I, like you, am not made of money. And while I personally love going out to get a fancy cocktail – or, like, 4 fancy cocktails – from time to time, my wallet is not always quite so enthusiastic.
Given that drinking anywhere in Chicago is so often times so damn expensive, I’m guessing that you might feel the same way.
So, in a last-ditch effort to give your bank account and mine a much needed respite, here are the cheapest drinks I could find in the city.
No need to thank me, you’re already welcome.
Estelle’s
Photo Credit: Estelle’s Instagram
2013 W North Ave –1/2 off everything 5pm–7pm M-F, $5 Tito’s cocktails on Thursdays
Estelle’s is one helluva neighborhood bar – and it’s definitely got the drink specials to match. Their daily happy hour runs from 5pm–7pm, Mondays through Fridays, and offers half off EVERYTHING but food and shots, meaning your average cocktail is only gonna cost you about 5 bucks. As if that wasn’t enough, Estelle’s also offers $5 Tito’s mixed drinks on Thursday, $4 Ferent Branca shots on Monday (for when you’re feeling fancy) and a $7 High Life + Four Rose combo on Sundays. I mean, why would you ever spend more than $10 on a cocktail when this exists?
Big Star
Photo Credit: Big Star Instagram
1531 N Damen Ave – $8 Margaritas
Okay, so I get that an $8 drink might not seem cheap, but in a city where speciality cocktails regularly cost me upwards of $10, 8 bucks is a miracle. Plus, Big Star’s rockin tacos, amazing backyard-bbq vibe AND the options to switch your tequila for mezcal in any drinks makes this spot a cheap-drink keeper.
Antique Taco
Photo Credit: Antique Taco Instagram
1360 N Milwaukee Ave –$8 Margarita
Sorry not sorry about all the margarita love.
Not only does Antique Taco offer an $8 classic marg at each of its three locations, but they also do a mean rosemary and seasonal option for the same price. As an added benefit for all my cheap-o’s out there, margarita pitchers at Antique Taco are also just $30. Gimme please.
Kincade’s
Photo Credit: Kincade’s Facebook
950 W Armitage – so, so many specials
Okay, deep breath – Kincade’s offers: $3 Miller Lite and Coors Light drafts on Tuesdays, $1 domestic bottles on Wednesdays, $1o domestic PITCHERS on Thursdays, a $4 draft o’ the day on Fridays AND, last but not least, $6 Tito’s cocktails and Bloody Mary’s on Sundays.
Did you catch all that? ‘Cause this perpetually full sports bar is pretty much the cheap drink Mecca.
Bar Lupo
Photo Credit: Bar Lupo Instagram
217 W Huron – $4 beer and wine, $5 spritzes 3pm–6pm M–F
A self-described punk-rock Italian restaurant, Bar Lupo doesn’t necessarily look like it would have cheap drinks – but, oh boy, it does. On weekday afternoons from three to six, Bar Lupo partakes in what the Italians call Aperitivo – or, in English, a really good happy hour. While in Italy Aperitivo will usually get you some kind of free food with your pre-dinner drinks, Bar Lupo stick to libations only, offering $4 beers and wines and $5 spritzes.
Delilah’s
Photo Credit: Delilah’s Instagram
2771 N Lincoln Ave – again, so many specials
Delilah’s is Lincoln Park’s resident beer bar, and features nearly 200 different drafts and bottles for you to take for spin. In a concerted effort to get you to drink as much awesome beer as humanly possible, Delilah’s offers up cheap as hell daily specials such as: $1 beer and $2 Jim Beam on Mondays, $3 High Life bottles on Tuesdays, $3 PBR longnecks and $3 W.L. Weller Special Reserve on Wednesdays, $3 Point Ale pints on Thursdays, $3 Labatt Blue on Fridays, $3 Chang Thai Lager on Saturdays and $3 Genesee Cream Ale Pints on Sundays.
Why you would ever buy another beer for more than $3 again I don’t know.
Boleo
Photo Credit: Boleo Instagram
122 W Monroe St – $8 Botanas and Cocktails during happy hour
There is nothing I love more than getting a sweet deal at an expensive restaurant – and happy hour at Boleo is just that. This swanky rooftop bar is usually mixin up $12 cocktails, but starting at 5pm on Wednesday and Thursday nights that price is slashed nearly in half to accommodate cheap-drinkers like yours truly. Plus, Boleo’s happy hour goes until about 8pm, meaning I can have my deal with dinner this time around.
Beauty Bar
Photo Credit: Beauty Bar Facebook
1444 W Chicago Ave – rotating specials
Beauty Bar Chicago is the king of creative specials. From their Sunday Nickel & Dimed deal (which offers 50-cent beer with a free slice of pizza) or their Soundtrack of Your Life series (which boasts $1 Old Styles and, again, free pizza), Beauty Bar is pretty much guaranteed to have some kind of drink deal every night of the week. For more information and current deals, check their events calendar here.
The Owl
Photo Credit: The Owl Instagram
2521 N Milwaukee – 1/2 off cocktails and beers from 6pm – 8pm
The Owl is Logan Square’s original hipster haven. Serving up good drinks, excellent beer and uber chill vibes (if chill vibe can even be “uber”), The Owl’s daily Early Bird Special is a must for anyone trying to save a couple bucks. What’s more, this laid back watering hole also offers $5 Absolut wells on Sunday and $2 beers on Tuesday.
Joe’s on Weed
Photo Credit: Joe’s Instagram
940 W Weed – $9 domestic pitchers, $18 domestic buckets and $8 Bloody Mary’s on Sundays
A classic sports bar, live music venue and country hot spot all rolled into one, there should be no doubt in your mind that Joe’s is offering some sweet drink deals on the cheap. Though their specials rotate pretty regularly, the best deal we could find was the bar’s Sunday/Game Day special, which lists pitchers for under 10 bucks, buckets for under $20 and loaded Bloody Mary’s for the low, low price of just $8.
The Kerryman
Photo Credit: The Kerryman Facebook
661 N Clark – lots o’ daily drink deals
The Irish know how to drink. This is just common knowledge. So it really shouldn’t come as a shock when I tell you that The Kerryman – an Irish pub – has some of the best damn cheap drinks in town. Their specials include, but are not limited to: half price BOTTLES of wine and $5 glasses on Tuesdays, $4 Stella Artois, Blue Moon and Jameson all day Wednesday, $6 Grey Goose Moscow Mules on Wednesday during happy hour, $6 Ketel One cocktails all day Thursday, $5 prosecco during happy hour on Thursday, $4 Guinness and $6 Tito’s Martinis during Happy Hour on Friday AND $5 mimosas and Bloody Mary’s Saturday & Sunday. Whew.
The Whistler
Photo Credit: The Whistler Instagram
2421 N Milwaukee – cocktails usually start around $6
The Whistler is a relatively upscale stage/gallery/bar/restaurant in Wicker Park where they could easily be charging you 12 bucks a drink. And they totally do. That being said, being the kind, gentle souls that they are, The Whistler’s daily drinks menu usually includes at least one drink under the $8 mark, meaning that even the brokest of folk can swing by and enjoy this cool space.
The Barrelhouse Flat
Photo Credit: Barrelhouse Flat Instagram
2624 N Lincoln Ave – $8 happy hour
The Barrelhouse Flat is one of those fancy-pants, dark-lit cocktail bars that you’d usually only go to for a special occasion. But with a stellar happy hour on Sundays and Mondays between 6 and 8pm, you definitely don’t have to. Offering many of the same cocktails as on their regular menu, everything The Barrelhouse Flat happy hour is $8 and under, including the mac and cheese.
So go on, girl – get yourself that fancy old fashioned, you can totally afford it here.
Jack and Ginger’s
Photo Credit: Jack and Ginger’s Facebook
2048 Armitage Ave – daily drink deals, $5 Jack and Ginger’s DAILY!
Jack and Ginger’s is a neighborhood dive, through and through. Stop by any night of the week to cash in on some of their fantastic deals :
Monday: $4 shots, $10 domestic pitchers
Tuesday: $4 flavored vodka, $1 ALL DRAFTS
Wednesday: $3 select Goose Island, $3 “J” shots (Jim, Jack, Jose, Jager – you get the idea)
Thursday: $5 all bombs, $13 domestic buckets
Friday: $4 well drinks, $2off Bulleit Whiskey
Saturday: $5 Ketel One drinks, $4 Bloody Mary’s and mimosas, $2.50 retro cans
Sunday: $4 Bloody Mary’s and Mimosas, $10 domestic pitchers, $2.50 domestic drafts
Roger’s Park Social
Photo Credit: Roger’s Park Social Instagram
6920 N Glenwood – $5 Happy Hour
From 4pm – 7pm, Mondays through Fridays, Roger’s Park Social is serving up a $5 happy hour special. The menu features house wines, $1 off domestic beers, and a “pick your own mule” deal that lets you choose whether your feelin vodka, tequila or whiskey that day.
Big Chicks
Photo Credit: Big Chicks Facebook
5024 N Sheridan – select drinks for $5 and under all week long
Big Chicks is a no muss, no fuss LGBTQ bar offering squeal-worthy drink deals all wee long. Stop by on Sundays for $3 vodka lemonades, $5 Dark and Stormys on Tuesdays, $1 off all local craft beers on Wednesdays or, if your feelin extra cheap, $3 PBRs on Fridays.
Brando’s Speakeasy
Photo Credit: Brando’s Instagram
343 S Dearborn St – late night and happy hour specials
This speakeasy and karaoke lounge offers cheapskates like myself both happy hour and late night specials on a daily basis. Some of Brando’s best deals and steals include $4 Moscow mules, $6 Grey Goose Martinis, $5 margaritas, $5 palomas and 1/2 off Revolution beers. And that’s just on Tuesdays. Check out their website for daily deal updates here.
The Franklin Room
Photo Credit: The Franklin Room Instagram
675 N Franklin – $1 beer and wine menu
Last, but certainly not least, the piece de resistance – the $1 beer and menu at The Franklin Room. Though it may only be served from 11:30 am to 2pm, Mondays through Fridays, this standard bar and restaurant does offer a full menu of drinks for just one dollar a piece. In addition to cheap-as-hell beers and wines, for those of us looking for something just a little harder, the menu also includes $3 martinis. I should probably mention that you have to buy lunch in order to cash in on the deal, but who cares, $1 drinks are worth it.
Featured Image Credit: Antique Tacos Instagram
