From delicious firework shows and pop up bars, to staycations in the city and Chicago’s hottest rooftop bars, we’ve rounded up some of the best happenings and offers for Labor Day weekend this year. Whether Chicagoans are going on a road trip, enjoying a staycation or celebrating with close family and friends, these fun activities and specials are sure to entertain locals and visitors alike on one of the last big weekends of the summer!

Enjoy the final summer days this Labor Day weekend at Offshore Rooftop, the world’s largest rooftop deck as recognized by the Guinness Book of World Records and one of Chicago’s most exciting hotspots located at Navy Pier! This year-round rooftop destination offers Chicagoans and travelers alike a full-service bar and world-class kitchen, along with cozy fire pits, a gaming area, and multiple large gathering spaces for you and your friends. Enjoy some of their latest libations such as their Melondramatic, Left on Red, and Dark Side of the Moon, while you enjoy the best seats for the final show of the Navy Pier fireworks this Saturday evening. For more information and to reserve your table today, please visit here.

Looking for a last minute Labor Day weekend staycation? Look no further than Sable at Navy Pier, the first hotel to break ground and make waves on one of the city’s most iconic and historic landmarks! Offering sweeping, unparalleled views of Lake Michigan and the Chicago skyline, the hotel is a destination truly unlike any other. This high-end oasis combines lush accommodations with elegance and comfort, with each room boasting floor to ceiling windows with unparalleled lake and skyline views, along with corner room upgrades, serenity beds, and spacious living room areas. Those looking to get away without getting away will be in for the ultimate treat on Navy Pier. Sable at Navy Pier is offering their final Saturday Firework Package for guests to have a spectacular stay with a front row view to the Navy Pier fireworks that conclude this weekend. To book an upcoming staycation this upcoming summer season, please click here.

Celebrate Labor Day weekend in an unforgettable way right on the water with City Cruises Chicago! Enjoy the final Fireworks Display on Navy Pier during one of City Cruises’ Fireworks Premier Plus Dinner Cruise on the Chicago River, a Chicago Seadog Lakefront Fireworks Cruise and more. Other spectacular options to check out this weekend include a Chicago Seadog River & Lake Architectural Tour, a weekend Premier Plus Lunch Cruise on the Chicago River, a Dinner Cruise on Lake Michigan and more. For more information or to book your cruise today, please click here.

Enjoy a Labor Day weekend getaway to The Rose Hotel Chicago O’Hare with a shopping spree at the Fashion Outlets of Chicago just around the corner! Book The Rose’s Fashion Outlets of Chicago Shopping Package which includes a Fashion Outlets Savings Pass, Complimentary Coat/Bag Check at the shopping mall, 3 p.m. Late Checkout, Continental Breakfast, Free Overnight Parking, and a Complimentary Shuttle to Fashion Outlets of Chicago. To book your stay or to learn more, please visit here.

Summer is wrapping up! If you are looking for a dynamic artistic exhibit as a place to take your family this weekend, the Louvre Fantastique exhibit in Oak Brook is an amazing opportunity. Offering projections, interactive art pieces, animated and virtual reality aspects, this exhibition is something exciting for families of all ages to experience while also learning about French art and history. All patrons will also have an audio guide at hand just for them as another way of learning about these masterpieces. The Louvre Fantastique pop-up is currently open and running Wednesday through Sundays through October! To find out more about this one-of-a-kind field trip opportunity click HERE!

For friends and couples looking for a new hot spot to check out this weekend, make sure to visit Kōmo Chicago, a boundless Japanese fine dining destination on West Loop’s Restaurant Row, 738 W Randolph St. Executive Chef Macku provides precision thoughtfully woven into each dish and delivers the utmost attention to the quality of each ingredient. A contemporary design that seamlessly pays homage to Japanese culture, Kōmo takes fine dining to another level amidst an already impressive culinary scene in the city’s most famous dining districts.

Feeling lucky this holiday weekend? The legendary Horseshoe Hammondlocated just a quick 20-minute drive from downtown Chicago right along Lake Michigan at 777 Casino Center Drive in Hammond, Indiana, ranked as one of the top 2022 Best Places to Work by the Indiana Chamber of Commerce for the twelfth consecutive year, is the ultimate destination with plenty to enjoy! This one stop entertainment haven is known to offer visitors the highest limits, featuring over 40 progressive jackpots starting at over $50,000. Grab your date and enjoy access to over 847 slot machines, 104 table games, over 1,100 penny machines, 15 poker tables, an impressive roster of restaurants, plus The Venue which hosts some of the hottest live entertainers including Fantasia this weekend!

Ditch the typical hangout this weekend, and instead enjoy a fun experience and good vibes at Puttshack Oakbrook Center! Puttshack is the world’s first and only upscale, tech-infused mini golf experience that is perfectly complemented with an array of global food and beverage offerings you and your date can share between games. Couples, families and friends are all welcome, and will be surrounded by an all-around high-energy and will allow for plenty room for that Insta selfie. For more information, purchase a gift card, or book your upcoming game, please visit

Dinos, paleontologists, and masterminds alike are invited to Replay Lincoln Park, 2833 N. Sheffield Ave., for the bar’s biggest pop-up experience yet: Jurassic Bar. This all-immersive pop-up is running through Labor Day weekend so don’t miss out! Jurassic Bar offers fans the opportunity to enter the island of Isla Nublar, encountering an array of deadly dinosaurs, custom-built vehicles, island foliage, and other nods to the film series along with Jurassic Park-themed trivia and plot-inspired cocktails fit for even the most daring explorers you know, and much more. This event is 21+ and all of the games are free, with no reservations, tickets, or tokens required.

Soak in the last of the Summer sun and catch the last of Chicago’s fireworks shows this weekend overlooking Lake Michigan on the gorgeous patio of Lirica restaurant, located right on Navy Pier. The Latin and Iberian-inspired eatery led by Executive Chef Jen Zambrano features an all-day menu of delicious fare and handcrafted cocktails ranging from flavor-filled small shareables to mouthwatering entrees including Lirica’s Signature Paella. To make a reservation, please visit the restaurant’s website.

With so many fun things to do this long weekend, leave the city parking woes behind and check-in to the new dual-branded Canopy by Hilton Chicago Central Loop and Hilton Garden Inn Chicago Central Loop to take advantage of their new “Park for Twenty Two” packages. Enjoy self-parking Thursday through Sunday with your stay at a discounted rate of just $22 per night. The package boasts a savings of $23 per night on parking and to add to the convenience, includes in-and-out privileges. To book the package at Canopy by Hilton Chicago Central Loop, please visit their website. To book the package at the Hilton Garden Inn Chicago Central Loop, please visit their website.

Game of Irons is hole-in-one fun for all-ages, open all Labor Day weekend long in the Oak Brook Promenade. Illinois’ largest indoor virtual golf simulator experience offers an oasis for avid golfers and beginners alike, featuring 16 simulator bays with GOLFZON Arcade Gaming, Driving Range capabilities and access to over 200 of the World’s most beautiful courses. The golf-lover’s getaway also features a full restaurant and bar with incredible Happy Hour deals available to enjoy on Labor Day from 3-6 pm including $3 Draft Beers, $18 Buckets of Domestics, $4 Glasses of Wine and various small plates for just $5. To enjoy BOGO on an hour of play, use code HERON. To book a bay, please visit their website.

Shop til you drop over the long weekend and take advantage of the holiday sales at the Roosevelt Collection Shops. The South Loop lifestyle center is home to a variety of retailers including H&M, Old Navy, Ulta Beauty, Victoria’s Secret, Francesca’s, The Container Store, Kido and more, plus incredible eats including The X Pot and Pacino’s Authentic Italian. Catch one of the latest new flicks at the Showplace ICON after a long day of shopping, or chill out on their spacious communal outdoor rooftop with incredible city views. For a full list of happenings at the Roosevelt Collection Shops, please visit their website.

Long weekends call for double the amount of brunch! Enjoy a delicious Latin-American inspired Sunday brunch from 10 am – 2 pm at the city’s most colorful restaurant, Carnivale. Dive into Dulce de Leche Pancakes or savor a scratch-made Seafood Paella in their iconic main dining room or out on their spacious patio overlooking the West Loop. To make a reservation, please visit the restaurant’s website. Another West Loop must-try, Fulton Market Kitchen offers brunch service in their part-restaurant, part-art gallery, full-style venue on Saturdays and Sundays. In addition to a variety of artful takes on classic brunch items, the vibrant hotspot offers a range of unique handcrafted cocktails and lo to no ABV drinks to enjoy with your meal. To make a reservation, please visit their website.

There is no better place to spend a long weekend than on a gorgeous patio in the heart of the city! Tzuco, the Mexican-French concept from Michelin Star Chef Carlos Gaytán, has recently introduced vibrant new dishes to the menu, featuring pure ingredients and extraordinary flavors that tell the story of their origin, including Charred Avocado Salad and Heirloom Tomatoes. Creating an over-the-top, floral outdoor oasis in the middle of River North, Tzuco has also debuted a new installation on their patio, featuring thousands of blooming burnt orange and magenta Bougainvillea, and beautiful Willow and Wisteria tree branches adorning the restaurant façade. Reservations are available on Resy. For more information, please visit or call (312) 374-8995.

Kick off the college football season this weekend at Gaelic Park Chicago (6119 W. 147th Street, Oak Forest, IL 60452) this Saturday, September 3rd  with the Notre Dame football game against Ohio State. Tailgating at Gaelic Park’s Carraig Pub Beer Garden begins at 5:30 pm leading up to kickoff at 6:30 pm. Fans can partake in great specials like $6 pints of Guinness (the official beer of Notre Dame Football) and $9.75 Irish Sausage and Chips. Prizes will also be given out for the best dressed Notre Dame fans. An impressive, covered bar, casual seating areas, umbrellas, multiple TVs, and beautifully landscaped space make this the perfect spot to catch the game. Draft beer, wine and liquor selections are plentiful as are non-alcoholic beverages. A special beer garden food menu will also be available.

Spend the long weekend outdoors at the Chicago Firehouse Restaurant! Formerly Engine Company 104 of the Chicago Fire Department, Chicago Firehouse Restaurant, the landmark restaurant at 1401 South Michigan Avenue features both a lush backyard patio providing a quaint escape in the city as well as an outdoor veranda affording picturesque views of the South Loop skyline. Take advantage of the restaurant’s Happy Hour from 4:30 – 5:30 p.m. Tuesday – Saturday. Enjoy items such as Oysters on the Half Shell, Signature Lobster BisqueBuffalo Chicken Sliders, House Wines and Beers, all for $5. For more information or to make a reservation, visit

After a long and hot season of summer fun, Raging Waves, Illinois’ largest waterpark located at 4000 N. Bridge St. in Yorkville, will close out their 15th year of delivering family fun on Monday, September 5, 2022. Through the long Labor Day Weekend, guests are invited to experience various attractions including 32 water slides, a wave pool, three kiddie pool areas, relaxing lazy river, 43 private cabanas, and more. Thrill seekers will be able to experience the six-lane mat racing water slide, aptly named Aussie Mat Dash. The first Proslide RallyRACER™ in Illinois and one of three in the world, the Aussie Mat Dash can be found at the south end of the park, near The BoomerangCyclone and the Hungry Croc Restaurant. Tickets are available online at

Pops for Champagne, the nation’s most acclaimed champagne bar, is celebrating their 40th Anniversary this month by serving a rotating $40 pour of unique champagne, not typically served by the glass, such as 2006 Pierre Moncuit Cuvée Elizabeth, 2008 Pierre Paillard La Grande Récolte, and 2013 Vintage Louis Roederer, throughout the year, in addition to opening their underground speakeasy, Watershed, after extensive renovations. Watershed has been completely remodeled, from updated furniture and flooring, to an enhanced sound system, while honoring the historic features of the property. Watershed will also introduce a ‘seasonal’ cocktail menu where every season focuses on a different television show, paying homage to the meaning of “watershed” in broadcasting, which is the time of day after which programming aimed towards mature or adult audiences is permitted.