Chicago Food & Drink Events

May 2019

Chicago is a foodie's dream. Each month, there's a new batch of food and drink events that offer a taste of the city's scorching-hot culinary scene. You can take part in exclusive tastings, cocktail classes, talks with celebrity chefs, pop-up dinners, and more. Here's a preview of just a few of Chicago's upcoming food and drink events: 

James Beard Eats Week and Awards

JBF event at Eden
Photo courtesy Eden

April 26 – May 6

This culinary celebration includes more than 100 Chicago restaurants, who will be offering special dishes and menus leading up to the James Beard Awards on Monday, May 6. Explore the full list of participating restaurants, then check out the awards-inspired events throughout the city (like cool pop-ups and chef collaborations).

Wine Spectator Grand Tour

Wine Spectator at Navy Pier
Photo courtesy Wine Spectator Magazine

May 2

If you’re a wine lover, you’ll definitely feel at home at Wine Spectator’s Grand Tour at Navy Pier. Attendees can mingle with winemakers and sample over 240 unique wines rated 90+ by the editors of Wine Spectator Magazine. A $200 general admission ticket ($325 for VIP) includes tastings of red, white, rosé, and sparkling along with light food, dessert, and a souvenir wine glass to take home. Purchase tickets and find more information here.

Kentucky Derby Party at Tavern on Rush

Mint julep at tavern on rush
Photo courtesy Tavern on Rush

May 4

Grab your Derby Day hat and head to Chicago’s Gold Coast to celebrate the 145th Kentucky Derby. Tavern on Rush will be hosting its 8th annual day-long derby viewing party with $8 mint juleps and food specials throughout the day. Be sure to come dressed in your Southern best as Tavern on Rush will be hosting a Best Hat contest with a first place prize of $1,000 and a second place prize of $500. Click here for more information.

Chicago Beer Classic

Chicago Beer Classic
Photo courtesy Chicago Beer Classic 

May 4

Who wouldn’t want to spend a spring Saturday sampling hundreds of Chicago beers in the middle of Soldier Field? With over 30 breweries pouring 150 craft beers, food, games, and more, the Chicago Beer Classic is a can’t-miss event for beer lovers. General admission tickets are sold for $69 and VIP for $89. Guests can choose from two different sessions: 11:30 a.m. – 2:30 p.m. or 4:30 p.m. – 7:30 p.m. Purchase tickets and find additional details here.

Cinco on the Street Festival at Broken English Taco Pub

Broken English
Photo courtesy Broken English Taco Pub

May 4 – 5

Broken English Taco Pub is taking it to the streets for their first-ever Cinco on the Street Festival. Celebrate Cinco de Mayo with tacos, tequila tastings, live music, luchadors, and more in Chicago’s picturesque Lincoln Park neighborhood. A $5 suggested donation will benefit the Stefani’s Children’s Foundation. VIP packages are available as well, starting at $30 and include two tacos, two margaritas, and a tequila tasting. Click here to purchase tickets.

Flower Cupcake Icing Class at Magnolia Bakery

Magnolia Bakery
Photo courtesy Magnolia Bakery

May 11

Just in time for Mother’s Day weekend, Magnolia Bakery is offering a one-of-a-kind class for all cupcake lovers in Chicago. Attendees will learn how to make Magnolia Bakery’s flower cupcakes, including how to decorate them like a pro with pastel buttercream. The $75 ticket includes six cupcakes you’ll make and decorate during class, the recipes for vanilla cupcakes and vanilla buttercream, cupcake decorations, sprinkles, an at-home starter cupcake icing kit, and more. Reserve your sweet spot here.

Lincoln Park Food Truck Social

Lincoln Park Food Truck Social
Photo courtesy Food Truck Social

May 11

The Lincoln Park Zoo will host over 25 Chicago-based mobile eateries for their annual Food Truck Social. From grilled cheese to fried chicken, lobster, pierogis, cupcakes, and so much more, don’t miss your chance to sample some of the city’s finest meals on wheels. Expect plenty of live music, activities, and drinks available for purchase, too. Tickets are $10 (food not included) and can be purchased here.

Illinois Craft Beer Week

Bar at Band of Bohemia Chicago

May 10 – 17

Come celebrate Craft Beer Week in the country’s brewing capital. The week will feature tons of fun events throughout the city that showcase Chicago’s vibrant brewing scene. Kick off the week at the Beer Under Glass tasting event at the Garfield Park Conservatory. Explore all the events here.


Photo courtesy StarEvents

May 17 – 19

Lakeview’s 24th annual Mayfest is a jam-packed weekend of live music and local food and drinks, the perfect way to celebrate the start of festival season. You can find the big top Mayfest tent located right at the corner of Ashland Avenue and Barry Street in Lakeview. Admission is $10 and you can purchase tickets here or at the gate.

Wine Tasting Experience at Spiaggia

May 21

You can’t go wrong with a combination of wine, charcuterie, and cheese — and downtown hot spot Spiaggia is combining all three for a wine tasting experience on May 21. Led by the restaurant’s sommeliers, guests will have the opportunity to sample six different wines from around the globe paired with small bites. Tickets are $55 and can be purchased here.

Mole de Mayo Festival

Mole de Mayo
Photo courtesy Star Events: Mole de Mayo

May 24 – 26

This year marks the 10th anniversary of Mole de Mayo Festival, a popular street fest in the Pilsen neighborhood that celebrates the traditional Mexican sauce. See local chefs and restaurants compete to be crowned best mole in Chicago, then check out the live music, an open-air mercado and a lucha libre wrestling ring. There’s a suggested donation of $5 for individuals and $10 for families. Find out more details here.

Summer Cocktail Fest on the Beach

Shore Club Chicago

May 24

Kick off summer with a drink in hand and your toes in the sand. The swanky Shore Club will be hosting their Summer Cocktail Festival from 6 – 9 p.m. on Friday, May 24. The sun-soaked event will include three hours of seasonal cocktail tastings, giveaways, and stunning views of Lake Michigan. Get your tickets here.

Pizza Film Screening with Spacca Napoli

May 29

If you’re a fan of all things Italy, then you’ll want to mark your calendars for May 29 at the Music Box Theatre. Filmmaker Matteo Troncone will be screening his film Arrangiarsi: Pizza...and the Art of Living, which chronicles his experience traveling in Naples, the craft of making pizza, and so much more. The $17 ticket ($20 at the door) includes a pre-show reception with appetizers and prosecco from Spacca Napoli, the film screening, and a Q&A with Matteo. Grab your tickets and read more information here.

Friday Night Flights

wh friday night flights

May 31

Friday Night Flights is back with an exciting lineup of craft beer tasting events. This summer series highlights the city's dynamic local brewing scene throughout Chicago's vibrant neighborhoods.The kick-off event will be help at Gallagher Way outside Wrigley Field. Get your tickets today.

Lincoln Park Greek Fest

Lincoln Park Greek Fest

May 31 – June 2

Sample the many flavors of Greece at this beloved summer street fest. The weekend will feature cultural celebrations, traditional live music, a craft fair — and lots and lots of food. Dig into grilled meats, homemade sweets, hummus, gyros, rotisserie lamb, and so much more. Get more information here.

Featured Partners