New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.Roam Around
![Romantic 25th Anniversary Getaway in Chicago](https://storage.googleapis.com/bd-app-dev-375714.appspot.com/itineraries/018f124f-ea6c-7a2c-86be-362f6ba21dd6/location719.jpg)
Romantic 25th Anniversary Getaway in Chicago Itinerary
Last updated: 2024 Jun 14Love and Luxury in the Windy City
Morning
Start your special day with a delightful breakfast at the renowned Au Cheval, known for its delicious dishes. After breakfast, take a romantic stroll hand in hand along the Chicago Riverwalk, enjoying the serene views of the river and the city's architecture.
Afternoon
For lunch, savor a meal at The Purple Pig, offering a cozy and intimate atmosphere. Afterward, visit the Art Institute of Chicago, where you can admire world-class art with your loved one. The museum's serene ambiance is perfect for a romantic afternoon.
Evening
In the evening, have a memorable anniversary dinner at The Signature Room at the 95th, a fine dining restaurant with panoramic views of the city. After dinner, take a romantic Chicago River Guided Sunset Cocktail & Architecture Tour, where you can enjoy the city's skyline as the sun sets.
Bedtime
Find amazing hotels in Chicago.
![Visit Chicago Riverwalk in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/3f/5c/d3.jpg)
4.72Chicago Riverwalk
Book Now
![Visit Chicago Riverwalk in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/3f/5c/d3.jpg)
Chicago Riverwalk
Book Now
![Visit Art Institute of Chicago in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/33/15/da.jpg)
4.61Art Institute of Chicago
Book Now
![Visit Art Institute of Chicago in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/33/15/da.jpg)
Art Institute of Chicago
Book Now
![Visit Chicago River Guided Sunset Cocktail & Architecture Tour in Chicago](https://cdn.getyourguide.com/img/tour/4b8877882d559ae9.jpeg/21.jpg)
4.24Chicago River Guided Sunset Cocktail & Architecture Tour
Book Now
![Visit Chicago River Guided Sunset Cocktail & Architecture Tour in Chicago](https://cdn.getyourguide.com/img/tour/4b8877882d559ae9.jpeg/21.jpg)
Chicago River Guided Sunset Cocktail & Architecture Tour
Book Now
Cherished Moments and Culinary Delights
Morning
Enjoy a relaxed morning with a brunch at Lula Cafe, a cozy spot with a laid-back atmosphere. After brunch, take a leisurely walk in the picturesque Millennium Park, home to the famous Cloud Gate sculpture.
Afternoon
For a unique experience, have a late lunch at The Publican, known for its communal dining and rustic fare. Afterward, take a Chicago Architecture Center Cruise on Chicago's First Lady, learning more about the city's architectural wonders.
Evening
Conclude your anniversary trip with a romantic and unforgettable dinner at Alinea, a three-Michelin-star restaurant offering a multi-sensory dining experience. After dinner, take a private evening Chicago Helicopter Tour of the Skyline to see the city lights from above, creating a perfect end to your celebration of love.
Bedtime
Find amazing hotels in Chicago.
![Visit Millennium Park in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/5c/00.jpg)
4.69Millennium Park
Book Now
![Visit Millennium Park in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/5c/00.jpg)
Millennium Park
Book Now
![Visit Chicago Architecture Center Cruise on Chicago's First Lady in Chicago](https://cdn.getyourguide.com/img/tour/6466a49b23b5a.jpeg/21.jpg)
4.46Chicago Architecture Center Cruise on Chicago's First Lady
Book Now
![Visit Chicago Architecture Center Cruise on Chicago's First Lady in Chicago](https://cdn.getyourguide.com/img/tour/6466a49b23b5a.jpeg/21.jpg)
Chicago Architecture Center Cruise on Chicago's First Lady
Book Now
![Visit Chicago Private Helicopter Tour of Chicago Skyline in Chicago](https://cdn.getyourguide.com/img/tour/7130c77be2a975cd.jpeg/21.jpg)
4.50Chicago Helicopter Tour of the Skyline
Book Now
![Visit Chicago Private Helicopter Tour of Chicago Skyline in Chicago](https://cdn.getyourguide.com/img/tour/7130c77be2a975cd.jpeg/21.jpg)
Chicago Helicopter Tour of the Skyline
Book Now
Top Chicago Travel Videos