New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.Roam Around
![5-Day Chicago Adventure: Architecture, Culture, and Culinary Delights](https://storage.googleapis.com/bd-app-dev-375714.appspot.com/itineraries/018df614-dea9-7f8f-9a42-38df3f6a204b/location624.jpg)
5-Day Chicago Adventure: Architecture, Culture, and Culinary Delights Itinerary
Last updated: 2024 Jun 14Iconic Landmarks and River Cruise
Morning
Start your Chicago adventure with a delicious breakfast at Lou Malnati's Pizzeria, famous for its deep-dish pizza. Afterward, embark on the Chicago River 1.5-Hour Guided Architecture Cruise to admire the city's stunning skyline and learn about its architectural marvels.
Afternoon
For lunch, head to The Purple Pig, known for its Mediterranean-inspired cuisine. Afterward, visit the iconic The Magnificent Mile for some shopping and explore the historic Wrigley Building.
Evening
Enjoy a delightful dinner at Gibsons Bar & Steakhouse, a classic Chicago steakhouse. Afterward, take a leisurely stroll along the beautiful Chicago Riverwalk to soak in the city's vibrant atmosphere.
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 The Magnificent Mile in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/3f/bb/eb.jpg)
4.65The Magnificent Mile
Book Now
![Visit The Magnificent Mile in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/3f/bb/eb.jpg)
The Magnificent Mile
Book Now
![Visit Wrigley Building in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/81/cd.jpg)
4.39Wrigley Building
Book Now
![Visit Wrigley Building in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/81/cd.jpg)
Wrigley Building
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
Museums and Cultural Delights
Morning
Start your day with a hearty breakfast at Lula Cafe, a popular spot for brunch. Then, visit the renowned Art Institute of Chicago to explore its impressive art collection.
Afternoon
For lunch, savor the flavors of Spain at Cafe Ba-Ba-Reeba!. Afterward, visit the fascinating Field Museum to learn about natural history and anthropology.
Evening
Indulge in a fine dining experience at Girl & the Goat, known for its innovative cuisine. Afterward, take a relaxing evening walk in Grant Park and enjoy the city lights.
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 Field Museum in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/33/16/53.jpg)
4.56Field Museum
Book Now
![Visit Field Museum in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/33/16/53.jpg)
Field Museum
Book Now
![Visit Grant Park in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/54/eb.jpg)
4.70Grant Park
Book Now
![Visit Grant Park in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/54/eb.jpg)
Grant Park
Book Now
Sky-high Views and Culinary Delights
Morning
Enjoy a delightful breakfast at Little Goat Diner, a cozy diner with a creative menu. Then, head to the Skydeck Chicago at Willis Tower (Sears Tower) to experience breathtaking views of the city from the glass-floored Ledge.
Afternoon
For lunch, visit Eataly Chicago, a vibrant Italian marketplace with various dining options. Afterward, take a thrilling ride on the Chicago Navy Pier Centennial Wheel and explore the attractions at Navy Pier.
Evening
Dine at RPM Italian, a modern Italian restaurant known for its elegant ambiance and delicious cuisine. Afterward, enjoy a cocktail at 360 Chicago Observation Deck (Formerly John Hancock Observatory) while taking in the city's glittering skyline.
Bedtime
Find amazing hotels in Chicago.
![Visit Skydeck Chicago at Willis Tower (Sears Tower) in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/ed/38/5d.jpg)
4.27Skydeck Chicago at Willis Tower (Sears Tower)
Book Now
![Visit Skydeck Chicago at Willis Tower (Sears Tower) in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/ed/38/5d.jpg)
Skydeck Chicago at Willis Tower (Sears Tower)
Book Now
![Visit Chicago Navy Pier Centennial Wheel Regular & Express Ticket in Chicago](https://cdn.getyourguide.com/img/tour/05cb0a307913c9a4.jpeg/21.jpg)
4.43Chicago Navy Pier Centennial Wheel
Book Now
![Visit Chicago Navy Pier Centennial Wheel Regular & Express Ticket in Chicago](https://cdn.getyourguide.com/img/tour/05cb0a307913c9a4.jpeg/21.jpg)
Chicago Navy Pier Centennial Wheel
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 (Formerly John Hancock Observatory)
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 (Formerly John Hancock Observatory)
Book Now
Cultural Immersion and Opera Night
Morning
Start your day with a delightful breakfast at Big Star, a lively spot known for its tacos and margaritas. Then, visit the historic Chicago Theatre for a guided tour and learn about its rich history.
Afternoon
For lunch, head to Portillo's Hot Dogs, a Chicago institution famous for its hot dogs and Italian beef sandwiches. Afterward, explore the vibrant neighborhood of Pilsen and visit the National Museum of Mexican Art.
![Visit Chicago Theatre in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/80/84.jpg)
4.71Chicago Theatre
Book Now
![Visit Chicago Theatre in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/80/84.jpg)
Chicago Theatre
Book Now
University Exploration and Indian Cuisine
Morning
Start your day with a delicious Indian breakfast at Xoco, known for its authentic Mexican and Indian-inspired dishes. Then, visit the prestigious University of Chicago and explore its beautiful campus and renowned Oriental Institute Museum.
Afternoon
For lunch, indulge in the flavors of India at Mirch Masala, a popular spot for traditional Indian cuisine. Afterward, take a leisurely walk in the picturesque Hyde Park and visit the Museum of Science and Industry.
Evening
Conclude your Chicago adventure with a farewell dinner at Giordano's, famous for its stuffed deep-dish pizza. Reflect on your trip and savor the memories of the Windy City.
Bedtime
Find amazing hotels in Chicago.
![Visit Blue Mountains National Park in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/3f/5d/67.jpg)
4.90University of Chicago
Book Now
![Visit Blue Mountains National Park in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/12/3f/5d/67.jpg)
University of Chicago
Book Now
![Visit Three Sisters in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/a6/5c.jpg)
4.65Hyde Park
Book Now
![Visit Three Sisters in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/a6/5c.jpg)
Hyde Park
Book Now
![Visit Museum of Science and Industry in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/60/79.jpg)
4.31Museum of Science and Industry
Book Now
![Visit Museum of Science and Industry in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/60/79.jpg)
Museum of Science and Industry
Book Now
Top Chicago Travel Videos