New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.Roam Around
![Diverse Delights of Chicago: From Architecture to Local Haunts](https://storage.googleapis.com/bd-app-dev-375714.appspot.com/itineraries/018f6ce9-5ece-788d-b0c2-f6ed75aa5055/location388.jpg)
Diverse Delights of Chicago: From Architecture to Local Haunts Itinerary
Last updated: 2024 Jun 14Architectural Marvels and Skyline Views
Morning
Start your day with a delightful brunch cruise on Lake Michigan aboard the Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise. Enjoy the scenic views and a delicious meal.
Afternoon
After brunch, head to the iconic Willis Tower Skydeck and The Ledge for a thrilling experience of standing on a glass balcony 1,353 feet above the city. Then, take a Chicago Architecture Center Cruise on Chicago's First Lady to learn about the city's renowned architecture.
Evening
In the evening, savor a gourmet dinner at Alinea, a three-Michelin-star restaurant known for its innovative cuisine. Afterward, take a leisurely stroll along the Chicago Riverwalk to admire the city lights.
Bedtime
Find amazing hotels in Chicago.
![Visit Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise in Chicago](https://cdn.getyourguide.com/img/tour/5d2f88cdb02a1.jpeg/21.jpg)
4.34Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise
Book Now
![Visit Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise in Chicago](https://cdn.getyourguide.com/img/tour/5d2f88cdb02a1.jpeg/21.jpg)
Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise
Book Now
![Visit Chicago Willis Tower Skydeck and The Ledge Ticket in Chicago](https://cdn.getyourguide.com/img/tour/4ef29da092a9da31.jpeg/21.jpg)
4.41Willis Tower Skydeck and The Ledge
Book Now
![Visit Chicago Willis Tower Skydeck and The Ledge Ticket in Chicago](https://cdn.getyourguide.com/img/tour/4ef29da092a9da31.jpeg/21.jpg)
Willis Tower Skydeck and The Ledge
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 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
Cultural Immersion and Local Flavors
Morning
Enjoy a relaxed morning with a visit to the Art Institute of Chicago, home to a world-class collection of art. Afterward, have a casual lunch at Pequod's Pizza, famous for its deep-dish pizza.
Afternoon
Spend the afternoon exploring the vibrant neighborhood of Wicker Park. Visit local home shops and enjoy the unique atmosphere. Stop for a coffee at Asado Coffee Co. to recharge.
Evening
For dinner, experience the lively ambiance of Big Star, known for its tacos and whiskey selection. Afterward, join a Chicago Gangsters and Food Tasting Walking Tour to discover the city's history and culinary scene.
Bedtime
Find amazing hotels in Chicago.
![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 Gangsters and Food Tasting Walking Tour in Chicago](https://cdn.getyourguide.com/img/tour/a235eca02656a614.jpeg/21.jpg)
4.67Chicago Gangsters and Food Tasting Walking Tour
Book Now
![Visit Chicago Gangsters and Food Tasting Walking Tour in Chicago](https://cdn.getyourguide.com/img/tour/a235eca02656a614.jpeg/21.jpg)
Chicago Gangsters and Food Tasting Walking Tour
Book Now
Sports, Spirits, and Spectres
Morning
Start your day with a visit to the Wrigley Field, the iconic home of the Chicago Cubs. After the game, have a late lunch at Lou Malnati's Pizzeria for a taste of classic Chicago deep-dish pizza.
Afternoon
In the afternoon, take a break from the city and enjoy a relaxing time at the Lincoln Park Zoo. Explore the zoo's diverse wildlife and beautiful surroundings.
Evening
For a unique experience, join a Chicago River Guided Sunset Cocktail & Architecture Tour. Sip on cocktails as you learn about the city's architecture and enjoy the sunset. After the tour, have a casual dinner at Portillo's Hot Dogs, a Chicago institution.
Bedtime
Find amazing hotels in Chicago.
![Visit Wrigley Field in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/31/bd/97.jpg)
4.86Wrigley Field
Book Now
![Visit Wrigley Field in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/31/bd/97.jpg)
Wrigley Field
Book Now
![Visit Lincoln Park & Zoo in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/62/3b.jpg)
4.29Lincoln Park Zoo
Book Now
![Visit Lincoln Park & Zoo in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/62/3b.jpg)
Lincoln Park Zoo
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
Ghostly Tales and Hidden Gems
Morning
Embark on a Chicago Discover the Gangsters & Ghosts of the City's Past tour to uncover the darker side of Chicago's history. After the tour, have a comforting breakfast at Lula Cafe.
Afternoon
Spend the afternoon exploring the unique shops and boutiques in the Andersonville neighborhood. Discover hidden gems and enjoy the local atmosphere. Stop for a light lunch at Xoco, known for its Mexican street food.
Evening
In the evening, continue the ghostly theme with a visit to one of Chicago's haunted bars, such as the The Green Mill. Enjoy a drink and listen to live jazz at this historic venue.
Bedtime
Find amazing hotels in Chicago.
![Visit Chicago Gangsters and Ghosts Guided Walking Tour in Chicago](https://cdn.getyourguide.com/img/tour/b6ede3f022029447.jpeg/21.jpg)
4.68Chicago Discover the Gangsters & Ghosts of the City's Past
Book Now
![Visit Chicago Gangsters and Ghosts Guided Walking Tour in Chicago](https://cdn.getyourguide.com/img/tour/b6ede3f022029447.jpeg/21.jpg)
Chicago Discover the Gangsters & Ghosts of the City's Past
Book Now
Farewell to the Windy City
Morning
On your last day, take a Chicago River 1.5-Hour Guided Architecture Cruise to admire the city's skyline from the water. After the cruise, have a relaxed brunch at The Publican.
Afternoon
Spend your final afternoon at the 360 Chicago Observation Deck, formerly known as the John Hancock Observatory. Enjoy panoramic views of the city and Lake Michigan. Consider having a late lunch at The Purple Pig, known for its Mediterranean-inspired cuisine.
Evening
End your trip with a memorable dinner at Girl & the Goat, a popular restaurant offering a creative menu. After dinner, take a leisurely walk along the Riverwalk to soak in the city's atmosphere one last time.
Bedtime
Find amazing hotels in Chicago.
![Visit Chicago River 1.5-Hour Guided Architecture Cruise in Chicago](https://cdn.getyourguide.com/img/tour/b4b30c0c6eccc80e.jpeg/21.jpg)
4.77Chicago River 1.5-Hour Guided Architecture Cruise
Book Now
![Visit Chicago River 1.5-Hour Guided Architecture Cruise in Chicago](https://cdn.getyourguide.com/img/tour/b4b30c0c6eccc80e.jpeg/21.jpg)
Chicago River 1.5-Hour Guided Architecture Cruise
Book Now
![Visit 360 Chicago Observation Deck (Formerly John Hancock Observatory) in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/a7/0e/e7.jpg)
4.17360 Chicago Observation Deck
Book Now
![Visit 360 Chicago Observation Deck (Formerly John Hancock Observatory) in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/a7/0e/e7.jpg)
360 Chicago Observation Deck
Book Now
Top Chicago Travel Videos