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Roamy - 2:17 AM👋 Hi, I'm Roamy, your AI Concierge! I'm here to help craft the perfect trip and answer your questions. Let's get started! 📅 To customize your itinerary, phrase your desired changes as a request. 👇 Examples: • "Make it 4 days" • "Recommend vegetarian options on Day 2" 🤔 Got questions? I've got answers! 👇 Examples: • "Am I supposed to tip in this country?" • "What are good transportation options to get here?"
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Your ai trip Illinois

day 1
calendarOctober 5
Exploring the Windy City

MORNING

Start your day with a delicious breakfast at Wildberry Pancakes and Cafe. Afterward, head to
Millennium Park
to see the famous Cloud Gate sculpture, also known as "The Bean." Take a leisurely stroll through the park and enjoy the beautiful scenery.

AFTERNOON

For lunch, try the deep-dish pizza at Lou Malnati's Pizzeria. Afterward, visit the
Art Institute of Chicago
to admire its impressive collection of artworks. Take your time exploring the museum and don't miss the iconic "American Gothic" painting.

EVENING

Enjoy a romantic sunset cruise along the Chicago River with the
Chicago 1.5-Hour Romantic Sunset Cruise
. Take in the breathtaking views of the city's skyline as the sun sets. For dinner, indulge in a gourmet meal at Alinea, a renowned Michelin-starred restaurant known for its innovative cuisine.

BEDTIME

Bedtime. Find amazing hotels in Chicago
day 2
calendarOctober 6
Architecture and Culture

MORNING

Start your day with a delicious breakfast at Yolk - South Loop. Afterward, embark on a 1.5-hour guided architecture cruise along the Chicago River with
Chicago River Architecture Cruise Skip-the-Ticket-Office
. Learn about the city's iconic buildings and architectural history.

AFTERNOON

For lunch, try the famous Chicago-style hot dogs at Portillo's Hot Dogs. Afterward, visit the
Field Museum
to explore its fascinating exhibits on natural history and anthropology.

EVENING

Enjoy a dinner at The Purple Pig, a popular restaurant known for its Mediterranean-inspired dishes. Afterward, catch a live performance at the historic
Chicago Theatre
.

BEDTIME

Bedtime. Find amazing hotels in Chicago
day 3
calendarOctober 7
Sky-high Views and Navy Pier

MORNING

Start your day with a delicious breakfast at Lula Cafe. Afterward, head to
360 Chicago Observation Deck (Formerly John Hancock Observatory)
for panoramic views of the city. Don't miss the thrilling experience of "The Tilt," a glass-enclosed platform that tilts outward from the building.

AFTERNOON

For lunch, try the mouthwatering burgers at Au Cheval. Afterward, visit
Navy Pier
to enjoy its attractions, including the Centennial Wheel and the Chicago Children's Museum.

EVENING

Indulge in a seafood dinner at The Signature Room at the 95th, located on the 95th floor of the John Hancock Center. Afterward, take a stroll along the
Chicago Riverwalk
and enjoy the vibrant atmosphere.

BEDTIME

Bedtime. Find amazing hotels in Chicago
day 4
calendarOctober 8
Exploring Evanston

MORNING

Start your day with a delicious breakfast at Lula Cafe. Afterward, visit the Bahá'í House of Worship, a stunning architectural masterpiece and a place of tranquility and reflection.

AFTERNOON

For lunch, try the mouthwatering burgers at Au Cheval. Afterward, explore the beautiful campus of Northwestern University and visit the Mary and Leigh Block Museum of Art to admire its impressive collection.

EVENING

Enjoy a dinner at The Stained Glass and savor their delicious American cuisine. Afterward, catch a performance at the Piven Theatre Workshop.

BEDTIME

Bedtime. Find amazing hotels in Evanston, Illinois
day 5
calendarOctober 9
Frank Lloyd Wright's Legacy

MORNING

Start your day with a delicious breakfast at Lula Cafe. Afterward, take a guided tour of the Frank Lloyd Wright Home and Studio to learn about the famous architect's life and work.

AFTERNOON

For lunch, try the mouthwatering burgers at Au Cheval. Afterward, visit the Frank Lloyd Wright's Unity Temple, a masterpiece of modern architecture.

EVENING

Enjoy a dinner at Hemmingway's Bistro and savor their delicious French cuisine. Afterward, take a leisurely walk through the charming streets of Oak Park and admire the beautiful historic homes.

BEDTIME

Bedtime. Find amazing hotels in Oak Park, Illinois
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