
2 hours
Chicago: Paint Night & Cocktails at Trendy Venues
Unleash your creativity with a fun paint and sip experience in Chicago. Enjoy a relaxed atmosphere with music, drinks, and plenty of laughs as you create your own masterpiece.
Au Cheval (late night) is a new american late-night spot in Chicago.
Editorially verified May 18, 2026 by Elliot Marsh, TableJourney editor. Source.

2 hours
Unleash your creativity with a fun paint and sip experience in Chicago. Enjoy a relaxed atmosphere with music, drinks, and plenty of laughs as you create your own masterpiece.

Guided tour · 3 hours
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 ...

Water activity · 2h 30m
An unforgettable celebration of holiday cheer and fine dining awaits on our Christmas Eve Dinner Cruise on Lake Michigan. Enjoy a 3-course plated dinner, an on board D...
Address: 800 W Randolph St, Chicago, IL 60607
The Wieners Circle in Chicago is the Lincoln Park late-night hot dog counter on Clark, with char dogs, cheese fries and staff-customer banter past 02:00.
TryChar dog with everything, cheese fries
TipChar dog with everything; the chocolate milkshake is the closing order for the walk back up Clark.
Ghareeb Nawaz in Chicago is the West Ridge Pakistani halal counter on Devon, with $7 chicken biryani open until 02:00, the only Devon plate at that hour.
Try$7 chicken biryani special
TipCash only. Bring a container; the biryani plate feeds two with leftovers for the morning.
The Aviary in Chicago is the Achatz-Kokonas modernist cocktail bar on Fulton Market with a 21:30 late seating, edible-ice cocktails and the Office speakeasy.
TryModernist cocktails
TipBook the 21:30 Wednesday or Thursday seating; the room is at half capacity, the cocktails come faster.
Ramen-san in Chicago is Lettuce Entertain You's River North ramen room on Hubbard, open Thursday to Saturday until 02:00, with tonkotsu and the spicy garlic.
TrySpicy garlic ramen
TipThe spicy garlic ramen at 01:30 is the call after a Loop show. The pork bun on the side is the wing.
Matchbox in Chicago is the four-foot-wide West Town cocktail bar on Milwaukee serving stiff classic cocktails until 02:00, a 30-seat triangle since 1995.
TryOld Fashioned, Gimlet
TipCash and glass only. Order an Old Fashioned; the slim bartender pour is the house standard you do not modify.