant offering innovative cuisine.
Field Museum: Cost estimate $26-40 | Time spent: 3-4 hours
Museum of Science and Industry: Cost estimate $16-26 | Time spent: 3-4 hours
High-end dinner: Cost estimate varies | Time spent: 2-3 hours
Wednesday, November 8: Navy Pier and Lakefront Beauty
Start your day by visiting Navy Pier, a vibrant entertainment destination along Lake Michigan. Embark on a luxurious boat tour, offering stunning views of the city skyline. Explore the various attractions on the pier, including the Chicago Children's Museum and the IMAX Theater. In the afternoon, indulge in retail therapy at cutting-edge stores along the Magnificent Mile. End your day with a sophisticated dinner at an upscale restaurant with lakefront views.
Navy Pier: Cost estimate varies | Time spent: 3-4 hours
Retail therapy on Magnificent Mile: Cost estimate varies | Time spent: 3-4 hours
Thursday, November 9: Cultural Delights and Theater
In the morning, explore Chicago's vibrant neighborhoods, such as Wicker Park or Lincoln Park. Discover upscale boutiques, art galleries, and charming cafes. For the afternoon, immerse yourself in culture at the Chicago Theatre District. Catch a matinee show or explore the historic theaters. In the evening, savor a gourmet dinner at a fine dining establishment.
Neighborhood exploration: Cost estimate varies | Time spent: 3-4 hours
Chicago Theatre District: Cost estimate varies | Time spent: 2-3 hours
Gourmet dinner: Cost estimate varies | Time spent: 2-3 hours
Friday, November 10: The Art of Luxury and Departure
On your last day, indulge in the art of luxury shopping on Oak Street. Browse exclusive designer boutiques, jewelers, and art galleries. Enjoy a lavish lunch at a trendy restaurant and treat yourself to a spa session or a rejuvenating treatment before departing from Chicago. Reflect on your luxurious journey and cherish the memories as you bid farewell to the Windy City.
Luxury shopping on Oak Street: Cost estimate varies | Time spent: 3-4 hours
Trendy lunch: Cost estimate varies | Time spent: 1-2 hours
Spa session or relaxation: Cost estimate varies | Time spent: 2-3 hours
Hidden Gems and Local Favorites
If you're looking for off the beaten path attractions and places cherished by locals, consider visiting Garfield Park Conservatory. This hidden gem showcases stunning botanical displays and tranquil greenhouses. For a unique luxury experience, book a private helicopter tour for unparalleled views of the city's skyline. These less-known treasures will add a touch of exclusivity and adventure to your itinerary.