Maxwell Street Market, Chicago's oldest market, runs on six select Sundays from May to October on Maxwell Street between Halsted and Union, free, with food, crafts and live entertainment.
Dates and details checked September 29, 2026 by Elliot Marsh against the organiser's site.
Hotels in Chicago around 4 October 2026, dates pre-filled. Prices and availability open on the partner site.
Maxwell Street Market runs 4 October. These are the food tours and tastings in Chicago to book for the days around it; most cancel free up to 24 hours ahead.
Guided tour · 3 hours
Taste the finest examples of Artisan, Neapolitan, Detroit Style, and Chicago deep-dish pizza on this professionally guided walking tour that takes you to highly-rated ...
Guided tour · 3 hours
Discover Chicago’s trendiest dining scene on a guided walk. Taste chef-driven dishes, sip craft brews, and explore West Loop’s hidden gems.
Guided tour · 4 hours
Taste your way around the world on this Chicago bike & food tour! Ride through historic West Side neighborhoods & Lakefront Trail while sampling incredible global cuis...
Address: Maxwell Street between S. Halsted St. and S. Union Ave., Chicago, IL 60607
23-26 Jul 2027
Fiesta del Sol
Mexican food festival, Pilsen
10-12 Sep 2027
Chicago German-American Oktoberfest
German food, beer, sausage
8-12 Jul 2027
Windy City Smokeout
Barbecue and country music
3-6 Sep 2027
Taste of Polonia
Polish
5-7 Jun 2027
Ribfest Chicago
Barbecue ribs
28-30 Aug 2027
Taste of Greektown
Greek
