Labor Day Dining and Drinking Guide

As August winds down and summer makes way for fall, Labor Day marks the unofficial end of the season. Sigh. In this case, you'll want to make the most of it and send summer off properly with these Labor Day specials and events. 


Old Town Pour House
Old Town Pour House

Bid summer adieu in style with some Labor Day brunch at Old Town Pour House. The bar and restaurant will serve a special holiday menu on Monday, September 7, from 11:30 a.m. until 2:30 p.m. Featured specials include shrimp and grits, breakfast tacos, brisket and gravy, and drinks like Beerlinis (Voveti Prosecco, peach puree, seasonal beer) and Bromosas (Stoli, Two Brothers Ebel’s Weiss, Prosecco, Voveti, orange juice, Red Bull). 

The Dawson’s final City Limits event of the season takes place Sunday, September 6. The restaurant’s concert series winds down with Latin folk rock band Radio Free Honduras, plus Mai Tais and peel & eat shrimp. It all goes down from 4:00 p.m. until 7:00 p.m. on the spacious patio. 

Speaking of shrimp, Wicker Park’s Wixter Market is offering Labor Day discounts and specials all weekend long. The sustainable, flash-frozen seafood shop will be doling out discount bags of “All Natural, GAA Certified Jumbo Shrimp” to guests who purchase a one- or two-pound bag of the product, from September 1 through September 6. Additionally, anyone who participates in the offer will receive a grilled shrimp recipe from Michael Sheerin of Embeya. 

In other Labor Day brunch news, One Off Hospitality is getting in on the holiday action with brunch at Nico Osteria and Publican Quality Meats. The former will serve brunch from 9:00 a.m. until 4:30 p.m. on September 7, featuring an early peek at the restaurant’s late summer cocktail menu. Available for the day, Head Bartender Matty Eggleston’s Blackberry Bunga Bunga contains a collection of fins mixed with fresh and sous vide blackberries, citrus, mint, eucalyptus, cocoa, and cardamom. It’s available by the glass of the pitcher. Meanwhile, Publican Quality Meats will be open for brunch from 10:00 a.m. until 3:30 p.m., in case you’re looking to end your summer on a meaty note. 

Labor Day weekend marks the second annual Hot Dog Takeover at Rockit Burger Bar. From September 4 through September 7, the Wrigleyville beef bastion will transform their signature burgers into burger-inspired hot dogs. On the menu: the Motherclucker made with a Vienna beef dog, applewood-smoked bacon, cheddar, bourbon BBQ sauce, and a pretzel bun; the Truffle Mushroom with a beef dog, mushrooms, Gruyere, sauteed mushrooms, truffle creme fraiche, and a side of truffle fries; the Hottie featuring a Vienna dog, breaded stuffed jalapenos, habanero Jack cheese, and ghost pepper aioli; and the BBQ Bourbon with buttermilk blue cheese, grilled red onion, housemade bourbon BBQ sauce and bacon aioli. To drink, Rockit Burger Bar will feature $5 Budweiser Tall Boys and $5 ‘Merica shots. 

Raise a glass to summer at Lottie’s Pub with some Labor Day booze specials. Between noon and 4:00 p.m. on September 7, the Bucktown bar will be slinging $1 mimosas, $3 Bloody Marys, $3 Absolut mason jars, and $3 Jamesons.             

Celebrate Labor Day in style at City Winery as part of their fourth annual country-themed Labor Day Bubbly-Q event on September 7. From 2:00 p.m. until 9:00 p.m., the 5,000 square foot courtyard patio and indoor concert venue play host to wine specials, live music, and a pig roast. For $15, guests get a special red, white, and blue limited edition split of Chandon bubbly. Musical performances will include The Hoyle Brothers, Angela Perley & The Howlin’ Moons, and Junior Brown.                           

- Matt Kirouac