Festivals near Woodstock, IL.

Deerfield Art Festival

• Jun. 6 - Jun 7, 2026
• 821 Park Ave - Deerfield, IL USA

• Other / General

The Deerfield Art Festival is filling Park Avenue with 100 original artists on June 6-7! Start your family or friend’s day downtown with coffee and b ....

2026 Milwaukee Highland Games, bringing Scotland to Milwaukee!

• Jun. 6 - Jun 6, 2026
• Franklin Beer Garden at Croatian Park - Franklin, WI USA

• Other / General

• $10 - $25

Milwaukee Highland Games — June 6, 2026! Get ready for a full day of Scottish culture, competition, music, and family fun at Croatian Park in Frankli ....

Apna Bazaar Season 2

• May. 30 - May 30, 2026
• Waterford Banquet \u0026 Conference Center - Elmhurst, IL USA

Apna Bazaar Season 2 is a high-energy, influencer-backed community expo happening on May 30, 2026 at Waterford Banquets in Elmhurst, IL. Building on ....

The Magnificent Mile Spring Art Fest

• May. 30 - May 31, 2026
• 875 North Michigan Avenue - Chicago, IL USA

• Other / General

The Magnificent Mile™ Spring Art Fest showcases the original art of 60 juried artists from around the country in a variety of mediums, highlighting je ....

Barrington Art Festival

• May. 23 - May 24, 2026
• South Cook Street \u0026 East Station Street - Barrington, IL USA

• Other / General

Welcome the return of summer at the 17th annual Barrington Art Festival, Memorial Day Weekend! Start your family or friend’s day downtown with coffee ....

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 ....

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 ....

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 ....

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 ....

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 ....

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  ....

Deer Park Art Show

• May. 2 - May 3, 2026
• 20530 N Rand Rd - Deer Park, IL USA

• Other / General

Deer Park Art Show fills the streets of Deer Park Town Center with thousands of original works of art from 75 artists May 2-3. There’s something for e ....

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 ....

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 ....

Eat the Neighborhood Foraging and Nature Walk -- Schaumburg

• Apr. 19 - Apr 19, 2026
• Olympic Park - Schaumburg, IL USA

• Food / Wine / Beer

• $25 - $50

Sunday, April 19, 2026 10:00?AM 12:00?PM Olympic Park (map) FIRST SUBURBAN TOUR OF THE SEASON Join Chicago's only full time professiona ....

Eat the Neighborhood: Foraging and Nature Walk

• Apr. 18 - Apr 18, 2026
• North Pond - Chicago, IL USA

• Food / Wine / Beer

• $25 - $50

FIRST CITY TOUR OF THE SEASON! Join Chicago's only full time professional forager Dave Odd for a walk around the north pond in Lincoln Park to see ....

Jazz Prayer - Where Jazz meets Spirit

• Apr. 17 - Apr 17, 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 ....

Jazz Prayer - Where Jazz Meets Spirits

• Apr. 17 - Apr 17, 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 ....