These 136 activities are worth leaving the house for.
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October 27 at 8pm
The Green Mill · Uptown • $$
Step back into 1920s Chicago as the Cellar Boys revive hot jazz and swing inside the Green Mill, a Prohibition-era club dripping with old world charm. Six multi-instrumentalists trade cornet, clarinet, banjo, and tuba like it's 1929.
October 31 (This weekend)
After Chicago · Fulton Market District
Fulton Street's moody, candlelit cocktail den transforms into a Halloween haunt where bespoke drinks and a theatrical atmosphere make October 31 feel deliciously sinister.
Sheffield & DePaul • $$
This neighborhood brewpub pairs rotating craft beers with an unexpectedly ambitious menu of Creole and Mexican fusion dishes. The vibe is laid-back, but the selection is serious.
Bridgeport • $
A Bridgeport institution since 1938, Shinnick's pours drinks behind a bar built in the late 1880s. It's the kind of no-frills Irish pub where Sox fans gather and the owners treat you like family.
Kasey's Tavern · Chicago Loop • $
The dive bar you were looking for: 130+ beers, a Belgian focus, and zero pretension in a historic 1889 space. Expect dark wood, friendly bartenders, and an unhurried atmosphere that turns strangers into regulars.
Goose Island • $$
Motel Bar channels a mid-century supper club vibe that feels nostalgic yet fresh. Settle into the warm, retro dining room for craft cocktails and a full menu that leans upscale without losing its neighborhood haunt comfort.
Browse Chicago neighborhood by neighborhood, get ideas just for you, or ask me anything.
136 activities · Page 1 / 3
Wed, Oct 28 · 5:00 PM
Chicago Magic Lounge · Ravenswood
Free
Wed, Oct 28 · 7:00 PM
Hillgrove Tap · Tinley Park
$$
Sat, Nov 7 · 3:00 PM
The Green Mill · Uptown
$$
Fri, Nov 13 · 8:00 PM
Cuzin's Tavern, Gaming & Pizza Tinley Park · Tinley Park
$$
Fri, Nov 13 · 5:00 PM
The Green Mill · Uptown
$$
Wed, Dec 16 · 3:30 PM
Robert R. McCormick School of Engineering and Applied Science at Northwestern · Evanston
$75
Fri, Feb 5 · 3:00 PM
Fitzgerald's Sidebar · Berwyn
Free
Fri, Apr 2 · 3:00 PM
FitzGerald's · Berwyn
Free
Mary Jo McGuire's · Lincoln Park
$$
Mrs. Murphy & Sons Irish Bistro · North Center
$$
Uptown Lounge & Coffee Shop · Uptown
$
The Dandy Crown · West Town
$$
West Town
$
Chicago Loop
The Leavitt Street Inn & Tavern · Bucktown
Wrigleyville
$
Chicago Loop
$$
Broadview
$
North Center
$$
Logan Square
$
Lincoln Park
Chicago Loop
$$$
Logan Square
Bucktown
$$
Fulton Market District
$
Bucktown
$$
Lake View
West Town
$$
West Town
$$
West Town
$$$
Riverside
Avondale
$
Off Color Brewing Taproom The Mousetrap · Goose Island
Irving Park
$
North Center
$$
Roscoe Village
$
Lincoln Park
River North
Lincoln Park
$$
Lake View East
$$
Near South Side
$$$
Berwyn
$
West Town
$$
West Town
$
West Loop
$$$$
Sheffield & DePaul
$$
River North
Berwyn
$
Fulton Market District
Logan Square
$
Meeting House Tavern · Uptown
$
Uptown
$$
Hopewell Brewing Company · Logan Square
Tinley Park
$$
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.
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.
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.
You can browse these pages without an account. Sign in to save activities and help me learn your taste, so future suggestions have a better starting point.
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.