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7 Days Exploring Chicago's Landmarks, Museums, and Food Scene

7 Days Exploring Chicago's Landmarks, Museums, and Food Scene Itinerary

Last updated: 2024 Jun 14

Exploring Chicago's Iconic Landmarks

Morning
Start your day with a delicious breakfast at Cafe Ba-Ba-Reeba!. Then, embark on a guided tour of the iconic Wrigley Field to learn about its history and significance.
Afternoon
Indulge in a deep-dish pizza experience at Lou Malnati's Pizzeria. After lunch, visit the renowned Art Institute of Chicago Guided Tour for a deep dive into art and culture.
Evening
Enjoy a delightful dinner at The Purple Pig known for its unique dishes. End the day with a relaxing Chicago Architecture River Cruise Skip-the-Ticket Line to admire the city's skyline from the water.
Bedtime
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Wrigley Field

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Chicago Art Institute of Chicago Guided Tour

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Chicago Architecture River Cruise Skip-the-Ticket Line

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Museum and Culinary Delights

Morning
Savor a scrumptious breakfast at Au Cheval. Then, explore the fascinating exhibits at the House of Blues for a blend of music and art.
Afternoon
Have a fulfilling lunch at Girl & the Goat known for its innovative cuisine. Afterward, take a leisurely stroll through the Chicago Loop to experience the city's vibrant atmosphere.
Evening
Dine at the famous Gibsons Bar & Steakhouse for a classic steakhouse experience. Wrap up the day with a visit to The Signature Room at the 95th for breathtaking views of the city lights.
Bedtime
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House of Blues

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Chicago Loop

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Cultural Exploration and Adventure

Morning
Start your day with a hearty breakfast at Xoco. Then, embark on a unique adventure with the Chicago Lakefront and Museum Campus Segway Tour to explore the city's lakefront and museums.
Afternoon
Enjoy a delightful lunch at Big Star known for its tasty tacos. After lunch, dive into the city's history with a Chicago Secret Interiors Architecture Walking Tour to discover hidden gems.
Evening
Experience a culinary journey at RPM Italian with its modern Italian cuisine. End the day with a thrilling Chicago Prohibition Speakeasies Bus Tour or Walking Tour to uncover Chicago's hidden past.
Bedtime
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Chicago Lakefront and Museum Campus Segway Tour

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Chicago Secret Interiors Architecture Walking Tour

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Chicago Prohibition Speakeasies Bus Tour or Walking Tour

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Artistic Marvels and Gastronomic Delights

Morning
Kick off the day with a delightful breakfast at Beatrix. Then, explore the stunning art at Marina City for a unique architectural experience.
Afternoon
Enjoy a delicious lunch at Kuma's Corner known for its gourmet burgers. After lunch, immerse yourself in the city's art scene with a Chicago Art Institute Skip-the-Line Tour with Guide for an insightful tour.
Evening
Dine at Frontera Grill for a taste of authentic Mexican cuisine. Conclude the day with a relaxing Chicago River 1.5-Hour Guided Architecture Riverboat Tour to admire the city's architectural wonders.
Bedtime
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Marina City

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Chicago Art Institute Skip-the-Line Tour with Guide

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Chicago River 1.5-Hour Guided Architecture Riverboat Tour

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Exploration and Adventure Continues

Morning
Start your day with a delicious breakfast at Crisp. Then, embark on an exciting Chicago Craft Brewery Tour by Barrel Bus to taste local brews and learn about the brewing process.
Afternoon
Indulge in a satisfying lunch at Parachute known for its unique Korean-American fusion cuisine. After lunch, explore the city's neighborhoods with a Chicago Lakefront Neighborhoods Bike Tour for a scenic ride.
Evening
Dine at Smoque BBQ for a mouthwatering barbecue experience. End the day with a fun Chicago 1-Hour Escape Room Adventure for a thrilling challenge.
Bedtime
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Chicago Craft Brewery Tour by Barrel Bus

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Chicago Lakefront Neighborhoods Bike Tour

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Chicago 1-Hour Escape Room Adventure

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Culinary Delights and Urban Exploration

Morning
Enjoy a delightful breakfast at The Bristol. Then, embark on a culinary adventure with the Chicago Secret Food Tour to taste a variety of local specialties.
Afternoon
Have a delicious lunch at Green Street Smoked Meats known for its flavorful barbecue. After lunch, explore the city's urban landscape with a Chicago Ultimate City Attractions Bike Tour for a comprehensive tour.
Evening
Dine at Honey Butter Fried Chicken for a unique twist on classic fried chicken. Conclude the day with a visit to Chicago Treasures of the Golden Age Walking Tour to discover hidden gems.
Bedtime
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Chicago Secret Food Tour

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Chicago Ultimate City Attractions Bike Tour

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Chicago Treasures of the Golden Age Walking Tour

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Final Day of Exploration

Morning
Start your day with a tasty breakfast at Lula Cafe. Then, discover the city's history with a Chicago Board of Trade Building tour for insights into Chicago's financial district.
Afternoon
Enjoy a delightful lunch at Longman & Eagle known for its creative American fare. After lunch, explore the city's architectural wonders with a Amazing Lakefront Segway Tour of Chicago for a unique perspective.
Evening
Savor a gourmet dinner at Monteverde for a taste of Italian excellence. End your Chicago adventure with a visit to Chicago Downtown Donut Tour with Tastings for a sweet farewell.
Bedtime
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Chicago Board of Trade Building

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Amazing Lakefront Segway Tour of Chicago

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Chicago Downtown Donut Tour with Tastings

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