Chicago Wine Bar Deals, $5 Glasses & Wine Happy Hours
50 wine bar deals at 17 restaurants across Chicago
Find the best wine bar food and drink deals across Chicago. Popular spots include City Winery, Cellar Door, Middle Brow. The cheapest drink deal is Limoncello Fizz shot for $2.00. Browse happy hours, daily specials, and more at wine bar restaurants near you.
Wine Bar Deals
Outside Voices
Happy Hour Wednesday-Friday until 6 PM with $8 Pavette 'Pinot Noir' and $8 Bernier 'Sauvignon Blanc'
Ed & Jean's Tavern
Happy Hour Daily until 6pm: Select cocktails and wines $10, Select beers and punch $5
Middle Brow
Happy Hour Wed-Fri 4-6pm and Sat-Sun 3-4pm with $5 beer, $6 wine, and a selection of bread, salad, and pizza, including half-price sausage and olive or mushroom Neapolitan pie.
Middle Brow
Happy Hour Wed-Fri 4-6pm and Sat-Sun 3-4pm, including $5 beer, $6 wine, and a selection of bread, salad, and pizza deals.
Outside Voices
Happy Hour Wednesday-Friday until 6 pm with $8 Pavette 'Pinot Noir', $8 Brisa Suave 'Vinho Verde Rose', and a rotating bottle special
Middle Brow
Happy Hour: Wednesday-Friday 4-6pm, Saturday-Sunday 3-4pm (includes half-price sausage and olive or mushroom Neapolitan pies, and select $5 wine)
The Oakville Grill & Cellar
Happy Hour: Mon-Fri 4-6pm in the bar area only, featuring $6 Wines by the Glass, $9 Martinis, $8 Spritzes, and featured snacks like Grilled Cheese, Crispy Chicken Sliders, and a Green Chili Cheeseburg
Ed & Jean's Tavern
Daily Happy Hour: $10 Select Handcrafted Cocktails + Wines, $5 Select Beers & Punch (until 6pm)
Printer's Row Wine Shop
Tuesday Night Vinyl Happy Hour (5-7pm): House red and white at $10 a glass, no corkage fee
Volo Restaurant Wine Bar
Happy Hour Specials until 6 PM nightly (Tue-Sat 4-6pm): $1 Oysters, $2 Limoncello "Fizz" Shots, $3 Off Volo Flatbreads, $4 Happy Hour Toasts, $5 Craft Beer, $6 Wines On Tap, $7 Happy Hour Spritz Menu,
Last checked 30d agoCity Winery
Happy Hour: Monday - Friday, 4 PM - 6 PM: 50% off all City Winery Made Wine, Fun-guy Flatbread - $10.50, Hot Honey Pizza - $11, Lox n' Flatbread - $12
Last checked 21d agoCity Winery
Happy Hour: Monday through Thursday from 4-7 PM and Fridays from 2-5 PM: half off select small plates, $10 glasses of Rosé and Sauvignon Blanc, and $10 featured cocktails
Last checked 21d agoCellar Door
Happy Hour (Tuesday-Saturday): 4 PM - 5 PM with $2 off any beer or seltzer and $3 off any cocktail (excluding flights)
Verified todayPrinter's Row Wine Shop
Tuesday Night Vinyl Happy Hour (5-7pm): House red and white at $10 a glass, no corkage fee, vinyls spinning all night
Verified todayCellar Door
Wednesday: $4 Stella Artois Drafts, $6 Organic Nortico Alvarinho, $6 Organic Chateau Sainte-Marie Bordeaux Red Blend, Team Trivia at 7pm
Cellar Door
Thursday: $2 off Draft Beer, $5 Flybird Wine Margarita & Paloma, $5 Organic Non-alcoholic Free Spirits Spicy Lime Margarita, $10 Glasses of Quilt Cabernet, Music Bingo at 7pm
Volo Restaurant Wine Bar
Legendary Happy Hour — Tue–Sat 4–6 PM
Volo's legendary happy hour, Tuesday through Saturday 4 PM–6 PM. $1 fresh oysters, $2 limoncello fizz shots, $3 off artisan flatbreads, $4 happy hour toasts, $5 select craft beers, $6 small-batch wines on tap, $7 happy hour spritz menu, $8 house-made flavorful sangrias.
The Grillroom Chophouse & Wine Bar
Happy Hour at the bar Monday-Friday, with items like a $12 Old Fashioned, oysters, meatballs, and Tuscan toast
Cellar Door
Wednesday: Team Trivia at 7pm, $2 off draft beer, $5 Flybird Wine Margarita & Paloma (normally $9), $5 Organic non-alcoholic Free Spirits Spicy Lime Margarita, $10 Glasses of Quilt Cabernet (normally
Verified todayCity Winery
Happy Hour
Half-price wines on tap, flatbreads, and dips with pita
The Grillroom Chophouse & Wine Bar
Happy Hour
Weekday happy hour with discounted drinks and appetizers including oysters, meatballs, tuscan toast, and filet skewers
Bar area only
SourceFlight 22 Wine Bar
Happy hour specials Mon-Fri: $2 off all glasses of wine, 10% off bottles
Printer's Row Wine Shop
Happy Hour (5-7 pm) with house red and white wine at $8 a glass and no corkage fee
Ed & Jean's Tavern
Daily Happy Hour: $10 Select Handcrafted Cocktails + Wines, $5 Select Beers & Punch
Checked 8d agoVolo Restaurant Wine Bar
Happy Hour Specials (until 6 PM nightly): $1 Oysters, $2 Limoncello "Fizz" Shots, $3 Off Volo Flatbreads, $4 Happy Hour Toasts, $5 Craft Beer, $6 Wines On Tap, $7 Happy Hour Spritz Menu, $8 House-made
Verified todayThe Oakville Grill & Cellar
2nd Annual Grand Sonoma Wine Tasting
Join us on Saturday, March 7, from 2:00–4:30 PM, in partnership with the Sonoma County Winegrowers Alliance. Sip wines from 40+ Sonoma County wineries, enjoy chef-curated bites, and take in sweeping city views from the 17th floor of 167 Green.
Specific event date: March 7th. Tickets required.
SourceThe Oakville Grill & Cellar
Happy Hour: Monday – Friday, 4:00 PM – 6:00 PM in the bar area only. Specials include select California wines, choice beer, signature cocktails (Aperol Spritz, Oakville Margarita), and snacks such as
The Oakville Grill & Cellar
Happy Hour: Monday – Friday, 4:00 PM – 6:00 PM in the bar area only, featuring select California wines, choice beer, signature cocktails (Aperol Spritz, Oakville Margarita), and snacks (Oakville Smash
City Winery
Happy Hour: Monday-Friday, 4-7 PM, with half-off City Winery wine and half-off cheesy pizzas
Middle Brow
Brunch: Every Saturday and Sunday from 9am (includes bagels and specials like Nova Lox)
City Winery
Happy Hour: Half-off tap wine, flatbreads, and a variety of dips served with pita, Monday through Friday from 4pm–7pm
City Winery
Weekend Brunch: Every Saturday and Sunday from 10 AM – 3 PM, with a DIY mimosa bar
Middle Brow
Happy Hour: Wednesday-Friday 4:00 PM - 6:00 PM, Saturday-Sunday 3:00 PM - 4:00 PM
City Winery
Happy Hour: Monday through Friday 4-7 pm: half-price on famous wines on tap, fabulous flatbreads, and a variety of dips served with pita
Last checked 21d agoCity Winery
Happy Hour & Summer Fridays: Mondays through Thursdays 4-6 PM for Happy Hour food and drink specials, or Summer Fridays from 2-5 PM
Last checked 21d agoDial Tone
Happy Hour
$10 cocktails, $6 beer, $10 wine. GF/Celiac: No hh apps
Grapes and Grains
Happy Hour
$11 cocktails. GF/Celiac: No hh apps
Liva at Chicago Winery
Happy Hour
$7 cocktails, $9 wine, $7-10 apps. GF/Celiac: Yes
Outside Voices Wine Bar
Happy Hour
$8 wine, $50 charcuterie board and wine bottle
Webster's Wine Bar
Happy Hour
$9 cocktails, $9 wine
Bronzeville Winery
Bronzeville Winery Happy Hour
Happy hour at the bar Wed and Thu 4-6pm
Cellar Door
Friday: $15 glasses of Baron Fuente 'Grande Reserve' Champagne Brut (normally $22)
Verified todayCellar Door
Saturday: $15 glasses of Baron Fuente 'Grande Reserve' Champagne Brut (normally $22)
Verified todayThe Grillroom Chophouse & Wine Bar
Happy hour offers drink specials from 4-6pm on weekdays
Volo Restaurant Wine Bar
Happy Hour Specials Until 6 PM Nightly (Wed-Sat, 4:00pm-6:00pm)
Lush Wine Bar
Happy Hour Monday to Thursday 3:30 PM to 6 PM
The Oakville Grill & Cellar
Weekend Brunch: Saturdays & Sundays, 9:00 AM – 3:00 PM.
City Winery
Brunch: Saturday-Sunday, 10 AM-3 PM, with a DIY mimosa bar
Lush Wine Bar
Happy Hour: Monday to Thursday 3:30 PM to 6 PM
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Frequently Asked Questions
- Where can I find wine bar food deals in Chicago?
- Chicago has 50 wine bar food deals at 17 restaurants. Top spots include City Winery, Cellar Door, Middle Brow.
- What are the best wine bar restaurant deals in Chicago?
- Outside Voices offers Happy Hour Wednesday-Friday until 6 PM with $8 Pavette 'Pinot Noir' and $8 Bernier 'Sauvignon Blanc'. Ed & Jean's Tavern offers Happy Hour Daily until 6pm: Select cocktails and wines $10, Select beers and punch $5. Middle Brow offers Happy Hour Wed-Fri 4-6pm and Sat-Sun 3-4pm with $5 beer, $6 wine, and a selection of bread, salad, and pizza, including half-price sausage and olive or mushroom Neapolitan pie..
- What's the cheapest wine bar deal in Chicago?
- The cheapest deal is Limoncello Fizz shot for $2.00. Browse all 50 wine bar deals for more.