Ring Around Chicago (Friday): Join Brian & Kenzie on Friday from 10a-11a at the ~MYSTERY LOCATION~ for a chance to win a Hearts On Fire Acclaim Engagement Ring valued at $8,000 from James & Sons Fine Jewelers. Contest rules can be found here.

White Sox host the Astros (Friday-Sunday): The struggling White Sox host the Houston Astros for a three-game series at home this weekend.

Strawberry Festival in Bridgeview (Friday-Sunday): This year’s event promises to be bigger and better than ever before with delicious food, strawberries, a petting zoo, and so much more. Tickets can be purchased here.

Chicago Mayfest in Lincoln Park (Friday-Sunday): Two stages will showcase Chicago’s most acclaimed musicians while festival goers enjoy a variety of delicious summertime food and all the libations needed to light up your weekend. You won’t want to miss this celebration of the sights, sounds and tastes of Chicago’s glorious Summer Season. Now with the Armitage Art Show on in the heart of the festival, you’ll get to experience Chicago’s top artists as they showcase and sell their work and feature interactive art demonstrations! Get details here.

Whose Line Is It Anyway? Live at the Studebaker Theater (Friday-Sunday): “Whose Live Anyway?” is 90 minutes of hilarious improvised comedy and song all based on audience suggestions. The Emmy-nominated TV show now takes the stage for multiple shows live at the Studebaker Theater this weekend.

WhiskyFest at the Hyatt Regency in the Loop (Friday): Take a trip around the world while tasting single malt and blended Scotch, Irish, bourbon, rye, Tennessee, Japanese, Canada and craft-distilled whiskies at this annual brown-spirits blowout. Tickets can be purchased here.

The Great Penguin Party at Shedd (Friday): Hell. Yes. Party alongside Wellington, Edward and Annie at the Shedd Aquarium’s roaring ’20s-themed soiree The Great Penguin Party, where guests can sip drinks from an open bar and hear live music. Penguins will be wearing tuxedos, but you can dress how you’d like. Tickets can be purchased here.

Lincoln Roscoe Spring Art and Craft Fair (Saturday-Sunday): Returning to Chicago on Saturday, May 13 and Sunday, May 14, this northside event features art for the home including fabulous paintings, sculptures, and fiber pieces, as well as décor, jewelry and more; all hand made by artists and artisans. Live music all weekend long, painting classes, selfie stations, festival food, interactive art activities for kids hosted by local businesses, as well as the brand new “Kids Art Stop” where artists invite children to stop at their booth to learn more about the art making process, make this a fun-filled event. Secure your spot here.

Fire host the St. Louis City SC (Saturday): The Chicago Fire host the fierce St. Louis squad on Saturday at Soldier Field.

NASCAR Watch Party at Stadium Club at The Max (Sunday): Join Q101 to watch The GOODYEAR 400 and cheer on your favorite drivers at our official watch party! Join us at Stadium Club at the Max located at 4740 Vernom Ave, in McCook on Sunday, May 14th from 2pm – 5pm for a watch party filled with high-speed thrills, delicious food, and unbeatable company. Get ready for the green flag with a cold drink in hand and a group of friends by your side.