What to Eat, Drink, See & Do in May
I know it may not feel like it yet, but we PROMISE summer is almost upon us. So, as the weather warms and patio season nears, treat yourself to a night out! Whether it’s drinking a beer with your buddies from college, dressing up for high tea or listening to live music while sipping a cocktail, Chicago is starting the summer months off with a bang! We’ve compiled a list of some of the best events to check out this month to make it extra easy to enjoy…
Run the for Roses at The Kentucky Derby @ Hampton Social on May 7 {Multiple Locations}
We may not be in Kentucky and there may be no space for horses in the city, but that doesn’t mean we can’t celebrate the Kentucky Derby anyway. On May 7, Hampton Social will be celebrating the derby the right way, with live music, Rosé Mint Juleps, and live viewing of this year's biggest race at all their locations!
Take a Bartending Class at City Winery on May 8 {1200 West Randolph Street, Chicago; 312.733.9463}
If you’ve ever wanted to be a bartender, check out one of City Winery’s bartending classes and become a pro mixologist in just one session. Plus, their spring class happens to take place this weekend on Mother’s Day, making it the perfect last-minute Mother’s Day gift so you and your mom both enjoy a good drink! All tools will be provided and you’ll get to spend the evening enjoying three unique cocktails.
Drink at the Bottleneck Craft Beer Week from May 16-22 {Multiple Locations}
Beer-lovers are going to want to head to one of Old Town Pour Houses locations this month for Craft Beer Week! In addition to Old Town Pour House, you can also visit Sweetwater Tavern and South Branch for $2 off Bottlenectar drafts, Bottleneck’s collab brew with Goose Island, along with their choice of flights to sample craft brews from across Chicagoland and the Midwest. This annual event will also include delicious pairings as well as a special menu, with items like Italian Beef Flatbread with beer jus dipping sauce that pairs perfectly with Dovetail’s Vienna Lager.
Dig in to Rodney Scott & Big Star’s Whole-Hog BBQ on May 22 {1531 North Damen Avenue, Chicago; 773.235.4039}
For one day only, legendary (and Netflix-famous) BBQ master Rodney Scott is headed to Chicago to team up with Big Star’s Chef Paul Kahan & his crew. Scott will be making and serving his renowned whole-hog barbecue as well as signing copies of his cookbook “Rodney Scott’s World of Barbecue: Every Day is a Good Day.” Spend your Sunday enjoying some great company and amazing food!
Indulge in Afternoon Tea at The Peninsula, Fridays through Sundays at 2:30 and 4:30PM {108 East Superior Street, Chicago; 312.337.2888}
Start your summer off on a classy note by throwing on some fancy dress and making a reservation for Afternoon Tea at The Peninsula Chicago Hotel. Afternoon tea will be offered Fridays through Sundays, with seatings available at 2:30 and 4:30 pm. Served in the heart of The Peninsula, there’s a rotating menu depending on the season and an arrangement of various teas, scones, tea sandwiches and desserts to share with your table. You’ll feel like royalty!
Have a Happy Hour at Boleo, Wednesday-Saturday from 5-6PM {122 West Monroe Street, Chicago; 312.750.9007}
If you’re tired of the same old song and dance when it comes to your happy hour, head to Boleo for a taste of the sultry beats of South America. Stop by from 5-6PM Wednesday through Saturday and enjoy drinks like the Boleo Handshake, their beer of the day choice, shots and more! While you’re there, make sure to try some of their appetizers including their Yaquitas (crispy yucca fries with rocoto aioli).
Bake CBD Cake Cookies from Budzy Box
Let’s face it, there’s never a bad time to bake and eat a cookie. Grab some of your friends for a movie night and cook a batch of the CBD Cake Cookies from Budzy Box. With only simple, honest and DELICIOUS ingredients including CBD isolate, you’ll be sure to end your day on a high note with these. Plus, the mix comes from a local, woman and Black-owned business, all of which we love to see!
Boogie to Live Music at The Whistler {2421 North Milwaukee Avenue , Chicago; 773.227.3530}
With all that’s been going on in the world recently, nothing sounds better than listening to live music with some friends in our favorite city. One of Logan Square's best hangouts is serving craft cocktails and pumping up the live music. All summer long The Whistler will be featuring an all-star lineup of live musicians with music ranging from French disco to Dixieland to lo-fi hip hop and beyond.
By Madison Freeman, Special Correspondent