Festivals near Highland, IN.

Altezza Rooftop opens May 28 in Streeterville with Italian-inspired cocktails

• May. 28 - Aug 31, 2026
• Altezza Rooftop Bar Chicago - Chicago, IL USA

• Food / Wine / Beer

Named for the Italian word meaning both physical elevation and noble stature, Altezza Rooftop will seamlessly blend the timeless Italian art of living ....

Randolph Street Market Festival returns for its 2026 season

• May. 23 - May 24, 2026
• 1341 W Randolph St - Chicago, IL USA

• Other / General

• $10 - $25

The Randolph Street Market Festival returns to Chicago’s West Loop for the launch of its 2026 season with the 23rd Annual Garden Party Market on Satur ....

Prairie Arts Festival

• May. 23 - May 24, 2026
• Al Larson Prairie Center For the Arts - Schaumburg, IL USA

• Arts (Arts & Crafts)
• Community (Community / Social)
• Food / Wine / Beer
• Holiday (Memorial Day)
• Music

• FREE!!

The Village of Schaumburg hosts the Prairie Arts Festival which is an outdoor fine art & fine craft exhibition and sale featuring artists, li ....

Adults Night Out: Block Party at Lincoln Park Zoo

• May. 22 - May 22, 2026
• Lincoln Park Zoo - Chicago, IL USA

• $10 - $25
• $25 - $50

Start the summer off right at Lincoln Park Zoo! Adults Night Out: Block Party is exclusively for the 21+ crowd to enjoy the zoo with games, music, and ....

Viceroy Spirited Series featuring Don Julio

• May. 22 - May 22, 2026
• Somerset - Chicago, IL USA

• Food / Wine / Beer

• $100 - $250

Join us for the much-anticipated return of the Don Julio Dinner, part of the ongoing Viceroy Spirited Series. Now in its fifth instalment since the se ....

Summer Kickoff at Lincoln Park Zoo

• May. 22 - May 25, 2026
• Lincoln Park Zoo - Chicago, IL USA

Sunshine season starts here! Celebrate the start of warmer weather and sunnier days at Lincoln Park Zoo’s Summer Kickoff, a free and family-friendly c ....

Andersonville Wine Walk

• May. 17 - May 17, 2026
• 5344 N Clark St - Chicago, IL USA

• Food / Wine / Beer

• $25 - $50

Every year the Andersonville Spring Wine Walk turns businesses throughout the district into wine-tasting destinations. Thank you to our event partner: ....

Lincoln Roscoe Art & Craft Fair

• May. 16 - May 17, 2026
• 3329 N Lincoln Ave - Chicago, IL USA

• Other / General

This event, hosted by Special Service Area 27, is free and takes place on Lincoln Avenue between Roscoe and Melrose Streets. Returning to Chicago on M ....

Jazz Prayer - Where Jazz meets Spirit

• May. 15 - May 15, 2026
• Good Shepherd Lutheran Church - Oak Park, IL USA

• Music

Experience the rhythm of the soul where music, spirit, and community come together. Jazz Prayer is a unique Oak Park tradition — part concert, part re ....

Asha Bhosle Tribute - An Evening Of Timeless Melodies - Schaumburg

• May. 15 - May 15, 2026
• Haridham Chicago: Hindu-Swaminarayan Temple & Cultural Center (YDS Chicago) - Schaumburg, IL USA

• Arts (Performing Arts)
• Music

• $25 - $50

About Event Asha Bhosle Tribute An Evening of Timeless Melodies A celebration of the legendary voice and her evergreen hits. Save the DateFrid ....

Jazz Prayer - Where Jazz Meets Spirits

• May. 15 - May 15, 2026
• Good Shepherd Lutheran Church - Oak Park, IL USA

• Music

Experience the rhythm of the soul where music, spirit, and community come together. Jazz Prayer is a unique Oak Park tradition — part concert, part re ....

Now Open: Mexican Radio Brings Bold, Regional Mexican Cuisine to the Loop

• May. 15 - Dec 31, 2026
• Mexican Radio - Chicago, IL USA

• Food / Wine / Beer

Mexican Radio is now open in the heart of the Loop, offering a vibrant destination for regionally inspired Mexican cuisine from acclaimed chef Dudley ....

Mother's Day in Somerset

• May. 10 - May 10, 2026
• Somerset - Chicago, IL USA

• Food / Wine / Beer

• $50 - $100

Celebrate Mother’s Day in Somerset with a vibrant and abundant brunch experience, thoughtfully designed to make every mom feel cherished and celebrate ....

Pilsen Ukulele Party (PUP)

• May. 9 - May 9, 2026
• Pilsen Arts and Communtit House - Chicago, IL USA

• Music

Pilsen Uke Party (PUP) A FREE joyful, one-day ukulele festival in Pilsen, Chicago at Pilsen Arts and Community House (PACH), A non-profit art gallery ....

Northbrook Art in the Park

• May. 9 - May 10, 2026
• 1810 Walters Ave - Northbrook, IL USA

• Other / General

Village Green Park in downtown Northbrook is your home base for a fantastic summer day! Grab a coffee on Shermer Road with friends or family, then soa ....

2026 Cinco de Miler

• May. 9 - May 9, 2026
• 400 W Montrose Harbor Dr - Chicago, IL USA

• Sports / Fitness

• $25 - $50

Mark your calendars for May 9, 2026, because the Cinco de Miler 5-Mile Run is back, bringing the perfect blend of fitness, fun, and fiesta! Lace up yo ....

2026 Lincoln Park Uncorked: An Armitage – Halsted Wine Stroll

• May. 7 - May 7, 2026
• Wintrust Bank - Lincoln Park - Chicago, IL USA

• Food / Wine / Beer

• $50 - $100

Stroll through one of Chicago’s most charming corridors while enjoying curated wine tastings and bites from local favorites. Armitage, between Kenmor ....

Touch a Truck Family Festival

• May. 3 - May 3, 2026
• NIPSTA - Glenview, IL USA

• Other / General

• $10 - $25

Be part of the BIGGEST event of the season! 40+ vehicles for kids to climb and explore, plus music, train rides, food trucks and more at this outdoor ....

BOLLYWOOD DHAMAAL- WITH DINNER BUFFET - Schaumburg

• May. 2 - May 2, 2026
• Bawarchi Biryanis Schaumburg - Schaumburg, IL USA

• Music

About Event Get ready for an electrifying night of music, dance, and delicious food at Bollywood Dhamaal with Dinner Buffet! Hosted by  ....

Asian American Arts Chicago Presents 2026 Festival “EVOLUTION,” May 2 and 3

• May. 2 - May 3, 2026
• Lookingglass Theatre Water Tower Water Works - Chicago, IL USA

• Other / General

• $10 - $25

Asian American Arts Chicago (AAAC) announces the 2026 Festival schedule and that tickets are now on sale for EVOLUTION: Asian American Arts Festival, ....

Art Attack at Commune + Market

• Apr. 26 - Apr 26, 2026
• Commune + Market - Three Oaks, MI USA

This April, Lubeznik Center for the Arts (LCA) is joining the excitement of Art Attack in Michigan's Harbor Country. Each year, art lovers flock to S ....

10th Annual Chicago Rum Festival Returns

• Apr. 25 - Apr 25, 2026
• Logan Square Auditorium - Chicago, IL USA

• Other / General

• $50 - $100

The Chicago Rum Festival will celebrate its 10th anniversary on April 25, 2026, at the iconic Logan Square Auditorium (2539 N Kedzie Blvd, Chicago, IL ....

Art Attack at Commune + Market

• Apr. 25 - Apr 25, 2026
• Commune + Market - Three Oaks, MI USA

This April, Lubeznik Center for the Arts (LCA) is joining the excitement of Art Attack in Michigan's Harbor Country. Each year, art lovers flock to S ....

Eat the Neighborhood: Foraging and Nature Walk - Wolf Lake, Indiana

• Apr. 25 - Apr 25, 2026
• Bairstow Trailhead Parking Lot - Hammond, IN USA

• Food / Wine / Beer

• $25 - $50

Saturday, April 25, 2026 10:00?AM 12:00?PM Bairstow Trailhead Parking Lot (map) Join Chicago's only full time professional forager Dave ....

Artisan Market 4/19

• Apr. 19 - Apr 19, 2026
• 442 S Grove Ave - Oak Park, IL USA

• Food / Wine / Beer

It's Sugar Beet Food Co-op's Owner Apreciation Month in April. Among other events such as a seed starting class by Driftless Seeds, we're hosting a bi ....