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Labor Day Trivia at aliveOne

  • Monday, September 2; open at 5 p.m.; trivia at 7:30 p.m.
  • $4 to $8 drink specials

After the Labor Day barbecues, patrons can head to aliveOne, which will open at 5 p.m. with a half-price happy hour until 7 p.m. At 7:30 p.m., "Whaddayaknow" will host a FREE music-themed trivia night.

In addition to FREE pool all evening, specials will include a $7 Hamm's and Old Grand-Dad shot combo, $4 Fernet shots, and a specialty $8 cocktail for Labor Day called "The McGuire" featuring Crown Royal, Yellow Chartreuse, lemon juice, Regan's orange bitters.

Labor Day Weekend End-Of-Season Party at Castaways

  • Saturday, August 31 through Monday, September 2

Chicagoans can say goodbye to summer with a weekend-long beach party for Labor Day at Castaways. The North Avenue Beach hotspot will feature live entertainment by DJ's from The DJ Firm from 1 p.m. to 7 p.m. Saturday through Monday. Entertainment includes DJ Medic, DJ Kaila Troy, DJ Daily, DJ Jem, Sye Young and more. While enjoying the music, guests can sip on beach bar drinks like frozen pina and strawberry coladas, spiked iced tea, margaritas, sangria and more.

Easy Bar's Labor Day Specials

  • Monday, September 2; open at 8 p.m.
  • $5 to $6 drink specials

Easy Bar will open from 8 p.m. to 2 a.m. on Labor Day and offer specials like $6 glasses of wine, $5 Espolon Tequila shots, $5 Stoli Lime drinks, and Tecate with a Jimador tequila shot for $6. Guests can enjoy their drinks and the final days of summer on Easy Bar's dog-friendly sidewalk patio with seating for 15 to 20 guests.

Labor Day Specials at Estelle's 

  • Monday, September 2; open at 10 p.m.
  • $3.50 to $7 food and drink specials

Chicagoans looking for a casual spot late-night spot to wind down after Labor Day weekend can head to Estelle's at 10 p.m. on Monday, September 2. Estelle's will offer their signature F*ck Your Patio cocktail (Chicago Distilling Finn's Gin, Apologue Aronia, demerara and lemon juice) for $7 each along with half- price burgers, a $3.50 rotating draft and $4 Fernet Branca shots. Estelle's is open until 4 a.m. on Labor Day.

FREE Ice Cream for Kids at Kizuki in Lincoln Park

  • Now through Monday, September 2
  • Complimentary Japanese Black Sesame Ice Cream

To help Chicago kids beat the heat this Labor Day weekend, Kizuki will give away FREE Japanese Black Sesame soft serve ice cream at their Lincoln Park NEWCITY location with any purchase (one per child).

Labor Day Weekend at the Miller Lite Beer Garden

  • Friday, August 30 to Monday, September 2

The Miller Lite Beer Garden, on Chicago's lakefront at the East End of Navy Pier, will kick off Labor Day weekend with happy hour on Friday, August 30 from 4 p.m. to 6 p.m. featuring $4 16-ounce Miller Lite drafts, $5 16-ounce Peroni drafts, $5 Capeline Strawberry Lemonade, $5 Henry's Hard Sparkling Water, $6 Smirnoff Vodka Lemonades, $6 Bacardi Mai Tais, $9 Double Cheeseburgers with fries, $6 Supreme Nachos and $4 Cheese Pizzas.

The Miller Lite Beer Garden will also continue its "Live on the Lake!" music series featuring local bands all weekend long (lineup below). On Saturday, August 31, patrons can enjoy the fireworks on Navy Pier at 10:15 p.m. 

Saturday, August 31
2 p.m. to 4:30 p.m.: Local Motive
5:30 p.m. to 8 p.m.: NuBlu Band
9:10 p.m. to 11:30 p.m.: Mike & Joe

Sunday, September 1
2 p.m. to 4:30 p.m.: AfroZap
4:30 p.m. to 7 p.m.: DJ Papa G
5:30 p.m. to 8 p.m.: Kofi and the New Roots

Monday, September 2
2 p.m. to 8 p.m.: Bitter Jester Music Festival 

Labor Day Weekend Prix Fixe Dinner for Two and All Day "Power Hour" at Morton's 

  • Thursday, August 29 through Monday, September 2 
  • $99 per couple three-course prix fixe (exclusive of tax and gratuity)
  • $5.50 to $10 "Power Hour" specials

For Chicagoans staying in town over Labor Day weekend, Morton's in Chicago, Naperville, Northbrook, Rosemont and Schaumburg will offer a special three-course prix fixe menu from Thursday, August 29 through Monday, September 2. Highlights include Lobster Bisque, 8-ounce Center-Cut Filet Mignon, New Zealand Ora King Salmon, Morton's Legendary Hot Chocolate Cake and more. The menu will be paired with a choice of Butter Block Chardonnay or Communion Pinot Noir.

All Morton's locations will also celebrate the long Labor Day weekend with a special all day "Power Hour" at the bar featuring specially priced beer, wine, martinis and cocktails and their legendary bar bites. Bar bite highlights include Iceberg Wedge Bites, Mini Crab Cake BLTs, Prime Cheeseburgers, Petite Filet Mignon Sandwiches, Filet Mignon Trio and more.

Labor Day Weekend Doggie Dining for a Cause at Onward

  • Friday, August 30 through Sunday, September 1 (CLOSED on Monday, September 2)

Guests who visit Onward in Rogers Park over Labor Day weekend can dine with their dogs for a good cause. The restaurant will offer a special "Bone Appetit" menu featuring Sweet Potato Strips ($4), Frozen Peanut Butter & Banana ($4) and Watermelon ($4) for dogs to enjoy on Onward's new sidewalk patio with seating for 24. A portion of proceeds from the dog menu sales will benefit One Tail at a Time Dog Rescue.

Executive Chef Patrick Russ has created special al fresco menu selections including Southern Crawfish Arancini ($12), Beef & Pork Kofta ($15), Softshell Crab Sandwich ($16) and more (menu available upon request). Guests can enjoy new cocktails like Frosé (rosé, vodka, Luxardo bitter, lime and pineapple syrup; $12), the Stellar Sip (tequila, cava, saline water, lemon, simple syrup, cucumber, mint; $13), the Killer Queen (rosé gin, still rosé, Luxardo bitter, pineapple syrup, lime juice, mint; $13), and a Bergamotto Punch Per Due (Italicus, chardonnay, pineapple syrup, citrus, cucumber and mint, served in a copper pineapple; $20). Assistant General Manager and Bar Director Vicente Romero has also curated a "Rosé Menu" featuring seven picks available by the glass or bottle (ranging from $12 to $60) including Proyecto Hermanas, Summer Water, Terre Gaie and more.

Labor Day Weekend Brunch at Parlay

  • Saturday, August 31 and Sunday, September 1
  • $50 per person ($30 bottomless brunch buffet and $20 mimosa package) 

Parlay at Joy District will host a Labor Day weekend brunch buffet available from 11 a.m. to 3 p.m. For $50 per person, guests will enjoy a brunch buffet and mimosa bar. Highlights include a carving station, seafood table and charcuterie, chili and pizza bar, waffle station, egg station, and dessert selections like cake pops, tartlets, brownies and a variety of Rice Krispie treats from Fruity Pebbles to Lucky Charms. There is also a cereal bar and a donut wall with flavors like powdered sugar, sprinkles, chocolate and vanilla. For reservations, visit

Late Night Labor Day at Remedy

  • Monday, September 2; open at 9 p.m.
  • $5 to $8 drink specials

Remedy will at 9 p.m. on Labor Day and offer some post-barbecue specials like $5 3 Floyds beers and a Miller High Life bottle with an Evans Williams shot for $8. Remedy will be open until 4 a.m. on Labor Day.

Labor Day Late Night Specials at The Owl

  • Monday, September 2; open at 10 p.m.
  • $3 to $5.50 drink specials

Guests looking for a low-key or late night Labor Day party can enjoy drink specials at The Owl including $5 boozy popsicles, half-price El Jimador margaritas, and $3 Bud, Miller Lite and High Life. The Owl is open until 4 a.m. on Labor Day.

Labor Day Weekend Grilling Classes at Weber Grill Academy in Lombard

  • Friday, August 30 and Saturday, August 31
  • $50 to $90 per person

On Friday, August 30 and Saturday, August 31, the new Weber Grill Academy in Lombard will offer two hands-on classes for Labor Day weekend grilling. Led by the Weber Grill Masters and Chefs, guests will have the opportunity to practice skills on either a Weber charcoal kettle grill or a Weber gas grill. Along with the recipes, chefs will teach guests the correct grill set up, grilling techniques and timing.

Gourmet Burger Blends

  • Friday, August 30 from 6:30 p.m. to 8:30 p.m.
  • $50 per person

Weber Grill chefs will teach guests about types of burger mixes and blends as well as toppings. Menu items will include custom blend Beef Burgers, Lamb Burgers and Turkey Burgers with a selection of toppings and condiments, Sweet Potato Fries with lemon aioli and Grilled Caprese Salad with red onion and balsamic reduction. To reserve, visit:!-Gourmet-Burger-Blends/

Reef & Beef: Classic Surf and Turf Grilling 

  • Saturday, August 31 from 6 p.m. to 8 p.m.
  • $90 per person

Guests will learn how to grill a Surf and Turf dinner featuring grilled cold-water Lobster Tail and Filet Mignon. Weber Grill chefs will teach basic grill set-up for steak, seafood and plank grilling, what to look for when purchasing steaks from the butcher/grocer, and how to grill proteins to the proper temperature. Menu items will include Grilled Romaine Caesar Salad with shrimp, hand-cut seven-ounce Filet Mignon, Grilled Lobster Tail with basil lemon butter, Grilled Asparagus, and Grilled Lemon Pound Cake with grill-roasted seasonal fruit  and whipped Cream. To reserve, visit:

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Courtesy of Ivy Tac


With the end of summer around the corner, etta is throwing a Labor Day Party.

The party starts at 12 p.m. on Monday, September 2. There will be a bottomless rosé tub and the full dinner menu featuring wood-fired pizzas, pastas, and entrées like the pig picnic and dry-aged ribeye for the table.

Shore Club (North Avenue Beach)

This Labor Day weekend, guests will be offered the ‘Merica Package ($750) that includes a fully stocked Yeti cooler at The Oasis, which boasts sunbed, daybed and cabana offerings in a lounge area. Shore Club will also offer The Frozen ($14) – a specialty frozen cocktail consisting of Pina Colada, Strawberry Daiquiri and blue Frozignon Blanc, for a red, white and blue experience to end the summer.

Rosé Tub
Courtesy of etta

MAD Social 

Kick off your Labor Day weekend with MAD Social’s (1140 W Madison) Friday Brunch service. Their full brunch menu is served from 11am-3pm and Bottomless Mimosas and Bloody Marys from 11am-2pm. Guests will be offered the brunch menu inside or on their dog-friendly patio, which seats 32.

Brunch menu highlights from Executive Chef Josue Salmeron:

  • SHORT RIB BENEDICT -braised Korean style short ribs, toasted pretzel buns, brussels sprouts kimchi, togarashi hollandaise, house potatoes

  • PANCAKES - buttermilk pancakes, salted caramel whipped butter, fresh berries, maple syrup

  • BREAKFAST SANDWICH - chicken and prosciutto sausage blend, baby greens, fried egg, dijonnaise, tomato, smoked gouda, served with breakfast potatoes .

  • CHICKEN & WAFFLES - churro waffle, chicken breast milanese, MAD hot sauce, crisp pork belly, maple syrup

  • SHORT RIB BENEDICT - braised Korean style short ribs, toasted pretzel buns, brussels sprouts kimchi, togarashi hollandaise, house potatoes

Bar Cargo 

Saturday & Sunday Brunch is served from 11am-2:30pm. Enjoy it inside or on their beer garden patio, which features their revamped walk up bar. The front patio space is dog-friendly and welcomes pups of all sizes. 

-$25 bottomless brunch buffet featuring Roman style pizza and brunch favorites 

-$25 bottomless mimosas and bloody marys 

Courtesy of Kailley Lindman

Tuco & Blondie

3358 N Southport Ave, Chicago, IL 60657

Tuco & Blondie will serve up a Mexican-style brunch on Labor Day from 10am-3pm! They will be offering $1 mimosas to the first 50 guests. Grab a seat on the patio or inside to indulge in the Chilaquiles or Breakfast Burrito. On the way out, guests can snag a free ice cream cone for the kids, and enjoy an adult cone for $1. All ice-cream proceeds go to local schools! 

Crosby's Kitchen

3455 N Southport Ave, Chicago, IL 60657

The brunch mecca of the Southport Corridor will also be offering $1 mimosas to the first 50 guests to pair with their monkey bread! Brunch is served from 8:30am-3pm on Labor Day. 

The Smoke Daddy

Wrigleyville: 3636 N Clark St, Chicago, IL 60613

Wicker Park: 1804 W Division St, Chicago, IL 60622

Smoke Daddy's family-style brunch offerings ($19 per person) and bottomless mimosas or Bloody Mary's ($18 @ Wrigleyville and $17 @ Wicker Park) are a recipe for Labor Day bliss. They'll be serving unlimited monkey bread, hash browns, bacon, sausage, fruit and a platter of pancakes until you say stop-and all you need to do is pick an entrée (and your closest Smoke Daddy location). Smoke Daddy will serve brunch from 10am-2pm at both locations on Labor Day.

Smoke Daddy Brunch Spread 2
Courtesy of 4 Star Restaurant Group

City Tap Kitchen & Craft 

To celebrate Labor Day, City Tap Kitchen & Craft is channeling the nostalgic tune of summer camp and hosting an Adult Summer Camp Monday Funday, based off the 2001 Wet Hot American Summer. Guests will be able to play patio games, a tie-dye station, camp-themed food and drink specials, s’mores, and tastings sponsored by Absolute Juice. Food options include:

Labor Day Menu (served cafeteria style)

  • Corn Dog 
  • Meatloaf 
  • Chicken Nuggets
  • Sloppy Joes 
  • Vegetable Lasagna 
  • French Fries 
  • Mashed Potatoes and Gravy
  • Mac n Cheese 
  • Corn on the Cob 
  • Potato Salad
  • Coleslaw  

City Tap has also put a boozy twist on a childhood favorite: Capri Suns! Dubbed the “CampriSun,” the cocktail is a vodka-based play on the classic summer sangria, served camp style in a Capri Sun Style pouch with fresh-cut fruit.


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