Roam Around - AI Travel Planner
You’re now chatting
with Roamy!
Our AI travel planner
with Roamy!
Our AI travel planner
You’re now chatting with Roamy! Our AI travel planner
Your ai trip Illinois
day 1
October 5
October 5Exploring 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 stroll along the Chicago Riverwalk
and enjoy the beautiful views of the city's architecture.AFTERNOON
For lunch, indulge in deep-dish pizza at Lou Malnati's Pizzeria. Afterward, visit the
Art Institute of Chicago
to admire its extensive collection of artworks. Take a walk along the iconic Magnificent Mile
and do some shopping at the various high-end stores.EVENING
Enjoy a delicious dinner at The Purple Pig, known for its Mediterranean-inspired dishes. Afterward, catch a show at the historic
Chicago Theatre
or explore the vibrant nightlife in the River North neighborhood.BEDTIME
Bedtime. Find amazing hotels in Chicago
day 2October 6
October 6Cultural Exploration
MORNING
Start your day with a visit to the
Field Museum
to learn about natural history and anthropology. Afterward, grab a quick bite at Portillo's Hot Dogs for a classic Chicago-style hot dog.AFTERNOON
Explore the
Navy Pier
and enjoy the various attractions, including the Ferris wheel and boat tours. For lunch, try the delicious barbecue at Smoque BBQ. In the afternoon, take a guided architecture cruise along the Chicago River
to learn about the city's iconic buildings.EVENING
For dinner, experience the culinary delights of Alinea, a three-Michelin-star restaurant known for its innovative cuisine. Afterward, head to
360 Chicago Observation Deck (Formerly John Hancock Observatory)
to enjoy panoramic views of the city at night.BEDTIME
Bedtime. Find amazing hotels in Chicago
day 3October 7
October 7Exploring the Suburbs
MORNING
Take a short trip to Evanston and start your day with breakfast at Yolk - South Loop. Explore the beautiful campus of Northwestern University and visit the Bahá'í House of Worship, a stunning architectural masterpiece.
AFTERNOON
Enjoy a leisurely walk along the shores of Lake Michigan at Clark Street Beach. For lunch, try the delicious Italian cuisine at Nando Milano Trattoria. Afterward, visit the Evanston Art Center to admire local artwork.
EVENING
Head back to Chicago and have dinner at Giordano's for their famous stuffed deep-dish pizza. End the day with a comedy show at The Second City, known for launching the careers of many famous comedians.
BEDTIME
Bedtime. Find amazing hotels in Evanston
day 4October 8
October 8Frank Lloyd Wright Tour
MORNING
Take a trip to Oak Park and start your day with breakfast at L'Appetito. Explore the historic neighborhood and visit the Frank Lloyd Wright Home and Studio, where the famous architect lived and worked.
AFTERNOON
Enjoy a guided tour of the various Frank Lloyd Wright-designed houses in Oak Park. For lunch, try the delicious Mexican cuisine at Cafe Ba-Ba-Reeba!. Afterward, visit the Ernest Hemingway Birthplace Museum to learn about the famous writer's early life.
EVENING
Head back to Chicago and have dinner at Gibsons Bar & Steakhouse, known for its prime steaks and lively atmosphere. Afterward, enjoy a drink at The Signature Room at the 95th, located on the 95th floor of the John Hancock Center, offering breathtaking views of the city.
BEDTIME
Bedtime. Find amazing hotels in Oak Park
day 5October 9
October 9Final Day in the Windy City
MORNING
Start your day with a visit to the
Shedd Aquarium
to explore the underwater world. Afterward, grab a quick breakfast at Eataly for some delicious Italian pastries.AFTERNOON
Take a stroll along the
Chicago River 1.5-Hour Guided Architecture Cruise
and learn about the city's architectural history. For lunch, try the famous Chicago-style hot dogs at Gene & Georgetti. In the afternoon, visit the Adler Planetarium
to learn about astronomy and space exploration.EVENING
Enjoy a farewell dinner at Garrett Popcorn Shops and indulge in their famous Chicago-style popcorn. End the trip with a visit to The Second City for a comedy show or head to The Gage for a drink and live music.
BEDTIME
Bedtime. Find amazing hotels in Chicago
Rate This Itinerary
Share trip
CopiedExplore Near By Towns
