Le Midi Wine
West Town • $$
A laid-back neighborhood wine bar with a beautifully curated selection and snacky small plates to amuse your bouche. Grab a glass, book a tasting, or take a bottle to go.
Wine Bars in Chicago worth going out for.
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TAAN
West Town • $$$
Thai flavors meet wine-bar polish at this Humboldt Park date-night favorite. Order the Whole Deep Fried Sea Bass with Fish Sauce Caramel, then let the friendly staff guide the rest.
Good Funk on the River
Chicago Loop • $$
Wine without the stuffiness: Goodfunk pours natural bottles and offbeat flights to a funk soundtrack, with hand-carved charcuterie and a riverfront patio attached to Beatnik.
The Glunz Tavern
Near North Side • $$
Step back to 1888 at this Old Town tavern attached to one of Chicago's oldest wine merchants. Expect European fare, rare wines, and a cozy old-world vibe perfect for gathering with friends.
Gilda
West Town • $$$$
Gilda channels San Sebastián energy with Basque pintxos and a curated wine list. Expect a compact, shareable menu built for grazing, sipping, and lingering over hard-to-find bottles.
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13 activities · Page 1 / 1
All activities
Sat, Dec 26 · 5:00 PM
Chicago Wine Fest at Hubbard Inn – Tastings Included
Hubbard Inn · River North
$31.26
Sat, Nov 7 · 2:00 PM
Spilt Milk
Logan Square
$
Bronzeville Winery
Bronzeville
$$
Mama Delia
West Town
$$$
Easy Bar
West Town
$
City Winery Chicago
Fulton Market District
Hopsmith
Rush & Division
$$
sip. Wine Bar & Restaurant
Tinley Park
$$
Wine in other cities
Frequently asked questions
Where do I start with Chicago’s live-performance scene?
Check what’s playing at Steppenwolf Theatre Company for theatre, or Sleeping Village for live music. Read about the actual production or listen to the artist before choosing. You don’t need to recognise a name for it to be your kind of evening.
How do I turn a Chicago event into a whole evening?
Choose the show first, then make plans nearby. Leave enough room between dinner and curtain time to enjoy both. Tell me where you’re staying and whether you’re taking transit, and I can help narrow the search to an evening that fits together.
How can Outgoing help me find something I’ll actually want to do?
Tell me when you’re free, where you’ll be, and what sounds appealing. “Live music near me, somewhere I can sit, under $30” gives me more to work with than “something fun.” You can keep narrowing it down with me.
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Is Outgoing free?
Outgoing is free to use. Events have their own admission prices, including some that are free. Check the listing for prices and booking details before making plans.