Chicago Fine Art Fairs, Art Galleries, and Craft Shows

Welcome to the Chicago Art Fair Calendar, offering info on the top juried art fairs, craft shows, art galleries, art exhibits, exhibitions, art festivals, and plein air painting competitions in Chicago and Chicagoland for all seasons in Naperville, Oak Park, Wilmette, Evanston, Riverside, Skokie, Oak Brook, Batavia, Geneva, Northbrook, LaGrange, and more!

Please double-check show dates and times before you go! Don't forget your sun protection, comfy shoes, and a tote bag to carry your purchases.

Paintings by Leslie Emery of Madison, WI

2025

December

December 4-7, 2025
Chicago, Illinois

24th Annual One of a Kind Holiday Show
Held at the Merchandise Mart on the 7th floor
Thursday - Saturday, 10am-7pm; Sunday, 10am-5pm
600+ artists

For more info: www.oneofakindshowchicago.com/holiday/

2026

June

June 13 & 14, 2026
Winnetka, Illinois

North Shore Art League's 14th Annual Art in the Village
Held at Hubbard Woods Park, 939 Green Bay Road in Winnetka
Saturday & Sunday, 10am-5pm
70 artists

For more info: www.northshoreartleague.org

June 27 - 28, 2026
Naperville, Illinois

66th Naperville Woman's Club Fine Art & Artisan Fair
Held at 523 W. Webster in Naperville
Saturday & Sunday, 10am-5pm
110+ artists

For more info: www.nwcfineartfair.org