1.The Press Room
West Loop
This candlelit cellar bar sits inside a 1900s former publishing house in West Loop, all exposed brick and warm light. Swing by for happy hour Tuesday through Thursday, 4-6pm.
Happy hour Tue-Thu, 4-6pmVisit site →
Chicago Wine Bar Date Spots
Chicago has no shortage of wine bars, but not every one is still open, still good, or actually date-worthy. These five, from a converted 1900s publishing house in West Loop to a Logan Square staple pouring since 1994, are verified by a real person so you're not showing up to a closed door or a place that changed its whole vibe. Grab a glass, split a flight, and let the night slow down a little.
✓ Verified July 2026
2.Volo
Roscoe Village
Work through a wine flight on the city's best hidden garden patio, tucked away in Roscoe Village. Open Tuesday through Saturday, 4-11pm, with a $1 oyster and $6 wine happy hour from 4-6pm
Tue-Sat, 4-11pmVisit site →
3.Bar Sotto
The Loop
The Loop spot pours a free Italian wine tasting every Wednesday from 5-7pm, with a new bottle featured each week, so there's always something new to try together.
Wednesdays, 5-7pmVisit site →
4.Rootstock
Humboldt Park
A dark, tiny neighborhood bar in Humboldt Park with an extremely extensive wine selection, making it an easy, low-key pick any night Monday through Saturday from 5pm.
Mon-Sat from 5pmVisit site →
5.Webster's Wine Bar
Logan Square
Chicago's first wine bar has been pouring by candlelight in Logan Square since 1994. It's open nightly from 5pm (Friday and Saturday from 4pm) for an easy, romantic glass. Has a rotating wine flight selection every Wednesday from $27.
Open nightly from 5pm (Fri-Sat 4pm)Visit site →
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