Randolph Street Market Festival 2027: May 23-Sep 27

Stay for the festival

Hotels in Chicago around 23 May to 27 September 2027, dates pre-filled. Prices and availability open on the partner site.

Expedia hotels for these dates Holidu hotels in Chicago from USD 95/night LateRooms hotels in Chicago from 114/night

Editor's tip. Saturday is the bigger day; the antique-dealer tables fill the indoor armory and the food vendors line the outdoor side lot.

Plan the days around it

Eat your way around Chicago while you are in town

Randolph Street Market Festival runs 23 May to 27 September. These are the food tours and tastings in Chicago to book for the days around it; most cancel free up to 24 hours ahead.

Chicago: Downtown Pizza Guided Walking Tour with Tastings

★ 5.0 (11)

Guided tour · 3 hours

Chicago: Downtown Pizza Guided Walking Tour with Tastings

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 ...

from$73 Check dates

Chicago: West Loop Culinary Walk with Chef Tastings

★ 5.0 (5)

Guided tour · 3 hours

Chicago: West Loop Culinary Walk with Chef Tastings

Discover Chicago’s trendiest dining scene on a guided walk. Taste chef-driven dishes, sip craft brews, and explore West Loop’s hidden gems.

from$129 Check dates

Chicago: Westside Food Tasting Bike Tour with Guide

★ 4.8 (16)

Guided tour · 4 hours

Chicago: Westside Food Tasting Bike Tour with Guide

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...

from$99 Check dates

See all 248 bookable experiences in Chicago