All Weekend

SWAY Dispensary is encouraging you to relax this Labor Day weekend by offering some sweet deals. Put some pep in your step with 30% off SWAYs Boogie, and 30% off SWAY Afters!

Colette Collection Sale: This Clark Street boutique is having a HUGE Labor Day Sale! Score huge markdowns on dozens of clothes and accessories! Closed on Monday, but the sale is running the entire week.

Saturday, August 30

Wingout Chicago at Gallagher Way: On Saturday and Sunday, Wingout Chicago is taking over Gallagher Way! This chicken wing-centered festival is bringing together the city’s finest wings for a weekend of wing sampling, live music, drinks, competitions, and more. Immerse yourself in this all-out wing extravaganza where Chicago’s best wing restaurants showcase their most delicious creations – from classic buffalo and sweet-and-spicy to wood-smoked, jerk, honey chili, and dozens more tantalizing flavors you won’t find anywhere else. Special guest, Sean Evans from Hot Ones will be joining the fun on Sunday! Think you can handle the heat? Get tickets here

Live Music at Tin Roof: Tin Roof has two stages, and both are going to be bumping on Saturday night! Nashville artist Matt Bennett will be rocking all night long, starting at 10:30 pm, and DJ Baby Phace will be rocking the back room starting at 11 pm.

Live Music at Stolen Saddle: Following the Cubs game, Tim Swann Band is playing at Wrigleyville’s three-story country bar, starting at 10 pm. Tim Swann has had many musical influences throughout the years, from country to rock to folk & gospel. Raised in a Pentecostal home, music was a part of everyday life & he spent 30 years playing and singing in churches, and just recently connected with several friends to work on polishing some original music & doing covers ranging from Johnny Cash to The Jackson 5 to Adele.

System of a Down Tribute Band: Join the unofficial System of a Down warm up party at The Cubby Bear, starting at 8:30 pm! Peephole will be headlining, with Back and Fourth opening, as well as Lions of the Tone Age. Get tickets in advance here

Hard Working Pop Queens Drag Brunch at Lark: Venus Carangi and Pixel are hosting a Labor Day Weekend Drag Brunch for three days! From 11 am to 3 pm on Saturday, Sunday, and Monday, come out and sip bottomless. Bottomless drink choices include Mimosa, Bellini, Bloody Mary, Sangria, Ketel One Botanicals Spritz, and Nutrl Vodka Seltzers. You can switch and change during the course of your brunch package. All guests get a breakfast sweet treat plate to begin, and you get your choice of 7 different brunch menu items! Click here to book your spot.

Ohio State Watch Party: Old Crow Smokehouse is hosting a watch party for Ohio State vs Texas! The game starts at 11 am. Specials for the game include $6 GLBC Beers and half-off apps.

You Better Work Brunch at Kit Kat Lounge: You better brunch! Join Kit Kat divas Kylee Hunter and Angelicia Maria at Kit Kat Lounge for drag brunch on both Saturday and Sunday. Seating times are at 10:30 am, 1 pm, and 3:15 pm. Click here for reservations

Unlimited Dosas at Rangoli Kabob: The only thing better than a soft and flaky Dosa is UNLIMITED soft and flaky dosas! Rangoli Kabob on Belmont is offering unlimited dosas for just $16.99 from noon to 4 pm on both Saturday and Sunday.

Bottomless Brunch at The River: Get bottomless at The River! On Saturday from 11 am to 3 pm, it’s only $39.95 for bottomless drinks, a brunch entree, and a cereal buffet. Make reservations here

Sidewalk Sale at Goldplaited Boutique: Save big this Labor Day. Goldplaited the Boutique is having a sidewalk sale, with racks that are 25% off, 40% off, and 70% off! On Saturday they are open from 10 am to 7 pm.

Trigger Happy: Annoyance Theater Signature Improv: Annoyance founder Mick Napier created the Trigger Happy form out of a desire to make improv look as slick and beautifully put together as a scripted show. Through a language invisible to the audience, the fully improvised show magically comes to life. There is truly nothing else like it. Get tickets here

Music Bingo Brunch: On Saturday afternoons, Cheesies is mixing together bingo, music, and delicious grub. From 11 am to 2pm, enjoy a $25 bottomless brunch, and play Music Bingo from 1 to 3 pm! Sing along, mark off songs on your bingo card, and let the good vibes roll.

Sunday, August 31

Wingout Chicago at Gallagher Way: On Saturday and Sunday, Wingout Chicago is taking over Gallagher Way! This chicken wing-centered festival is bringing together the city’s finest wings for a weekend of wing sampling, live music, drinks, competitions, and more. Immerse yourself in this all-out wing extravaganza where Chicago’s best wing restaurants showcase their most delicious creations – from classic buffalo and sweet-and-spicy to wood-smoked, jerk, honey chili, and dozens more tantalizing flavors you won’t find anywhere else. Special guest, Sean Evans from Hot Ones, will be joining the fun on Sunday! Think you can handle the heat? Get tickets here

The Mighty Ducks Cast Meet and Greet at Sluggers: DUCKS FLY TOGETHER! For the first time ever, eight cast members of The Mighty Ducks are coming to Wrigleyville! Don’t miss this once-in-a-lifetime meet & greet on Sunday, August 31st at Sluggers World Class Sports Bar and Dueling Pianos, from 2:00 PM to 7:00 PM. Doors open at 1:30 PM. Let’s form the Flying V and spend the day with the PeeWee Champion Ducks and a few Junior Goodwill Games USA Ducks as we celebrate one of the greatest hockey movies of all time. Meet and Greet tickets are available here

Full Band Karaoke: Brand new to Cheesie’s Wrigleyville, full band karaoke is on Sunday nights starting at 7 pm! Warm up those vocal cords and get ready to feel like a rock star.

Lost Never Found Drag Brunch: Get lost at drag brunch! Hosted by Rachel Slurrz, bring cash and get ready to party like you have a three-day weekend. The show starts at 1 pm! Click here to book reservations

Hard Working Pop Queens Drag Brunch at Lark: Venus Carangi and Pixel are hosting Labor Day Weekend Drag Brunch for three days! From 11 am to 3 pm on Saturday, Sunday, and Monday, come out and sip bottomless. Bottomless drink choices include Mimosa, Bellini, Bloody Mary, Sangria, Ketel One Botanicals Spritz, and Nutrl Vodka Seltzers. You can switch and change during the course of your brunch package. All guests get a breakfast sweet treat plate to begin, and you get your choice of 7 different brunch menu items! Click here to book your spot.

Labor Day QUEEN at Metro and Smartbar: The whole building is celebrating Labor Day! QUEEN returns to Metro and Smart Bar featuring: Derrick Carter * Ladymonix * DJ Lady D * Mystic Bill * Michael Serafini * Shaun Wright. Hosted by: Lucy Stoole * Nico Guest Hosts: Boy J * Ari Blakk Diamond. Decorations by: Boxboy Rich. $25-$30 Advance / $30 Door / $20 Student Door. Get tickets here

Kirkwood Party: Kirkwood Bar and Grill is partying on a Sunday like you don’t have work in the morning! There will be an in house DJ spinning at night, and specials include $7 Michelob Ultra, Miller Lite or Garage Beer Stadium cups, and $8 Vegas Bombs and Green Tea shots.

Industry Night at Replay Lincoln Park: Service industry workers get 50% off drinks every Sunday over at Replay Lincoln Park!

Sidewalk Sale at Goldplaited Boutique: Save big this Labor Day. Goldplaited the Boutique is having a sidewalk sale, with racks that are 25% off, 40% off, and 70% off! On Sunday they are open from 10 am to 6 pm.

Anime Night: Every Sunday night, Cheesies hosts Anime Sundays. Watch some of the best anime movies from 7 pm to 11 pm, and treat yourself to a stacked grilled cheese while you’re there.

Monday, September 1

WOOGMS Labor Day Parade: Lakeview’s longest-running tradition — the WOOGMS Parade — is returning September 1st. Since 1963 this family and pet-friendly event has delighted our neighborhood, a parade where “Everybody Marches and Nobody Watches.” Bring your strollers and scooters and join the Jesse White Drum Corps on a fun march around the neighborhood. Watch the fabulous tumblers perform at the end of the parade. Come join the WOOGMS Parade 11 am on September 1st at the intersection of Wellington and Pine Grove.

Cubs Game: On Labor Day, Monday, The Cubs are playing at home against the Braves for a 3:05 pm game! Get tickets here

Bottomless Brunch at Drews: Let’s get bottomless! Drew’s on Halsted is hosting their infamous bottomless mimosa brunch on Labor Day. For just $49, sip all the mimosas you can handle, AND the price includes an entrée! Brunch is served from 10 am to 3 pm. Make reservations here

Thali at Rangoli Kabob: In celebration of Labor Day, Rangoli Kabob will be serving up delicious Thali! Both vegetarian and non-vegetarian Thali will be available.

Super Smash Bos Ultimate Tournament: Think you got game? Every Monday night, Replay Lincoln Park hosts Super Smash Brothers Ultimate Tournament. The tournament starts at 7 pm, and it’s a $5 bracket fee with cash prizes up for grabs. No cover- walk on in! Sign ups start at 6 pm.

Cheesies: Open on Labor Day from 11 am to 2 am, come sip on Monday specials! Domestic drafts and well cocktails are $5, and happy hour is from 3:30 to 5:30 pm.

Bottomless Mimosa Brunch at El Mariachi Tequila Bar & Grill: It’s hard to beat a $20 bottomless mimosa brunch! El Mariachi Tequila Bar and Grill is opening at 10 am on Labor Day, and will be open until 10 pm. To make the holiday even more special, they are serving $7 house margaritas all day long. Make a reservation here