Where to Celebrate Labor Day 2026

Avondale

• Central Park Bar

Celebrate the long weekend with a relaxed Labor Day happy hour at Central Park Bar in Avondale. On Monday, September 7, the neighborhood spot opens at 4 p.m. and invites guests to enjoy half-price drinks (excluding shots) from 4 to 7 p.m. while soaking up the holiday on one of the area's largest patios. At 7 p.m. guests can enjoy a few rounds of FREE Bingo until 10 p.m. Weather permitting, the Labor Day festivities will take place in the 3,500-square-foot Backyard Bar, featuring a covered outdoor bar, bumper pool, picnic tables, porch swings, a photo booth, a claw machine, and a cozy fire pit. Whether you're gathering with friends or simply looking to make the most of the final days of summer, Central Park Bar offers the perfect setting to relax, sip, and celebrate.

• Tune-Up

Chicagoans can make the most of Labor Day weekend at Tune-Up in Avondale, where guests can soak up the final unofficial weekend of summer on the spacious outdoor patio. Patrons that arrive early can enjoy Tune Up’s signature half-price happy hour from 4 p.m. to 7 p.m. and enjoy seasonal specials like the Frozen Patio Paloma with Astral tequila, St. Germain, Squirt, grapefruit juice & lime juice and ‘Tune it up’ by adding Ghost habanero tequila floater on top. Other seasonal libations include the ErotiColada with Bacardi, Green Chartreuse, pineapple, lime juice, Dead Beat Beet with Los Vecinos mezcal, Giffard Ginger of the Indies, Supasawa, lemon juice, beet syrup, celery bitters and more. Tune-Up's expansive patio offers a setting to enjoy the long holiday weekend. 

Beverly

• Sanders BBQ Supply Co.

Sanders BBQ Supply Co. will be open on Labor Day weekend and are offering catering and take-out opportunities for backyard parties, from their signature Ribs and Pulled Pork Sandwich to sides like Mac n’ Cheese and Sweet Potato Cornbread. 

Gold Coast

• The Bellevue

Spend Labor Day Weekend dining al fresco at The Bellevue in Chicago’s Gold Coast. The neighborhood will have its Friday brunch service leading into the long holiday weekend, followed by patio dining throughout Labor Day Monday. Guests can enjoy elevated American fare, seasonal cocktails, and brunch favorites from the restaurant’s expansive 100-seat patio, which offers an open-air setting with partially enclosed spaces for added comfort. Whether stopping in for a leisurely brunch, afternoon cocktails, or a relaxed holiday dinner, The Bellevue offers an easy escape just steps from the lakefront and downtown festivities. Menu Highlights Banana Espresso Martini with Tito’s Vodka, Belissimo Coffee Liqueur, Espresso, Banana Syrup, Gravlox Platter with Cured Salmon, Cream Cheese, Red Onion Cucumber, Capers, Dill, Plain Bagel, and Prime Skirt Steak (6oz) & Eggs with Hash Browns & Toast. 

• Carmine's

Carmine’s on Rush is giving Chicagoans a reason to stretch Labor Day weekend just a little longer with The Last Spritz of Summer, a one-day-only afternoon celebration on Monday, Sept. 7. From open until 4 p.m., guests can settle in on the second floor patio overlooking Rush Street and sip a trio of $12 cocktails, including an Aperol Spritz, Hugo Spritz and Lemon Ice, bringing a taste of an Italian summer to the heart of the Gold Coast. 

• Shore Club

Shore Club will host Labor Day Weekend at the Oasis from September 5–7, inviting guests to celebrate the unofficial end of summer. Throughout the three-day weekend, guests can enjoy live music, bottle service, private cabanas, cocktails, and lakefront views. Reservations are recommended and are now open through their website.

Lakeview

• Cody's Public House

Cody’s Public House in West Lakeview invites college football fans to kick off college football season and Labor Day with a weekend full of games beginning Saturday, September 5. Cody's will open at 11 a.m. on Saturday for the ESPN College GameDay featured matchup with full game sound. Fans can enjoy game day specials including $5 Mimosas, $6 22-ounce Miller Lite cups, $7 Walk of Shame Bombs and $30 Surfside Buckets.

Lincoln Park

• aliveOne

After a day of Labor Day celebrations, aliveOne in Lincoln Park will keep the holiday weekend going with an evening of free music trivia, drink specials, and free pool. The bar opens at 8 p.m. on Monday, September 7, offering $7 Old Style and whiskey shot combos, $1 off domestic beers, and music trivia hosted by Whaddayaknow Trivia. Following trivia, guests are invited to stick around for complimentary pool throughout the rest of the evening. 

Logan Square

• Remedy

Remedy will celebrate Labor Day with a late-night party on Monday, September 7, featuring drink specials and a complimentary hot dog special. Open from 10 p.m. to 4 a.m., Remedy will offer guests a free hot dog (while supplies last) with the purchase of a $5 Malört shot.

• The Owl

Guests looking for a late-night Labor Day party can head to The Owl in Logan Square from 10 p.m. until 4 a.m. on Monday, September 7. Guests can sip on cocktails for only $10 each all evening like the Smokey Kiss with Union mezcal, Cynar, sweet vermouth, the Tipsy Rose with Dolin strawberry aperitif, Sfumato rhubarb amaro, bubbles, sparkling rosé and more. 

Magnificent Mile

• Casa Chi by Chef Richard Sandoval

Make the most of Labor Day Weekend with a visit to Casa Chi, a destination for Japanese-Peruvian Nikkei cuisine, cocktails, and dining experiences. Guests can kick off the celebration with Happy Hour, available from 4–7 pm, featuring specialty cocktails, bubbles, wine, and shareable bites before enjoying sushi and small plates. For a girls’ gathering, try Casa Chi’s “Girl Dinner” experience starting at 7 pm, featuring a seasonal margarita or Champagne, a starter of swordfish dip or guacamole, and a three-piece omakase selection for $35 per person. Walk-ins Welcomed, Reservations on OpenTable.

• Sweetwater Tavern & Grille

Sweetwater Tavern & Grille invites everyone to its weekend brunch this Labor Day (it’s the weekend brunch extended for Labor Day and starting one hour earlier, at 10 a.m.). Served until 3 p.m., guests can dig into signature favorites like Stuffed French Toast, Avocado Toast, Chilaquiles, and Chicken & Waffles alongside the Breakfast Burger, Brisket Biscuits & Gravy, and Steak & Eggs. Kids are covered with Breakfast Tacos, Pancakes, and French Toast Sticks. The restaurant also offers a variety of cocktails, mocktails plus Mimosa flights and breakfast shots. 

River North

• Sifr

Celebrate Labor Day with a Middle Eastern dining experience at Sifr, where Chef Sahil Sethi showcases wood-fired flavors inspired by the spice-scented bazaars of the Middle East. Gather with friends and family to enjoy the restaurant's $60 Chef's Tasting Menu or explore a selection of tasteful mezze, hearth-roasted specialties, and shareable à la carte dishes. Walk-ins Welcomed, Reservations on SevenRooms.

• The Smith

Celebrate Labor Day Weekend at The Smith Chicago in River North with brunch and cocktails that keep the holiday vibes going. Gather friends and family for weekend brunch featuring favorites like Vanilla Bean French Toast, Shrimp & Grits, and signature Potato Waffle Benedicts before raising a glass during Martini Hour. Available weekdays from 3–6 p.m. at the bar, Martini Hour features $12 handcrafted martinis, including the new Caprese, Dirty Blue Olive, new Pickle Rick, and Espresso Martini, paired with oysters and bar bites. Walk-ins Welcomed, Reservations on OpenTable.

• Olio e Più

Guests at Olio e Più can kick off the holiday with brunch favorites and Bottomless Bubbles ($25 pp) during brunch service before easing into Aperitivo Hour from 4–7 PM at the bar and patio, featuring $10 classic cocktails, wines, and bites. The celebration also includes the restaurant’s Martini Monday offering, featuring $10 martinis including Espresso, Dirty, Cosmopolitan, Lemon Drop, and French martinis. The restaurant’s expansive 64-seat corner patio brings a slice of the Italian Riviera to River North, complete with classic bistro seating, lush greenery, and sidewalk views along Dearborn and Illinois Streets. With spritzes, handmade pastas, and one of the neighborhood’s most transportive outdoor dining setups, Olio e Più offers an easy escape for the long holiday weekend. Brunch menu highlights include Toast Francese with mixed berries, vanilla mascarpone cream, maple syrup, Uovo Benedetto with focaccia bread, crispy bacon, fondue, and Uovo Prosciutto e Patate with poached eggs, roasted potatoes, prosciutto, garlic-paprika mayonnaise.

• The Gwen Hotel 

Celebrate Labor Day weekend above the city at The Gwen, where guests can soak up the final days of summer on the hotel’s outdoor terrace. On Saturday, September 5, kick off the long weekend with The Gwen’s signature Tipsy Tea starting at noon, featuring a take on traditional afternoon tea with sweet and savory bites, cocktails and plenty of rosé. Stick around for drinks and bites on the terrace, offering an open-air setting in the heart of downtown for one last summer weekend.

The Loop

• Kindling

Mark the end of summer with a dining experience at Kindling, where Chef Jonathon Sawyer showcases the art of live-fire cooking in the heart of Chicago. Open for lunch and dinner, guests can enjoy Kindling’s wood-fired favorites, seasonal dishes, fresh seafood, steaks, and craft cocktails while soaking up the final days of summer on the restaurant’s outdoor patio. Walk-ins Welcomed, Reservations on OpenTable.

• Cindy’s Rooftop

Send off summer with cocktails, seasonal dishes and skyline views at Cindy’s Rooftop. Perched atop Chicago Athletic Association overlooking Millennium Park and Lake Michigan, Cindy’s offers a spot to soak up the final days of summer. On Saturday, September 5, guests can also catch Navy Pier’s final summer fireworks show of the season at 10 p.m. from the rooftop—a quintessential Chicago way to toast Labor Day weekend.

• The Grillroom Chophouse & Wine Bar

Chicagoans can get a head start on Labor Day weekend at The Grillroom Chophouse & Wine Bar with a special Labor Day Weekend Kick-Off Happy Hour on Friday, September 4 and Saturday, September 5 from 4 p.m. to 6 p.m. Before the holiday crowds arrive, guests can unwind on The Grillroom's patio overlooking Monroe Street while enjoying signature cocktails, wines, and shareable bites in the heart of downtown Chicago. Happy Hour specials include $10 select wines and House Margaritas, $12 Barrel-Aged Old Fashioneds, and a variety of crowd-pleasing small plates, including East Coast Oysters, Meatballs, Tuscan Toast, and Filet Skewers. For those looking for a more substantial meal, guests can also enjoy The Grillroom's Summer Grill Board ($69), designed for sharing or as a satisfying entrée. The board features sliced steak, grilled shrimp, grilled asparagus, corn on the cob, house-made chimichurri, and garlic butter, bringing together the flavors of summer. Patrons can pair the Grill Board with The Smoke Show ($12), a smoky-sweet cocktail made with Reposado Tequila, Mezcal, pineapple juice, fresh lime juice, and agave, finished with a charred pineapple garnish.

• LondonHouse Chicago

LondonHouse Chicago invites guests to celebrate Labor Day at LH Rooftop, located on the hotel’s 22nd floor. Guests can take in panoramic skyline views while enjoying signature cocktails, elevated dining and a DJ spinning from 4 p.m. to midnight on Labor Day. 

Wicker Park

• Easy Bar

Easy Bar, located in Wicker Park, will open at 4 p.m. on Monday, September 7 to celebrate Labor Day with half-price happy hour from 4 p.m. to 6 p.m. Guests can also enjoy evening-long drink specials including $4 Montucky Cold Snacks, $5 Espolón Blanco Shots, $5 Underbergs and $5.50 Domestic bottles and cans. Weather permitting, guests are invited to relax on Easy Bar’s intimate, dog-friendly sidewalk patio, which offers seating for 15 to 20 guests and a laid-back neighborhood atmosphere.

• Estelle's

Estelle's in Wicker Park is giving late-night diners another way to celebrate Labor Day with a special burger offering on Monday, September 7. Beginning at 10 p.m., guests can enjoy Estelle's annual Labor Day hang with half-price build-your-own burgers with the purchase of a drink.

Wrigleyville

• The Graystone Tavern

College football fans can kick off Labor Day weekend at The Graystone Tavern in Wrigleyville with wall-to-wall game day action plus food and drink specials for two matchups including the Kansas State Wildcats on Saturday, September 5 at 6 p.m. and Washington Huskies on Sunday, September 6 at 3 p.m. Fans can enjoy team-inspired food and drink specials throughout the weekend. Graystone will air both games across 15 TVs throughout the bar and weatherproofed patio, complete with overhead string lights, and classic outdoor games including bags, giant Jenga, and giant Connect 4.

Multiple Locations

• Farm Bar

Celebrate the long Labor Day Weekend with fresh, locally sourced fare at Farm Bar in Lakeview or Ravenswood. Whether joining for a leisurely weekend brunch or settling in for a relaxed dinner, guests can enjoy Midwest-inspired comfort food, seasonal ingredients harvested from Farm Bar's own Brown Dog Farm, and handcrafted cocktails. Walk-ins Welcomed, Reservations on OpenTable for Ravenswood and Lakeview.

• Sweet Mandy B's

Just in time for backyard barbecues and long weekend gatherings, Sweet Mandy B’s Lincoln Park and Streeterville locations will be dishing out holiday specials starting Friday, September 4, and will remain open on Labor Day, Monday, September 7, from 9 a.m. to 4 p.m. Specials will include patriotic 6-packs of Sweet Mandy B’s cupcakes (three classic yellow and three chocolate) topped with red, white, and blue star sugars. 

• DineAmic Hospitality

DineAmic Hospitality is celebrating Labor Day with brunch, cocktails, and holiday dining across several of its Chicago restaurants. Bandit and Bar La Rue will all offer Monday brunch, while LYRA will open early on Sunday with an all-day Happy Hour. NAIA will also be open for lunch on Labor Day, giving guests even more ways to enjoy the long holiday weekend.

Suburbs

• Sankyu Sushi & Izakaya

Sankyu Sushi & Izakaya will be open on Labor Day weekend and are offering sushi platters, takeout packages, and catering. 

• Old Town Pour House

Old Town Pour House invites everyone to its weekend brunch this Labor Day (it’s the weekend brunch extended for Labor Day and starting one hour earlier, at 10 a.m.). Served until 3 p.m., guests can dig into signature favorites like Stuffed French Toast, Avocado Toast, Chilaquiles, and Chicken & Waffles alongside the Breakfast Burger, Brisket Biscuits & Gravy, and Steak & Eggs. Kids are covered with Breakfast Tacos, Pancakes, and French Toast Sticks. The restaurant also offers a variety of cocktails, mocktails plus Mimosa flights and breakfast shots. Served from 10 a.m. until 3 p.m. on Saturday, Sunday and Monday, Labor Day, September 1, the weekend brunch is available at at their suburban locations in Oak Brook and Naperville.

• Puttshack

Labor Day Weekend (September 4–7) guests can receive 25% off gameplay using promo code LDW25. Puttshack is also rolling out several fall specials including $9 After 9 every Saturday night where guests can score 9 holes of tech-infused mini golf for just $9 with promo code 9AFTER9, plus enjoy $9 mixed drinks and $9 shareables. Happy Hour is also offered Monday through Friday, 3–6 PM for guests to enjoy $1 wings, $3 draft beers, $10 cocktails, $5 white queso & chips, and a $10 Signature Skirted Double Cheeseburger. Puttshack has also introduced Dirty Sodas with flavors including Peaches and Cream, Island Creamsicle, Strawberry Fields, Milk Bar Cookie Monster.