Below is a list of regularly scheduled tastings at Chicago area wine bars and shops. Many are free or low-cost, but it is always a good idea to contact the shop/wine bar ahead of time to be sure.
Tip: Many wine shops switch up tasting schedules and add tastings as opportunity permits. The best way to stay abreast of these changes is to follow the shop on social media and subscribe to their online newsletter, if they have one.
(If following a shop on Instagram, be sure to check out their stories, which is where upcoming events are often featured.)
This list is hardly comprehensive, though I hope it will eventually become so. Please let me know if you’d like to recommend a spot or need to correct any information.
57th Street Wines holds tastings on Thursdays from 5-7 pm and Saturday afternoons (times vary). Tastings are usually themed, and occasionally the schedule switches up a bit, so check out their website and call ahead to avoid disappointment. (Hyde Park)
Augusta Food & Wine offers free tastings on Thursdays between 6-8 pm. No sign-up is required. (Lincoln Square)
BottlesUp! First Friday tastings take place the first Friday of every month and include free wine tastings plus new, in-store art. (Lakeview)
Door 24 holds regular tastings every Friday from 5:30 - 7:30 pm. These are free, and no sign-up is required. Get on their social media pages for updates on their Friday night lineup! (Bucktown)
Ella Elli holds a monthly “20 for 20” tasting (20 wines for sampling, tickets are $20). Their kitchen is open during the tasting for snacks. Reservations are required and space is limited. (Southport)
Galleria Liquors holds free wine tastings at both its locations on Fridays from 5:30 pm - 8:30 pm and Saturdays from 3 - 6 pm. (Southport & Old Town)
In Fine Spirits holds regular free wine tastings on Wednesdays from 5-7 pm and Saturdays from 3-6 pm with an occasional Thursday tasting (which will be announced on their social media and in their newsletter). (Andersonville)
Konbini & Kanpai holds regular wine tastings (often on Wednesdays and usually free), plus additional tastings of beer, sake, and spirits throughout the month. I strongly recommend checking out their online calendar and getting on their mailing list so that you can stay informed. (Lakeview)
Independent Spirits is holding wine tastings from 5-7 pm on Fridays. Tastings are free, and information about the tastings appears on social media. Tastings are free and there is no charge. (Edgewater)
Perman Wine Selections offers an informal Saturday tasting: Visit the shop, ask what is open, and Craig Perman pours you a taste. The store is open from 11 am to 7 pm. (Near North)
Picnic Wine & Provisions holds wine tastings from 5-8 pm on Thursdays. The cost is $5 (free for wine club members) reservations are appreciated but not required. (Rogers Park)
Red & White Wines continues to offer tastings each Saturday from 2-5 pm. The cost is $10 and their wine club members get to participate at no added cost. The Red & White Wines newsletter usually releases information about the tastings the day before. I recommend getting on the mailing list so that you’ll know what to expect. (Bucktown)
Taste Food & Wine hosts $5 tastings on Tuesdays and Fridays from 5:30 - 7:30 pm. 10% off the featured tasting bottles if you take one home that evening. Snacks are available at an additional charge. (Rogers Park)
Table, Donkey and Stick holds its “Terrior Tuesdays” every, you guessed it, Tuesday, selling a wine or wines by a featured producer by the glass at wholesale cost. Events sometimes include wine producers as special guests. (Logan Square)
The Wine Goddess: $5 tastings every Saturday from 3-5 pm. Tastings feature four different wines. (Evanston)
Uvae Fromagerie & Tasting Room offers free hosted tastings from 6-8 pm on Tuesdays. Cork Dork Thursdays and Somm Pick Saturdays offer more extensive wine knowledge. Sign up and pay for your tickets online.
Uvae Fromagerie also offers pre-set wine flights of four one-ounce pours for $10 whenever the tasting room is open. (Andersonville)
Vin Chicago: Tastings on Saturdays from 12-4 pm at all three stores (Chicago, Barrington, and Highland Park). Free. No RSVP is necessary. Check out Vin’s Instagram for more details.
Winestyles: Weekly tastings on Thursdays from 6-8 pm. Tickets are $10 and can be reserved online.