3 Days of Chicago Luxury: The Ultimate High-End Itinerary

3 Days of Chicago Luxury: The Ultimate High-End Itinerary

luxury-inspired image of a woman seen from behind, walking along Chicago's Magnificent Mile

Want to experience Chicago at its most lavish? 

Here’s a 3-day itinerary that takes you through the city’s top spots, Michelin-star meals, and VIP experiences. 

Staying at The Peninsula Chicago on Magnificent Mile, you’ll be surrounded by high-end comforts, amazing service, and unbeatable city access.

Day 1: Cruise, Art, and Michelin Dining

a woman, fully dressed in fashionable attire, standing on the deck of a private yacht during a VIP river cruise

Morning
Start your first day in style with a VIP river cruise on a private yacht by Chicago’s First Lady Cruises. 

Glide through the Chicago River and out to Lake Michigan, soaking up skyline views from the comfort of your own space. Perfect for kicking off the trip.

Lunch
Next, make your way to Alinea for lunch. Known for its creativity and modern flair, this 3-star Michelin spot is a whole experience in itself. 

Expect unexpected flavors and dishes that feel more like art than food.

Afternoon
After lunch, head to the Art Institute of Chicago for a private, guided tour. 

Skip the lines, dive into some of the world’s best collections, and learn about masterpieces from your personal guide.

Dinner
End the night with a multi-course tasting menu at Smyth. This Michelin 3-star restaurant offers seasonal dishes that bring out the best of each ingredient. Ideal way to wrap up Day 1.

Day 2: Sky-high Views and Iconic Shopping

woman sitting at a high-rise bar with a panoramic view of the Chicago skyline

Morning
Get your heart racing with the TILT experience at 360 CHICAGO Observation Deck. 

Standing 94 floors up, you’ll tilt out over the edge for unbeatable views of the city below. 

Afterward, grab a cocktail at CloudBar to calm your nerves and enjoy that view a little longer.

Lunch
Head over to Monteverde for lunch, where the handmade pasta steals the show. Their Italian dishes, crafted with a Midwestern twist, have won over locals and travelers alike.

Afternoon
Spend your afternoon exploring the Magnificent Mile. It’s shopping heaven for anyone after designer brands, luxury goods, or simply wanting to take in the architecture.

Dinner
Tonight’s dinner is at Ever, a 2-star Michelin spot known for its 8-10 course tasting menu. 

Each dish is a mini adventure, full of flavor and precision. It’s all about indulging in something truly unforgettable.

Day 3: Spa Day, Baseball VIP, and Korean Fine Dining

woman receiving a luxurious face mask treatment at The Peninsula Chicago spa

Morning
Start your final day with a relaxing spa treatment at The Peninsula. From massages to facials, it’s all about recharging before your last Chicago outing.

Lunch
Lunch at Oriole, a 2-star Michelin gem, is a real treat. This modern American restaurant is known for pushing boundaries, so you can expect an exciting range of flavors.

Afternoon
In the afternoon, head over to Wrigley Field for a private, behind-the-scenes tour of the historic Chicago Cubs stadium. 

Get an insider’s look at one of baseball’s most iconic ballparks, with VIP access to parts of the stadium most fans never see.

Dinner
Finish your trip with a modern Korean fine-dining experience at Jeong. 

The tasting menu here is a fantastic mix of Korean flavors and refined technique—perfect for closing out your luxury Chicago adventure.

Extra Tips

  1. Use the Peninsula’s concierge services to help secure reservations and tour bookings.
  2. Book dining and VIP experiences at least a month in advance.
  3. Consider a private limo service for seamless travel between locations.
  4. Don’t forget to check out a performance by the Chicago Symphony Orchestra if you have an extra night.

With this itinerary, you’re set for three days of pure luxury. From Michelin dining to personalized tours, this trip is about experiencing Chicago at its finest. Enjoy every bit of the indulgence!


Related Post : 3 Days in Chicago on a Mid-Budget – Get the Full Experience Without Going Overboard

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