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![Exploring the Architecture and Cuisine of Chicago](https://storage.googleapis.com/bd-app-dev-375714.appspot.com/itineraries/018af6fa-1b1b-7285-9012-d9a3e4caf677/location726.jpg)
Exploring the Architecture and Cuisine of Chicago Itinerary
Last updated: 2024 Jun 14Discovering Chicago's Architecture
Morning
Start your day with a delicious breakfast at Egg Harbor Cafe to fuel up for a day of exploring. After breakfast, embark on the Chicago River 1.5-Hour Guided Architecture Cruise to admire the city's stunning architecture from the water.
Afternoon
For lunch, head to Cooper's Hawk Winery & Restaurant for a delightful meal paired with their own handcrafted wines. Afterward, visit the iconic Willis Tower Skydeck and The Ledge for breathtaking views of the city.
Evening
In the evening, join the Chicago Gangsters and Ghosts 2-Hour Walking Tour to uncover the city's intriguing history of crime and paranormal activity. End the day with a delicious dinner at Cucina Paradiso, where you can savor authentic Italian cuisine.
Bedtime
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![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
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![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
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![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
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![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
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![Visit Chicago Gangsters and Ghosts Guided Walking Tour in Chicago](https://cdn.getyourguide.com/img/tour/b6ede3f022029447.jpeg/21.jpg)
4.68Chicago Gangsters and Ghosts 2-Hour Walking Tour
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![Visit Chicago Gangsters and Ghosts Guided Walking Tour in Chicago](https://cdn.getyourguide.com/img/tour/b6ede3f022029447.jpeg/21.jpg)
Chicago Gangsters and Ghosts 2-Hour Walking Tour
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Cruising and Sunset Cocktails
Morning
Start your day with a scrumptious brunch at Wild Onion Tied House. Afterward, embark on the Chicago 1.5-Hour Lake and River Architecture Cruise to explore the city's architectural wonders from a different perspective.
Afternoon
For a unique dining experience, indulge in a gourmet lunch cruise on Lake Michigan with Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise. Enjoy a delicious meal while taking in the stunning views of the city skyline.
Evening
As the sun sets, join the Chicago River Guided Sunset Cocktail & Architecture Tour for a relaxing cruise along the Chicago River. Sip on cocktails and admire the illuminated architecture. For dinner, head to Szechwan Beijing for delectable Chinese cuisine.
Bedtime
Find amazing hotels in Chicago.
![Visit Chicago 1.5-Hour Lake and River Architecture Cruise in Chicago](https://cdn.getyourguide.com/img/tour/4e4f6c4b8b2f172c.jpeg/21.jpg)
4.75Chicago 1.5-Hour Lake and River Architecture Cruise
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![Visit Chicago 1.5-Hour Lake and River Architecture Cruise in Chicago](https://cdn.getyourguide.com/img/tour/4e4f6c4b8b2f172c.jpeg/21.jpg)
Chicago 1.5-Hour Lake and River Architecture Cruise
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![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
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![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
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![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
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![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
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Exploring City Landmarks
Morning
Start your day with a hearty breakfast at Delia's Kitchen. Afterward, visit the Chicago Architecture Center Cruise on Chicago's First Lady for an informative and engaging architectural tour.
Afternoon
For lunch, head to Poor Phil's Bar & Grill for delicious pub food and a wide selection of craft beers. Afterward, explore the city's landmarks on a Chicago CityPASS® Save 48% or More on 5 Top Attractions.
Evening
Enjoy a romantic dinner at The Maple Tree Inn, known for its mouthwatering Cajun and Creole cuisine. After dinner, catch a live performance at The Green Mill, a historic jazz club.
Bedtime
Find amazing hotels in Chicago.
![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
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![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
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![Visit Chicago CityPASS® with Tickets to 5 Top Attractions in Chicago](https://cdn.getyourguide.com/img/tour/502c0203b722e66c.jpeg/21.jpg)
4.61Chicago CityPASS® Save 48% or More on 5 Top Attractions
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![Visit Chicago CityPASS® with Tickets to 5 Top Attractions in Chicago](https://cdn.getyourguide.com/img/tour/502c0203b722e66c.jpeg/21.jpg)
Chicago CityPASS® Save 48% or More on 5 Top Attractions
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Sunset Cruise and Skyline Views
Morning
Start your day with a tasty breakfast at Papaspiros. Afterward, embark on a Chicago 1.5-Hour Romantic Sunset Cruise for a romantic and picturesque experience on Lake Michigan.
Afternoon
For lunch, head to Burger Antics for creative and delicious burgers. Afterward, visit the Chicago Architecture Center to further explore the city's architectural marvels.
Evening
Enjoy a delightful dinner at Valente's Restaurant, known for its authentic Italian dishes. End the day with a visit to The Signature Lounge at the 96th, located on the 96th floor of the John Hancock Center, for breathtaking views of the city skyline.
Bedtime
Find amazing hotels in Chicago.
![Visit Chicago 1.5-Hour Romantic Sunset Cruise in Chicago](https://cdn.getyourguide.com/img/tour/640f9f6880eb7.jpeg/21.jpg)
4.61Chicago 1.5-Hour Romantic Sunset Cruise
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![Visit Chicago 1.5-Hour Romantic Sunset Cruise in Chicago](https://cdn.getyourguide.com/img/tour/640f9f6880eb7.jpeg/21.jpg)
Chicago 1.5-Hour Romantic Sunset Cruise
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![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
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![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
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![Visit Philadelphia’s Magic Gardens in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/99/59.jpg)
4.83The Signature Lounge at the 96th
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![Visit Philadelphia’s Magic Gardens in Chicago](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/99/59.jpg)
The Signature Lounge at the 96th
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Exploring Oak Park's Charm
Morning
Start your day with a delicious breakfast at Brookfield Family Restaurant. Afterward, explore the architectural gems of Oak Park, including the Frank Lloyd Wright Home and Studio and the Unity Temple.
Afternoon
For lunch, head to New Hong Kong Restaurant for flavorful Chinese cuisine. Afterward, visit the Ernest Hemingway Birthplace Museum to learn about the famous writer's early life.
Evening
Enjoy a relaxing dinner at Lou Malnati's Pizzeria, known for its deep-dish pizza. End the day with a leisurely stroll through the charming streets of Oak Park.
Bedtime
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![Visit Maruyama Park (Maruyama Koen) in Oak Park, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/96/cb.jpg)
4.76Unity Temple
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![Visit Maruyama Park (Maruyama Koen) in Oak Park, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/96/cb.jpg)
Unity Temple
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![Visit Bali Zoo in Oak Park, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/99/30.jpg)
4.92Ernest Hemingway Birthplace Museum
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![Visit Bali Zoo in Oak Park, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/99/30.jpg)
Ernest Hemingway Birthplace Museum
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