Luxury Chicago Architecture, Art & Lakefront Exploration

Begin your stay in Chicago with a private guided vehicle tour before exploring Millennium Park, the Riverwalk, Skydeck, and Magnificent Mile boutiques.

1. 08:30|09:30
   

   Food

   Breakfast at RL Restaurant

   08:30 – 09:30

   Enjoy an elegant morning breakfast in a classic club-style setting near Michigan Avenue.

2. 09:45|12:15
   

   Sightseeing

   Private Chicago Guided Tour with Hotel Pickup

   09:45 – 12:15

   Explore key city landmarks with a personal driver and knowledgeable local guide.

   • entryINR 51572
3. 12:30|13:45
   

   Food

   Lunch at The Purple Pig

   12:30 – 13:45

   Dine on Mediterranean-inspired small plates and wine along Michigan Avenue.

4. 14:00|15:15
   

   Sightseeing

   Explore Millennium Park

   14:00 – 15:15

   Walk through the park to view Cloud Gate and the Jay Pritzker Pavilion.

   • entryFree
5. 15:30|16:30
   

   Outdoor

   Chicago Riverwalk Stroll

   15:30 – 16:30

   Stroll along the pedestrian riverfront past waterfront cafes and high-rise architecture.

6. 16:45|18:00
   

   Sightseeing

   Skydeck Chicago Experience

   16:45 – 18:00

   Ascend Willis Tower for panoramic views over four states from glass balconies.

   • entryFree
7. 18:15|19:15
   

   Shopping

   Shopping at Magnificent Mile

   18:15 – 19:15

   Browse luxury flagships along North Michigan Avenue.

8. 19:30|21:00
   

   Food

   Dinner at Gibsons Bar & Steakhouse

   19:30 – 21:00

   Savor prime steaks and cocktails in an iconic Chicago dining institution.

Combine a private photography shoot and exclusive museum tour with lakefront cycling and Navy Pier visits.

1. 08:30|09:30
   

   Food

   Breakfast at Pierrot Gourmet

   08:30 – 09:30

   Start the day with European pastries and coffee at The Peninsula Chicago.

2. 09:45|10:45
   

   Sightseeing

   1 Hour Photoshoot in Chicago

   09:45 – 10:45

   Capture professional vacation portraits against dramatic city backdrops.

   • entryINR 17930
3. 11:00|12:20
   

   Sightseeing

   Visit the Art Institute of Chicago

   11:00 – 12:20

   Examine world-renowned Impressionist and Modern art collections.

   • entryFree
4. 12:30|13:45
   

   Food

   Lunch at Terzo Piano

   12:30 – 13:45

   Enjoy fine dining with city views located in the museum's Modern Wing.

5. 14:00|16:00
   

   Sightseeing

   Private Tour Art Institute of Chicago Guided Museum

   14:00 – 16:00

   Gain tailored insights from an expert art historian on a private gallery walk.

   • entryINR 50397
6. 16:15|17:30
   

   Outdoor

   Biking along Lakefront Trail

   16:15 – 17:30

   Ride along the shore of Lake Michigan enjoying skyline vistas.

7. 17:45|19:15
   

   Sightseeing

   Visit Navy Pier

   17:45 – 19:15

   Walk the historic pier to view the lake and skyline attractions.

   • entryFree
8. 19:30|21:00
   

   Food

   Dinner at RPM Seafood

   19:30 – 21:00

   Dine on multi-level riverfront patios featuring premium seafood.

Immerse yourself in Chicago's famous architectural legacy via walking, boating, and kayaking experiences.

1. 08:00|09:00
   

   Outdoor

   Chicago River Yoga Walk Tour

   08:00 – 09:00

   Combine mindful movement and local geography on a quiet river walk.

2. 09:15|10:15
   

   Food

   Breakfast at Beatrix

   09:15 – 10:15

   Sample fresh juices, pastries, and healthy breakfast dishes in River North.

3. 10:30|12:00
   

   Sightseeing

   Loop Architecture tour in Chicago

   10:30 – 12:00

   Discover historic skyscrapers and modern towers in the financial heart of the city.

   • entryINR 33951
4. 12:30|13:45
   

   Food

   Lunch at Luke's Lobster City Hall

   12:30 – 13:45

   Enjoy high-grade lobster rolls and seafood soups near the financial district.

5. 14:00|15:30
   

   Outdoor

   Chicago Architectural Boat Tour

   14:00 – 15:30

   Cruise down the Chicago River as docents explain the design history of iconic structures.

6. 15:45|17:00
   

   Sightseeing

   Skydeck Chicago Experience

   15:45 – 17:00

   Return for late-afternoon skyline views from high above the city grid.

   • entryFree
7. 17:15|18:45
   

   Outdoor

   Kayaking on Chicago River

   17:15 – 18:45

   Paddle along skyscraper canyon walls under historic drawbridges.

8. 19:30|21:00
   

   Food

   Dinner at Maple & Ash

   19:30 – 21:00

   Indulge in upscale wood-fired steaks and raw bar selections in the Gold Coast.

Engage in creative art classes, explore upscale retail stores, and visit Lincoln Park's green spaces.

1. 08:30|09:30
   

   Food

   Breakfast at Wildberry Pancakes & Cafe

   08:30 – 09:30

   Enjoy gourmet pancakes and breakfast specialties in downtown Chicago.

2. 09:45|11:15
   

   Shopping

   Fluid Bear Public Art Class in Chicago

   09:45 – 11:15

   Craft your own custom fluid art bear keepsake during a guided creative workshop.

3. 11:30|12:30
   

   Shopping

   Shopping at Magnificent Mile

   11:30 – 12:30

   Shop designer boutiques and luxury department stores along North Michigan Avenue.

4. 12:45|14:00
   

   Food

   Lunch at Chicago Cut Steakhouse

   12:45 – 14:00

   Savor riverside lunch dining featuring prime cuts and fresh seafood.

5. 14:15|16:30
   

   Sightseeing

   Adventure at Lincoln Park Zoo

   14:15 – 16:30

   Stroll through historic grounds featuring exotic wildlife and lush gardens.

   • entryFree
6. 16:45|18:00
   

   Outdoor

   Biking along Lakefront Trail

   16:45 – 18:00

   Enjoy a seaside cycle around Lincoln Park and North Avenue Beach.

7. 18:15|19:15
   

   Sightseeing

   Visit Navy Pier

   18:15 – 19:15

   Unwind near the water while taking in dusk views of Lake Michigan.

   • entryFree
8. 19:30|21:00
   

   Food

   Dinner at Boka

   19:30 – 21:00

   Experience Michelin-starred contemporary American cuisine in Lincoln Park.

Participate in a guided walking game, admire city park sculpture, and end with a world-renowned dining experience.

1. 08:30|09:30
   

   Food

   Breakfast at Eggy's Diner

   08:30 – 09:30

   Order hearty breakfast classics in modern urban surroundings.

2. 09:45|12:00
   

   Outdoor

   Chicago Magnificent Mile Scavenger Hunt Walking Tour and Game

   09:45 – 12:00

   Uncover hidden architectural details on a gamified walking tour of Michigan Avenue.

3. 12:30|14:00
   

   Food

   Lunch at Lou Malnati's Pizzeria

   12:30 – 14:00

   Taste authentic Chicago deep-dish pizza prepared fresh.

4. 14:15|15:30
   

   Sightseeing

   Explore Millennium Park

   14:15 – 15:30

   Walk past Lurie Garden and modern architectural landmarks.

   • entryFree
5. 15:45|17:00
   

   Outdoor

   Chicago Riverwalk Stroll

   15:45 – 17:00

   Relax along public seating and riverfront art installations.

6. 17:15|18:30
   

   Outdoor

   Chicago Architectural Boat Tour

   17:15 – 18:30

   Enjoy late afternoon light reflecting off glass facades along the river route.

7. 18:45|19:25
   

   Shopping

   Shopping at Magnificent Mile

   18:45 – 19:25

   Pick up souvenirs or fashion items before dinner.

8. 19:30|21:00
   

   Food

   Dinner at Alinea

   19:30 – 21:00

   Dine on an innovative multi-course tasting menu at a world-famous restaurant.

Explore city history via self-guided storytelling tours, animal encounters, and active water sports.

1. 08:30|09:30
   

   Food

   Breakfast at Goddess and the Baker

   08:30 – 09:30

   Order specialty coffee drinks, breakfast sandwiches, and fresh pastries.

2. 09:45|11:15
   

   Sightseeing

   Chicago Self-Guided Audio Tour

   09:45 – 11:15

   Listen to curated audio commentary highlighting downtown culture and secrets.

   • entryINR 902
3. 11:30|12:30
   

   Sightseeing

   Wind City Wanderlust: A Chicago Family Odyssey

   11:30 – 12:30

   Follow a thematic sightseeing trail showcasing key historical points.

   • entryINR 20676
4. 12:30|13:45
   

   Food

   Lunch at The Gage

   12:30 – 13:45

   Dine on upscale gastropub fare steps away from Millennium Park.

5. 14:00|15:30
   

   Sightseeing

   Adventure at Lincoln Park Zoo

   14:00 – 15:30

   Visit historic animal habitats and lush botanical displays.

   • entryFree
6. 15:45|17:15
   

   Outdoor

   Kayaking on Chicago River

   15:45 – 17:15

   Enjoy a guided or open paddle past stunning riverfront developments.

7. 17:30|19:00
   

   Sightseeing

   Visit the Art Institute of Chicago

   17:30 – 19:00

   View masterworks of painting and sculpture in quiet evening galleries.

   • entryFree
8. 19:30|21:00
   

   Food

   Dinner at Sepia

   19:30 – 21:00

   Sample Michelin-starred American dishes made with local organic ingredients.

Conclude your trip with a festive scavenger hunt, shopping, and an evening dinner cruise across Lake Michigan.

1. 08:30|09:30
   

   Food

   Breakfast at Yolk Streeterville

   08:30 – 09:30

   Enjoy generous breakfast plates and custom omelets in the center of town.

2. 09:45|11:45
   

   Outdoor

   Experience the season with a scavenger hunt in Chicago with Holly Jolly Hunt

   09:45 – 11:45

   Participate in a seasonal outdoor scavenger hunt around city landmarks.

3. 12:00|13:15
   

   Sightseeing

   Explore Millennium Park

   12:00 – 13:15

   Take final photographs near Cloud Gate and the park plaza.

   • entryFree
4. 13:30|14:30
   

   Food

   Lunch at Portillo's

   13:30 – 14:30

   Try famous Chicago-style hot dogs and Italian beef sandwiches.

5. 14:45|16:00
   

   Outdoor

   Chicago Riverwalk Stroll

   14:45 – 16:00

   Take a quiet afternoon walk along the river promenade.

6. 16:15|17:30
   

   Sightseeing

   Visit Navy Pier

   16:15 – 17:30

   Board your evening lake vessel from the historic pier docks.

   • entryFree
7. 17:45|19:15
   

   Shopping

   Shopping at Magnificent Mile

   17:45 – 19:15

   Pick up final gifts and luxury goods along Michigan Avenue.

8. 19:30|21:00
   

   Food

   Dinner aboard Lake Michigan Cruise

   19:30 – 21:00

   Savor plated gourmet dishes while cruising the city shoreline.

9. 21:00|22:30
   

   Sightseeing

   Christmas Eve Plated Dinner Cruise on Lake Michigan

   21:00 – 22:30

   Experience festive plated dining with grand views of illuminated skyscrapers.

   • entryINR 16719