21 Ways to Spend Labor Day Weekend in Chicago

Photograph by Gautam Krishnan

As the Chicago sun bids a gradual farewell to summer, Labor Day emerges as the ideal occasion for a fitting send-off. Whether you seek a delightful family meal or an invigorating adventure, our curated collection of ideas guarantees a perfect match for your preferences!



Unleash your taste buds’ adventure at Barrio. Starting at 10:30am on September 4th, Barrio serves up an imaginative fusion of traditional Mexican flavors with intriguing American influences. This Labor Day, let Barrio take you on a journey of binding cultures, where every dish feels especially creative.


Inside of Bandit

Step into the heart of West Loop’s vibrancy at Bandit. As Labor Day arrives, Bandit opens its doors at 10am, inviting you to relish in its farm-to-table delights and soak in the relaxed, welcoming atmosphere. Whether you’re seeking a leisurely brunch or an early lunch, Bandit promises an experience that blends exceptional food with a low-key, high-vibe ambiance!

Bar Siena

Transport yourself to the streets of Italy without leaving Chicago this Labor Day. Bar Siena opens its doors at 10am, welcoming you to an expansive spread of Italian street food and artisanal pizzas. Beyond the delectable cuisine, the ambiance of Bar Siena whisks you away to a European escape right in the heart of the city.

Old Town Pour House

Turn your Labor Day into a rockin’ good time at Old Town Pour House. From 11am to 3pm, they’re rolling out their legendary Rock ‘N Roll brunch! With a staggering selection of 90 beers on tap and a brunch menu that pushes creative boundaries, Old Town Pour House promises an experience that’s equal parts indulgent and electrifying!

Sweetwater Tavern and Grille

Elevate your brunch game while soaking in city views at Sweetwater Tavern and Grille. On Labor Day, from 10am to 3pm, their brunch offerings promise to please your taste buds with inventive delights like Stuffed French Toast and Breakfast Chimichangas. The fusion of flavors, combined with the elegant atmosphere, guarantees a brunch experience that’s as visually enchanting as it is delicious!

Siena Tavern

3 Girls Toasting at Siena Tavern

Experience a slice of Italian sophistication at Siena Tavern. From 10am, the doors swing open, revealing a world of upscale, classic Italian fares crafted to perfection. The intersection of impeccable service, luxurious ambiance, and delightful dishes is sure to provide a fabulous Labor Day experience. 

The Hampton Social

This Labor Day, gather with friends or family at The Hampton Social for a brunch that’s nothing short of exceptional. From 11am to 3pm, indulge in a selection of delectable items like Grandma Swan’s Pancakes, Sunrise Beach Bowl, and Bananas Foster French Toast. The combination of warm ambiance and flavorful dishes promises a satisfying dining experience!

Sable Hotel & Offshore Rooftop

Elevate your Labor Day Weekend with a dash of luxury at Sable Hotel’s Offshore Rooftop. Experience the dazzling Navy Pier fireworks show from the top of the world’s largest rooftop! Book their special Saturday package, which treats you to a Champagne toast for two, delectable specialty chocolate truffles, an elevated room placement on a high floor, and a leisurely late checkout!

Stan’s Donuts

Le Stan donut at Stan's Donuts

Celebrate an iconic Chicago Labor Day Weekend tradition at Stan’s Donuts! Dive into the spirit of the season by treating yourself to their latest masterpiece. This time, it’s the Lemon Blueberry Le Stan – a sensational donut that oozes with the essence of summer. Picture this: a classic Le Stan donut, generously filled with blueberry lemon zest jam, crowned with a delightful lemon drizzle. Perhaps it’s too intense for the imagination; guess you’ll have to see it for yourself!

Farm Bar

Savor the final days of summer this Labor Day Weekend at Farm Bar, nestled in Chicago’s Lakeview neighborhood. They’re extending their hours on Monday, September 4th, offering lunch and brunch on their dog-friendly patio. From 11am, you can relish their regular menu along with four brunch additions: Short Stack, Eggs Benedict, Wisconsin Pimento Sandwich, and Farm Bar BLT. 

Tutore Cooking School

Making Pasta at Tutore Cooking School

Make this Labor Day weekend memorable by learning the art of Italian cooking at Tutore Cooking School. Founded by renowned chefs Dean Zanella and James De Marte, the school is hosting pasta making classes with a heartfelt twist. 100% of the proceeds will directly support families affected by the Maui wildfires. Your participation will aid the restaurant staff of Chef Peter Marriman’s Big Island Restaurant, helping them rebuild after the devastating fires. Sign up for classes and contribute to this meaningful cause.

Chicago Burger Company

Bid adieu to summer in style at Chicago Burger Company’s Bourbon & Brisket-themed party over Labor Day Weekend. Head to their riverwalk patio on Saturday, September 2nd, from 12pm to 5pm. Enjoy patio games, food and drink specials, and signature favorites. Quench your thirst with $4 White Claws and $15 White Claw buckets, Hornitos Canned Margarita Cocktails, and Tattersall Single Barrel Bourbon cocktails. Dishes like BBQ Smoked Brisket and Smoked Chicken await, along with Tattersall Bourbon samplings from 12pm to 2pm.


Cocktail at LYRA

Discover a holistic dining endeavor rooted in Greek wellness at Lyra. As Labor Day dawns, Lyra opens its doors for a special dinner from 3pm to 9pm, inviting you to explore a menu that delights while also nourishing your body. The earth-toned, indoor-meets-outdoor space creates a tranquil atmosphere that complements the fresh, holistic fare on offer.

Chicago Winery

Gear up for a sensational Labor Day Weekend with Chicago Winery’s Picnic Party Packs. These packs come complete with Rosé and Sauvignon Blanc bottles, a Chef’s Whim for four, a bamboo serving tray with tongs, and a stylish LIVA at Chicago Winery logoed tote bag. And here’s a delightful twist: when you enjoy bottomless mimosas during their brunch, you’re also contributing to a noble cause. 10% of the proceeds from mimosas will be donated to PAWS Chicago!

Things to Do

Tabú & Tetto

Unleash the good times at Tabú and Tetto Chicago during the CHI BOOGIE Labor Day weekend event. Immerse yourself in positive vibes, live music, plus fabulous food and cocktails. With an incredible lineup of artists including Brian Fisher, J Stereo, Khali Melon, Perry A, and Will Galvan, the festivities kick off on Sunday, September 3rd. Party it up from 4pm to 10pm on Tetto, and continue the excitement at Tabú from 10pm until closing!

Performers at Chicago Jazz Music Festival

Jazz Music Festival 

The Chicago Jazz Music Festival is returning to enhance another groovy Labor Day weekend. Click here to learn more about this free festival!

The Chicago Riverwalk

The Chicago Riverwalk is a grand way to spend time off as there is a plethora of things to do. From fruity cocktails to enlightening vistas, there is something for everyone. Peruse CP’s Riverwalk guide and plan your Labor Day itinerary!

Island Party Boats

Use this three-day-weekend as an excuse to party atop the waters of Lake Michigan! Island Party Boats is one of CP’s favorite ways to spend time off-land. Their plethora of various rental boats, charters, and cruises offers floating fun that is fit for everyone!

Shoreline Sightseeing

Shoreline Sightseeing on Chicago River

Shoreline Sightseeing effortlessly unveils some of Chicago’s best angles on their tours. Spending Labor Day weekend sailing on Lake Michigan is surely a fitting way to celebrate the end of summer. Despite the national holiday, the company’s typical fares and schedules are available, allowing families to spend time off in a splendid manner. Schedule your outing here

WingOut Chicago Festival

From Classic Buffalo and Honey Chili to Spicy Garlic and Southern BBQ, WingOut Chicago Festival will supply. Spend your Labor Day Weekend munching on some of Chicago’s most renowned wings. Jake Melnick’s, Joker’s Cajun Smokehouse, The Wild Hare, The Cubby Bear, Offset BBQ, and more will decorate the festival with their expertise! Get your tickets here!

Navy Pier

As one of the city’s biggest tourist attractions, many Chicagoans forget that Navy Pier remains one of the best ways to spend a summer weekend. The endless food, drink, and venture options lead this attraction to be a reliable way to have fun. Read through CP’s Navy Pier article to find what will fit your plan best.

Notify of
Inline Feedbacks
View all comments
Would love your thoughts, please comment.x

Discover more from Concierge Preferred

Subscribe now to keep reading and get access to the full archive.

Continue reading