For many Labor Day Weekend marks the de facto end of summer. For others, it’s a weekend filled with outdoor activities, the start of football season, and, of course, more bar and restaurant specials than you know what to do with. In Chicago, patio and rooftop season is still very much in full swing. Say you find yourself bopping around the city during LDW 2021and looking for the next ice cold beer or delicious plate of food, check out these 7 restaurants running deals.

But here at UrbanMatter we want to take it one deeper for you. If you’re a suburbanite, or an out-of-towner looking for a weekend getaway in the city, we’ve added 4 Chicagoland area hotels putting on events for the weekend festivities to boot.

Eat. Sleep. Breathe. It’s really that easy.



On your left! Bring your party to Recess this Labor Day and make sure one of them knows how to ride a bike. You’ll need your best rider to help you mix a pitcher of margaritas on Recess’ new Fender Blender Patron Bike, which serves six for $75. You’ll also enjoy being out on Chicago’s largest patio one last time for Summer 2021 before they need to bring back the outdoor heaters. Reserve your party’s table now for Labor Day by visiting

The Smith

Just in time for the holiday weekend and last moments of summer, Chicago residents can now soak up the sun with The Smith’s Picnic Totes! The $48 tote serves two guests and includes Toasted Sesame Hummus & Vegetables, a Caesar Salad, potato chips, chocolate chip cookies, and choice of two sandwiches, either the Grilled Chicken, BLT+E, The Smith Burger or the Veggie Burger Royale. Looking to upgrade? Diners can also add the Lobster Roll for an additional +$15 per person.


Logan Square’s new Midwestern salumeria just launched dinner service every Friday, Saturday and Sunday, perfect for celebrating the holiday weekend. Available weekends from 5:30 to 10 p.m, the dinner menu features dishes like their signature Lardon Salad, decadent Crispy Duck Leg Confit and Steak Frites. Reservations are available on Resy. This new dinner service adds onto Lardon’s daily offerings, including coffee and pastries starting at 7 a.m., lunch from 11 a.m. to 4 p.m. and house-cured meat and artisanal cheeses until close.


Looking to plan the perfect picnic with your friends or family this Labor Day Weekend? Nonnina is offering the ultimate “RiverWalk Package” which features a large salad, 12-inch sub, and a bottle of wine for $35.

Farm Bar

Lakeview’s favorite neighborhood spot is opening early on Labor Day itself, giving you a chance to ward off the Monday scaries before heading back to work on Tuesday. Monday Brunch specials include: Midwestern farm-to-table favorites like monkey bread and buttermilk pancakes with Wisconsin-made apple brandy maple syrup, plus the Farm Bar-favorite breakfast sandwich—which features slow-roasted pork belly on French toast with a sunnyside farm egg, strawberry jam, melted Monterey Jack cheese and spicy potatoes. Any meal is paired perfectly with an espresso martini, seasonal watermelon mimosa or cider sangria.

PB&J: Pizza, Beer, & Jukebox

This Labor Day weekend, kick off the festivities at West Loop hotspot, PB&J, with a variety of special frozen drinks! Sip on a frozen “Sour Watermelon” featuring Pink Lemonade Smirnoff, Lemon and Red Bull Watermelon Edition, or the Chi Colada, a mix of Captain Morgan, Pineapple and Coconut. Lastly, diners can sit on the expansive patio and soak in the sun while enjoying the best of both worlds with the new “West Loop Vice”, a mixture of both the Sour Watermelon and Chi Colada. Looking to start the weekend festivities early? Finally, end the Dog Days of Summer with a Splash! Join PB&J at their “Puppy Pool Party” on Wednesday, September 1st.

El Che Meat & Provisions

As your family plans to gather for your Labor Day cookout, El Che Steakhouse & Bar’s retail marketplace is offering everything needed for a successful BBQ with take-home grilling kits. The Weekender Kit ($57) includes a 4 pack short ribs, 2 morcilla links, 2 chorizo links, 4-pack BabyGold Beer—part of his partnership at iconic Berwyn establishment Fitzgeralds—plus 4 oz each of housemade Chimichurri, Chimichurri Rojo, Salsa Criolla. Steak lovers can take home the Ultimate Steak Box ($220) which includes 8oz Filet, 14oz Ribeye 16oz Tira de Asado, 16oz New York Strip, 32oz Bone-In Ribeye and 1/2 Pint Chimichurri. Finally, before the summer ends the Beat the Heat Wine Box ($45) offers three must-try South American wine bottles, best served chilled. Book via Toast here.


The Blackstone 

Stay at The Blackstone, an architectural icon rooted in Chicago’s past, and book the hotel’s “End of Summer Escape” flash rate for Labor Day Weekend. Enjoy 20% off the best available rate on bookings now through September 9, starting at just $211. Just a short walk away from Millennium Park, the Museum Campus and Lake Michigan, you can experience art, history and nature from one location. In addition to this great end of summer rate, The Blackstone is offering two new packages: “Chicago Fire’d Up” that has fans in mind and turns the soccer game into an amazing overall experience and “Soulful Chicago,” a customized tour that transports guests to the golden twenties where they will hear stories of Chicago’s past.

Radisson Blu Aqua Hotel 

Experience luxury this Labor Day Weekend by booking Radisson Blu Aqua Hotel’s Suite Retreat Package.” Relax with a stay in an Ambassador Suite and receive 20% off the best available rate, breakfast for two and a 2 p.m. late check-out. During your stay enjoy not one but two pools. Ideal for any type of weather, the indoor and outdoor pools offer the best of both worlds. The outdoor terrace also includes the city’s largest recreation deck, a running track, indoor basketball court, media and game rooms, and an 8,000-square-foot fitness center with state-of-the-art equipment. For those that want to explore, the hotel is located minutes from the Magnificent Mile, Millennium Park, Grant Park, and Navy Pier.

Sheraton Grand

Sheraton Grand is the perfect place to stay when visiting the city this Labor Day Weekend. A blend of refined comfort and stylishly appointed accommodations, the hotel offers striking views of the lake, river and Chicago skyline. Celebrate the start to the holiday weekend on Friday from 5 p.m. to 8 p.m. and experience the hotel’s new concert series, “Riverfront Riffs.” Listen to local musician Dave Herrero sing the blues along the Riverwalk outside of Chicago Burger Company while enjoying tasty dishes and refreshing beverages. If traveling with the family, the hotel’s location steps away from Millennium Park and Navy Pier offers daytime adventures and a refreshing pool to come back to after a fun-filled day.

Hotels of Oak Brook

Escape the city over the holiday weekend and celebrate Labor Day in Oak Brook. A serene suburb setting just beyond city limits, the Hotels of Oak Brook offer a great alternative to downtown Chicago. Just 15 miles west of the city, Oak Brook is home to six outdoor parks, one of the Midwest’s hottest shopping destinations Oak Brook Center and seven hotel options for all budgets. While visiting experience the largest exhibition of original Frida Kahlo works in the Chicagoland area in over 40 years or Human+Nature Exhibit at Morton Arboretum.

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