Luxury Chicago Highlights & Lakefront Escape

Start your luxury tour of Chicago with a private guided overview, classic downtown park strolls, elevated dining, and panoramic skyline vistas.

1. 08:00|09:00
   

   Food

   Breakfast at Pierrot Gourmet at The Peninsula

   08:00 – 09:00

   Enjoy a Parisian-style breakfast with fresh pastries and espresso in a luxury setting.

2. 09:15|11:45
   

   Sightseeing

   Private Chicago Guided Tour with Hotel Pickup

   09:15 – 11:45

   Embark on a private guided tour exploring Chicago's landmark sights with door-to-door comfort.

   • entryINR 51572
3. 12:00|13:00
   

   Sightseeing

   Explore Millennium Park

   12:00 – 13:00

   Walk through Millennium Park to see iconic installations like Cloud Gate and the Crown Fountain.

   • entryFree
4. 13:15|14:30
   

   Food

   Lunch at The Gage

   13:15 – 14:30

   Dine on upscale American fare situated steps from Millennium Park.

5. 14:45|16:00
   

   Outdoor

   Chicago Riverwalk Stroll

   14:45 – 16:00

   Stroll along the lively Chicago Riverwalk and take in the surrounding architecture.

6. 16:15|17:30
   

   Sightseeing

   Skydeck Chicago Experience

   16:15 – 17:30

   Head up Willis Tower to experience thrilling views on The Ledge glass balconies.

   • entryFree
7. 17:45|19:15
   

   Shopping

   Shopping at Magnificent Mile

   17:45 – 19:15

   Browse premier designer boutiques and luxury flagships along Michigan Avenue.

8. 19:30|21:30
   

   Food

   Dinner at Gibsons Bar & Steakhouse

   19:30 – 21:30

   Savor classic prime steaks and seafood at a legendary Gold Coast establishment.

Combine morning active river tours with a private guided museum visit and evening pier vistas.

1. 08:00|09:15
   

   Food

   Breakfast at Wildberry Pancakes & Cafe

   08:00 – 09:15

   Fuel up with gourmet breakfast specialties and fresh squeezed juices.

2. 09:30|10:45
   

   Outdoor

   Chicago River Yoga Walk Tour

   09:30 – 10:45

   Enjoy a gentle wellness walk combined with mindful yoga poses along the riverfront.

3. 11:00|12:30
   

   Outdoor

   Kayaking on Chicago River

   11:00 – 12:30

   Paddle along the Chicago River gorge for an active perspective of the city's skyscrapers.

4. 12:45|14:00
   

   Food

   Lunch at Terzo Piano

   12:45 – 14:00

   Enjoy Italian-inspired cuisine overlooking Millennium Park at the Art Institute.

5. 14:15|16:30
   

   Sightseeing

   Private Tour Art Institute of Chicago Guided Museum

   14:15 – 16:30

   Explore world-class Impressionist and modern masterpieces with a dedicated art historian guide.

   • entryINR 50397
6. 16:45|18:00
   

   Sightseeing

   Visit the Art Institute of Chicago

   16:45 – 18:00

   Spend additional self-guided time browsing special exhibits and contemporary galleries.

   • entryFree
7. 18:15|19:15
   

   Sightseeing

   Visit Navy Pier

   18:15 – 19:15

   Take an evening walk along Lake Michigan at Chicago's landmark pier.

   • entryFree
8. 19:30|21:30
   

   Food

   Dinner at RPM Seafood

   19:30 – 21:30

   Indulge in fresh luxury seafood dishes with sweeping views of the Chicago River.

Discover Chicago's architectural heritage by land and water, complemented by a private art studio session.

1. 08:00|09:15
   

   Food

   Breakfast at Three Arts Club Cafe

   08:00 – 09:15

   Dine under glass chandeliers inside a magnificent restored courtyard showroom.

2. 09:30|11:30
   

   Sightseeing

   Loop Architecture tour in Chicago

   09:30 – 11:30

   Walk through the historic Loop district studying pioneering skyscraper design.

   • entryINR 33951
3. 11:45|12:45
   

   Outdoor

   Chicago Architectural Boat Tour

   11:45 – 12:45

   Glide along the river canyon aboard an open-air river boat while experts detail building histories.

4. 13:00|14:15
   

   Food

   Lunch at Chicago Cut Steakhouse

   13:00 – 14:15

   Enjoy a refined prime steak lunch on the riverfront terrace.

5. 14:30|16:00
   

   Shopping

   Fluid Bear Public Art Class in Chicago

   14:30 – 16:00

   Create your own custom fluid art bear keepsake in a guided design session.

6. 16:15|17:30
   

   Outdoor

   Biking along Lakefront Trail

   16:15 – 17:30

   Cycle along the paved Lakefront Trail with views of Lake Michigan and park greenery.

7. 17:45|19:15
   

   Sightseeing

   Adventure at Lincoln Park Zoo

   17:45 – 19:15

   Stroll through the historic and beautifully landscaped zoo grounds in Lincoln Park.

   • entryFree
8. 19:30|21:30
   

   Food

   Dinner at Alinea

   19:30 – 21:30

   Experience world-renowned three-star Michelin avant-garde gastronomy.

Capture luxury memories with a personal photographer before exploring high-end shopping districts and urban games.

1. 08:00|09:15
   

   Food

   Breakfast at RL Restaurant

   08:00 – 09:15

   Enjoy refined morning dishes surrounded by classic equestrian art at Ralph Lauren's flagship restaurant.

2. 09:30|10:30
   

   Sightseeing

   1 Hour Photoshoot in Chicago

   09:30 – 10:30

   Work with a professional photographer to capture portraits at Chicago's most photogenic landmarks.

   • entryINR 17930
3. 10:45|12:45
   

   Outdoor

   Chicago Magnificent Mile Scavenger Hunt Walking Tour and Game

   10:45 – 12:45

   Embark on an interactive discovery game solving clues along Michigan Avenue.

4. 13:00|14:15
   

   Food

   Lunch at The Purple Pig

   13:00 – 14:15

   Sample Mediterranean small plates, house-cured meats, and curated wines.

5. 14:30|16:30
   

   Shopping

   Shopping at Magnificent Mile

   14:30 – 16:30

   Continue exploring exclusive fashion boutiques and department stores along the Avenue.

6. 16:45|18:00
   

   Outdoor

   Chicago Riverwalk Stroll

   16:45 – 18:00

   Unwind with a peaceful late afternoon walk past waterfront cafes and historic bridges.

7. 18:15|19:15
   

   Sightseeing

   Explore Millennium Park

   18:15 – 19:15

   Revisit Millennium Park during twilight hours for stunning evening lighting.

   • entryFree
8. 19:30|21:30
   

   Food

   Dinner at Maple & Ash

   19:30 – 21:30

   Dine on wood-fired steaks and seafood in a high-energy, sophisticated setting.

Wrap up your trip with engaging guided tours, lake breezes, and high-altitude farewell dining.

1. 08:00|09:15
   

   Food

   Breakfast at Meli Cafe

   08:00 – 09:15

   Savor farm-fresh egg dishes, pancakes, and fresh juices.

2. 09:30|11:30
   

   Sightseeing

   Wind City Wanderlust: A Chicago Family Odyssey

   09:30 – 11:30

   Enjoy a curated, narrative-driven exploration of Chicago's cultural landmarks.

   • entryINR 20676
3. 11:45|12:45
   

   Sightseeing

   Chicago Self-Guided Audio Tour

   11:45 – 12:45

   Listen to immersive historical audio tales while wandering at your own comfortable speed.

   • entryINR 902
4. 13:00|14:15
   

   Food

   Lunch at Lou Malnati's Pizzeria

   13:00 – 14:15

   Experience Chicago's famous buttery deep-dish pizza.

5. 14:30|16:00
   

   Sightseeing

   Visit Navy Pier

   14:30 – 16:00

   Enjoy afternoon lakefront views and attractions along Navy Pier.

   • entryFree
6. 16:15|17:30
   

   Outdoor

   Biking along Lakefront Trail

   16:15 – 17:30

   Take a final leisurely bike ride along the shores of Lake Michigan.

7. 17:45|19:15
   

   Sightseeing

   Skydeck Chicago Experience

   17:45 – 19:15

   Catch golden hour views over the city horizon from Willis Tower.

   • entryFree
8. 19:30|21:30
   

   Food

   Dinner at BOKA

   19:30 – 21:30

   Celebrate your journey with Michelin-starred seasonal tasting menus in Lincoln Park.