May's Best Chicagoland Events -
May’s Best Chicagoland Events

Chicagoland rejoice! Its officially spring, and the temperatures outside are beginning to agree with the calendar. Now’s the time to plan for longer days and warm nights. Take a look at the best events happening in your region this May.


Tinley Park’s annual Gateway Classic’s Spring Fling & Open House is back with music, food, vendors and, of course, classic cars. The fun happens this Sat., May 9 from 9 a.m. – 5 p.m.  Click here for more information. 

22nd Century Media’s Women’s Expo: LADY takes over Tinley Park Convention Center this Sat., May 10 from 10 a.m. – 4 p.m. with vendors, motivational speakers, cooking demonstrations, photo booths and more. Find more information on their event page here. 

Rail Fest returns to Homewood on Sat., May 16 from 9 a.m. – 4 p.m. This event is fun for all ages and features every kind of train collectible, raffles, food and even scale models of trains available for rides. More information can be found here.


Bring out every member of your family (including the ones with tails) for Township’s Annual Family and Pet Spring Fling in Frankfort. The event on Sat., May 9, begins at 11:30 a.m. and includes raffles, demonstrations, vendors and activities for your family and pet. Click for details.

Spark the imagination of your little one at Lockport’s Pixies Fairies & Pirates on the Farm event on May 16. Tinkerbell and Captain Hook will be in attendance. See all the magical details here.

Join other fans of timeless music for  Centennial Sinatra – A Tribute Celebrating the Life Music of Frank Sinatra at Rialto Square Theatre in Joliet . This night of music with Steve Lippia is scheduled for Thu., May 14, 7:30 p.m. Read more here.


What’s Blooming on Harrison? Find out at this family-oriented event that has delighted Oak Park residents since 1999. Artist demonstrations, live music, dance performances and an art fair span two days for this May 15 – 16 event. All the colorful details can be found here.

Fine Line Arts Festival is an event for everyone in St. Charles! Head to the Creative Arts Center on Sat., May 30 from 9 a.m. – 4 p.m. for a fun, outdoor day of hands-on art experience. More information on all the fun found here.


The first ever Evanston Literary Festival will happen May 11 – 18. Visit the event’s website for a full schedule of speakers and venues.

The May 16 – 17 Skokie Festival of Cultures, known for attracting more than 450,000 visitors, brings residents ethnic folk music, dance, arts and crafts, food, merchandise, children’s games and cultural booths all representing 14 different cultures. Visit the website to learn more.

Coming to the beautiful Chicago Botanic Garden in Glencoe, Grapevines and Wines. The spring tasting event returns this year on Thurs., May 28 from 6 – 8 p.m. To get tickets and learn more click here.

The 58th Annual Des Plaines River Canoe and Kayak Marathon and Minithon supplies yearly thrills for lovers of the outdoors in Libertyville. This event  is scheduled for Sun., May 17th at 8:00 A.M. Read more here.

Rosemont’s series of free weekly concerts, Rockin’ the Park, kicks of Sun., May 24 at 7 p.m. This Hawaiian-themed pub crawl and concert features classic cover bands, food and beverages, plus nightly fireworks. Concerts following the kick off will occur on Thursday nights. For the full schedule, visit this page.


Three days of chocolate. Need we say more? The hours of Long Grove‘s Chocolate Festival have been extended this year for maximum sugar-bliss. Enjoy three sweet days of fun from May 15 – 17. More information here.

Barrington’s art festival returns Memorial Day weekend (May 23 – 24) along Cook and Station Streets from 10 a.m. – 5 p.m. The festival showcases more than 130-juried artists from around the world, live music, kid-friendly activities, food and fun. Read all about it here.


Chicago Craft Beer Week is scheduled for May 14 – 24 and features more than 10 days of barley and hops spanning more than 300 venues across the area. Get started early with American Beer Classic on May 9 at Soldier Field. If beer isn’t your thing, take advantage of the Roscoe Village Wine Stroll on May 28 in Roscoe Village.

The Chicago Underground Film Festival is scheduled for May 13 – 17 at the famous Logan Theatre in Logan Square. See a full scheduled here.

Navy Pier fireworks kick off this month on May 23 at 10:15 P.M. You can enjoy the city’s best fireworks every Wednesday and Sunday through September 5.

Take advantage of the rare chance to bike Lake Shore Drive at the annual Bike the Drive event on May 24.

Love music? This summer is filled with events. May kicks off the melodic fun with the Belmont- Sheffield Music Festival (May 23 – 24) in Lincoln Park, Do Division Street Fest (May 29 – 31) in Wicker Park and Chicago Gospel Music festival (May 29 – 31) in Grant Park.