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 works.
You are traveling solo
Solo, Old Town works.
You care about the visual experience
For beauty & photography, Old Town delivers.
Think twice if
You are watching the budget
On a budget, weigh it — Old Town isn't cheap for what it is.
You only have one day
Old Town is a real time commitment — fit it in only if it's a priority.
You are traveling with kids
With kids, it depends on the day.
You prefer local life to spectacle
For local authenticity, Old Town is hit or miss.
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.