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![5 Days in Chicago Adventure](https://storage.googleapis.com/bd-app-dev-375714.appspot.com/itineraries/019014c5-29e0-79c2-b238-832615d612f3/location745.jpg)
5 Days in Chicago Adventure Itinerary
Last updated: 2024 Jun 14Exploring Iconic Chicago
Morning
Start your adventure with a visit to Millennium Park, one of Chicago's most iconic landmarks. Stroll through the park and marvel at the famous Cloud Gate sculpture, also known as 'The Bean.' This is a great spot for photos and to enjoy the vibrant atmosphere of downtown Chicago. For breakfast, head to The Gage, a highly-rated restaurant known for its hearty brunch options and proximity to Millennium Park.
Afternoon
After exploring Millennium Park, take a short walk to Art Institute of Chicago. This world-renowned museum houses an impressive collection of art from various periods and cultures. Don't miss the chance to see famous works like Grant Wood's 'American Gothic' and Georges Seurat's 'A Sunday on La Grande Jatte.' For lunch, dine at The Dearborn, which offers delicious American cuisine in a stylish setting.
Evening
In the evening, immerse yourself in Chicago's vibrant nightlife by visiting House of Blues. Enjoy live music performances in an intimate setting while savoring Southern-inspired dishes at their restaurant. This venue is perfect for experiencing Chicago's rich musical heritage and lively atmosphere.
Bedtime
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House of Blues
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Architectural Wonders & River Cruise
Morning
Begin your day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). Take the elevator up to the Skydeck on the 103rd floor for breathtaking views of the city skyline. Step out onto The Ledge, a glass balcony extending four feet outside the building, for an exhilarating experience. For breakfast, stop by Lou Mitchell's, a historic diner known for its classic American breakfast fare.
Afternoon
Next, explore more of Chicago's architectural marvels with a visit to Chicago Riverwalk. Stroll along this scenic promenade that runs parallel to the Chicago River and admire stunning views of skyscrapers and historic buildings. Enjoy lunch at Café Bonhomme, which offers Mediterranean-inspired dishes with beautiful riverfront views.
Evening
Cap off your day with an unforgettable experience on the water by taking part in Chicago Architecture Boat Tour with Drinks. Cruise along the Chicago River while learning about the city's architectural history from knowledgeable guides. Sip on cocktails as you take in panoramic views of iconic buildings illuminated against the night sky.
Bedtime
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![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)
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Skydeck Chicago at Willis Tower (Sears Tower)
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Chicago Riverwalk
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4.85Chicago Architecture Boat Tour with Drinks
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Chicago Architecture Boat Tour with Drinks
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Cultural Gems & Foodie Delights
Morning
Start your day by visiting Field Museum, one of America's premier natural history museums. Explore fascinating exhibits featuring dinosaur skeletons, ancient artifacts, and cultural treasures from around the world. For breakfast or brunch before heading there, try Yolk - South Loop, known for its creative twists on classic breakfast dishes.
Afternoon
After immersing yourself in natural history at Field Museum, head over to nearby Grant Park where you can relax amidst lush greenery or take leisurely walks around Buckingham Fountain – one of largest fountains worldwide! Enjoy lunch at nearby eatery called The Gage offering upscale pub grub right across Michigan Avenue from Grant Park entrance making it convenient spot refuel during exploration time!
Evening
End your day with some fun-filled activities like participating in unique culinary experiences such as joining guided tour called Chicago Secret Food Tour which takes participants through hidden gems within city’s diverse neighborhoods sampling delectable local treats along way ensuring memorable gastronomic journey awaits all food enthusiasts alike!
Bedtime
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Field Museum
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![Visit Chicago Secret Food Tour in Chicago](https://cdn.getyourguide.com/img/tour/5cc316bc76de2.jpeg/21.jpg)
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Sports and Skyline Adventures
Morning
Kick off your day with a visit to Wrigley Field, one of the oldest and most iconic baseball stadiums in the United States. Take a guided tour to learn about the history of the Chicago Cubs and explore areas usually off-limits to the public, such as the dugout and press box. For breakfast, head to Southport Grocery & Cafe, a cozy spot known for its delicious brunch options and proximity to Wrigley Field.
Afternoon
After soaking in some baseball history, make your way to 360 Chicago Observation Deck (Formerly John Hancock Observatory). Located on the 94th floor of the John Hancock Center, this observation deck offers stunning views of Chicago's skyline and Lake Michigan. Don't forget to try TILT, an exhilarating experience that tilts you out over Michigan Avenue from 1,000 feet up! For lunch, dine at The Signature Room at the 95th, located just one floor above the observation deck, offering upscale American cuisine with panoramic views.
Evening
In the evening, immerse yourself in Chicago's vibrant nightlife by visiting Navy Pier. Enjoy a leisurely stroll along this iconic pier, which features shops, restaurants, and entertainment options. Consider taking part in Chicago: Lake Michigan Educational 'Tall Ship Windy' Cruise, where you can sail on a traditional tall ship while learning about Chicago's maritime history. For dinner, indulge in some deep-dish pizza at Giordano's, a local favorite located near Navy Pier.
Bedtime
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Wrigley Field
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![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)
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360 Chicago Observation Deck (Formerly John Hancock Observatory)
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Navy Pier
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![Visit Chicago: Lake Michigan Educational "Tall Ship Windy" Cruise in Chicago](https://cdn.getyourguide.com/img/tour/630aa8dc6cbc1.jpeg/21.jpg)
5.00Chicago: Lake Michigan Educational 'Tall Ship Windy' Cruise
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Chicago: Lake Michigan Educational 'Tall Ship Windy' Cruise
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Artistic Explorations & Farewell
Morning
Chicago Cultural Center is your first stop today. This stunning building is known for its beautiful architecture and free cultural events. Explore its galleries showcasing local artists' work or attend one of their many performances or lectures if available during your visit! For breakfast beforehand head over nearby café called Toni Patisserie & Café offering French-inspired pastries coffee perfect way start morning right!
Afternoon
Museum of Science and Industry awaits you next! Spend hours exploring interactive exhibits covering everything from space exploration technology advancements human body more making it educational yet fun experience all ages alike! Grab quick bite eat museum’s own Brain Food Court which offers variety food options suit every palate ensuring no one goes hungry while discovering wonders science together family friends alike!
Evening
Second City provides perfect ending note trip through laughter comedy shows performed by talented comedians who’ve gone become household names entertainment industry today! Before heading show enjoy dinner nearby restaurant called RPM Italian serving modern Italian dishes crafted using freshest ingredients ensuring delightful dining experience before laughing night away iconic comedy club located heart Old Town neighborhood!
Bedtime
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Museum of Science and Industry
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Second City
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Second City
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