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Ultimate 10-Day Chicago Exploration Itinerary
Last updated: 2024 Jun 14Iconic Chicago Landmarks
Morning
Start your Chicago adventure with a visit to the famous The Magnificent Mile. Enjoy some shopping and marvel at the architecture. Afterward, take a stroll to the historic Wrigley Building.
Afternoon
For lunch, head to Giordano's, a renowned spot for deep-dish pizza. Afterward, take a walk to Millennium Park to see the iconic Cloud Gate sculpture, also known as "The Bean."
Evening
In the evening, enjoy a relaxing dinner at The Signature Room at the 95th, where you can savor delicious food with a stunning view of the city.
Bedtime
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4.65The Magnificent Mile
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4.65The Magnificent Mile
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4.39Wrigley Building
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4.39Wrigley Building
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Museum and Skyline Views
Morning
Spend your morning at the Art Institute of Chicago, home to a world-class collection of art. Afterward, take a walk to the nearby Grant Park.
Afternoon
For lunch, try the famous burgers at Au Cheval. Afterward, visit the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for panoramic views of the city.
Evening
Enjoy a delightful dinner at Girl & The Goat, known for its innovative cuisine and vibrant atmosphere.
Bedtime
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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4.70Grant Park
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4.70Grant Park
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Lakefront and Navy Pier
Morning
Start your day with a relaxing walk or bike ride along the Chicago Lakefront Trail. Take in the beautiful views of Lake Michigan.
Afternoon
For lunch, enjoy a meal at The Purple Pig, a popular spot for Mediterranean-inspired dishes. Afterward, explore Navy Pier and take a ride on the Centennial Wheel.
Evening
Have dinner at RPM Italian, a modern Italian restaurant with a lively atmosphere.
Bedtime
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4.48Navy Pier
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4.48Navy Pier
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Gangsters and Ghosts
Morning
Embark on a Chicago Gangsters and Ghosts Guided Walking Tour to learn about the city's dark history.
Afternoon
For lunch, try the authentic Mexican cuisine at Big Star. Afterward, take a break at Lincoln Park.
4.68Chicago Gangsters and Ghosts Guided Walking Tour
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4.68Chicago Gangsters and Ghosts Guided Walking Tour
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4.29Lincoln Park
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4.29Lincoln Park
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Science and Industry
Morning
Spend the morning exploring the Museum of Science and Industry, a fascinating museum with interactive exhibits.
Afternoon
For lunch, head to Lou Malnati's Pizzeria for a taste of classic Chicago deep-dish pizza. Afterward, take a walk in the nearby Hyde Park.
4.31Museum of Science and Industry
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4.31Museum of Science and Industry
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Cultural Immersion
Morning
Start your day with a visit to the Chicago Cultural Center, a historic building with stunning architecture.
Afternoon
For lunch, try the gourmet sandwiches at Xoco, a popular spot by chef Rick Bayless. Afterward, explore the vibrant neighborhoods of Wicker Park and Bucktown.
Evening
Enjoy a dinner at The Publican, a bustling beer hall with a focus on seasonal fare.
Bedtime
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4.71Chicago Cultural Center
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4.71Chicago Cultural Center
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4.84Wicker Park
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4.84Wicker Park
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Rooftop Views and River Cruise
Morning
Start your day with a leisurely brunch at Little Goat Diner, a favorite spot for comfort food.
Afternoon
Take a Chicago River 1.5-Hour Guided Architecture Cruise to see the city's famous buildings from the water. Afterward, visit the Chicago Architecture Center.
Evening
Enjoy a sunset cocktail at Cindys Rooftop, where you can take in panoramic views of the city.
Bedtime
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4.77Chicago River 1.5-Hour Guided Architecture Cruise
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4.77Chicago River 1.5-Hour Guided Architecture Cruise
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4.46Chicago Architecture Center
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4.46Chicago Architecture Center
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Art and Food Tour
Morning
Spend the morning at the Field Museum, exploring its world-renowned natural history exhibits.
Afternoon
For lunch, try the gourmet street food at Au Cheval. Afterward, take a Chicago Art and Food Walking Tour to sample the city's culinary delights.
Evening
Have dinner at Gibsons Bar & Steakhouse, a classic Chicago steakhouse known for its prime cuts of meat.
Bedtime
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4.56Field Museum
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4.56Field Museum
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4.67Chicago Art and Food Walking Tour
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4.67Chicago Art and Food Walking Tour
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Final Day of Exploration
Morning
Take a Chicago Lake Michigan Skyline Cruise to enjoy the city's skyline from the water.
Afternoon
Spend your last afternoon in Chicago visiting the Adler Planetarium and taking a walk in Graceland Cemetery.
Evening
For your final dinner in Chicago, indulge in a steak at Gibsons Bar & Steakhouse, a local favorite.
Bedtime
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4.59Chicago Lake Michigan Skyline Cruise
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4.59Chicago Lake Michigan Skyline Cruise
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4.61Adler Planetarium
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4.61Adler Planetarium
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Departure Day
Morning
On your last morning in Chicago, take a walk along the Chicago Riverwalk and enjoy the views of the city.
Afternoon
For a farewell lunch, head to The Purple Pig to savor Mediterranean-inspired dishes. Afterward, take a Chicago River Guided Sunset Cocktail & Architecture Tour to end your trip on a high note.
Evening
Departure from Chicago.
Bedtime
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4.72Chicago Riverwalk
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4.72Chicago Riverwalk
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4.24Chicago River Guided Sunset Cocktail & Architecture Tour
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4.24Chicago River Guided Sunset Cocktail & Architecture Tour
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