AI Travel Planner

AI Travel PlannerRoam AroundAI Travel Planner


5-day trip to Chicago Itinerary

Starting date
Rate This Itinerary
day 1

Exploring the City's Landmarks

Chicago Itinerary - February 29

Morning. Start your day with a delicious breakfast at Lula Cafe. Afterward, head to Millennium Park to see the famous The Bean and enjoy the beautiful gardens. Take a stroll along the Chicago Riverwalk and admire the stunning architecture of the city.
Afternoon. For lunch, try the mouthwatering deep-dish pizza at Lou Malnati's Pizzeria. Afterward, take a guided architecture cruise on the Chicago River to learn about the city's iconic buildings and skyline.
Evening. Enjoy a delightful dinner at The Purple Pig, known for its Mediterranean-inspired dishes. Afterward, take a leisurely walk along The Magnificent Mile and indulge in some shopping.
day 2

Museums and Cultural Experiences

Chicago Itinerary - March 1

Morning. Start your day with a visit to the Art Institute of Chicago, one of the oldest and largest art museums in the country. Explore the impressive collection and don't miss famous artworks like Grant Wood's "American Gothic" and Vincent van Gogh's "The Bedroom."
Afternoon. For lunch, head to Eataly Chicago and enjoy a variety of Italian specialties. Afterward, visit the Field Museum to learn about natural history and see fascinating exhibits like Sue, the largest and most complete Tyrannosaurus rex skeleton.
Evening. Indulge in a fine dining experience at Alinea, a three-Michelin-star restaurant known for its innovative and artistic cuisine. Afterward, catch a show at the historic Chicago Theatre.
day 3

Neighborhood Exploration

Chicago Itinerary - March 2

Morning. Start your day with a hearty breakfast at Longman & Eagle. Afterward, explore the vibrant neighborhoods of Wicker Park and Bucktown. Visit local boutiques, art galleries, and enjoy the unique street art.
Afternoon. For lunch, try the delicious tacos at Big Star. Afterward, visit the Garfield Park Conservatory, a stunning botanical garden with a variety of plant species from around the world.
Evening. Enjoy a casual dinner at Kuma's Corner, known for its gourmet burgers. Afterward, head to Logan Square and explore the lively bar scene.
day 4

History and Sports

Chicago Itinerary - March 3

Morning. Start your day with a visit to the Chicago History Museum to learn about the city's rich history. Explore exhibits on the Great Chicago Fire, the Prohibition era, and more.
Afternoon. For lunch, try the mouthwatering barbecue at Smoque BBQ. Afterward, visit Wrigley Field, home of the Chicago Cubs. Take a guided tour of the stadium and learn about the team's history.
Evening. Enjoy a classic steak dinner at Gibsons Bar & Steakhouse. Afterward, catch a game at the United Center, home of the Chicago Bulls and Chicago Blackhawks.
day 5

Relaxation and Farewell

Chicago Itinerary - March 4

Morning. Start your day with a leisurely breakfast at Revival Food Hall. Afterward, take a walk along the Lakefront Trail and enjoy the beautiful views of Lake Michigan.
Afternoon. For lunch, try the delicious Mexican cuisine at Xoco. Afterward, visit Navy Pier and take a ride on the Centennial Wheel for panoramic views of the city.
Evening. Enjoy a farewell dinner at Au Cheval, known for its mouthwatering burgers. Afterward, take a sunset cocktail and architecture tour on the Chicago River to admire the city's skyline one last time.
Rate This Itinerary
Share trip

Explore itineraries for nearby towns in Illinois