Chicago’s Best Bars for Drinking on Off-Nights


Chicago’s Best Bars for Drinking on Off-Nights
Chicago’s Best Bars for Drinking on Off-Nights

Courtesy of Bordel
Courtesy of Bordel

We all know the weekend starts at 4:45pm on Thursday, but what about going out in Chicago on a more traditionally tame Sunday, Monday, Tuesday, or Wednesday night? Whether you work over the weekend or just want to treat every night like the weekend, you can enjoy yourself without the need to rub elbows with tourists and “industry” types at Downtown clubs and lounges. If you’re looking for a helluva time that you definitely (probably) won't regret the next day, hit up Chicago’s best off-night bars.

Courtesy of Roof on the Wit (edited)


Lincoln Park

Early in the day, this Lincoln Park mainstay (and Eddie Vedder hangout) hosts a popular brunch buffet that’s stocked with fried chicken. The party keeps on rolling into the night, so throw back a few Bloody Marys and get ready to rock out with live-band karaoke, and hopefully a tipsy, goat-mumbling Eddie Vedder.

ROOF on theWit


ROOF only throws its Sunday bashes throughout the summer -- that time of year when the sun is actually out -- which probably adds to the midday energy at this cranked-up day party. Sparklers, bros donning tank tops, dolled-up women rocking their best heels, and plenty of Corona bottles are all on display here. The music is loud, the views are great, and the vibe is fun.

Smart Bar


Every Sunday night at "Queen!," Michael Serafini's high-energy gay night, he and partner-in-crime Garrett David keep the weekend-party going by spinning house, disco, and tech on vinyl.

Big Chicks


Barbecue buffet. $3 vodka lemonades. Solid crowd. ‘Nuff said.

Gallery Cabaret


On Sunday evenings, Gallery Cabaret is here to do wonders for your dating life by offering one of the cheapest dinner-and-a-show options in town. There’s a free buffet that’s stocked with decent food (donations accepted), the beer is cheap, and there’s an open mic that hosts musicians ranging from “pretty good” to “at least we have beer.”


Slippery Slope

Logan Square

Considering the massive lines you’ll encounter here on weekend nights, hitting the Slope on a weekday will make you feel like you’re freely waltzing into the joint through the kitchen, Swingers style. The bar doesn’t get too packed, instead drawing a thirsty crowd that shows up for $1 mugs of Hamm’s. If you’re looking to keep it on the level, there’s free skee-ball and karaoke to keep you occupied.


Noble Square

evilOlive has been crushing it on Monday nights for years, stretching back to its scenester-packed "Rehab" parties, where a typical night could include downing shots with Flosstradamus and shooting pool with Hollywood Holt. Nowadays, the weekly "Porn and Chicken" bash keeps things turnt until 4am, and you can probably guess what the catering and entertainment options are. (Yes, it’s porn on the TVs and fried chicken to snack on.)

Beauty Bar

Noble Square

Hosting the entertaining weekly "Salonathon," Beauty Bar is an excellent choice for those looking to get a little weird early in the week. Cheap beer-and-shot specials keep bar-goers lubricated, while a lineup of writers, musicians, and weirdos keep things interesting. In the same night, you can see live music, a contortionist, and a Fifty Shades of Grey parody-reading by a guy who is dressed in a dog costume. For real.

Empty Bottle

Ukrainian Village

Not only does Empty Bottle book quality bands on Monday nights throughout the year, but it doesn’t even charge a cover for the vast majority of them. The venue’s "Free Music Mondays" series can draw a packed house when there’s an up-and-coming band stopping in, which can sometimes feel as if you’ve suddenly time-traveled into a Saturday night show. Oh, and $6 for a shot and a beer isn’t too shabby either.


Lincoln Park

The Monday night crowd at Delilah’s isn’t always wall to wall, but it sure is a thrifty bunch with great taste in music. "Punk Rock Mondays" is the bar’s weekly bash, during which visitors can expect plenty of punk rock on the speakers, free games of pool upstairs, and cheap booze. Like, really cheap. Domestic beers-for-$1-and-whiskey shots-for-$2 cheap. After all, nothing’s more punk rock than being fiscally responsible.

The Owl (edited)

The Owl

Logan Square

One of four bars that offer the same Tuesday night special, The Owl draws a packed house on Tuesday nights thanks to its ridiculous deal: select craft beer pints for $2 or $3. The menu changes weekly, but the crowd comes out year-round, because apparently craft beer aficionados will hike through a snowstorm in order to save a few bucks. Hey, if there’s one thing that’s worth hiking through a snowstorm, it’s definitely beer.


Wicker Park

Offering the same deal as The Owl (select craft beer pints for $2 or $3), Tuesday nights at Estelle’s are slammed like Andre the Giant at WrestleMania. Besides the great beer deal, you can score some pretty decent bar food -- like the avocado-topped Point Break burger -- and hit up the great jukebox, which is locked and loaded with LCD Soundsystem and Band of Gypsys.


Lincoln Park

aliveOne offers the same deal as The Owl and Estelle’s on its bustling Tuesday nights (select craft beer pints for $2 or $3), but it also has something that the other two bars don’t: a jukebox that’s stocked with live-music albums. Which you’ll either love, or absolutely hate, because can we all just admit that live-music albums are worse than going to your date’s apartment and discovering dozens of mannequins?

Easy Bar

Wicker Park

Hey, guess what the special is at Easy Bar on Tuesdays. Just guess. Yuuuuuup: it’s select craft beer pints for $2 or $3. Easy Bar doesn’t get as busy as Estelle’s, but that can be a good thing if you don’t feel like waiting to order, sitting 5ft from a deep fryer, or wondering why the men’s bathroom door has been broken for seven years. (Seriously Estelle’s, fix that door!)

Joe’s on Weed

Lincoln Park

Say what you will about bros and broettes, but they sure do know how to party. Witness them in their natural, sports-saturated habitat at Joe’s on Weed, which throws a super-fun Tuesday night bash that’s fueled by serious drink specials: $2 vodka drinks, $2 domestic pitchers, $1.50 Bud Light and Coors Light cans, and $5 pizzas, among others. Yes, $2 pitchers are a thing outside of Flint, Michigan and heaven.

Blue Line (edited)


Ukrainian Village

The throwback, vaudeville-inspired cocktail lounge above Black Bull is one of our favorite secret bars. However, it looks like the worst-kept secret in town on Wednesday nights, when scenesters, industry peeps, and thirsty locals stop in to check out live music and DJs at the weekly "Speakeasy" bash.


Logan Square

Cole’s is the kind of no-fuss bar that really doesn’t need any event to keep it busy on any particular night of the week. However, Wednesday nights are dependably happening because there’s a great standup open mic night in the back, and also because Logan Square locals like to go out a lot. It’s science.


Lincoln Park

Spend enough time in Lincoln Park and you’ll soon realize that you’re trapped in a discombobulating vortex where every bar in the neighborhood is actually the same bar, with the same games on TV, Buffalo wing baskets, and mix of sloppy white-collared paper-pushers and overly thirsty DePaul coeds. Kincade’s knows this, and totally owns it by putting on rowdy Wednesday nights with its $1 domestic bottles special. Props.

Blue Line Lounge

Wicker Park

You may not like martinis, and it’s probably because they’re served in the stupidest glass ever made. On the other hand, you may be into drinking on a budget or just chatting up fellow martini drinkers. If that’s the case, swing by the Blue Line Lounge and get sauced on specialty martinis, which pack a punch and will set you back only $5 a pop.

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Raf has no problem with going out on Tuesdays and Netflixing on Fridays. Hit him up with movie recommendations: @raffosho.

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Previous Venue Next Venue Venue Description
1. Stanley's Kitchen & Tap 1970 N Lincoln Ave, Chicago, IL 60614 (Sheffield Depaul)

This neighborhood dive bar has everything you could want for your local watering hole, cheap booze, DJs, dance floor and if you're lucky an appearance by the Naked Guy.

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2. Roof on the Wit 201 N State St, Chicago, IL 60601 (Loop)

Do you like models, bottle service, and DJs? If so, theWit's rooftop lounge is for you. More than just a glitzy bar, the 27th-floor hotspot features a retractable roof (it's open year-round, after all), a 3D video-mapping wall, and a sleek bar that turns into a runway. The food and drink menu is equally fit for a glam squad, serving up flatbreads, seafood towers, fancy craft cocktails, and punch bowls.

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3. Smart Bar 3730 N Clark St, Chicago, IL 60613 (Lakeview)

Smart Bar has a great sound system, as well as frequent DJs and awesome drinks.

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4. Big Chicks 5024 N Sheridan Rd, Chicago, IL 60640

At this friendly, uptown bar, art-lined walls greet a lively hometown crowd with bar eats and cheap drinks.

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5. Gallery Cabaret 2020 N Oakley Ave, Chicago, IL 60647 (Bucktown)

With a prime spot in Chicago's Bucktown neighborhood, Gallery Cabaret is one of the premier destinations in the city for live music, comedy nights, and poetry readings.

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6. Slippery Slope 2357 N Milwaukee Ave, Chicago, IL 60647 (Logan Square)

Skee-ball, tamales, and and an expansive, crimson-lit dance floor await at this two-story club made to replace what Bonny's once was. The beer is cheap, the wine is boxed, and we promise this will probably be one of the only times you'll hear "Mother-In-Law" (a tamale-chili combo) and not be filled with dread.

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7. Evil Olive 1551 W Division St, Chicago, IL 60622 (West Town)

Looking for a way to cure the Monday blues? Check out Evil Olive for their reputable Monday night "Porn and Chicken" party. Think half-naked women on the bartop, lots of dancing, and of course good ol' fried chicken. What an amazing way to kick off the work week.

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8. Beauty Bar 1444 W Chicago Ave, Chicago, IL 60642 (Ukrainian Village)

An outpost of the NY-based chain of wild, multicolored nightclubs, Beauty Bar is designed to resemble an old-school salon from the '60s, mixed with a dance-heavy dive bar. Among blow-drying and nail-painting stations, the bartenders even sling specialty hair-themed cocktails, like Bed Head (Sauza Blue Silver tequila shaken with pineapple and lime juices) and The Blowout (Jim Beam rye or bourbon whiskey, dekuyper ginger, liqueur, lemon).

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9. Empty Bottle 1035 N Western Ave, Chicago, IL 60622 (Ukrainian Village)

Empty Bottle's got awesome live music, a photobooth, and a cheap booze selection.

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10. Delilah's 2771 N Lincoln Ave, Chicago, IL 60614 (Lincoln Park)

Delilah's is a neighborhood bar with over 400 whiskeys, located in Chicago's Lincoln Park.

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11. The Owl 2521 N Milwaukee Ave, Chicago, IL 60647

From the folks behind laid-back landmarks Easy Bar and Estelle's, The Owl sports a similarly dive-y vibe, with dim amber lighting, a softly curving, 40-stool'd bar, and, held over and spruced up from the previous occupants, a retro-looking waterfall, which you're sure to go chasing...with a beer!

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12. Estelle's 2013 W North Ave, Chicago, IL 60647 (Wicker Park)

Estelle's... where $2 beer Tuesday's live-on, and the jukebox is chock full of tunes that'll make you feel like you're back in college again.

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13. aliveOne 2683 N Halsted St, Chicago, IL 60614

This rite of passage bar for Chicagoans has a live music jukebox, shows in the back room and a crowd of 20-somethings who are always game for a good night.

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14. Easy Bar 1944 W Division St, Chicago, IL 60622

The guys behind Estelle’s and Alive One bring you this trendy, easygoing bar in Wicker Park. Cozy up inside the wood-laden space sporting dark red walls, and knock back a few rounds from its solid beer list, which features draft, bottle, and can options from Belgium to Chicago. You can also sip on cocktails like the “Choice Words," made with Four Roses bourbon, Chartreuse, lemon, and Luxardo maraschino. There's a jukebox bumping hits from the likes of Otis Redding, Jack White, and Alabama Shakes that are sure to set the mood.

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15. Joe's on Weed 940 W Weed St, Chicago, IL 60642

Donning a sports vibe and the related bros and broettes crowd, Joe’s on Weed hosts a Tuesday night bash that’s fueled by serious drink specials: $2 vodka drinks, $2 domestic pitchers, and $5 pizzas, among other offerings.

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16. Bordel 1721 W Division St, Chicago, IL 60622 (Wicker Park)

Bordel remains a charming cocktail lounge that stands firmly against the soul-crushing waves of party buses, thanks to the second-story establishment's unmarked door. Once inside, visitors can expect classic cocktails, table service that serves up booze in a tea set, and live performances that range from burlesque to flamenco dancing.

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17. Cole's 2338 N Milwaukee Ave, Chicago, IL 60647 (Logan Square)

Cole's is a down-home dive serving up cheap brews, great tunes, and a stellar crowd.

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18. Kincade's 950 W Armitage Ave, Chicago, IL 60614

This casual bar offers wing baskets, streaming TV, a standard neighborhood bar drinks menu, and a non-standard Wednesday nights special with $1 domestic bottles.

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19. Blue Line Lounge & Grill 1548 N Damen Ave, Chicago, IL 60647 (Wicker Park)

Never empty but always uncrowded, this Wicker Park grill and lounge has a serious selection of board games and massive booths to play ‘em all in, not to mention tasty 'tails and a trendy ambience.