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21-Day Chicago Adventure Itinerary
Last updated: 2024 Jun 14Exploring Downtown Chicago
Morning
Start your day with a visit to Millennium Park, where you can see the iconic Cloud Gate sculpture and enjoy the beautiful gardens. This park is a must-visit for anyone coming to Chicago and offers a peaceful start to your trip.
Afternoon
Head over to The Magnificent Mile for some shopping and sightseeing. This famous stretch of Michigan Avenue is home to numerous shops, restaurants, and landmarks. For lunch, stop by Girl & The Goat, known for its innovative dishes and vibrant atmosphere.
Evening
In the evening, take a stroll along Chicago Riverwalk. This scenic walkway offers stunning views of the city's architecture and is perfect for an evening walk. For dinner, enjoy some classic Chicago-style pizza at Lou Malnati's Pizzeria.
Bedtime
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4.69Millennium Park
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4.69Millennium Park
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4.65The Magnificent Mile
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4.65The Magnificent Mile
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Cultural Gems and Historic Sites
Morning
Begin your day with a visit to the Art Institute of Chicago. This world-renowned museum houses an impressive collection of art from various periods and cultures. It's a great way to immerse yourself in Chicago's rich cultural scene.
Afternoon
After exploring the museum, head over to Grant Park for a relaxing afternoon. This large urban park offers plenty of green space and beautiful views of Lake Michigan. For lunch, try some delicious seafood at Joe's Seafood Prime Steak & Stone Crab.
Evening
In the evening, catch a show at the historic Chicago Theatre. This iconic venue hosts a variety of performances throughout the year. Before the show, have dinner at The Purple Pig, known for its Mediterranean-inspired small plates.
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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Architectural Wonders and Scenic Views
Morning
Start your day with a visit to the famous Skydeck Chicago at Willis Tower (Sears Tower). Enjoy breathtaking views of the city from one of its tallest buildings.
Afternoon
Next, explore the architectural marvels along Chicago Loop. Take in the stunning buildings that define Chicago's skyline. For lunch, head over to Portillo's Hot Dogs for some classic Chicago-style hot dogs.
Evening
In the evening, visit Navy Pier, one of Chicago's most popular attractions. Enjoy rides, games, and beautiful views of Lake Michigan. For dinner, indulge in some gourmet burgers at Au Cheval.
Bedtime
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4.27Skydeck Chicago at Willis Tower (Sears Tower)
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4.27Skydeck Chicago at Willis Tower (Sears Tower)
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4.83Chicago Loop
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4.83Chicago Loop
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Historic Landmarks and Entertainment
Morning
Begin your day with a tour of the historic Rookery Building. Designed by Frank Lloyd Wright, this building is an architectural masterpiece.
Afternoon
Afterward, take a leisurely walk through Lincoln Park & Zoo. This free zoo is home to various animals and offers beautiful gardens as well. For lunch nearby try out some BBQ at Smoque BBQ
Evening
End your day with an exciting experience at House of Blues where you can enjoy live music in an intimate setting . Before heading there , have dinner at Frontera Grill , known for its authentic Mexican cuisine .
Bedtime
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4.73Rookery Building
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4.73Rookery Building
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4.29Lincoln Park & Zoo
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4.29Lincoln Park & Zoo
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Sports and Science Day
Morning
Kick off your day with a visit to Wrigley Field, one of the oldest baseball stadiums in the country. Even if it's not baseball season, the guided tours are fascinating and offer a glimpse into Chicago's sports history.
Afternoon
After the stadium tour, head over to Museum of Science and Industry. This museum is packed with interactive exhibits that are fun for all ages. For lunch, grab a bite at Gibsons Bar & Steakhouse, known for its hearty steaks and classic American fare.
Evening
In the evening, take in a show at Second City, Chicago's famous comedy club. Before the show, enjoy dinner at The Purple Pig, which offers Mediterranean-inspired small plates perfect for sharing.
Bedtime
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4.86Wrigley Field
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4.86Wrigley Field
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4.31Museum of Science and Industry
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4.31Museum of Science and Industry
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History and High Points
Morning
Start your day with a visit to Chicago Board of Trade Building. This historic building is an architectural gem and offers guided tours that delve into its rich history.
Afternoon
Next, explore Chicago Pedway, an underground network of tunnels that connect various parts of downtown Chicago. It's a unique way to see the city from a different perspective. For lunch, stop by Portillo's Hot Dogs for some classic Chicago-style hot dogs.
Evening
In the evening, head over to 360 Chicago Observation Deck (Formerly John Hancock Observatory) for stunning views of the city skyline. For dinner, try out some delicious seafood at Joe's Seafood Prime Steak & Stone Crab.
Bedtime
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4.87Chicago Board of Trade Building
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4.87Chicago Board of Trade Building
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4.94Chicago Pedway
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4.94Chicago Pedway
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Aquatic Adventures and Cultural Insights
Morning
Begin your day with a visit to Shedd Aquarium, one of the largest indoor aquariums in the world. It's home to thousands of marine animals and offers various interactive exhibits.
Afternoon
After exploring the aquarium, take a walk along Lake Michigan at Adler Planetarium. The planetarium itself is also worth visiting if you have time. For lunch nearby try out some BBQ at Smoque BBQ
Evening
End your day with an exciting experience at House of Blues where you can enjoy live music in an intimate setting . Before heading there , have dinner at Frontera Grill , known for its authentic Mexican cuisine .
Bedtime
Find amazing hotels in Chicago, Illinois.
4.75Shedd Aquarium
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4.75Shedd Aquarium
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4.61Adler Planetarium
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4.61Adler Planetarium
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Historic Landmarks and Entertainment
Morning
Begin your day with a tour of the historic Rookery Building. Designed by Frank Lloyd Wright, this building is an architectural masterpiece.
Afternoon
Afterward, take a leisurely walk through Lincoln Park & Zoo. This free zoo is home to various animals and offers beautiful gardens as well. For lunch nearby try out some BBQ at Smoque BBQ
Evening
4.73Rookery Building
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4.73Rookery Building
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4.29Lincoln Park & Zoo
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4.29Lincoln Park & Zoo
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Architectural Marvels and River Views
Morning
Start your day with a visit to Marina City. These iconic twin towers are a marvel of modern architecture and offer unique views of the city.
Afternoon
After exploring Marina City, take a stroll along the Chicago River. This picturesque river is lined with beautiful buildings and offers plenty of photo opportunities. For lunch, head over to The Purple Pig for some Mediterranean-inspired small plates.
Evening
In the evening, enjoy a performance at the Chicago Theatre. This historic venue hosts a variety of shows throughout the year. Before the show, have dinner at Gibsons Bar & Steakhouse, known for its hearty steaks and classic American fare.
Bedtime
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4.84Marina City
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4.84Marina City
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4.61Chicago River
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4.61Chicago River
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Science, Industry, and Nightlife
Morning
Museum of Science and Industry is your first stop today. This museum is packed with interactive exhibits that are fun for all ages.
Afternoon
Grant Park is perfect for a relaxing afternoon. This large urban park offers plenty of green space and beautiful views of Lake Michigan. For lunch, try some delicious seafood at Joe's Seafood Prime Steak & Stone Crab.
Evening
House of Blues awaits you in the evening where you can enjoy live music in an intimate setting. Before heading there, have dinner at Frontera Grill, known for its authentic Mexican cuisine.
Bedtime
Find amazing hotels in Chicago, Illinois.
4.31Museum of Science and Industry
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4.31Museum of Science and Industry
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4.70Grant Park
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4.70Grant Park
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History and High Points
Morning
Chicago Board of Trade Building is an architectural gem offering guided tours that delve into its rich history.
Afternoon
Chicago Pedway, an underground network of tunnels that connect various parts of downtown Chicago, offers a unique way to see the city from a different perspective. For lunch, stop by Portillo's Hot Dogs for some classic Chicago-style hot dogs.
Evening
360 Chicago Observation Deck (Formerly John Hancock Observatory) offers stunning views of the city skyline in the evening. For dinner, try out some delicious seafood at Joe's Seafood Prime Steak & Stone Crab.
Bedtime
Find amazing hotels in Chicago, Illinois.
4.87Chicago Board of Trade Building
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4.87Chicago Board of Trade Building
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4.94Chicago Pedway
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4.94Chicago Pedway
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Art and Skyline Views
Morning
Start your day with a visit to the Art Institute of Chicago. This world-renowned museum houses an impressive collection of art from various periods and cultures. It's a great way to immerse yourself in Chicago's rich cultural scene.
Afternoon
After exploring the museum, head over to Grant Park for a relaxing afternoon. This large urban park offers plenty of green space and beautiful views of Lake Michigan. For lunch, try some delicious seafood at Joe's Seafood Prime Steak & Stone Crab.
Evening
Skydeck Chicago at Willis Tower (Sears Tower) awaits you in the evening where you can enjoy breathtaking views of the city from one of its tallest buildings. For dinner, indulge in some gourmet burgers at Au Cheval.
Bedtime
Find amazing hotels in Chicago, Illinois.
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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Cultural Insights and Entertainment
Morning
Chicago Cultural Center is your first stop today. This landmark building offers free art exhibits and cultural events.
Afternoon
Chicago Riverwalk is perfect for a scenic afternoon walk. This picturesque walkway is lined with beautiful buildings and offers plenty of photo opportunities. For lunch, head over to The Purple Pig for some Mediterranean-inspired small plates.
Evening
Second City awaits you in the evening where you can enjoy live comedy performances. Before heading there, have dinner at Gibsons Bar & Steakhouse, known for its hearty steaks and classic American fare.
Bedtime
Find amazing hotels in Chicago, Illinois.
4.71Chicago Cultural Center
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4.71Chicago Cultural Center
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4.72Chicago Riverwalk
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4.72Chicago Riverwalk
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Exploring Chicago's Iconic Landmarks
Morning
Start your day with a visit to Water Tower Place. This iconic shopping destination offers a variety of stores and is a great place to pick up some souvenirs.
Afternoon
Next, head over to The Magnificent Mile for some more shopping and sightseeing. This famous stretch of Michigan Avenue is home to numerous shops, restaurants, and landmarks. For lunch, stop by Girl & The Goat, known for its innovative dishes and vibrant atmosphere.
Evening
In the evening, take a stroll along Chicago Riverwalk. This scenic walkway offers stunning views of the city's architecture and is perfect for an evening walk. For dinner, enjoy some classic Chicago-style pizza at Lou Malnati's Pizzeria.
Bedtime
Find amazing hotels in Chicago, Illinois.
4.62Water Tower Place
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4.62Water Tower Place
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4.65The Magnificent Mile
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4.65The Magnificent Mile
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Cultural Immersion and Scenic Views
Morning
Begin your day with a visit to the Chicago Cultural Center. This landmark building offers free art exhibits and cultural events.
Afternoon
After exploring the cultural center, take a walk through Grant Park. This large urban park offers plenty of green space and beautiful views of Lake Michigan. For lunch, try some delicious seafood at Joe's Seafood Prime Steak & Stone Crab.
Evening
In the evening, head over to the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for stunning views of the city skyline. For dinner, indulge in some gourmet burgers at Au Cheval.
Bedtime
Find amazing hotels in Chicago, Illinois.
4.71Chicago Cultural Center
Book Now
4.71Chicago Cultural Center
Book Now
4.70Grant Park
Book Now
4.70Grant Park
Book Now
Architectural Wonders and Nightlife
Morning
Start your day with a visit to the historic Rookery Building. Designed by Frank Lloyd Wright, this building is an architectural masterpiece.
Afternoon
Next, explore the architectural marvels along Chicago Loop. Take in the stunning buildings that define Chicago's skyline. For lunch, head over to Portillo's Hot Dogs for some classic Chicago-style hot dogs.
Evening
In the evening, catch a show at the historic Chicago Theatre. This iconic venue hosts a variety of performances throughout the year. Before the show, have dinner at The Purple Pig, known for its Mediterranean-inspired small plates.
Bedtime
Find amazing hotels in Chicago, Illinois.
4.73Rookery Building
Book Now
4.73Rookery Building
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4.83Chicago Loop
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4.83Chicago Loop
Book Now
Science Exploration Day
Morning
Kick off your day with a visit to the fascinatingMuseum of Science and Industry[1213],which features interactive exhibits that are fun for all ages.
Afternoon
After exploring science head over toSoldier Field[6901],home of Chicago Bears football team.Take guided tour if available.For lunch nearby try out BBQ atSmoque BBQ
Evening
End your day with an exciting experience atHouse of Blues[6906]where you can enjoy live music in an intimate setting.Before heading there have dinner atFrontera Grill,known for its authentic Mexican cuisine.
Bedtime
Find amazing hotels in Chicago, Illinois.
4.31Museum of Science and Industry[1213]
Book Now
4.31Museum of Science and Industry[1213]
Book Now
4.76Soldier Field[6901]
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4.76Soldier Field[6901]
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Final Day of Chicago Exploration
Morning
Start your final day with a visit to Field Museum. This natural history museum is one of the largest in the world and offers fascinating exhibits on everything from dinosaurs to ancient cultures.
Afternoon
After exploring the museum, take a leisurely walk through Millennium Park. Enjoy the beautiful gardens and iconic sculptures one last time. For lunch, stop by Girl & The Goat, known for its innovative dishes and vibrant atmosphere.
Evening
In the evening, take a relaxing cruise along Lake Michigan with Chicago Christmas Eve Gourmet Dinner Cruise Lake Michigan. Enjoy stunning views of the city skyline while dining on gourmet cuisine. It's a perfect way to end your Chicago adventure.
Bedtime
Find amazing hotels in Chicago, Illinois.
4.56Field Museum
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4.56Field Museum
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4.69Millennium Park
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4.69Millennium Park
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Aquatic Adventures
Morning
Begin your day with a visit toShedd Aquarium[1210],one of the largest indoor aquariums in the world.It’s home to thousands of marine animals and offers various interactive exhibits.
Afternoon
After exploring the aquarium,take a walk along Lake Michigan atAdler Planetarium[1209].The planetarium itself is also worth visiting if you have time.For lunch nearby try out some BBQ atSmoque BBQ
Evening
End your day with an exciting experience atHouse of Blues[6906]where you can enjoy live music in an intimate setting.Before heading there,have dinner atFrontera Grill,known for its authentic Mexican cuisine.
Bedtime
Find amazing hotels in Chicago,Illinois.
4.75Shedd Aquarium[1210]
Book Now
4.75Shedd Aquarium[1210]
Book Now
4.61Adler Planetarium[1209]
Book Now
4.61Adler Planetarium[1209]
Book Now
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