Things to Do in Chicago and DuPage – Weekend Guide (May 8 – May 10, 2026)

Looking for plans in Chicago this weekend? From live performances and immersive exhibits to outdoor markets and sports, here are some of the top events happening across the city.

Chicago Weekend Highlights

May 8, 2026 – Friday Highlights

MAY8

HISTORY & CULTURE

Free and Independent

Explore the origins of America through historical texts and insights into the Declaration of Independence.

Event details

Friday, May 8
Daytime Hours

Newberry Library
60 W Walton St

MAY8

COMMUNITY

Chicago Water Week

A citywide series of events focused on water, sustainability, and community engagement.

Event details

Friday, May 8
All Day

Various Locations
Chicago, IL

MAY8

EXHIBIT

I AM WILD: A Charley Harper Exhibit

A vibrant exhibit showcasing wildlife and habitats through bold, graphic artwork.

Event details

Friday, May 8
Daytime Hours

Chicago Children’s Museum
700 E Grand Ave

MAY8

THEATRE

CHICAGO the Musical

The iconic Broadway hit returns with its signature jazz, drama, and unforgettable performances.

Event details

Friday, May 8
Evening Showtimes

Auditorium Theatre
50 E Ida B Wells Dr

MAY8

FOOD & NIGHTLIFE

SAUCED Night Market

A lively evening market featuring local vendors, food, drinks, and music.

Event details

Friday, May 8
5:00 PM – 10:00 PM

Ignite Glass Studios
401 N Armour St

May 9, 2026 – Saturday Highlights

MAY9

SPORTS

Chicago Fire FC vs. New York Red Bulls

Catch an exciting MLS matchup in the heart of the city.

Event details

Saturday, May 9
Match Time Varies

Soldier Field
1410 Special Olympics Dr

MAY9

THEATRE

The 8th Dwarf

A creative and whimsical stage production offering a fresh take on a classic tale.

Event details

Saturday, May 9
Showtimes Vary

Bughouse Theater
1910 W Irving Park Rd

MAY9

EXPERIENCE

Dinner Detective Murder Mystery Show

An interactive dinner experience where guests solve a live-action mystery.

Event details

Saturday, May 9
Evening Event

Magnificent Mile Area
165 E Ontario St

MAY9

FAMILY & OUTDOORS

Glow Wild

A nighttime lantern festival transforming the zoo into a glowing, immersive experience.

Event details

Saturday, May 9
Evening Hours

Brookfield Zoo
3300 Golf Rd

MAY9

SPORTS

Chicago White Sox vs. Seattle Mariners

Enjoy a classic baseball game with an energetic crowd atmosphere.

Event details

Saturday, May 9
Game Time Varies

Guaranteed Rate Field
333 W 35th St

May 10, 2026 – Sunday Highlights

MAY10

THEATRE

CHICAGO the Musical

Another chance to experience one of Broadway’s longest-running shows.

Event details

Sunday, May 10
Showtimes Vary

Auditorium Theatre
50 E Ida B Wells Dr

MAY10

EXPERIENCE

Theater of the Mind

An immersive theatrical experience blending storytelling, sound, and sensory design.

Event details

Sunday, May 10
Timed Entry

Reid Murdoch Building
333 N LaSalle St

MAY10

MARKET

Wicker Park Farmers Market

A popular neighborhood market featuring local produce, food vendors, and handmade goods.

Event details

Sunday, May 10
Morning – Afternoon

Wicker Park
1425 N Damen Ave

MAY10

FOOD & DINING

Mother’s Day: Brunch, Bubbles & Blooms

Celebrate Mother’s Day with an elevated brunch experience in a stylish setting.

Event details

Sunday, May 10
Brunch Hours

Brass Tack
11 E Walton St

MAY10

FAMILY

Goodnight Moon

A charming live adaptation of the beloved children’s book, perfect for families.

Event details

Sunday, May 10
Showtimes Vary

Chicago Children’s Theatre
100 S Racine Ave

DUPAGE WEEKEND HIGHLIGHTS

Looking for something closer to home in the western suburbs? DuPage offers relaxing weekend activities including nature experiences, live music, and local events.

May 8, 2026 – Friday Picks (DuPage)

MAY8

FOOD & EXPERIENCE

Spring Tea at Hotel Arista

Enjoy an elegant afternoon tea experience featuring pastries, desserts, and seasonal flavors.

Event details

Friday, May 8
Afternoon Seating

Hotel Arista
Naperville

MAY8

FOOD & DRINK

Happy Hour at The Drake Oak Brook

Relax with drinks and small bites in a refined lounge setting to kick off the weekend.

Event details

Friday, May 8
Happy Hour

Devon Seafood + Steak
Oak Brook Terrace

MAY8

CHARITY EVENT

Cocktail for a Cure

Sip for a cause at this charity-driven cocktail experience supporting cancer research.

Event details

Friday, May 8
Evening Event

Le Méridien
Oak Brook

MAY8

LIVE MUSIC

Live Music at Church Street Brewing

A laid-back evening with local live music and craft beer favorites.

Event details

Friday, May 8
Evening

Church Street Brewing
Itasca

MAY8

EXHIBIT

Cabinet of Curiosities Exhibit

Explore fascinating artifacts and historical pieces at the DuPage County Historical Museum.

Event details

Friday, May 8
All Day

DuPage County Historical Museum
Wheaton

May 9, 2026 – Saturday Picks (DuPage)

MAY9

WORKSHOP

Build a Bouquet: Mother’s Day Event

Create a custom floral arrangement as a thoughtful and hands-on Mother’s Day activity.

Event details

Saturday, May 9
Event Hours Vary

Downtown Naperville
Naperville

MAY9

SPORTS

Bensenville Mother’s Day Soccer Tournament

A fun, family-friendly sports event running throughout the weekend.

Event details

Saturday, May 9
All Day

Bensenville Fields
Bensenville

MAY9

ENTERTAINMENT

Mortal Kombat: Flawless Victory Event

A unique themed event for fans of gaming and pop culture.

Event details

Saturday, May 9
Evening Event

Hollywood Blvd Cinema
Woodridge

MAY9

FAMILY

Mother Nature’s Day at Cosley Zoo

Celebrate conservation, community, and nature with family-friendly activities.

Event details

Saturday, May 9
Daytime Hours

Cosley Zoo
Wheaton

MAY9

FOOD & DRINK

Spring Wine Tasting at The Morton Arboretum

Sip and stroll through scenic landscapes while enjoying curated wine selections.

Event details

Saturday, May 9
Timed Entry

The Morton Arboretum
Lisle

May 10, 2026 – Sunday Picks (Mother’s Day Highlights – DuPage)

MAY10

FOOD & DINING

Bolingbrook Golf Club Mother’s Day Champagne Brunch

An upscale brunch experience with classic dishes and champagne service.

Event details

Sunday, May 10
Brunch Hours

Bolingbrook Golf Club
Bolingbrook

MAY10

BRUNCH

Downers Grove Annual Mother’s Day Brunch

A popular local brunch featuring buffet stations and live music.

Event details

Sunday, May 10
Reservation Required

Osteria by Capri
Downers Grove

MAY10

FOOD & DINING

Mother’s Day Brunch at Harry Caray’s

Enjoy a lively brunch atmosphere with Italian-inspired favorites.

Event details

Sunday, May 10
Brunch Seating

Harry Caray’s
Lombard

MAY10

BREWERY

Mother’s Day at Two Brothers Tap House

Celebrate with brunch, drinks, and a relaxed brewery vibe.

Event details

Sunday, May 10
Brunch + Drinks

Two Brothers Tap House
Warrenville

MAY10

DINING

Mother’s Day Celebration at Crowne Plaza

A full dining experience with brunch specials and festive offerings.

Event details

Sunday, May 10
Dining Experience

Crowne Plaza / Glen Prairie
Glen Ellyn

Weekend Wrap-Up

Chicago is packed this weekend with a mix of culture, entertainment, and can’t-miss experiences across the city, from major events like Chicago Water Week and live performances like CHICAGO the Musical, to unique experiences like night markets, art exhibits, and even true crime tours, plus games from the Chicago Fire and White Sox and plenty of family-friendly shows and museum exhibits, while DuPage County offers a more relaxed, community-focused vibe with a strong Mother’s Day theme, featuring hands-on activities like bouquet building, local markets, and family outings at Cosley Zoo on Saturday, followed by brunches, celebrations, and special experiences across Naperville, Downers Grove, and nearby suburbs on Sunday, including wine tastings at The Morton Arboretum and upscale champagne brunches, making it a well-rounded weekend whether you’re staying in the city or heading to the suburbs.

Explore more Chicago events, from winter festivals to culinary celebrations and performing arts.

See DuPage’s full event calendar for all events happening this weekend and beyond.

Also Read: Tickets Now Available for the Obama Presidential Center Ahead of June Opening

Stay Connected

Ranked among the top 1 percent of real estate teams in the Chicagoland market, Cory Tanzer and the Cory Tanzer Group are experts in helping buyers and sellers navigate today’s market across Downtown Chicago, the North Shore, and the Western Suburbs. Recognized for their neighborhood expertise in areas like University Village, University Commons, South Loop, and Pilsen, the team helps clients stay one step ahead by understanding where the Chicago market is moving next.

Embed Block

Add an embed URL or code.