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Ultimate 7-Day Chicago Adventure Itinerary
Last updated: 2024 Jun 14Iconic Chicago Sights and Skyline Views
Morning
Start your Chicago adventure with a delicious breakfast at Lou Malnati's Pizzeria, famous for its deep-dish pizza. Afterward, take a relaxing stroll along the beautiful Chicago Riverwalk to soak in the morning vibes of the city.
Afternoon
For lunch, head to The Purple Pig, a renowned restaurant offering a variety of Mediterranean-inspired dishes. Afterward, take a guided architecture cruise on the Chicago River 1.5-Hour Guided Architecture Cruise to marvel at the city's stunning skyline.
Evening
Enjoy a delightful dinner at The Signature Room at the 95th, offering breathtaking views of the city. Afterward, visit the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for a panoramic view of Chicago at night.
Bedtime
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4.72Chicago Riverwalk
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4.72Chicago Riverwalk
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4.77Chicago River 1.5-Hour Guided Architecture Cruise
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4.77Chicago River 1.5-Hour Guided Architecture Cruise
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Cultural Exploration and Culinary Delights
Morning
Start your day with a hearty brunch at Girl & The Goat, known for its innovative cuisine. Afterward, visit the Art Institute of Chicago to explore its impressive art collection.
Afternoon
For lunch, head to Xoco, a top spot for Mexican street food. Afterward, take a guided tour of the Chicago Theatre to learn about its rich history and architecture.
Evening
Indulge in a memorable dining experience at Au Cheval, famous for its mouthwatering burgers. Afterward, take a leisurely walk along The Magnificent Mile and explore the upscale shops and boutiques.
Bedtime
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4.61Art Institute of Chicago
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4.61Art Institute of Chicago
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4.71Chicago Theatre
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4.71Chicago Theatre
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Museums and Lakefront Relaxation
Morning
Enjoy a delightful breakfast at Lula Cafe, a cozy neighborhood spot. Afterward, visit the Field Museum to explore its fascinating exhibits.
Afternoon
For lunch, head to Eataly Chicago, a vibrant Italian marketplace with various dining options. Afterward, take a relaxing stroll in Grant Park and enjoy the scenic views of Lake Michigan.
Evening
Dine at RPM Italian, known for its modern Italian cuisine. Afterward, take a serene evening cruise on the Chicago Lake Michigan Skyline Cruise and admire the city's skyline from the water.
Bedtime
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4.56Field Museum
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4.56Field Museum
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4.70Grant Park
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4.70Grant Park
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Culinary Exploration and Riverfront Fun
Morning
Start your day with a delicious breakfast at Little Goat Diner, a popular spot for creative comfort food. Afterward, take a guided tour of the Wrigley Field to learn about its storied history.
Afternoon
Evening
Dine at Portillo's Hot Dogs, a Chicago institution known for its classic hot dogs and Italian beef sandwiches. Afterward, take a scenic evening walk along the Chicago River and enjoy the city lights.
Bedtime
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4.86Wrigley Field
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4.86Wrigley Field
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4.48Navy Pier
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4.48Navy Pier
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Gangsters, Ghosts, and Gourmet Dining
Morning
Enjoy a leisurely breakfast at Cafe Ba-Ba-Reeba!, a Spanish tapas restaurant. Afterward, embark on a Chicago Gangsters and Ghosts Guided Walking Tour to learn about the city's intriguing history.
Afternoon
For lunch, head to Gibsons Bar & Steakhouse, a classic Chicago steakhouse. Afterward, visit the Museum of Science and Industry to explore its interactive exhibits.
Evening
Dine at Smoque BBQ, known for its mouthwatering barbecue dishes. Afterward, take a gourmet dinner cruise on the Chicago Gourmet Brunch, Lunch, or Dinner River Cruise and enjoy the city's skyline from the water.
Bedtime
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4.68Chicago Gangsters and Ghosts Guided Walking Tour
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4.68Chicago Gangsters and Ghosts Guided Walking Tour
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4.31Museum of Science and Industry
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4.31Museum of Science and Industry
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Art, Architecture, and Sky-High Dining
Morning
Start your day with a delightful breakfast at Kuma's Corner, a rock 'n' roll-themed restaurant known for its burgers. Afterward, visit the Millennium Park to see the iconic Cloud Gate sculpture.
Afternoon
For lunch, head to Longman & Eagle, a Michelin-starred gastropub. Afterward, take a guided tour of the Wrigley Building to learn about its architectural significance.
Evening
Dine at Pequod's Pizza, famous for its caramelized crust deep-dish pizza. Afterward, visit the Skydeck Chicago at Willis Tower (Sears Tower) to experience the thrill of "The Ledge" glass floor balconies.
Bedtime
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4.69Millennium Park
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4.69Millennium Park
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4.39Wrigley Building
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4.39Wrigley Building
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Zoo, Helicopter Views, and Farewell Dinner
Morning
Enjoy a delightful breakfast at Lula Cafe, a cozy neighborhood spot. Afterward, visit the Lincoln Park & Zoo to see a variety of animals and enjoy a leisurely walk in the park.
Afternoon
For lunch, head to Girl & The Goat, known for its innovative cuisine. Afterward, take a private helicopter tour of the Chicago Skyline for a bird's-eye view of the city.
Evening
Dine at The Purple Pig, offering a variety of Mediterranean-inspired dishes. Afterward, take a farewell stroll along the Chicago Riverwalk and reminisce about your amazing Chicago adventure.
Bedtime
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4.29Lincoln Park & Zoo
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4.29Lincoln Park & Zoo
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4.50Chicago Skyline
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4.50Chicago Skyline
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