5-day itinerary
The Perfect 5 Days in Chicago
A balanced 5-day plan for Chicago, built around its top-rated sights and ordered so each day flows without backtracking — with a bite to eat and travel times between every stop. Like it? Make it your own in a couple of taps.
Make this Chicago itinerary yours
Customize it →The Big Highlights
Morning
Chicago Cubs Team Store
Stock up on authentic Chicago Cubs merchandise and wear your team pride all season long.
4 min walk · 0.3 km to the next stop
Afternoon
Chicago Water Tower
One of the few structures to survive the Great Chicago Fire, this Gothic limestone tower is a city icon.
5 min walk · 0.4 km to the next stop
Evening
Wilson
Clothing shop offering apparel and fashion retail selections.
Where to eat: Alinea — Fine Dining — a well-loved local spot.
Sights & Experiences
Morning
World of Whirlpool
Appliance retail store showcasing kitchen and home appliances.
13 min walk · 1 km to the next stop
Afternoon
Cloud Gate
Reflect yourself in Chicago's beloved giant mirrored bean, a dazzling landmark in Millennium Park.
5 min walk · 0.4 km to the next stop
Evening
Begin Route 66
Stand at the legendary birthplace of Route 66, where America's most iconic road trip adventure begins.
Where to eat: Mon Ami Gabi — French — a well-loved local spot.
Culture & Icons
Morning
Clarence Buckingham Memorial Fountain
One of the world's largest fountains, dazzling visitors with spectacular water displays in the heart of Grant Park.
14 min walk · 1 km to the next stop
Afternoon
Brachiosaurus Replica
Marvel at a life-sized Brachiosaurus replica towering over Chicago's lakefront parkland.
10 min drive · 2 km to the next stop
Evening
Pillar of Fire
A historic memorial in Chicago.
Where to eat: Lou Mitchell's Restaurant — American — a well-loved local spot.
Culture & Icons
Morning
Chicago Union Station
Marvel at the Beaux-Arts grandeur of Chicago's iconic train hub, a timeless crossroads of American travel.
10 min walk · 0.8 km to the next stop
Afternoon
Haymarket Memorial
A powerful bronze sculpture honoring the 1886 labor martyrs who shaped workers' rights worldwide.
14 min drive · 3.4 km to the next stop
Evening
Navy Pier
Chicago's beloved pier dazzles with skyline views, Ferris wheel thrills, and vibrant waterfront entertainment.
Where to eat: Al's Beef — Sandwiches — a well-loved local spot.
Culture & Icons
Morning
S.R. Crown Hall
Mies van der Rohe's glass-and-steel gem is a landmark of International Style architecture you must see.
20 min drive · 5.5 km to the next stop
Afternoon
Frederick C. Robie House
Frank Lloyd Wright's groundbreaking 1910 home that defined modern American architecture with its sweeping horizontal lines.
17 min walk · 1.2 km to the next stop
Evening
U-505 Submarine
Board a real German U-boat captured in WWII—the only one on display in the Western Hemisphere.
Where to eat: McDonald's — Burgers — a well-loved local spot.
Make it your own
Set your own dates and pace, swap any stop, and let the AI build a plan around your real flights and hotels.
Customize it →Built from Chicago's top-rated attractions. Opening hours, prices, and whether a spot still delivers can change — double-check anything time-sensitive before you go.