Get your deals on with this comprehensive list of 9 summer sidewalk sales on Chicago’s North Shore! This list is compiled in chronological order and was updated on June 19, 2026. Hours are 10am – 5pm unless otherwise noted.
Glencoe Sidewalk Sale
June 19–20
Annual sidewalk sale featuring discounts from Glencoe shops and businesses.
Sidewalk Sale Shop Northfield
July 10–11
Northfield shops offer sidewalk deals and summer markdowns.
The Wilmette Sidewalk Sale
July 10–11
Wilmette and Kenilworth merchants offer sidewalk specials and seasonal deals.
Lake Bluff / Lake Forest Summer Sale Celebration
July 16–18
Multi-day summer sale event spanning Lake Bluff and Lake Forest businesses.
Sidewalk Sale Shop Winnetka
July 17–18
Winnetka’s shopping district hosts its annual summer sidewalk sale.
Central Street Evanston Annual Sidewalk Sale
July 23–25
Central Street’s shops and boutiques host their yearly sidewalk sale.
Highland Park Chamber of Commerce Sidewalk Sale
July 24–25
Storewide discounts and sidewalk shopping throughout downtown Highland Park.
Sidewalk Sale & Chalk Art Contest @ Downtown Evanston
July 24–26, 9:00 am–3:00 pm
Downtown Evanston combines sidewalk shopping with a family-friendly chalk art contest.
Main Dempster – Summer Sidewalk Sale
July 24–26
Summer sidewalk sale along the Main-Dempster Mile shopping corridor.
