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Ultimate 16-Day Chicago Adventure with Iconic Landmarks and Culinary Delights Itinerary
Last updated: 2024 Jun 14City Icons and River Cruises
Morning
Begin your Chicago adventure with a delightful breakfast at LG's Bar & Kitchen, known for its cozy ambiance and hearty morning fare. Afterward, take a stroll along the iconic Chicago Riverwalk to admire the city's stunning architecture and the serene waters of the Chicago River.
Afternoon
For lunch, head to Elephant & Castle for a taste of their British-inspired dishes. Post-lunch, enjoy a Chicago 45-Minute Family-Friendly Architecture River Cruise to get a unique perspective of the city's famous landmarks from the water.
Evening
Dine at Bar Louie - Printers Row, a local favorite for its vibrant atmosphere and diverse menu. After dinner, take a leisurely walk to Navy Pier and experience the excitement of this historic landmark with its amusement rides and stunning views of Lake Michigan.
Bedtime
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4.72Chicago Riverwalk
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4.72Chicago Riverwalk
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4.68Chicago 45-Minute Family-Friendly Architecture River Cruise
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4.68Chicago 45-Minute Family-Friendly Architecture River Cruise
Book Now
Museum Marvels and Sky-high Views
Morning
Start your day with a visit to the renowned Art Institute of Chicago, where you can explore an impressive collection of art spanning centuries. Grab a quick bite at the museum cafe before heading to the nearby Millennium Park to see the famous "Bean" sculpture.
Afternoon
Enjoy a sophisticated lunch at LUXBAR, known for its upscale American cuisine. Afterward, take in the cityscape from the 360 Chicago Observation Deck (Formerly John Hancock Observatory) with your skip-the-line ticket, and if you're feeling adventurous, try the TILT experience for a unique thrill.
Evening
Dine at Bar Siena, where you can savor Italian dishes in a stylish setting. Cap off the evening with a visit to The Magnificent Mile, Chicago's premier shopping destination, and take a leisurely walk to admire the upscale stores and the beautiful architecture of the area.
Bedtime
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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4.69Millennium Park
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4.69Millennium Park
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Historic Buildings and Evening Entertainment
Morning
Enjoy a classic Chicago breakfast at Miller's Pub, a historic spot with a warm atmosphere. Afterward, take a guided tour of the Wrigley Building and learn about its architectural significance and the history of the city.
Afternoon
For lunch, head to Reviver, a contemporary American restaurant with a focus on seasonal ingredients. Post-lunch, immerse yourself in the world of crime and prohibition on the Chicago Gangsters and Ghosts Guided Walking Tour, exploring the city's darker history.
Evening
Dine at Untitled Supper Club, a speakeasy-style venue with live music and a menu that pays homage to the Prohibition era. After dinner, enjoy a live performance at the historic Chicago Theatre, known for its stunning architecture and top-notch entertainment.
Bedtime
Find amazing hotels in Chicago.
4.39Wrigley Building
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4.39Wrigley Building
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4.68Chicago Gangsters and Ghosts Guided Walking Tour
Book Now
4.68Chicago Gangsters and Ghosts Guided Walking Tour
Book Now
Science and Nature Exploration
Morning
Start your day with a visit to the Museum of Science and Industry, where you can explore fascinating exhibits and interactive displays. Grab a quick bite at the museum cafe before continuing your exploration.
Afternoon
For lunch, head to Five Star Bar, a casual spot known for its great burgers and beer selection. Afterward, visit the nearby Jackson Park to enjoy a leisurely walk and take in the natural beauty of the area.
Evening
Dine at Plymouth Restaurant & Rooftop Bar, where you can enjoy a meal with a view. After dinner, take a relaxing evening stroll at Soldier Field, home of the Chicago Bears, and soak in the atmosphere of this historic sports venue.
Bedtime
Find amazing hotels in Chicago.
4.31Museum of Science and Industry
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4.31Museum of Science and Industry
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4.76Soldier Field
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4.76Soldier Field
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Culinary Delights and Evening Cruise
Morning
Indulge in a gourmet breakfast at ROOF on theWit, known for its stunning views and delicious food. After breakfast, take a guided food tour with the Chicago Favorite Foods Guided Walking Tour, sampling a variety of local specialties.
Afternoon
For a unique lunch experience, visit First Draft, a self-pour beer and wine bar with a diverse menu. After lunch, relax and enjoy the sights on a Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise, where you can dine while taking in the beautiful skyline and lake views.
Evening
Conclude your day with a memorable dinner at Scofflaw, a popular spot known for its craft cocktails and elevated bar food. Afterward, take a peaceful evening walk at Lincoln Park & Zoo, one of the oldest and most beautiful zoos in the country.
Bedtime
Find amazing hotels in Chicago.
4.82Chicago Favorite Foods Guided Walking Tour
Book Now
4.82Chicago Favorite Foods Guided Walking Tour
Book Now
4.34Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise
Book Now
4.34Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise
Book Now
Cultural Immersion and Evening Entertainment
Morning
Start your day with a visit to the Field Museum, where you can explore the natural history and cultural exhibits. Grab a quick breakfast at the museum cafe before continuing your cultural journey.
Afternoon
For lunch, head to Emerald Loop Bar & Grill, a casual spot with a diverse menu. Afterward, take a stroll through the vibrant Taste of Chinatown Food Walking Tour, exploring the rich culinary and cultural heritage of the area.
4.56Field Museum
Book Now
4.56Field Museum
Book Now
4.79Taste of Chinatown Food Walking Tour
Book Now
4.79Taste of Chinatown Food Walking Tour
Book Now
Urban Exploration and Evening Drinks
Morning
Start your day with a hearty breakfast at Half Sour, a neighborhood spot with a relaxed vibe. After breakfast, take a self-guided tour of the Chicago Pedway System, exploring the underground passages and discovering hidden gems of the city.
Afternoon
For lunch, visit Timothy O'Toole's Pub Chicago, a classic Irish pub with a wide selection of beers. Afterward, take a walk through the lively Wrigleyville neighborhood, known for its sports bars and vibrant atmosphere.
Evening
Dine at Long Room Chicago, a cozy bar with a focus on craft beers and comfort food. After dinner, enjoy a drink at The Signature Lounge at the 96th, where you can take in panoramic views of the city skyline from the 96th floor of the John Hancock Center.
Bedtime
Find amazing hotels in Chicago.
Lakeside Serenity and Evening Elegance
Morning
Begin your day with a delightful breakfast at Miller's Pub, a historic spot with a warm atmosphere. Afterward, take a morning walk at North Avenue Beach, enjoying the peaceful lakefront and the iconic skyline views.
Afternoon
For lunch, head to Reviver, a contemporary American restaurant with a focus on seasonal ingredients. Post-lunch, explore the serene Alfred Caldwell Lily Pool, a hidden gem in the heart of the city.
Evening
Dine at Untitled Supper Club, a speakeasy-style venue with live music and a menu that pays homage to the Prohibition era. After dinner, enjoy a sophisticated evening at The Green Mill, a historic jazz club with a rich history and top-notch performances.
Bedtime
Find amazing hotels in Chicago.
Architectural Wonders and Evening Entertainment
Morning
Start your day with a visit to the Chicago River, where you can take a morning stroll and admire the city's iconic bridges and buildings. For breakfast, head to Elephant & Castle for a taste of their British-inspired dishes.
Afternoon
Enjoy a sophisticated lunch at LUXBAR, known for its upscale American cuisine. Afterward, take a guided tour of the Wrigley Building and learn about its architectural significance and the history of the city.
Evening
Dine at Bar Siena, where you can savor Italian dishes in a stylish setting. Cap off the evening with a visit to The Magnificent Mile, Chicago's premier shopping destination, and take a leisurely walk to admire the upscale stores and the beautiful architecture of the area.
Bedtime
Find amazing hotels in Chicago.
4.61Chicago River
Book Now
4.61Chicago River
Book Now
4.39Wrigley Building
Book Now
4.39Wrigley Building
Book Now
Museum Marvels and Sky-high Views
Morning
Start your day with a visit to the renowned Art Institute of Chicago, where you can explore an impressive collection of art spanning centuries. Grab a quick bite at the museum cafe before heading to the nearby Millennium Park to see the famous "Bean" sculpture.
Afternoon
Enjoy a sophisticated lunch at LUXBAR, known for its upscale American cuisine. Afterward, take in the cityscape from the 360 Chicago Observation Deck (Formerly John Hancock Observatory) with your skip-the-line ticket, and if you're feeling adventurous, try the TILT experience for a unique thrill.
Evening
Dine at Bar Siena, where you can savor Italian dishes in a stylish setting. Cap off the evening with a visit to The Magnificent Mile, Chicago's premier shopping destination, and take a leisurely walk to admire the upscale stores and the beautiful architecture of the area.
Bedtime
Find amazing hotels in Chicago.
4.61Art Institute of Chicago
Book Now
4.61Art Institute of Chicago
Book Now
4.69Millennium Park
Book Now
4.69Millennium Park
Book Now
Historic Buildings and Evening Entertainment
Morning
Enjoy a classic Chicago breakfast at Miller's Pub, a historic spot with a warm atmosphere. Afterward, take a guided tour of the Wrigley Building and learn about its architectural significance and the history of the city.
Afternoon
For lunch, head to Reviver, a contemporary American restaurant with a focus on seasonal ingredients. Post-lunch, immerse yourself in the world of crime and prohibition on the Chicago Gangsters and Ghosts Guided Walking Tour, exploring the city's darker history.
Evening
Dine at Untitled Supper Club, a speakeasy-style venue with live music and a menu that pays homage to the Prohibition era. After dinner, enjoy a live performance at the historic Chicago Theatre, known for its stunning architecture and top-notch entertainment.
Bedtime
Find amazing hotels in Chicago.
4.39Wrigley Building
Book Now
4.39Wrigley Building
Book Now
4.68Chicago Gangsters and Ghosts Guided Walking Tour
Book Now
4.68Chicago Gangsters and Ghosts Guided Walking Tour
Book Now
Science and Nature Exploration
Morning
Start your day with a visit to the Museum of Science and Industry, where you can explore fascinating exhibits and interactive displays. Grab a quick bite at the museum cafe before continuing your exploration.
Afternoon
For lunch, head to Five Star Bar, a casual spot known for its great burgers and beer selection. Afterward, visit the nearby Jackson Park to enjoy a leisurely walk and take in the natural beauty of the area.
Evening
Dine at Plymouth Restaurant & Rooftop Bar, where you can enjoy a meal with a view. After dinner, take a relaxing evening stroll at Soldier Field, home of the Chicago Bears, and soak in the atmosphere of this historic sports venue.
Bedtime
Find amazing hotels in Chicago.
4.31Museum of Science and Industry
Book Now
4.31Museum of Science and Industry
Book Now
4.76Soldier Field
Book Now
4.76Soldier Field
Book Now
Culinary Delights and Evening Cruise
Morning
Indulge in a gourmet breakfast at ROOF on theWit, known for its stunning views and delicious food. After breakfast, take a guided food tour with the Chicago Favorite Foods Guided Walking Tour, sampling a variety of local specialties.
Afternoon
For a unique lunch experience, visit First Draft, a self-pour beer and wine bar with a diverse menu. After lunch, relax and enjoy the sights on a Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise, where you can dine while taking in the beautiful skyline and lake views.
Evening
Conclude your day with a memorable dinner at Scofflaw, a popular spot known for its craft cocktails and elevated bar food. Afterward, take a peaceful evening walk at Lincoln Park & Zoo, one of the oldest and most beautiful zoos in the country.
Bedtime
Find amazing hotels in Chicago.
4.82Chicago Favorite Foods Guided Walking Tour
Book Now
4.82Chicago Favorite Foods Guided Walking Tour
Book Now
4.34Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise
Book Now
4.34Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise
Book Now
Cultural Immersion and Evening Entertainment
Morning
Start your day with a visit to the Field Museum, where you can explore the natural history and cultural exhibits. Grab a quick breakfast at the museum cafe before continuing your cultural journey.
Afternoon
For lunch, head to Emerald Loop Bar & Grill, a casual spot with a diverse menu. Afterward, take a stroll through the vibrant Taste of Chinatown Food Walking Tour, exploring the rich culinary and cultural heritage of the area.
4.56Field Museum
Book Now
4.56Field Museum
Book Now
4.79Taste of Chinatown Food Walking Tour
Book Now
4.79Taste of Chinatown Food Walking Tour
Book Now
Urban Exploration and Evening Drinks
Morning
Start your day with a hearty breakfast at Half Sour, a neighborhood spot with a relaxed vibe. After breakfast, take a self-guided tour of the Chicago Pedway System, exploring the underground passages and discovering hidden gems of the city.
Afternoon
For lunch, visit Timothy O'Toole's Pub Chicago, a classic Irish pub with a wide selection of beers. Afterward, take a walk through the lively Wrigleyville neighborhood, known for its sports bars and vibrant atmosphere.
Evening
Dine at Long Room Chicago, a cozy bar with a focus on craft beers and comfort food. After dinner, enjoy a drink at The Signature Lounge at the 96th, where you can take in panoramic views of the city skyline from the 96th floor of the John Hancock Center.
Bedtime
Find amazing hotels in Chicago.
Lakeside Serenity and Evening Elegance
Morning
Begin your day with a delightful breakfast at Miller's Pub, a historic spot with a warm atmosphere. Afterward, take a morning walk at North Avenue Beach, enjoying the peaceful lakefront and the iconic skyline views.
Afternoon
For lunch, head to Reviver, a contemporary American restaurant with a focus on seasonal ingredients. Post-lunch, explore the serene Alfred Caldwell Lily Pool, a hidden gem in the heart of the city.
Evening
Dine at Untitled Supper Club, a speakeasy-style venue with live music and a menu that pays homage to the Prohibition era. After dinner, enjoy a sophisticated evening at The Green Mill, a historic jazz club with a rich history and top-notch performances.
Bedtime
Find amazing hotels in Chicago.
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