Off the Clock
Chicago · Drinks after dinner

Drinks after dinner in Chicago.

Somewhere to carry on the conversation after dinner: good drinks, room to talk, and no nightclub noise.

Browse ChicagoNear the McCormick PlaceClient dinnersPrivate dining roomsWorking lunchesBreakfast meetingsDrinks after dinnerGroup activities

3 picks

Checked regularly. Confirm details with the venue when you book.
Drinks$$

VU Rooftop

133 E Cermak Rd (Hiltons at McCormick Place), South Loop · about 5 min walk from McCormick Place (estimate)

A big 22nd-floor bar next to McCormick Place, with lake and skyline views. An enclosed room keeps it open year-round, so it works for a drink after a show day in December.

DrinksViewsEasy walkBig groups
Fits
Largest room 85 standing; private events up to 100; buyout 550
Cost
$40–70 per person (est.)
Walk
About 5 min from the convention centre
Tip
Weeknights it opens at 4 PM and closes at 11 PM; call the private dining line, 312-256-2991, for a group area.
Reserve on OpenTable ↗
Website ↗Source ↗Map ↗Checked October 24, 2026
Drinks$$$

Vol. 39

39 S LaSalle St (Kimpton Gray), the Loop · about 15 min by cab from McCormick Place

A library-style cocktail lounge in the Kimpton Gray, with leather chairs and bookshelves. Calm enough to keep talking after a client dinner in the Loop.

DrinksQuietRelaxed
Fits
Semi-private area up to 20 standing; buyout up to 80
Cost
$70–120 per person (est.)
Tip
Closed Sundays; weeknights it runs 4 to 10 PM, so plan it as an early nightcap.
Reserve on OpenTable ↗
Website ↗Source ↗Map ↗Checked October 24, 2026
Drinks$$$

Cindy's Rooftop

12 S Michigan Ave (Chicago Athletic Association), the Loop · about 15 min by cab from McCormick Place

A glass-enclosed rooftop on the 13th floor of the Chicago Athletic Association, looking over Millennium Park and the lake. Fire pits warm the terrace in winter.

DrinksViewsBucket listPrivate room
Fits
Lakeview area 10 to 25 seated; The Library 10 to 55 seated; buyout up to 80
Cost
$70–120 per person (est.)
Tip
It gets busy, so book a table on OpenTable rather than walking in.
Reserve on OpenTable ↗
Website ↗Source ↗Map ↗Checked October 24, 2026

How far ahead to book

Our rule of thumb for groups. Individual venues vary, so confirm when you call.

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