United States:
Chicago, curated
5-day luxury tour of Chicago
Trip Overview
Day 1 - 5 | Chicago | The Langham Chicago | 4 nights
day 1 | Chicago
Renowned for its residential sense of calm and quietly sophisticated aesthetic, The Langham Chicago blends sculptural architecture with understated luxury, with sweeping views of the Chicago River and Lake Michigan. Steps from the Riverwalk and moments from the Magnificent Mile.
Arrival & Private Transfer. Greeting at the arrivals terminal and private transfer to The Langham Chicago, on the Chicago Riverwalk in the heart of downtown.
The Langham Club. A 4,000 square foot private lounge on the highest floor of the hotel, with floor to ceiling windows over Lake Michigan and the Chicago River. Breakfast, afternoon tea, evening cocktails and canapés are served in the Club dining room, with a dedicated ambassador team on hand throughout.
Dinner at Joe's Seafood, Prime Steak & Stone Crab. A Chicago institution renowned for its prime cuts, stone crab claws and the kind of old-school hospitality that keeps guests coming back.
day 2 | Chicago
One of the great encyclopedic museums in the world, before the doors open.
Private Tour of the Art Institute of Chicago. A privately guided visit with an art historian that begins before the museum opens to the public, so you have the galleries to yourselves in the first window of the morning. Founded in 1879, the Art Institute holds nearly 300,000 works spanning 5,000 years, from Impressionist masterpieces to ancient Asian bronzes. Its Modern Wing, designed by Renzo Piano, makes it the second largest art museum in the United States, and it holds what many consider the finest collection of Impressionist and Post-Impressionist painting outside of Europe.
Lunch. The museum's own café is a natural end to the morning. Across the street, The Gage serves sandwiches, fish and chips and more, and next door Cindy's Rooftop looks out over Millennium Park and Lake Michigan.
Dinner at The Alston. A stylish River North restaurant offering refined American cuisine in a warm, intimate setting.
day 3 | Chicago
Contemporary art in the morning, Frank Lloyd Wright in the afternoon.
Before-Hours VIP Access to the Museum of Contemporary Art. Private access to the MCA before it opens to the public, with a dedicated professor who brings context to the current exhibition. Established in 1967, the MCA is one of the world's largest institutions dedicated to contemporary art, with works by Andy Warhol, Francis Bacon, Alexander Calder, Jasper Johns and Kerry James Marshall in constant conversation with the cultural moment.
Private Tour of the Frederick C. Robie House. Widely considered the most impressive Frank Lloyd Wright building in Chicago, and a UNESCO World Heritage Site. The premier example of his Prairie School style: dramatic horizontal lines, cantilevered roofs, art glass windows and open-plan interiors, with site, furniture, ornament and architecture conceived as one coherent whole. Wright himself called it "a cornerstone of modern architecture."
Dinner at Hugo's Frog Bar & Fish House. A beloved Chicago classic known for exceptional seafood, a lively atmosphere and legendary frog legs.
day 4 | Chicago
Chicago's architecture is best understood from the water.
Morning at Leisure. Relax at the hotel or explore the city at your own pace.
Private Yacht Tour on the Chicago River with an Architectural Docent. Board a privately chartered yacht with a welcome drink and an open bar throughout. Led by an architectural docent, the journey reveals the skyline as a living museum, from Art Deco and Neo-Classical towers a century old to some of the tallest skyscrapers in the world. As the afternoon gives way to evening, the skyline shifts with the light in a way few visitors ever see at this pace.
Dinner at Coco Pazzo. A longstanding Chicago favorite serving rustic Tuscan cuisine, handmade pasta and an extensive Italian wine list.
day 5 | Departure
Private Transfer. Private transfer to the airport or Union Station for your onward journey.
Pricing & Inclusions
See our Booking Terms & Conditions here.
Starting at $800 per person per day
Based on two people in double occupancy and subject to increase depending on itinerary specifics and dates.
Accommodation: 4 nights at The Langham Chicago with access to The Langham Club.
Transport: Private airport transfers. Private vehicle at your disposal on touring days.
Tours & Activities: Private Art Institute tour with an art historian, before-hours MCA visit with a professor, private Robie House tour, private yacht tour on the Chicago River with an architectural docent.
Meals: All breakfasts.
Other: City taxes associated with your accommodations. Restaurant reservations and coordination.
Exclusions
Flights · Travel insurance · Tips

