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Roam Around

Ultimate Chicago Architecture and Culinary Experience Itinerary

Last updated: 2024 Jun 14

Iconic Chicago Landmarks and Skyline Views

Morning

Start your day with a delightful brunch at The Purple Pig, known for its Mediterranean-inspired small plates. Afterward, take a stroll along the Magnificent Mile and explore the upscale shops and historic architecture.

Afternoon

For the afternoon, visit the Art Institute of Chicago and immerse yourself in world-class art collections. Afterward, enjoy a late lunch at Giordano's for their famous deep-dish pizza.

Evening

In the evening, head to the 360 Chicago Observation Deck (Formerly John Hancock Observatory) for breathtaking views of the city at sunset. Followed by a gourmet dinner at Alinea, a three-Michelin-star restaurant offering a unique dining experience.

Bedtime

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4.65
Magnificent Mile
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4.61
Art Institute of Chicago
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Riverfront Architecture and Culinary Delights

Morning

Enjoy a leisurely breakfast at Lula Cafe, a cozy spot known for its farm-to-table dishes. Then, embark on the Chicago River 1.5-Hour Guided Architecture Cruise to learn about the city's iconic buildings.

Afternoon

After the cruise, have a seafood feast at Gibsons Bar & Steakhouse, a classic Chicago eatery. Then, take a walk along the Chicago Riverwalk and admire the views.

Evening

For dinner, savor the flavors of Mexico at Xoco, a restaurant by award-winning chef Rick Bayless. Afterward, experience the city's vibrant nightlife at a local bar in the River North area.

Bedtime

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4.77
Chicago River 1.5-Hour Guided Architecture Cruise
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4.72
Chicago Riverwalk
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Cultural Immersion and Sky-High Thrills

Morning

Start your day with a hearty breakfast at Wildberry Pancakes and Cafe, known for its delicious pancakes. Then, explore the Field Museum and delve into natural history and world cultures.

Afternoon

After the museum, enjoy a classic Chicago hot dog at Portillo's Hot Dogs. Then, visit the Willis Tower Skydeck and The Ledge for a thrilling experience on the glass-bottomed ledge.

Evening

Dine at The Signature Room at the 95th and enjoy a gourmet meal with panoramic views of the city. End your day with a leisurely walk around the Millennium Park and see the famous Cloud Gate sculpture.

Bedtime

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4.56
Field Museum
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4.41
Willis Tower Skydeck and The Ledge
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Gangsters, Ghosts, and Gourmet Food

Morning

Indulge in a luxurious brunch at The Publican, known for its oysters and charcuterie. Then, embark on the Chicago Gangsters and Ghosts Guided Walking Tour to learn about the city's dark past.

Afternoon

After the tour, have a late lunch at Girl & the Goat, a popular spot for creative small plates. Spend the afternoon exploring the trendy West Loop neighborhood.

Evening

For dinner, experience a unique culinary journey at Alinea, one of the best restaurants in the world. Afterward, if you're up for it, join a Prohibition Speakeasies Bus Tour for a taste of the city's hidden history.

Bedtime

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4.68
Chicago Gangsters and Ghosts Guided Walking Tour
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4.90
Prohibition Speakeasies Bus Tour
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Lakefront Serenity and Culinary Excellence

Morning

Enjoy a peaceful morning at Lincoln Park & Zoo, strolling through the gardens and visiting the animals. For brunch, head to Lula Cafe for their famous farm-to-table dishes.

Afternoon

After the zoo, take a relaxing Chicago Lake Michigan Skyline Cruise and admire the city's skyline from the water. Have a late lunch at The Purple Pig for a taste of Mediterranean flavors.

Evening

Dine at Au Cheval, known for its mouthwatering burgers. After dinner, take a leisurely walk along the Chicago Riverwalk and enjoy the evening views.

Bedtime

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4.29
Lincoln Park & Zoo
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4.59
Chicago Lake Michigan Skyline Cruise
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Architectural Wonders and Culinary Delights

Morning

Start your day with a visit to the Chicago Architecture Center to learn more about the city's iconic buildings. Afterward, have a delightful brunch at Little Goat Diner, a popular spot for comfort food.

Afternoon

Explore the Museum of Science and Industry, a fascinating museum with interactive exhibits. For a late lunch, head to Pequod's Pizza for their famous pan-style pizza.

Evening

Enjoy a gourmet dinner at Alinea, a three-Michelin-star restaurant known for its innovative cuisine. Afterward, take a walk around the historic Wrigley Building and enjoy the evening lights.

Bedtime

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4.46
Chicago Architecture Center
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4.31
Museum of Science and Industry
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Farewell to Chicago with Culinary Bliss

Morning

Spend your last morning in Chicago enjoying a leisurely breakfast at Lula Cafe. Take a final stroll along the Chicago Riverwalk and savor the views.

Afternoon

For your last meal in the city, indulge in a gourmet lunch at Alinea. Afterward, visit the 360 Chicago Observation Deck for one last look at the city before you depart.

Evening

Departure from Chicago. If time allows, have a farewell drink at a local bar, reminiscing about your wonderful time in the Windy City.

Bedtime

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