Labor Day Weekend is the official unofficial end of summer, and as bittersweet as that may be, Lakeview East has everything you need to celebrate one of the most anticipated weekends of the year. Check out some of the hottest Labor Day Weekend events happening in Chicago!

WOOGMS Labor Day Parade

This Labor Day, WOOGMS (Wellington / Oakdale Old Glory Marching Society) is hosting the annual WOOGMS Parade! In this parade, EVERYBODY marches, nobody watches. Be a part of history, as this is the 61st WOOGMS Labor Day parade. Bring your kids, their bikes and scooters, your pups, and friends along for this wonderful neighborhood event. It all starts at 11 am at the corner of Wellington and Pine Grove.

Restaurants Open & Serving Labor Day Deals

Almost Home Tavern: Right in the heart of Wrigleyville, just a block away from Wrigley Field, stop into Almost Home before, after, or during the game and score these deals: $20 Twisted Tea Pitchers, $20 Hardly Water Buckets, $10 Home-made Dorito Nachos, and $5 Dirty Monkey Shots!

Bamboo Club: A little karaoke never hurt anybody (well, maybe their eardrums). On Monday nights, Bamboo Club hosts karaoke night! From 7 to 10 pm, come sing your heart out and enjoy these karaoke night specials: Half off pizza, $25 buckets of SunnyD Vodka setlzers, and $5 Tiki Torch cocktails. Make your reservation here

Barcocina: Barcocina is serving a Labor Day Brunch for just $60! From 11 am to 3 pm, sip on bottomless modelos, skinny punch, house margaritas, mimosas, high noons, bloody marys, and micheladas! Included in the $60 is also a brunch entrée, as well as chips and salsa. Make your reservation here!

Duffy’s Tavern and Grille: Every Monday night, Duffy’s hosts a Monday night RAW watch party, and Labor Day is no exception! From 7 to 10 pm they will be airing the match, and will have slammin’ specials like all drafts for $5 and $56 Jameson shots.

El Mariachi Tequila Bar: El Mariachi has a $35 mimosa package with a brunch entree included, all weekend long, and on Labor Day! Also on Labor Day they are selling their house margaritas for $8! Make reservations here

El Nuevo Mexicano: El Nuevo is serving up a Bottomless Brunch all weekend long! From Friday through Monday, indulge in endless mimosas and a delicious entrée for just $25. Treat yourself to some of the best Mexican cuisine in the city at an unbeatable price!

Lost Never Found: Usually, LNF is closed on Mondays, but they are staying open for Labor Day! Enjoy one of the best happy hours in the city: Half off appetizers, half-off pizzas, $5 seltzers, $6 highballs, $7 spicy frozen margaritas, $8 martinis, and $8 LNF specialty cocktails! Happy Hour is at the bartop ONLY and is from 4 to 7 pm. Get there early, seats fill up really quickly!

Matilda: Matilda invites you to come celebrate Labor Day with $5 draft beers, and $10 burgers (the Matilda burger or the quinoa burger for the veg-heads)! Their doors open at 5 pm.

NOLA Kitchen & Bar: NOLA will have their regular happy hour deal, 50% off all house cocktails from 4-7 pm, and in addition to that, $4 domestic cans! Save some room for their delicious Cajun NOLA-style cuisine while you’re there, like blackened shrimp pasta, shrimp po boys, and chicken wings!

Savanna Restaurant: Sip, sip, hooray! Savanna invites you to come brunch with them on Labor Day, and to sip as many $8 mimosas you’d like, of any flavor!

Swift Tavern: Swift Tavern is opening at 4:30 pm for game day! Specials for the day are Pints & Pearls, which is $2 oysters, and $4 select pints of beer!

Labor Day Deals & Sales

CRAM Fashion: CRAM has a huge labor day sale all weekend long! Get 25% off ALL swimwear, tanks, and shorts, and even 75% off select summer items.

SWAY Dispensary: Save big this Labor Day at SWAY! Get 20% off edibles, and 15% off drinks this Monday only!

Colette Collection: The Colette cuties go big for every holiday, including Labor Day! Score up to 40% off some items the entire weekend, and join in on their Sip & Shop event on Friday night! There will be a tarot card reader and complimentary drinks! Can’t make it in person? Shop online, anytime!

Events on Saturday, August 31

Pearl Jam Plays Wrigley Field: Saturday is the LAST concert of the summer at Wrigley Field! Special guest Glen Hansard will be opening. Grab tickets to the Dark Matter World Tour, here!

Duffy’s Tavern & Grille: Duffy’s is celebrating the start of Michigan football season! Come in for the game and treat yourself to $7 Bud Light Stadium Cups, $6 Founders drafts, $7 Patron silver & Jameson shots, and $8 Go Blue Shots! They have over 30 DH TV’s and a halftime raffle. It all goes down Saturday, with a majority of seating opening at 4:30 pm.

Gman Tavern: Heading to Wrigley Field for the Pearl Jam concert? Gman is hosting a FREE preparty, with DJ Jill Hopkins! She’ll be spinning from 3:30 to 6:30 pm. Come rock out before the show!

Matilda: Matilda is celebrating the first Michigan Football Game of the season, on Saturday night! Drink specials for the big game: $4 Domestic Bottles, $5 Son of Juice Drafts, $5 Bells Lager for the Lakes Drafts, $5 High Noon, White Claw, Freshie Seltzers and $10 Journeyman Old Fashioned Cocktails⁠. Participate in the Halftime Raffle, prizes include a Signed Blake Corum jersey, Tickets to see Michigan @ Illinois this year, and a few pieces of Championship Gear! For every drink purchased, you will receive a raffle ticket.⁠ Get for an epic showdown as the Wolverines defend their title against Fresno State!

Events on Sunday, September 1

Cubby Bear: Every Sunday, Cubby Bear hosts Salsa Sundays! They have professional salsa instructors come to the bar, and teach you step by step how to get your salsa on. Dance lessons start at 8 pm, but doors open at 7 pm if you need a little liquid courage to get those hips moving.

Kirkwood Bar & Grill: Kirkwood is encouraging you to come party. because they know you are not working Monday. On Sunday night, they have a DJ spinning live, as well as some special Labor Day deals! $7 Bud Light and Miller Lite Stadium Cups, and $8 Vegas bombs and green tea shots!

Dog Day at Gallagher Way: The dog days of summer are coming to an end, but not just yet. On Sunday, September 1, kick off the fall season with friends, family, and, of course, your pup Gallagher Way is hosting Dog Day from 5 to 8 p.m. and enjoy: A pup cup station, Agility activities, Pop-jets, Bubbles, and more! This event is free, and does not require registration. Dogs attending the event with their owners are required to have updated vaccinations and to be on a leash. Owners are responsible for their dogs and legally responsible for any injuries caused by their dogs. Owner’s must immediately clean up after their dogs.

Metro: The Metro is hosting Labor Day QUEEN! on Sunday night, starting at 9 pm. Lucy Stoole and Nico will be your hosts for the evening, and Steve “Silk” Hurley, Derrick Carter, Michael Serafini, Mark Grusane, Jessica Jane, DJ wOLFY, and more TBA! Tickets are available at the door for $25 – $30, and students will be let in for $20 as long as they come in before midnight.

Old Crow Smokehouse: Old Crow is keeping the weekend alive and well by having live music starting at 9 pm, with Sunfallen taking the stage! Deals for the day are $5 bud lights. Drinking and dancing sounds like a great Sunday night to us!

All Things Drag

Kit Kat Lounge: Kit Kat has a STELLAR lineup this week! Shantell Demarco will be at Kit Kat from 6 pm to 11 pm on Friday and Saturday night. Then, on Saturday and Sunday morning, Kinley Preston and Angelica Maria are hosting a Sing-A-Long brunch, with bottomless mimosas of course! Book your spot here, and get ready to have a blast with the Kit Kat divas.

Lark: Lark is doing it big for Labor Day Weekend:

Take a day off! Join us for Labor Day Weekend Drag Brunch at Lark with Venus Carangi, Hector, and Danny!

Our drag brunch is a high-energy experience featuring floor shows from your favorite Chicago queens. Get ready for a wild time! Featuring themes each week and fun tableside interactions, Lark’s drag brunch on North Halsted is a fun experience for everyone.

How it works: Your brunch starts with a choice of bottomless drinks- Mimosa, Bellini, Bloody Mary, Sangria, 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!
  • Bottomless drinks, breakfast sweet starter, and choice of entrée from select menu
  • 90 minute bottomless drink package, 2hr seating
  • For non alcoholic options we have bottomless mocktails
  • Bring cash! Our performers appreciate tips.
  • All ages to attend, 21+ to drink

Make reservations to Lark, here!

Lost Never Found: Get lost at Lost Never Found, on Sunday at 11:30 am for their Gospel Drag Brunch! Hosts for the day are Rachel Slurrz and Siren, featuring Dymond Carrington, Sativa Diamond, Anya K, Thunderkat, and Dida Ritz.

• $30 Unlimited Mimosa package available

• $40 Unlimited mimosas & call cocktails package available

• Food will be ordered a la carte from a slightly limited menu

Make reservations here!

The River: Drag Me to The River! On Sunday, the legendary River Drag Brunch is taking place, with showtimes at 11 am, 1 pm, and 3 pm. Hosted by Kimberly Summer, Veronica Pop, and Boy J, sip on bottomless drinks and be prepared for a SHOW! Special guests of the week are Gadfire and Abigail Beverly Hillz, and the go-go dancers for the day are Mark Love and Julez. Grab your ticket here!