Old Town
A charming historic enclave of Victorian rowhouses, comedy, and tree-lined streets near the Gold Coast.
The call
Worth it if you are traveling as a couple and you are traveling solo.
Why
- 01
One of the prettiest, most strollable older neighborhoods — narrow Wells Street, preserved Victorian homes that survived the Great Fire, and Second City anchoring the nightlife.
Our read - 02
The honest catch is that it's small and residential; the pleasure is the architecture and a meal, not a list of attractions.
Our read
Is it a fit?
Go if
You are traveling as a couple
As a couple, Old Town is an easy yes.
You are traveling solo
Solo, Old Town is an easy yes.
You care about the visual experience
Old Town rewards a trip built around beauty & photography.
Think twice if
You are watching the budget
Old Town can strain a tight budget. Go only when it is a priority.
You only have one day
Keep Old Town only when it outranks a half-day elsewhere.
You are traveling with kids
With kids, Old Town needs the right timing and tolerance.
You prefer local life to spectacle
Old Town offers some local authenticity, but not enough to make it the reason to go.
The same streets, hour by hour
Quiet residential streets and cafes
Gentle strolling among Victorian homes
Dinner and the Second City comedy scene
Worth-it spots in the area
Plan it well
- Cost
- Free to explore
- Timing
- Late afternoon into evening, combined with dinner or a show.
- Allow
- 1.5–2.5 hours
- Accessibility
- Walkable sidewalks; some historic venues have steps.
- Getting there
- North of downtown near the Gold Coast; Brown/Purple Line Sedgwick stop.