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Ultimate 21-day Trip to Chicago Itinerary

Last updated: 2024 Jun 14

Exploring the Iconic Landmarks

Morning

Start your day by taking a 1.5-hour guided architecture cruise along the beautiful Chicago River. Marvel at the stunning skyscrapers and learn about the city's architectural history. After the cruise, head to Au Cheval for a delicious brunch.

Afternoon

Visit the famous Willis Tower Skydeck and The Ledge for breathtaking views of the city. Take some time to explore Millennium Park and take a selfie at the iconic The Bean. For lunch, indulge in some deep-dish pizza at Lou Malnati's Pizzeria.

Evening

Enjoy a leisurely walk along the Chicago Riverwalk and admire the city's skyline. For dinner, savor the flavors of Mediterranean cuisine at The Purple Pig. End the day with a visit to the historic Chicago Theatre and catch a live performance.

Bedtime

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Chicago's Cultural Gems

Morning

Start your day with a visit to the Art Institute of Chicago. Explore the impressive collection of artworks and take a guided tour to learn more about the masterpieces. Grab a quick bite at Xoco for lunch.

Afternoon

Immerse yourself in science and history at the Field Museum of Natural History. Spend the afternoon exploring the fascinating exhibits and learning about the world's natural wonders. For a snack, head to Big Star for some delicious tacos.

Evening

Experience the vibrant nightlife of Chicago by visiting 360 Chicago Observation Deck Sip and View. Enjoy panoramic views of the city while sipping on cocktails. For dinner, indulge in a mouthwatering steak at Gibsons Bar & Steakhouse.

Bedtime

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Chicago River and Navy Pier

Morning

Embark on a 45-minute family-friendly architecture river cruise along the Chicago River. Learn about the city's iconic buildings and bridges while enjoying the scenic views. Grab a quick breakfast at Little Goat Diner.

Afternoon

Head to Navy Pier and take a ride on the Centennial Wheel. Enjoy the carnival atmosphere and explore the various attractions. For lunch, try some Chicago-style hot dogs at Portillo's Hot Dogs.

Evening

Take a leisurely stroll along the pier and enjoy the sunset. For dinner, savor the flavors of Italian cuisine at Eataly Chicago. End the day with a thrilling ride at the Centennial Wheel.

Bedtime

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Museums and Science

Morning

Explore the fascinating exhibits at the Museum of Science and Industry. Spend the morning learning about science, technology, and innovation. Grab a quick lunch at Lula Cafe.

Afternoon

Visit the Shedd Aquarium and discover the wonders of the underwater world. Marvel at the diverse marine life and attend a live animal show. For a snack, head to Smoque BBQ for some mouthwatering barbecue.

Evening

Immerse yourself in history at the Chicago History Museum. Learn about the city's past and its impact on American history. For dinner, enjoy farm-to-table cuisine at Longman & Eagle.

Bedtime

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Gangsters and Ghosts

Morning

Embark on a Chicago Gangsters and Ghosts Walking Tour and explore the city's dark history. Learn about infamous gangsters and haunted locations. Grab a quick breakfast at Kuma's Corner.

Afternoon

Visit the 360 Chicago Observation Deck Skip-the-Line and enjoy panoramic views of the city. For lunch, try some gourmet burgers at Girl & the Goat.

Evening

Join a Chicago Mob and Crime Bus Tour and delve deeper into the city's notorious past. Learn about organized crime and visit famous crime scenes. For dinner, indulge in a fine dining experience at Alinea.

Bedtime

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River Cruise and Art

Morning

Take a 1.5-hour guided architecture riverboat tour along the Chicago River. Admire the city's stunning architecture and learn about its history. Grab a quick breakfast at Pequod's Pizza.

Afternoon

Visit the Art Institute of Chicago and explore the extensive collection of artworks. Take a guided tour to learn more about the artists and their masterpieces. For a snack, head to The Publican.

Evening

Enjoy a sunset cocktail and architecture tour along the Chicago River. Admire the city's skyline as you sip on delicious drinks. For dinner, try some traditional Chicago-style deep-dish pizza at Giordano's.

Bedtime

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Food and History

Morning

Embark on a Taste of Chinatown Food Walking Tour and explore the vibrant culinary scene of Chicago's Chinatown. Sample delicious Chinese dishes and learn about the neighborhood's history. Grab a quick breakfast at Frontera Grill.

Afternoon

Visit the Chicago Cultural Center and admire the stunning architecture and art exhibitions. For lunch, indulge in some delicious Mexican cuisine at Big Star.

Evening

Join a Prohibition Speakeasies Bus Tour and learn about Chicago's role during the Prohibition era. Visit hidden speakeasies and enjoy craft cocktails. For dinner, try some innovative American cuisine at The Publican.

Bedtime

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Golden Age and Theater

Morning

Take a Treasures of the Golden Age Walking Tour and explore the architectural gems of Chicago's Golden Age. Learn about the city's history and admire the stunning buildings. Grab a quick breakfast at Lula Cafe.

Afternoon

Visit the iconic Chicago Theatre and take a marquee tour to learn about its history and architecture. For lunch, try some delicious pub food at Revolution Brewing.

Evening

Immerse yourself in the world of theater by watching a live performance at the Chicago Theatre. For dinner, enjoy a steak dinner at Gibsons Bar & Steakhouse.

Bedtime

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Skyline Views and Museums

Morning

Visit the Skydeck Chicago at Willis Tower and experience the thrill of standing on The Ledge. Enjoy panoramic views of the city from the observation deck. Grab a quick breakfast at Little Goat Diner.

Afternoon

Explore the Adler Planetarium and learn about the wonders of the universe. For lunch, try some delicious Italian sandwiches at Xoco.

Evening

Visit the Field Museum of Natural History and immerse yourself in the world of dinosaurs and ancient civilizations. For dinner, indulge in some classic Chicago-style deep-dish pizza at Lou Malnati's Pizzeria.

Bedtime

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Parks and Zoos

Morning

Explore the beautiful Lincoln Park and visit the Lincoln Park Zoo. Enjoy a leisurely walk through the park and admire the diverse wildlife. Grab a quick breakfast at Lula Cafe.

Afternoon

Visit the Garfield Park Conservatory and immerse yourself in the lush greenery. For lunch, try some delicious barbecue at Smoque BBQ.

Evening

Take a relaxing stroll along the Chicago Riverwalk and enjoy the scenic views. For dinner, savor the flavors of farm-to-table cuisine at Lula Cafe.

Bedtime

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Architecture and History

Morning

Take a Chicago River Architecture Cruise Skip-the-Ticket-Office and admire the city's stunning architecture from the river. Learn about the iconic buildings and their history. Grab a quick breakfast at Pequod's Pizza.

Afternoon

Visit the Chicago Architecture Center Cruise on Chicago's First Lady and learn more about the city's architectural wonders. For lunch, try some delicious Mediterranean cuisine at The Purple Pig.

Evening

Explore the historic Rookery Building and admire its stunning architecture. For dinner, enjoy a steak dinner at Gibsons Bar & Steakhouse.

Bedtime

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Art and Shopping

Morning

Take a guided tour of the Art Institute of Chicago and explore the museum's extensive collection. Learn about the artists and their masterpieces. Grab a quick breakfast at Eataly Chicago.

Afternoon

Visit The Magnificent Mile and indulge in some retail therapy. Explore the high-end boutiques and department stores. For lunch, try some delicious Italian cuisine at Giordano's.

Evening

Enjoy a leisurely walk along the Chicago Riverwalk and admire the city's skyline. For dinner, savor the flavors of farm-to-table cuisine at The Publican.

Bedtime

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River Cruise and Food Tasting

Morning

Embark on a Chicago River 1.5-Hour Guided Architecture Riverboat Tour and learn about the city's iconic architecture. Enjoy the scenic views along the river. Grab a quick breakfast at Big Star.

Afternoon

Join a Favorite Foods Guided Walking Tour and explore the city's culinary scene. Sample delicious dishes from various local eateries. For a snack, head to Portillo's Hot Dogs.

Evening

Take a leisurely stroll along the Chicago Riverwalk and enjoy the vibrant atmosphere. For dinner, try some innovative American cuisine at The Publican.

Bedtime

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Museums and Ice Cream

Morning

Visit the Museum of Science and Industry and explore the interactive exhibits. Learn about science, technology, and innovation. Grab a quick breakfast at Lula Cafe.

Afternoon

Indulge your sweet tooth at the Museum of Ice Cream. Enjoy unique ice cream flavors and interactive installations. For lunch, try some delicious sandwiches at Xoco.

Evening

Explore the Chicago Cultural Center and admire the stunning architecture. For dinner, savor the flavors of Italian cuisine at Eataly Chicago.

Bedtime

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Hop-on Hop-off Tour and Lake Cruise

Morning

Explore the city at your own pace with a Big Bus Hop-on Hop-off Open-Top Sightseeing Tour. Visit the various attractions and landmarks. Grab a quick breakfast at Frontera Grill.

Afternoon

Take a Lake Michigan Buffet Brunch, Lunch or Dinner Cruise and enjoy breathtaking views of the city skyline from the lake. Indulge in a delicious meal on board. For a snack, head to Big Star.

Evening

Visit the Chicago Riverwalk and enjoy the vibrant atmosphere. For dinner, try some traditional Chicago-style deep-dish pizza at Pequod's Pizza.

Bedtime

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Torture Museum and Ghost Hunting

Morning

Visit the Medieval Torture Museum and learn about the dark history of torture. Explore the exhibits and artifacts. Grab a quick breakfast at Kuma's Corner.

Afternoon

Join a Medieval Torture Museum Ticket with Ghost Hunting and explore haunted locations in the city. Learn about paranormal activity and ghost stories. For lunch, try some delicious barbecue at Smoque BBQ.

Evening

Take a relaxing stroll along the Chicago Riverwalk and enjoy the scenic views. For dinner, savor the flavors of farm-to-table cuisine at Lula Cafe.

Bedtime

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Pedway and Secrets

Morning

Explore the Chicago Pedway and discover the hidden secrets of the city. Learn about the underground tunnels and unique architecture. Grab a quick breakfast at Little Goat Diner.

Afternoon

Join an Underground Pedway & Downtown Secrets Walking Tour and explore the hidden gems of downtown Chicago. For lunch, try some delicious Mexican cuisine at Big Star.

Evening

Take a leisurely walk along the Chicago Riverwalk and enjoy the vibrant atmosphere. For dinner, try some innovative American cuisine at The Publican.

Bedtime

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Iconic Buildings and Theater

Morning

Visit the iconic Wrigley Building and admire its stunning architecture. Learn about its history and significance. Grab a quick breakfast at Eataly Chicago.

Afternoon

Explore the Tribune Tower and learn about its architectural significance. For lunch, try some delicious Italian cuisine at Giordano's.

Evening

Immerse yourself in the world of theater by watching a live performance at the Chicago Theatre. For dinner, enjoy a steak dinner at Gibsons Bar & Steakhouse.

Bedtime

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Parks and Sports

Morning

Explore the beautiful Grant Park and enjoy a leisurely walk through the park. Admire the stunning views of the city skyline. Grab a quick breakfast at Frontera Grill.

Afternoon

Visit the iconic Wrigley Field and take a guided tour of the historic baseball stadium. For lunch, try some delicious pub food at Revolution Brewing.

Evening

Take a relaxing stroll along the Chicago Riverwalk and enjoy the scenic views. For dinner, savor the flavors of farm-to-table cuisine at The Publican.

Bedtime

Find amazing hotels in Chicago, Illinois.

Science and Nature

Morning

Visit the Museum of Science and Industry and explore the interactive exhibits. Learn about science, technology, and innovation. Grab a quick breakfast at Lula Cafe.

Afternoon

Explore the Adler Planetarium and learn about the wonders of the universe. For lunch, try some delicious Italian sandwiches at Xoco.

Evening

Take a relaxing stroll along the Chicago Riverwalk and enjoy the scenic views. For dinner, savor the flavors of farm-to-table cuisine at The Publican.

Bedtime

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Farewell to Chicago

Morning

Take a leisurely walk along the Chicago Riverwalk and enjoy the vibrant atmosphere. Grab a quick breakfast at Little Goat Diner.

Afternoon

Visit the Chicago River and take in the beauty of the city's iconic river. For lunch, try some delicious Chicago-style hot dogs at Portillo's Hot Dogs.

Evening

Enjoy a farewell dinner at Gibsons Bar & Steakhouse and reminisce about your amazing trip to Chicago.

Bedtime

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