Chicago Wine Bar Deals — $5 Glasses & Wine Happy Hours

50 wine bar deals at 15 restaurants across Chicago

Find the best wine bar food and drink deals across Chicago. Popular spots include Middle Brow, Ed & Jean's Tavern, Volo Restaurant Wine Bar. The cheapest drink deal is Limoncello Fizz shot for $2.00. Browse happy hours, daily specials, and more at wine bar restaurants near you.

15 restaurants

50 deals

Volo Restaurant Wine Bar

Legendary Happy Hour — Tue–Sat 4–6 PM

Last checked 22d ago

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.

Fresh oysters $1Artisan flatbreadsHappy hour toasts $4

Limoncello Fizz shot $2Select craft beers $5Small-batch wines on tap $6Happy hour spritz $7

Roscoe VillageTue-Sat 4PM-6PM4.6

City Winery

Happy Hour

Half-price wines on tap, flatbreads, and dips with pita

FlatbreadsVariety of dips served with pita

Famous wines on tap

West LoopMon-Fri 4PM-7PM4.2

Source Reserve on Resy

The Grillroom Chophouse & Wine Bar

Happy Hour

Weekday happy hour with discounted drinks and appetizers including oysters, meatballs, tuscan toast, and filet skewers

1/2 Dozen East Coast Oysters $12Meatballs $12Tuscan Toast $12Filet Skewers $16

Select Featured Wines $10House Margarita $10Tropical Storm $12Barrel-Aged Old Fashioned $12

The LoopMon-Fri 3PM-6PM4.5

Bar area only

The 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.

The LoopSat 2PM-4:30PM4.8

Specific event date: March 7th. Tickets required.

Dial Tone

Happy Hour

$10 cocktails, $6 beer, $10 wine. GF/Celiac: No hh apps

$10 cocktails $10$6 beer $6$10 wine $10

Old TownMon-Thu 4PM-6PM

Grapes and Grains

Happy Hour

$11 cocktails. GF/Celiac: No hh apps

$11 cocktails $11

West LoopWed-Fri 6PM-8PM

Liva at Chicago Winery

Happy Hour

$7 cocktails, $9 wine, $7-10 apps. GF/Celiac: Yes

$7 cocktails $7$9 wine $9

River NorthThu, Fri 5PM-6:30PM

Outside Voices Wine Bar

Happy Hour

$8 wine, $50 charcuterie board and wine bottle

$8 wine $8$50 charcuterie board and wine bottle $50

Logan SquareWed-Fri 5PM-6PM

Printer's Row Wine Shop

Happy Hour

$8 wine

South LoopTue 5PM-7PM4.6

Webster's Wine Bar

Happy Hour

$9 cocktails, $9 wine

$9 cocktails $9$9 wine $9

Logan SquareMon-Thu 5PM-6PM

Bronzeville Winery

Bronzeville Winery Happy Hour

Happy hour at the bar Wed and Thu 4-6pm

BronzevilleWed, Thu 4PM-6PM

The Oakville Grill & Cellar

Happy Hour

Select wines, beer, spritzes, martinis, margaritas, and exclusive snacks like Tempura Veggie Fries and Double Smash Burger, from $6-$10. Bar only.

Tempura Veggie Fries $6Double Smash Burger $10

Select wines/beer/cocktails $6

The LoopMon-Fri 4PM-6PM4.8

Bar only

LoyaltyActive Now

Middle Brow

Brėd Club - Limited Specialty Breads

Newsletter subscribers and consistent customers get first dibs on specialty, limited breads through the brėd club

Specialty limited breads - early access

Logan SquareEvery day4.4

Must be newsletter subscriber or consistent customer

Source Reserve on Resy

Daily SpecialActive Now

Middle Brow

Fresh Bagels with Coffee

Fresh bagels available Saturday morning with coffee shots

Logan SquareSat4.4

Source Reserve on Resy

City Winery

Chef & Winemaker Dinner Series

Monthly 4-course prix fixe experience featuring spring flavors paired with City Winery wines

4-course prix fixe dinner (Cream of Mushroom with Grilled Maitake, Roasted Carrots with Labneh/Gochujang Maple/Watercress, Beef Bourguignon with Red Wine, Strawberry Shortcake Trifle)

City Winery wine pairings

Reservations required

Source Reserve on Resy

The Grillroom Chophouse & Wine Bar

Happy Hour Menu

Happy hour menu available, with themed cocktails including the Hamiltini

The Grillroom Chophouse & Wine Bar

Tax Day Lunch Special

Tax Day special featuring choice of Chicory Salad or Tomato Bisque, choice of Prime Rib, Crispy Chicken, or Blackened Mahi Sandwich, and choice of Mini Crème Brûlée or Tiramisu

3-course lunch special (choice of salad/soup, sandwich, dessert) $22

Available April 15th only

Limited TimeActive Now

City Winery

Mother's Day Wine 3-Pack Gift

Special curated 3-pack of City Winery favorites for Mother's Day, featuring rosé and other wines

Curated 3-pack of City Winery favorites (includes rosé)

West LoopEvery day4.2

Source Reserve on Resy

Middle Brow

Pizza Stretching Class

Learn how to stretch pizza with guided wine tasting and pizza for $60

Pizza stretching class with pizza $60

Guided wine tasting

Logan Square4.4

Source Reserve on Resy

Middle Brow

Pizza Play - Make Your Own Pizza

Make-your-own pizza for kids/teens at the pizza counter

Make-your-own pizza

Logan SquareTue-Thu 4PM-6PM4.4

At pizza counter

Source Reserve on Resy

Event DrivenActive Now

Middle Brow

Beachwater Bagels Pop-up

Hot and fresh bagels pop-up every weekend morning until sold out

Logan SquareSat-Sun4.4

Until sold out

Source Reserve on Resy

Middle Brow

Dirt Cheap Wine Tasting

Wine tasting event with 6 heavy sample pours for $10, featuring slashed prices on bottles and food

Cheap food (unspecified)

Wine tasting - 6 heavy sample pours $10Cheap bottles to go

Logan SquareMon4.4

Special guests Communion Wines, link in bio for signup

Source Reserve on Resy

Middle Brow

Ramp Pizza Limited Return

Limited return of ramp pizza, available tonight only

Logan SquareSun4.4

Very limited availability

Source Reserve on Resy

Middle Brow

Bagels with Ramp Pimiento Cheese

Bagels served with ramp pimiento cheese

Bagels with ramp pimiento cheese

Logan SquareMon4.4

Source Reserve on Resy

Middle Brow

Cinnamon-Raisin White Bread

Limited remaining loaves of specialty cinnamon-raisin white bread, first come first served

Cinnamon-raisin white bread by Cakes Not Steaks

Logan SquareSun4.4

1-2 loaves remaining, first come first served

Source Reserve on Resy

City Winery

Cinco de Mayo Specials

Cinco de Mayo specials mentioned but no specific details provided

West LoopFri4.2

Source Reserve on Resy

ko-ze wine room

Mother's Day Floral Arrangement Workshop

Floral arrangement workshop with bubbly included, creating arrangements in mimosa-inspired spring tones

Glass of bubbly (included with workshop)

LombardSun 11AM-1PM4.8

Tickets required, Mother's Day only

Anfora Wine Merchants

La Colombera Timorasso Wine Tasting with Elisa Semino

Intimate wine tasting experience with Elisa Semino of La Colombera, featuring rare Timorasso wines from Piedmont. Tickets available via link in bio.

Elmwood Park4.6

Limited space, tickets required

Anfora Wine Merchants

April Showers Bring May Flowers Wine Tasting

Wine tasting featuring fragrant whites and elegantly perfumed reds with hints of jasmine, rose, violet. $5 tasting fee applies towards any bottle purchase from the lineup.

Wine tasting (fragrant whites and perfumed reds) $5

Elmwood Park4.6

Tasting fee applies towards bottle purchase from lineup, or until poured out

Limited TimeActive Now

Anfora Wine Merchants

Love your Mother Earth Month Wine Tasting

Earth Month wine tasting special - $5 to taste which applies towards any bottle you take home from the line-up. Bottles open until 5pm or until poured out.

Wine tasting (applies to bottle purchase) $5

Elmwood ParkEvery day4.6

$5 tasting fee applies towards any bottle purchase from the tasting line-up

Middle Brow

NEW WINE Party

Last checked 27d ago

Quarterly new wine party featuring 6 brand new wines that have never been shared with the public, with special guest wines by Communion Wines

6-8 wine pours (new wines) $10

Logan SquareThu 5PM-9PM4.4

May 21st only, features guest wines by Communion Wines

Source Reserve on Resy

Middle Brow

RUBGRØD Rye Bread Pre-order

Last checked 27d ago

Limited release of 50 RUBGRØD rye bread loaves, available for pre-order and walk-up on Thursday

RUBGRØD rye bread

Logan SquareThu4.4

Limited to 50 loaves, pre-order recommended as walk-up likely to sell out

Source Reserve on Resy

Printer's Row Wine Shop

Tuesday Vinyl Happy Hour

Last checked 23d ago

Weekly vinyl listening happy hour featuring music selections from staff including French synth pop, Japanese city pop, and African funk

South LoopTue 5PM-7PM4.6

Printer's Row Wine Shop

Candlelight Series - Zusslin Alsace Wines

Last checked 23d ago

Candlelight wine tasting event featuring Zusslin wines from Alsace with special by the glass menu and flight options

Zusslin Alsace wines by the glassZusslin Alsace wine flight

South LoopWed 6PM-8PM4.6

Volo Restaurant Wine Bar

Happy Hour

Last checked 22d ago

Happy hour featuring oysters, spritzes, wines on tap, and sangrias Tuesday through Saturday from 4-6 PM

SpritzesWines on tapSangrias

Roscoe VillageTue-Sat 4PM-6PM4.6

Volo Restaurant Wine Bar

Cabana Happy Hour

Last checked 17d ago

Daily happy hour featuring $1 oysters, $2 limoncello fizz shots, $3 off seasonal flatbreads, $4 happy hour toasts, $5 craft beers, $6 wine on tap, $7 spritz menu, $8 house-made sangria and more

Oysters $1Seasonal FlatbreadsHappy Hour Toasts $4

Limoncello Fizz Shots $2Craft Beers $5Wine On Tap $6Spritz Menu $7

Roscoe VillageEvery day 4PM-6PM4.6

Volo Restaurant Wine Bar

Soave Night Wine Event with Winemaker

Last checked 21d ago

Meet winemaker Enrico Marcato with complimentary welcome pours of 2024 iPrandi Soave DOC and special pricing on iPrandi Soave by glass and bottle all evening

Complimentary 2024 iPrandi Soave DOC welcome taste $0iPrandi Soave by the glass - special pricingiPrandi Soave bottles - special pricing

Roscoe VillageWed 6PM-11PM4.6

No cover charge, reservations strongly encouraged, 2-hour table limit prior to 7:30pm, available exclusively via Tock

Volo Restaurant Wine Bar

Soave Night Wine Event

Last checked 17d ago

Meet the winemaker Enrico Marcato with complimentary welcome pours and special pricing on iPrandi Soave by the glass and bottle all evening long

Complimentary welcome taste of 2024 iPrandi Soave $0

iPrandi Soave by the glassiPrandi Soave by the bottle

Roscoe VillageWed4.6

2-hour table limit prior to 7:30pm, reservations strongly encouraged

Limited TimeActive Now

Ed & Jean's Tavern

SOIF Natural Wine Collaboration

Checked 14d ago

Wine collaboration with middle brow and 3rd Coast SOIF Natural Wine Week Chicago 2025

Natural wine collaboration selections

Humboldt ParkEvery day4.8

Ed & Jean's Tavern

Star Union Distillery Rum Tasting

Checked 14d ago

Local pot still rum tasting event with Bob Windy featuring 5 rum tastings for $10

Star Union Distillery Local Pot Still Rum Tasting (5 tastes) $10

Humboldt Park4.8

Ed & Jean's Tavern

Easter Special

Checked 14d ago

Easter Sunday special featuring ham and cheese sandwiches and Easter spritzes available all day until 9pm

Ham and cheese sandwiches

Easter spritzes

Humboldt ParkSun 12AM-9PM4.8

Ed & Jean's Tavern

Martini Mondays

Checked 13d ago

Monday martini specials featuring hand crafted martinis for $10 and smaller mini martinis for $5

Hand Crafted Martinis $10Mini Martinis $5

Humboldt ParkMon4.8

Ed & Jean's Tavern

Tasting Tuesdays

Checked 13d ago

Tuesday tasting special offering 5 tastes for $10

Weekly special tastings (5 tastes) $10

Humboldt ParkTue4.8

Ask your server for details

Ed & Jean's Tavern

Wine Wednesdays

Checked 13d ago

Wednesday wine special featuring half price wine by the bottle

Wine by the bottle (half price)

Humboldt ParkWed4.8

Ask your server for details

Middle Brow

NANCY at Middle Brow - Bagels and Pastry Brunch

Verified 6d ago

Special collaborative brunch event with Nancy Silverton on Sunday, June 14th featuring bagels and pastries, presented by Resy

Bagels and pastry brunch

Logan SquareSun4.4

$10 reservation deposit required, must book through Resy

Source Reserve on Resy

Middle Brow

Record Release Event - Matt Gold & Dustin Laurenzi

Verified 6d ago

Free live music event featuring Matt Gold and Dustin Laurenzi with two sets, plus DJ set by Quin Kirchner. Special 'Devotional Fade' pizza available.

Devotional Fade pizza

Logan SquareSun4.4

Source Reserve on Resy

Middle Brow

Pizza Night

Verified 6d ago

Pizza night special

Logan SquareThu4.4

Source Reserve on Resy

Middle Brow

Happy Hour

Happy hour Wednesday through Friday 4-6pm

Logan SquareWed-Fri 4PM-6PM4.4

Source Reserve on Resy

Bronzeville Winery

Happy Hour

Wed & Thu 4-6pm at the bar. $10 bites, $10 cocktails, $10 wine. Bar snacks change regularly. Live music on plant-filled sidewalk patio.

$7 wine $7$7 cocktails $7

BronzevilleWed, Thu 4PM-6PM

Middle Brow

Happy hour from 4-6 p.m. with half-price sausage and olive or mushroom Neapolitan pie

Discovered via freshness check for Middle Brow

Logan Square4.4

Reserve on Resy

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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 15 restaurants. Top spots include Middle Brow, Ed & Jean's Tavern, Volo Restaurant Wine Bar.
What are the best wine bar restaurant deals in Chicago?: Volo Restaurant Wine Bar offers Legendary Happy Hour — Tue–Sat 4–6 PM. City Winery offers Happy Hour. The Grillroom Chophouse & Wine Bar offers Happy Hour.
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.