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Roam Around

21 Days of Chicago Adventures Itinerary

Last updated: 2024 Jun 30

Exploring the Heart of Chicago

Morning

Start your day with a visit to Millennium Park, one of Chicago's most iconic landmarks. Here, you can see the famous Cloud Gate sculpture (often referred to as 'The Bean') and enjoy the beautiful gardens and public art installations. After exploring the park, head over to The Goddess and Grocer for a delightful breakfast.

Afternoon

In the afternoon, take a tour from your wishlist: Chicago: Art Institute of Chicago Guided Tour. This guided tour will give you an in-depth look at one of the world's greatest art museums. Afterward, have lunch at The Gage, known for its upscale pub fare and great atmosphere.

Evening

As evening approaches, make your way to Navy Pier, where you can enjoy various attractions including rides, shops, and restaurants. Don't miss out on a ride on the Centennial Wheel for stunning views of the city skyline. For dinner, dine at Riva Crabhouse, which offers delicious seafood with a view.

Bedtime

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4.69
Millennium Park
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4.85
Chicago: Art Institute of Chicago Guided Tour
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Architectural Wonders and River Cruises

Morning

Begin your second day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). Experience breathtaking views from one of the tallest buildings in the Western Hemisphere. For breakfast, stop by Lou Mitchell's, a classic Chicago diner known for its hearty meals.

Afternoon

In the afternoon, embark on another wishlist tour: Chicago River: 1.5-Hour Guided Architecture Riverboat Tour. This tour provides an excellent overview of Chicago's architectural history as you cruise along the river. Have lunch afterward at Portillo's Hot Dogs, famous for its Chicago-style hot dogs and Italian beef sandwiches.

Evening

Spend your evening exploring The Magnificent Mile, Chicago's premier shopping district filled with high-end stores and boutiques. Enjoy dinner at Gibsons Bar & Steakhouse, renowned for its prime steaks and lively atmosphere.

Bedtime

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4.27
Skydeck Chicago at Willis Tower (Sears Tower)
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4.71
Chicago River: 1.5-Hour Guided Architecture Riverboat Tour
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Cultural Gems and Lakefront Views

Morning

Kick off your third day with a visit to Field Museum, home to Sue the T-Rex and countless other fascinating exhibits. Enjoy breakfast at Yolk, which offers creative takes on classic breakfast dishes.

Afternoon

Afterward, take part in another wishlist tour: Chicago: Lakefront Neighborhoods Bike Tour. This bike tour will take you through some of Chicago's most charming neighborhoods along Lake Michigan. For lunch, stop by Girl & The Goat, known for its innovative small plates.

Evening

Conclude your day with an evening stroll along the scenic Chicago Riverwalk. This pedestrian path offers beautiful views of the city’s architecture and vibrant nightlife. Have dinner at River Roast, where you can enjoy delicious American cuisine right by the river.

Bedtime

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Field Museum
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Chicago: Lakefront Neighborhoods Bike Tour
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Historic Landmarks and Hidden Gems

Morning

Start your day with a visit to Rookery Building, an architectural masterpiece designed by Frank Lloyd Wright. Enjoy breakfast at The Dearborn, known for its classic American dishes and stylish setting.

Afternoon

In the afternoon, take part in the wishlist tour: Chicago: Underground Pedway & Downtown Secrets Walking Tour. This tour will take you through Chicago's hidden underground pedestrian pathways and reveal some of the city's best-kept secrets. For lunch, head to The Purple Pig, famous for its Mediterranean-inspired small plates.

Evening

Spend your evening at House of Blues, where you can enjoy live music in a vibrant atmosphere. For dinner, dine at Smith & Wollensky, offering prime steaks and seafood with a view of the Chicago River.

Bedtime

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4.73
Rookery Building
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4.73
Chicago: Underground Pedway & Downtown Secrets Walking Tour
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Museums and Scenic Cruises

Morning

Museum of Science and Industry is your first stop today. This museum offers interactive exhibits that are perfect for all ages. Have breakfast at Valois Restaurant, a local favorite known for its hearty breakfasts.

Afternoon

Chicago: 1.5-Hour Lake and River Architecture Cruise is on the agenda for the afternoon. This cruise provides stunning views of Chicago's skyline from both the lake and river perspectives. Afterward, enjoy lunch at Pizza Capri, which offers delicious Italian cuisine.

Evening

Adler Planetarium is an excellent choice for an evening visit, especially if you're interested in astronomy. For dinner, head to The Signature Room at the 95th, located in the John Hancock Center, offering breathtaking views along with fine dining.

Bedtime

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Museum of Science and Industry
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4.75
Chicago: 1.5-Hour Lake and River Architecture Cruise
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Parks and Cultural Experiences

Morning

Lincoln Park & Zoo is a great way to start your day with nature and wildlife right in the heart of Chicago. Have breakfast at Toast, known for its creative brunch menu.

Afternoon

Chicago: Gangsters and Ghosts Guided Walking Tour will take you through some of Chicago's most infamous historical sites related to gangsters and ghosts. For lunch, stop by Frontera Grill, renowned for its Mexican cuisine by celebrity chef Rick Bayless.

Evening

Conclude your day with a visit to Second City, one of Chicago's most famous comedy clubs where many comedians got their start. Enjoy dinner at Tru, offering contemporary American cuisine in an elegant setting.

Bedtime

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4.29
Lincoln Park & Zoo
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4.68
Chicago: Gangsters and Ghosts Guided Walking Tour
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Sports and Skyline Views

Morning

Begin 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 its rich history and see behind-the-scenes areas. For breakfast, head to Southport Grocery & Cafe, known for its delicious pastries and brunch options.

Afternoon

In the afternoon, embark on the wishlist tour: Chicago: 360 Chicago Observation Deck General Admission. This observation deck offers stunning views of the city from the John Hancock Center. Afterward, enjoy lunch at The Purple Pig, famous for its Mediterranean-inspired small plates.

Evening

Spend your evening at United Center, home to the Chicago Bulls and Blackhawks. If there's a game or event happening, it's a must-see experience. For dinner, dine at Girl & The Goat, known for its innovative small plates and vibrant atmosphere.

Bedtime

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Wrigley Field
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Chicago: 360 Chicago Observation Deck General Admission
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Aquatic Adventures and Historic Buildings

Morning

Shedd Aquarium is your first stop today. This world-renowned aquarium houses thousands of marine animals and offers interactive exhibits. Have breakfast at Yolk, which offers creative takes on classic breakfast dishes.

Afternoon

Chicago: Architecture Boat Tour with Drinks is on the agenda for the afternoon. This tour provides an excellent overview of Chicago's architectural history while you enjoy a refreshing drink on board. Afterward, have lunch at Portillo's Hot Dogs, famous for its Chicago-style hot dogs and Italian beef sandwiches.

Evening

Palmer House Hilton is an excellent choice for an evening visit to explore this historic hotel with its stunning architecture and rich history. For dinner, head to The Gage, known for its upscale pub fare and great atmosphere.

Bedtime

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4.75
Shedd Aquarium
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4.85
Chicago: Architecture Boat Tour with Drinks
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Cultural Landmarks and Scenic Cruises

Morning

Art Institute of Chicago is your first stop today. This museum houses an extensive collection of art from around the world. Enjoy breakfast at The Goddess and Grocer, which offers delightful pastries and coffee.

Afternoon

Chicago: Lake Michigan Skyline Cruise will take you on a scenic cruise along Lake Michigan, offering breathtaking views of Chicago's skyline. For lunch, stop by Lou Malnati's Pizzeria, known for its deep-dish pizza.

Evening

Chicago Theatre is an iconic venue where you can catch a show or simply admire its beautiful architecture. Enjoy dinner at RPM Steak, offering prime steaks in a chic setting.

Bedtime

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Art Institute of Chicago
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4.59
Chicago: Lake Michigan Skyline Cruise
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Exploring the Loop and Riverwalk

Morning

Start your day with a visit to Chicago Loop, the central business district known for its stunning architecture and bustling atmosphere. Have breakfast at The Dearborn, which offers classic American dishes in a stylish setting.

Afternoon

In the afternoon, take part in the wishlist tour: Chicago: Treasures of the Golden Age Walking Tour. This tour will guide you through some of Chicago's most historic buildings and landmarks. For lunch, head to The Purple Pig, famous for its Mediterranean-inspired small plates.

Evening

Spend your evening exploring Chicago Riverwalk, a pedestrian path along the Chicago River offering beautiful views of the city’s architecture and vibrant nightlife. For dinner, dine at River Roast, where you can enjoy delicious American cuisine right by the river.

Bedtime

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4.83
Chicago Loop
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4.77
Chicago: Treasures of the Golden Age Walking Tour
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Science, Industry, and Skyline Views

Morning

Begin your day with a visit to Museum of Science and Industry, which offers interactive exhibits perfect for all ages. Enjoy breakfast at Valois Restaurant, a local favorite known for its hearty breakfasts.

Afternoon

Chicago: 1.5-Hour Scenic Sunset Lake Cruise is on the agenda for the afternoon. This cruise provides stunning views of Chicago's skyline as the sun sets over Lake Michigan. Afterward, have lunch at Pizza Capri, which offers delicious Italian cuisine.

Evening

Conclude your day with an evening visit to 360 Chicago Observation Deck (Formerly John Hancock Observatory). Enjoy breathtaking views from one of Chicago's tallest buildings. For dinner, head to The Signature Room at the 95th, located in the John Hancock Center, offering fine dining with panoramic views.

Bedtime

Find amazing hotels in Chicago, Illinois.

4.31
Museum of Science and Industry
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4.61
Chicago: 1.5-Hour Scenic Sunset Lake Cruise
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Cultural Experiences and Historic Tours

Morning

Kick off your day with a visit to Field Museum, home to Sue the T-Rex and countless other fascinating exhibits. Have breakfast at Yolk, which offers creative takes on classic breakfast dishes.

Afternoon

Afterward, take part in another wishlist tour: Chicago: Mob and Crime Bus Tour. This tour will take you through some of Chicago's most infamous historical sites related to gangsters and crime. For lunch, stop by Frontera Grill, renowned for its Mexican cuisine by celebrity chef Rick Bayless.

Evening

Conclude your day with an evening stroll along the scenic lakefront near Grant Park. Enjoy dinner at Tru, offering contemporary American cuisine in an elegant setting.

Bedtime

Find amazing hotels in Chicago, Illinois.