These 113 activities are worth leaving the house for.
Ask me what you're after.
October 24 at 1pm (Next weekend)
The Gman Tavern · Lake View East • Free
Dig through crates with Jam's resident DJs at this beloved Wrigleyville dive. Four staff spinners plus a special guest set mean four hours of vinyl-only discoveries in a room that actually feels like Chicago.
October 25 at 7pm (Next weekend)
Beat Kitchen · North Center • $$
Beat Kitchen nails the old-school rock club vibe without the grime. Expect cold drinks, better-than-expected food, and sightlines so good there's genuinely no bad spot.
Near South Side
Chef Emani Roberts turns brunch into an all-day affair at this South Loop hotspot. Come for the catfish and grits or chicken and waffles, stay for the full bar and seriously good gumbo.
Christmas Club Pop-Up Bar · Lake View East • $$
Wrigleyville's original holiday pop-up bar transforms into a seasonal wonderland. Expect a festive atmosphere with no cover charge and no reservations required for walk-ins.
River North • $$
Step through a hidden door at House of Blues and find yourself in a gilded lounge that feels like a rock star's private club. Complimentary champagne, ornate decor, and live entertainment make every night feel like an occasion.
Goose Island • $$
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.
113 activities · Page 1 / 2
Sun, Oct 18 · 12:00 PM
ROOF on theWit · Chicago Loop
Sun, Oct 18 · 11:00 AM
Tin Roof · Lake View East
$$
Mon, Oct 19 · 3:30 PM
Lil' Ba-Ba-Reeba! · River North
$$
Mon, Oct 19 · 8:00 PM
Chicago Magic Lounge · Ravenswood
Free
Tue, Oct 20 · 8:00 PM
The Green Mill · Uptown
$$
Fri, Oct 23 · 1:00 AM
The Green Mill · Uptown
$$
Thu, Nov 5 · 5:00 PM
The Green Mill · Uptown
$$
Fri, Nov 6 · 8:00 PM
Cobra Lounge · West Loop
$26-$33
Sun, Nov 29 · 7:00 PM
Beauty Bar Chicago · West Town
Free
Fri, Jan 8 · 3:00 PM
Fitzgerald's Sidebar · Berwyn
Free
Fri, May 7 · 3:00 PM
Fitzgerald's Sidebar · Berwyn
Free
Fri, Jun 4 · 3:00 PM
FitzGerald's · Berwyn
Free
Uptown Lounge & Coffee Shop · Uptown
$
The Green Mill · Uptown
$$
Lake View East
$$
West Town
$
Streeterville
$$
Revolution Brewing - Brewery & Taproom · Avondale
Near South Side
$$$
Forest Park
North Center
$$
Lake View East
Chicago Loop
$$$
Hoffman Estates
$$
West Town
$
Lake View East
$$
Riverside
West Town
$$$
Logan Square
$$$$
Irving Park
$
River North
$$
West Town
$$
Brookfield
$$
Bucktown
$$
Lincoln Park
Berwyn
Rush & Division
West Town
Lincoln Park
$$
Chicago Loop
$$
Sheffield & DePaul
Berwyn
$
Lake View East
West Town
$$
Schaumburg
River North
$$
Berwyn
$
Forest Park
$$
West Town
$$
Uptown
$$
West Loop
Chicago Loop
$$
Edison Park
$$
Logan Square
$$
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.