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7-Day Chicago Exploration with Iconic Landmarks and Culinary Delights Itinerary
Last updated: 2024 Jun 14City Icons and River Cruise
Morning
Begin your Chicago adventure with a hearty breakfast at Miller's Pub, a historic spot in the Loop. Afterward, take a stroll to the iconic Wrigley Building and enjoy the architecture.
Afternoon
For lunch, head to The Gage for a taste of their renowned gastropub fare. Spend your afternoon at the majestic Art Institute of Chicago, exploring its world-class art collection.
Evening
Dine with a view at Cindy's Rooftop, located in the Chicago Athletic Association Hotel. Afterward, take a leisurely Chicago Riverwalk to soak in the city's evening ambiance.
Bedtime
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4.39Wrigley Building
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4.39
Wrigley Building
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4.61Art Institute of Chicago
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4.61
Art Institute of Chicago
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4.72Chicago Riverwalk
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4.72
Chicago Riverwalk
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Museum Marvels and Skyline Views
Morning
Enjoy a delightful breakfast at The Franklin Room, known for its classic American dishes. Start your day with a visit to the interactive Museum of Science and Industry.
Afternoon
For lunch, head to Sweetwater Tavern & Grille and savor their diverse menu. Spend your afternoon at the serene Lincoln Park & Zoo, a perfect escape from the urban bustle.
Evening
Experience the city from above at the 360 Chicago Observation Deck (Formerly John Hancock Observatory), and then have a sophisticated dinner at 676 Restaurant & Bar.
Bedtime
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4.31Museum of Science and Industry
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4.31
Museum of Science and Industry
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4.29Lincoln Park & Zoo
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4.29
Lincoln Park & Zoo
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4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
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4.17
360 Chicago Observation Deck (Formerly John Hancock Observatory)
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Cultural Treasures and Navy Pier
Morning
Start with a breakfast at The Green Door Tavern, a historic speakeasy. Then, immerse yourself in the vibrant atmosphere of The Magnificent Mile for some morning shopping.
Afternoon
Enjoy a diverse lunch at Bar Siena in the heart of the city. Spend your afternoon at the family-friendly Navy Pier, exploring its attractions and taking a ride on the Centennial Wheel.
Evening
Dine at FireLake Grill House and Cocktail Bar and then catch a live performance at the Chicago Theatre, an iconic venue with a rich history.
Bedtime
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4.65The Magnificent Mile
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4.65
The Magnificent Mile
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4.48Navy Pier
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4.48
Navy Pier
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4.43Centennial Wheel
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4.43
Centennial Wheel
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4.71Chicago Theatre
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4.71
Chicago Theatre
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Culinary Delights and Lakefront Serenity
Morning
Start your day with a delicious breakfast at House of Blues Restaurant & Bar. Then, take a morning walk at the serene Grant Park, also known as Chicago's "front yard."
Afternoon
For lunch, head to Lockwood Restaurant & Bar and enjoy their farm-to-table offerings. Spend your afternoon at the Shedd Aquarium and be amazed by the aquatic wonders.
Evening
Enjoy a relaxing dinner cruise with the Chicago Gourmet Brunch, Lunch, or Dinner River Cruise, where you can indulge in fine dining while gliding along the Chicago River.
Bedtime
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4.70Grant Park
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4.70
Grant Park
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4.75Shedd Aquarium
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4.75
Shedd Aquarium
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4.60Chicago Gourmet Brunch, Lunch, or Dinner River Cruise
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4.60
Chicago Gourmet Brunch, Lunch, or Dinner River Cruise
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Historic Tours and Evening Breezes
Morning
Grab breakfast at State and Lake Chicago Tavern, then embark on a guided Chicago Gangsters and Ghosts Guided Walking Tour to uncover the city's intriguing past.
Afternoon
For lunch, head to Randolph Tavern and enjoy their pub-style cuisine. Afterward, take a leisurely Chicago River cruise to see the city's architecture from a different perspective.
Evening
Dine at Exchequer Restaurant & Pub, a historic spot known for its deep-dish pizza. Then, take an evening stroll at Millennium Park and admire the famous "Bean" (Cloud Gate) sculpture.
Bedtime
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4.68Chicago Gangsters and Ghosts Guided Walking Tour
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4.68
Chicago Gangsters and Ghosts Guided Walking Tour
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4.61Chicago River
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4.61
Chicago River
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4.69Millennium Park
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4.69
Millennium Park
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Park Promenades and Cultural Sojourn
Morning
Start with breakfast at The Beetle Bar and Grill, then enjoy a morning walk at the beautiful Marina City, known for its unique architecture and vibrant riverfront.
Afternoon
Have lunch at Bar Louie - Printers Row, and then spend your afternoon at the serene Tribune Tower and the nearby River, taking in the city's history and natural beauty.
Evening
Dine at Emerald Loop Bar & Grill, offering a wide range of dishes. Cap off the evening with a visit to the Chicago River for a peaceful end to the day.
Bedtime
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4.84Marina City
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4.84
Marina City
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4.61Tribune Tower
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4.61
Tribune Tower
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4.61River
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4.61
River
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4.61Chicago River
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4.61
Chicago River
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Farewell to Chicago with Sky-high Views
Morning
Enjoy a final breakfast at Five Star Bar, a local favorite. Then, take a private Helicopter Tour of Chicago Skyline for a breathtaking perspective of the city.
Afternoon
For lunch, head to Billy Goat Tavern (Millennium Park) and try their famous "Cheezborger." Spend your afternoon at the Underground Pedway & Downtown Secrets Walking Tour, discovering hidden gems and local lore.
Evening
Dine at Gilt Bar, an upscale spot with a cozy atmosphere. End your trip with a visit to the Skydeck Chicago at Willis Tower (Sears Tower) to witness the city lights from the tallest building in the Western Hemisphere.
Bedtime
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4.50Helicopter Tour of Chicago Skyline
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4.50
Helicopter Tour of Chicago Skyline
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4.73Underground Pedway & Downtown Secrets Walking Tour
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4.73
Underground Pedway & Downtown Secrets Walking Tour
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4.27Skydeck Chicago at Willis Tower (Sears Tower)
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4.27
Skydeck Chicago at Willis Tower (Sears Tower)
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