Things to Do in Chicago and DuPage – Weekend Guide (May 15 – May 17, 2026)

Chicago Weekend Highlights

Chicago’s mid-May calendar is packed with neighborhood festivals, Broadway productions, outdoor markets, foodie experiences, and cultural events as the city officially shifts into summer mode. From Lincoln Park street festivals to iconic theater downtown, this weekend offers something for every kind of Chicagoan, whether you're planning a date night, family outing, or exploring the city with friends.

May 15, 2026 – Friday Picks

MAY15

ART & HISTORY

Ink & Outrage: 18th-Century Satirical Prints in London & Dublin

Explore political satire and historic artwork at the Driehaus Museum through this fascinating exhibition featuring rare 18th-century prints and caricatures.

Event details

Friday, May 15
Museum Hours

Driehaus Museum
40 E Erie St

MAY15

IMMERSIVE EXPERIENCE

Minecraft Experience: Villager Rescue

Step inside an immersive Minecraft-inspired adventure at EXP Rosemont featuring interactive challenges, scavenger hunts, and hands-on gameplay.

Event details

Friday, May 15
Timed Entry

EXP Rosemont
Rosemont, IL

MAY15

CITY TOUR

Chicago Greeter – Loop InstaGreeter

Take a free guided walk through downtown Chicago and discover hidden gems, architecture, and local stories from volunteer city greeters.

Event details

Friday, May 15
Walking Tour

The Loop
Downtown Chicago

MAY15

TRUE CRIME TOUR

Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour

Experience Chicago’s darker history through a guided evening walking tour featuring infamous mob stories, haunted locations, and true crime legends.

Event details

Friday, May 15
Evening Tour

Downtown Chicago
Chicago, IL

MAY15

FESTIVAL

5th Annual Lincoln Park Mayfest

Kick off festival season with live music, food vendors, drinks, and neighborhood energy at one of Chicago’s most popular spring street festivals.

Event details

Friday, May 15
Festival Hours

Lincoln Park
Chicago, IL

May 16, 2026 – Saturday Highlights

MAY16

THEATRE & PERFORMING ARTS

Les Misérables

One of the world’s most celebrated musicals returns to Chicago with its powerful storytelling, unforgettable music, and award-winning production at the Cadillac Palace Theatre.

Event details

Saturday, May 16
Showtimes Vary

Cadillac Palace Theatre
151 W Randolph St

MAY16

FESTIVALS & COMMUNITY

Hyde Park Garden Fair

Chicago’s oldest community garden sale returns to Hyde Park with flowers, plants, gardening vendors, and seasonal inspiration across Kimbark Plaza.

Event details

Saturday, May 16
Daytime Hours

Kimbark Plaza
1208 E 53rd St

MAY16

TOURS & ATTRACTIONS

Iconic Foods of Chicago Food Tour

Taste the dishes that made Chicago famous with stops featuring deep dish pizza, Italian beef, hot dogs, Garrett Popcorn, and more throughout River North and Streeterville.

Event details

Saturday, May 16
12:00 p.m. – 3:00 p.m.

River North
Chicago, IL

MAY16

FESTIVAL

5th Annual Lincoln Park Mayfest

One of Chicago’s biggest neighborhood street festivals kicks off summer with live music, food vendors, art, drinks, and family-friendly activities along Armitage Avenue.

Event details

Saturday, May 16
12:00 p.m. – 10:00 p.m.

Lincoln Park
1000 W Armitage Ave

MAY16

CITY TOUR

Chicago Greeter – Loop InstaGreeter

Explore downtown Chicago with a free guided walking experience led by local volunteers sharing architecture, history, and hidden gems throughout the Loop.

Event details

Saturday, May 16
1:30 p.m. – 3:00 p.m.

Chicago Cultural Center
78 E Washington St

May 17, 2026 – Sunday Highlights

MAY17

FESTIVALS & COMMUNITY

5th Annual Lincoln Park Mayfest

Chicago’s popular spring street festival continues with live music, food vendors, drinks, local art, and neighborhood energy throughout Lincoln Park.

Event details

Sunday, May 17
12:00 p.m. – 9:00 p.m.

Lincoln Park
1000 W Armitage Ave

MAY17

TOURS & ATTRACTIONS

Street Foods of Pilsen Food Tour

Experience authentic neighborhood flavors, colorful murals, and local culture while exploring one of Chicago’s most vibrant food destinations.

Event details

Sunday, May 17
1:00 p.m. – 4:00 p.m.

Pilsen Neighborhood
Chicago, IL

MAY17

TOURS & ATTRACTIONS

Gateway to The West Loop Food Tour

Discover the restaurants, craft breweries, and culinary hotspots that transformed the West Loop into one of Chicago’s most talked-about dining districts.

Event details

Sunday, May 17
1:00 p.m. – 4:00 p.m.

West Loop
925 W Randolph St

MAY17

THEATRE & PERFORMING ARTS

FIRE HOUSE

A gripping immersive production staged inside Chicago’s oldest standing firehouse, blending live performance, history, and dramatic storytelling.

Event details

Sunday, May 17
8:00 p.m. – 9:30 p.m.

Firehouse Art Studio
1123 W Roosevelt Rd

MAY17

COMEDY & LIVE ENTERTAINMENT

That 90s Throwback Comedy Show

Relive the best of the 90s through stand-up comedy, trivia, nostalgic references, and interactive crowd moments at Chicago’s iconic comedy venue.

Event details

Sunday, May 17
8:00 p.m. – 9:30 p.m.

The Lincoln Lodge
2040 N Milwaukee Ave

DUPAGE WEEKEND HIGHLIGHTS

DuPage County is stepping into peak spring weekend season with outdoor festivals, family-friendly activities, live entertainment, and community events happening across the western suburbs. From local farmers markets and seasonal fairs to food events and outdoor experiences, this weekend offers plenty of reasons to explore beyond downtown Chicago. Whether you're staying local in Naperville, Wheaton, Downers Grove, or Elmhurst, there’s no shortage of ways to enjoy the warmer weather and kickoff-to-summer energy across the suburbs.

May 15, 2026 – Friday Highlights

MAY15

SPORTS & TOURNAMENTS

Big Bear Dragon's Lair Hockey Tournament

A competitive youth hockey tournament weekend bringing teams together for fast-paced action, championship games, and family-friendly entertainment.

Event details

Friday, May 15
All Weekend Event

Canlan Sports Romeoville
1581 W Normantown Rd

MAY15

COMMUNITY EVENTS

Cop on a Rooftop

Support Special Olympics Illinois during this fun community fundraiser featuring local police officers collecting donations from the rooftop.

Event details

Friday, May 15
Morning Event

Dunkin' Bensenville
1004 W Irving Park Rd

MAY15

GALAS & FUNDRAISERS

Furever Friends Gala

An elegant evening supporting DuPage animal welfare programs featuring dining, entertainment, fundraising activities, and community celebration.

Event details

Friday, May 15
Evening Gala

Chicago Marriott Oak Brook
1401 W 22nd St

MAY15

FESTIVALS & COMMUNITY

Lilac Time Festival

Celebrate springtime in Lombard with blooming lilacs, carnival rides, live entertainment, food vendors, and family-friendly activities.

Event details

Friday, May 15
Festival Hours Vary

Lilacia Park
150 S Park Ave

MAY15

LIVE MUSIC & NIGHTLIFE

Live Music: Tom & Amy Malouf

Enjoy an evening of live local music, classic favorites, and relaxed dining in a welcoming atmosphere at Arrowhead Restaurant & Bar.

Event details

Friday, May 15
Live Music Performance

Arrowhead Restaurant & Bar
26W151 Butterfield Rd

May 16, 2026 – Saturday Highlights

MAY16

MUSIC & PERFORMING ARTS

Rising Stars

Enjoy an inspiring concert competition showcasing talented young musicians performing alongside the Elmhurst Symphony Orchestra.

Event details

Saturday, May 16
3:00 p.m.

Elmhurst Christian Reformed Church
149 W Brush Hill Rd

MAY16

FAMILY & COMMUNITY

Summer Saturday: Garden Party

Families can enjoy sensory-friendly outdoor activities, games, music, and interactive experiences during this fun summer celebration.

Event details

Saturday, May 16
Daytime Event

Sensory Garden Playground
2751 International Dr

MAY16

ART & CULTURE

America 250 Summer Art Banner Exhibit

Explore a patriotic public art installation celebrating America’s 250th anniversary with colorful banners displayed throughout downtown West Chicago.

Event details

Saturday, May 16
Seasonal Exhibit

Downtown West Chicago
136 Main St

MAY16

HANDS-ON EXPERIENCES

Blacksmithing 101 – 2 Day Class

Learn traditional blacksmithing techniques through a hands-on workshop experience guided by skilled instructors at Naper Settlement.

Event details

Saturday, May 16
Workshop Hours Vary

Naper Settlement
523 S Webster St

MAY16

HISTORY & COMMUNITY

Illinois Humanities Community Conversations

Join meaningful discussions exploring shared history, identity, and civic engagement through this thoughtful community conversation series.

Event details

Saturday, May 16
Community Program

Naper Settlement
523 S Webster St

May 17, 2026 – Sunday Highlights

MAY17

PARADES & COMMUNITY

2026 Lombard Lilac Parade

Celebrate one of Lombard’s most beloved traditions with colorful floats, marching bands, community groups, and festive spring energy throughout downtown Lombard.

Event details

Sunday, May 17
Parade Hours Vary

Main Street – Lombard
1014 S Main St

MAY17

MUSIC & CULTURE

Pre-Concert Lecture: Carmina Burana

Learn more about the legendary Carmina Burana performance through an engaging pre-concert lecture exploring its history, themes, and musical significance.

Event details

Sunday, May 17
Lecture Time Vary

Elmhurst Public Library
125 S Prospect Ave

MAY17

FOOD & DINING

Family Style Sundays

Enjoy a curated Italian dining experience designed for sharing, featuring classic dishes, warm hospitality, and a relaxed Sunday atmosphere.

Event details

Sunday, May 17
Dining Hours Vary

Osteria by Capri
2111 Butterfield Rd

Weekend Wrap-Up

From Broadway performances and neighborhood festivals in Chicago to outdoor community events across DuPage County, this weekend delivered the perfect mix of entertainment, food, culture, and spring energy. As warmer weather continues to bring more people outdoors, both the city and suburbs are fully settling into summer event season with packed calendars and experiences for every type of weekend plan.

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

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