Cocktail bar happy hours in Chicago

7 Chicago bars and restaurants list Cocktail bar deals this week, last checked Nov 3, 2026. Cheapest listed: Dearly Beloved from $2.

7 places with Cocktail bar deals in Chicago

Chicago tonight Mexican16 Italian18 Pizza24 Japanese11 Sushi6 Seafood16 American79 Burger18 BBQ6 Sports bar6 Wine bar18

Cara Cara Club

2545 N Kedzie Blvd, Chicago

from $5

Monday · 5:00 PM – 12:00 AM

mystery shot, bartender's choice: $5

Monday · 5:00 PM – 7:00 PM

all house classic cocktails: $10
any mix & match highball: $10

Tuesday · 5:00 PM – 12:00 AM

all house classic cocktails: $10
any mix & match highball: $10
mystery shot, bartender's choice: $5
All day happy hour

+8 more times this week

Dearly Beloved

900 N Franklin St, Chicago · $$$

from $2

Wednesday · 4:00 PM – 6:00 PM

50% off select shareables: beef carpaccio, tuna tartare, red curry sweet potatoes, warm crab dip
oysters, orders of 6 or 12: $2
wine by the glass: $8
martinis: pornstar, lemon drop: $10
summer spritz drinks: $10

The Welcome Back Lounge

2423 N Milwaukee Ave, Chicago

from $5

Monday · 5:00 PM – 7:00 PM

draft beer: $5
mixed drinks (house spirits): $6
beer & a shot: $10
burger & fries: $13
Dine-in only

Tuesday · 5:00 PM – 7:00 PM

draft beer: $5
mixed drinks (house spirits): $6
beer & a shot: $10
burger & fries: $13
Dine-in only

Wednesday · 5:00 PM – 7:00 PM

draft beer: $5
mixed drinks (house spirits): $6
beer & a shot: $10
burger & fries: $13
Dine-in only

+2 more times this week

Mary Jo McGuire's

2251 N Lincoln Ave, Chicago

from $2

Monday · 4:00 PM – 11:59 PM

50% off tequila & margaritas
25% off wraps & chicken tortilla soup

Tuesday · 4:00 PM – 11:59 PM

hot dogs: $2
50% off draft beer

Wednesday · 4:00 PM – 11:59 PM

50% off whiskey, bourbon, rye & scotch
pizzas w/ 50c toppings: $12

+3 more times this week

Rounders Pub House

644 W Diversey Pkwy, Chicago · $$

from $3

Monday · 3:00 PM – 6:00 PM

Old Style draft: $3
Kona draft: $5
cocktails, Caesar salad: $10
spritz & a shot, burger & fries: $12

Tuesday · 3:00 PM – 6:00 PM

Old Style draft: $3
Kona draft: $5
cocktails, Caesar salad: $10
spritz & a shot, burger & fries: $12

Wednesday · 3:00 PM – 6:00 PM

Old Style draft: $3
Kona draft: $5
cocktails, Caesar salad: $10
spritz & a shot, burger & fries: $12

+2 more times this week

The L Station

186 N Wells St, Chicago

from $7

Wednesday · 5:00 PM – 8:00 PM

lemon drops: $7
lamb chops: $7

Barcocina Lakeview

2901 N Sheffield Ave, Chicago · $$

Monday · 4:00 PM – 6:00 PM

1/2 off margaritas: house marg, skinny punch, summer marg, house fire, smoke house
1/2 off beers: Modelo, Tecate, Corona Extra, Dos Equis, Pacifico, Negra Modelo
1/2 off dips & snacks: salsa, Barco guac, elotes, yucca tots, brussels sprouts

Tuesday · 4:00 PM – 6:00 PM

1/2 off margaritas: house marg, skinny punch, summer marg, house fire, smoke house
1/2 off beers: Modelo, Tecate, Corona Extra, Dos Equis, Pacifico, Negra Modelo
1/2 off dips & snacks: salsa, Barco guac, elotes, yucca tots, brussels sprouts

Wednesday · 4:00 PM – 6:00 PM

1/2 off margaritas: house marg, skinny punch, summer marg, house fire, smoke house
1/2 off beers: Modelo, Tecate, Corona Extra, Dos Equis, Pacifico, Negra Modelo
1/2 off dips & snacks: salsa, Barco guac, elotes, yucca tots, brussels sprouts

+2 more times this week

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FAQ

Where can I find Cocktail bar deals in Chicago?

7 places this week. Top-rated: Cara Cara Club (Monday 5:00 PM – 12:00 AM), Dearly Beloved (Wednesday 4:00 PM – 6:00 PM), The Welcome Back Lounge (Monday 5:00 PM – 7:00 PM), Mary Jo McGuire's (Monday 4:00 PM – 11:59 PM), Rounders Pub House (Monday 3:00 PM – 6:00 PM).

What are the cheapest Cocktail bar deals in Chicago?

Dearly Beloved from $2, Mary Jo McGuire's from $2, Rounders Pub House from $3, Cara Cara Club from $5, The Welcome Back Lounge from $5.