Plenty of things are happening in May: Mother’s day, AAPI heritage celebrations, national burger day/month celebrations, and the long Memorial Day weekend. While all the festivities are piling up, don’t forget Chicago has plenty of activities and destinations good for exploration on any ordinary day! Check out our list of things to do in Chicago this May, and as always, keep an eye open for our specialty round-ups coming up throughout the month!
Dining
May is destined to be a month of feasting, with many new restaurants opening up, hoping to catch the summer crowd. Later in the month, we will publish a list of new restaurants to try this season. But, for now, check out the must-go time-sensitive dining experiences in Chicago.
Smoke Sessions at Frontier
1072 N Milwaukee Ave, Chicago, IL 60642
From 7 PM-9 PM on Thursday, May 18th, guests can experience and taste the invigorating outcome of what happens when two of Chicago’s top chefs team up together to curate a one-of-a-kind menu, featuring 4 dishes and 4 cocktails! While guests are mingling and sipping cocktails on Frontier’s exceptional beer garden, Chef Jup and Chef Dominique will be presenting, preparing, and plating items like smoked salmon with chili-garlic brussels sprouts, wagyu beef brisket macaroni & cheese, smoked shrimp with ham hock risotto, and maple bacon ice cream cookie sandwiches for the guests to indulge in.
Duck Sel Dinner
Known as one of America’s coolest secret restaurants, Chef/Owner Donald Young is giving diners even more opportunities to get in on the secret experience of Duck Sel, his much-buzzed-about experiential culinary concept! In May, food lovers can witness Young’s culinary creativity come to life through surprising multicourse menus carefully curated for exclusive ticketed events held in a secret location on the following dates:
Friday, May 12 at 7 p.m. (15-course)
Saturday, May 13 at 5:30 p.m. (7-course)
Saturday, May 13 at 8:30 p.m. (15-course)
Sunday, May 14 at 6 p.m. (15-course) *Special Mother’s Day dinner
Friday, May 19 at 7 p.m. (15-course)
Saturday, May 20 at 5:30 p.m. (7-course)
Saturday, May 20 at 8:30 p.m. (15-course)
During the evening, Young will lead up to 16 guests on an exciting fine-dining journey unlike any other out there while serving up delicacies like Black Cod with carrot, kish mish and blossoms, Duck and Waffles with maple, good butter, and blueberries, Memories of Culver’s with “Reeses,” cookie dough and chocolate and more.
Dusek’s x Poilevey & Ascencio Collaboration Dinner
Dusek’s Tavern has been leading the wave with their latest collaboration dinner series, and the latest installment returns this month on May 17th. For May, Chefs Ryan Pfeiffer and Geoff Thompson of Dusek’s will be teaming up with Chefs Oliver Poilevey and Marcos Ascencio of LE Bouchon, Obelix, and Taqueria Chingon for a six-course prix fixe meal of inventive Mariscos dishes, served family style.
Pizza Omakase at Siena Tavern
51 W Kinzie St, Chicago, IL 60654
Chicago’s first Pizza Omakase will happen at Siena Tavern on Wednesday, May 17th. The pizza tasting, which includes an antipasti course and six pizza courses, will be served to guests right at Siena Tavern’s Crudo Bar & Chef’s Counter beginning at 6:00 pm. The two-hour meal will feature a variety of pies including Siena Tavern classics and seasonal preparations. Tickets to this first-of-its-kind dinner are $50 per person, with the option of a beverage pairing add-on from Bar Siena’s sommelier for $25.
Mother’s Day Brunch
Mother’s Day is right around the corner, and nothing is more suitable than taking your mom or mother-figure out for a lovely brunch. Whether you prefer patio seatings where you can enjoy the beautiful weather, a high-end environment within one of Chicago’s luxury hotels, or a celebration of ethnic cuisine, there is something for you in Chicago that will please you and your mom both.
Untitled Prime Rib Dinner
111 W Kinzie St, Chicago, IL 60654
Meat lovers, look over here! Untitled Supper Club in Chicago’s River North neighborhood is serving up Prime Rib every Wednesday featuring three different Prime Rib cuts, four unique sauces and a slew of classic sides. The three cuts diners can choose from include the English, the Queen and Capone. Cuts can be topped with the diner’s choice of sauces like a Classic Bearnaise, a Bourbon Peppercorn, a Grain Mustard Steak Sauce and Untitled’s House Horseradish Relish.
Wicker Park Patio Palooza
On Tuesday, May 23rd, from 6:00 pm to 9:00 pm, a handful of the neighborhood’s best showcase the patio party of the year by banding together to host Patio Palooza! For $35, this ticketed event allows outdoor dining enthusiasts to wander down one of the liveliest stretches of the city of Chicago to grab hosted small bites at hot spots like Smoke Daddy, The Perch, Fat Pour, Takito, and more. Start from either the east end at Bangers & Lace or from the west at Queen Mary—tickets are available at $35 in advance and are available for $45 on the day of the crawl.
Drinking
What is your favorite summer beverage? Some say it’s the season of light, fruity cocktails, while others are loyal to their rich, profound spirits. Either way, Chicago is the perfect place for a casual evening drink or an elegant tasting event. If you wonder where you should go for a drink this month, here are some recommendations from our (spirit-loving) editor.
Single Cask Launch at The M Room
450 N Clark St, Chicago, IL 60654
The M Room will host a launch party on May 11 at 5:30 pm to introduce The Macallan Exceptional Single Cask. Guests will be one of the few to try the rare 2017 and 2018 Exceptional Single Casks side-by-side tasting and enjoy indulgent appetizers, a champagne greeting, and our featured cocktail. An expert guest speaker will guide you through the experience. Tickets are $145 each.
10 Years of Three Dots and a Dash
Join Three Dots and a Dash as they welcome an acclaimed lineup of bartenders from around the world for Three Dots and a Decade, celebrating their 10th birthday and the James Beard Awards. To mark the occasion, original cocktails from each of the renowned bars will be available for a proper toast to ten. Tickets for Three Dots and a Decade are limited and start at $95, plus tax; each ticket includes 5 cocktails along with some tropical bites and musical entertainment.
Lottie’s 89th Anniversary
1925 W Cortland St, Chicago, IL 60622
With Lottie’s being a staple to the Bucktown community since its (alleged) transformation from grocery store to speakeasy during Prohibition, the neighborhood’s favorite watering hole is paying tribute to its long history here in the city with $0.89 burgers (11:00 am to 4:00 pm) and $0.89 cent drafts (all day) on Saturday, May 20th. Offerings include $8.89 pizzas, $6 Tullamore shots, and $7 Tullamore cocktails.
A Taste of Iberia
2024 N Halsted St, Chicago, IL 60614
Cafe Ba-Ba-Reeba! invites you to A Taste of Iberia featuring BBQ Wine. This collaboration with BBQ Wine, known for their Best Bubble Quality, is a love letter to the flavors that fill the Mediterranean coast. From 6:00 PM to 9:00 PM tour through the Iberian Peninsula with an evening of Spanish tapas complimented by Portuguese wine. A Taste of Iberia is a five-course evening where guests are invited to sip, savor and celebrate the cuisine and cultures of the Iberian Peninsula.
