Living in Old Town
Old Town is the historic triangle between the Gold Coast and Lincoln Park: crooked pre-fire streets, Second City comedy, Wells Street's restaurant row, and some of the most charming single-family blocks in the city. It trades at a premium for its location - walkable to downtown, the lake, and Lincoln Park at once.
The feel
Village-like in the landmark triangle - brick cottages and coach houses on Crilly Court and Menomonee - and lively on Wells Street, with Second City, the Spice House, and a deep restaurant bench. The Old Town Art Fair each June is the neighborhood's signature weekend.
Homes & what they cost
A small, supply-constrained market: condos $300Ks-$800Ks, townhomes and rowhouses $700K-$1.5M, and landmark-district single-family homes $1.5M-$3M+. New luxury towers on the eastern edge added full-amenity options near Division.
Who it suits
Buyers who want historic charm within walking distance of downtown, professionals splitting the difference between Gold Coast polish and Lincoln Park green, and long-hold owners - inventory here turns over slowly for a reason.
Getting around
Brown/Purple lines at Sedgwick, Red at Clark/Division, LSD at North Avenue, and a flat 20-minute walk to River North offices. North Avenue Beach is ten minutes on foot.
Old Town questions, answered straight
Is Old Town a good place to live?
Yes - it is one of the most walkable, historic, and centrally placed neighborhoods in Chicago, minutes from both downtown and Lincoln Park. Its small size keeps supply tight, so well-priced listings move fast and values hold.
How much does a home cost in Old Town?
As of mid-2026, condos generally run $300K-$800K, townhomes $700K-$1.5M, and landmark-triangle single-family homes $1.5M-$3M+. The historic district's constrained supply keeps per-square-foot pricing among the highest on the Near North Side.
What is Old Town known for?
Second City - the comedy theater that launched half of SNL - plus the pre-Chicago-fire streetscape of the landmark triangle, Wells Street's restaurants, and the Old Town Art Fair. It is one of the few neighborhoods where 1870s cottages sit ten minutes from the Magnificent Mile.