2-day itinerary
The Perfect 2 Days in Chicago
A balanced 2-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.
9 min walk · 0.7 km to the next stop
Afternoon
Wilson
Clothing shop offering apparel and fashion retail selections.
11 min drive · 2.3 km to the next stop
Evening
Haymarket Memorial
A powerful bronze sculpture honoring the 1886 labor martyrs who shaped workers' rights worldwide.
Where to eat: Alinea — Fine Dining — a well-loved local spot.
Culture & Icons
Morning
Begin Route 66
Stand at the legendary birthplace of Route 66, where America's most iconic road trip adventure begins.
9 min drive · 1.5 km to the next stop
Afternoon
Brachiosaurus Replica
Marvel at a life-sized Brachiosaurus replica towering over Chicago's lakefront parkland.
31 min drive · 8.9 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: Mon Ami Gabi — French — 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.