11 Chicago Restaurant and Hotel Deals for Labor Day Weekend


For many, Labor Day weekend marks the de facto end of summer in Chicago. For others, it’s a weekend filled with outdoor activities, the start of the football season and, of course, more bar and restaurant specials than you know what to do with. In Chicago, the patio and rooftop season is still in full swing. Say you find yourself scouring the city and looking for the next frozen beer or a delicious plate of food, check out these 11 restaurant and hotel deals available in Chicago for Labor Day weekend.

But here at UrbanMatter we want to go even further for you. If you’re a commuter or an out-of-town looking for a weekend city break, we’ve added 4 Chicagoland area hotels that host events for the weekend festivities.

To eat. To sleep. To breathe. It really is that easy.


To your left! Bring your group to Recess this Labor Day weekend in Chicago and make sure one of them knows how to ride a bike. You will need your best jumper to help you mix a pitcher of margaritas on the new Fender Blender Patron from Recess. Bicycle, which serves six for $ 75. You’ll also enjoy stepping out on Chicago’s largest patio one last time for the summer of 2021 before having to bring back the outdoor heaters. Reserve your Labor Day party table now by visiting https: //www.chicagoinrecess.com.

If you’re looking for Labor Day events in Chicago, now residents can soak up the sun with The Smith’s Picnic Totes! The $ 48 tote serves two people and includes grilled sesame hummus and vegetables, a Caesar salad, chips, chocolate chip cookies and a choice of two sandwiches, including grilled chicken, BLT + E , the Smith Burger or the Veggie Burger Royale. Looking to upgrade? Guests can also add the Lobster Roll for an additional $ 15 per person.

Logan Square’s new Midwestern salumeria has just launched a dinner service every Friday, Saturday and Sunday, perfect for celebrating the holiday weekend. Available weekends from 5:30 p.m. to 10 p.m., the dinner menu features dishes like their signature bacon salad, crispy duck leg confit, and steak fries. Reservations are available on Resy. This new table service is added to Lardon’s daily offer, including coffee and pastries from 7 a.m., lunch from 11 a.m. to 4 p.m. and homemade cold meats and artisan cheeses until closing.

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

Lakeview’s favorite neighborhood spot opens early on Labor Day, allowing you to stave off Monday fears before returning to work on Tuesday. Monday brunch specials at this Chicago restaurant include farm-to-table Midwestern favorites like monkey bread and buttermilk pancakes with Wisconsin apple brandy maple syrup, as well as Farm Bar’s favorite breakfast sandwich, which features slow roasted pork belly on French toast with a sunny farm egg, strawberry jam, melted Monterey Jack cheese and spicy potatoes. Any meal pairs perfectly with an espresso martini, seasonal watermelon mimosa or cider sangria.

This Labor Day weekend, kick off the festivities at the West Loop hotspot, PB&J, with a variety of frozen drink specials! Sip a frozen “Sour Watermelon” with Pink Lemonade Smirnoff, Lemon and Red Bull Watermelon Edition, or Chi Colada, a blend of Captain Morgan, pineapple and coconut. Finally, diners can sit on the expansive patio and soak up the sun while enjoying the best of both worlds with the new ‘West Loop Vice’, a blend of 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.

While your family plans to get together for your Labor Day meal, El Che Steakhouse & Bar’s retail market has everything you need for a successful barbecue with on-the-go grill kits. The Weekender Kit ($ 57) includes a pack of 4 ribs, 2 links of morcilla, 2 links of chorizo, a pack of 4 BabyGold beers – part of its partnership with the iconic establishment of Berwyn Fitzgeralds – plus 4 oz each of Chimichurri, Chimichurri Rojo, Salsa Criolla. Steak lovers can take home the Ultimate Steak Box ($ 220) which includes an 8oz Tenderloin, 14oz Ribeye, 16oz Tira de Asado, 16oz New York Strip, 32 oz with bone and 1/2 pint of Chimichurri. Finally, before the end of summer, the Beat the Heat Wine Box ($ 45) offers three must-have bottles of South American wine, best served chilled. Book via Toast here.


Stay at the Blackstone, an architectural icon steeped in Chicago’s past, and book the hotel’s “End of Summer Escape” flash rate for Labor Day weekend. Enjoy 20% off Best available rate on bookings until September 9, starting at just $ 211. Steps from Millennium Park, Museum Campus and Lake Michigan, you can experience art, history and nature all from one place. In addition to this great late summer rate, The Blackstone is offering two new packages: “Chicago Fire’d Up“which has the fans in mind and turns the football game into an incredible overall experience and”Chicago soul,”A personalized tour that transports guests to the Roaring Twenties where they will hear stories from Chicago’s past.

Experience luxury this Labor Day weekend by booking the Radisson Blu Aqua Hotel’s Suite Retreat Package.”Relax by staying in an Ambassador Suite and get 20% off the best available rate, breakfast for two and a 2pm late check-out. During your stay, enjoy not one but two swimming pools. Perfect for any weather, indoor and outdoor pools offer the best of both worlds. The outdoor patio also features the city’s largest recreation platform, 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 who want to explore, the hotel is located just minutes from the Magnificent Mile, Millennium Park, Grant Park and Navy Pier.

The Sheraton Grand is the perfect place to stay for sightseeing this Labor Day weekend. A blend of fine comfort and elegantly appointed guestrooms, the hotel offers breathtaking views of the lake, river and Chicago skyline. Celebrate the start of the holiday weekend on Friday 5-8pm and experience the hotel’s new concert series, “Riverfront Riffs”. Hear local musician Dave Herrero sing the blues along the Riverwalk outside the Chicago Burger Company while enjoying tasty food and refreshing drinks. If you’re traveling with the family, the hotel’s location just steps from Millennium Park and Navy Pier offers daytime adventures and a refreshing pool to come back to after a busy day.

Escape the city over the holiday weekend and celebrate Labor Day at Oak Brook. A serene suburb located just beyond the city limits, Oak Brook hotels provide a great alternative to downtown Chicago. Just 15 miles west of town, Oak Brook is home to six outdoor parks, one of the Midwest’s top shopping destinations in Oak Brook Center, and seven hotel options to suit all budgets. During your visit, discover the biggest exhibition by Frida Kahlo of origin has been working in the Chicagoland region for over 40 years or Human + Nature Exhibition at Morton Arboretum.

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