whattodowheretogo
HomeChicagoWeekend Guide
Weekend Guide · Chicago

Things to Do in Chicago This Weekend.

Hand-picked festivals, live shows, weekend markets, and outdoor escapes.

Want a tailored weekend guide schedule?

Our AI maps out verified venues, coordinates, and exact start times in Chicago.

Generate Itinerary
Live Pulse

Upcoming Events & Happenings

10 listings
live music$20

Kingston Mines Live Chicago Blues Weekend Showcase

Authentic, high-octane live Chicago blues across two continuous stages running until 4:00 AM at the world-famous Lincoln Park blues institution operating since 1968.

Sat, Aug 29 at 12:00 AMDetails
comedy$30

Stand-Up Comedy Showcase at Zanies Chicago

Intimate stand-up comedy showcase featuring top touring headliners and Chicago's sharpest club comedians in the historic Old Town venue.

Sat, Aug 29 at 12:00 AMDetails
nightlife$15

Late-Night Jazz Jam Session at The Green Mill

Historic Uptown cocktail lounge and former Prohibition-era speakeasy hosting late-night live jazz jam sessions and quartet performances rolling until 3:30 AM.

Sat, Aug 29 at 1:00 AMDetails
food drinkFree Entry

Green City Market Lincoln Park

Chicago's premier sustainable open-air farmers market connecting local Midwest farmers and artisan food makers with the community beneath Lincoln Park's tree canopy.

Sat, Aug 29 at 12:00 PMDetails
familyFree Entry

Navy Pier Summer Lakefront Fireworks

Award-winning choreographed fireworks lighting up Lake Michigan and the downtown skyline, free to view along the 3,300-foot pier promenade and surrounding lakefront parks.

Sun, Aug 30 at 3:00 AMDetails
food drinkFree Entry

Logan Square Farmers Market

Vibrant open-air Sunday community market along Milwaukee Avenue offering regional seasonal produce, local honey, artisan pastries, specialty coffees, and live street buskers.

Sun, Aug 30 at 1:30 PMDetails
live musicFree Entry

47th Annual Chicago Jazz Festival

A celebrated Labor Day weekend Chicago tradition organized by DCASE and the Jazz Institute of Chicago, featuring world-renowned jazz artists and local Chicago legends across Jay Pritzker Pavilion and park lawns.

Thu, Sep 3 at 4:00 PMDetails
live music$199

ARC Music Festival 2026

Chicago's premier electronic music festival returning for Labor Day weekend at Union Park, highlighting house and techno pioneers alongside global powerhouse headliners across multiple curated stages.

Fri, Sep 4 at 5:00 PMDetails
comedy$40

The Second City Mainstage 114th Revue

An evening of sharp satirical sketch comedy and fast-paced improv from the legendary comedy troupe that launched the careers of Tina Fey, Steve Carell, and Stephen Colbert.

Sun, Sep 6 at 3:00 AMDetails
nightlife$20

Labor Day Weekend Queen! at Smartbar

Chicago's legendary weekly Sunday LGBTQ+ underground house and disco party at Smartbar, featuring resident selector Derrick Carter, Michael Serafini, and Shaun J. Wright on the subterranean Funktion-One sound system.

Mon, Sep 7 at 3:00 AMDetails
Curated Selection

Hand-Picked Venues & Spots in Chicago

Millennium Park (Cloud Gate)

4.8

Chicago's premier civic center featuring Cloud Gate, Crown Fountain, and Jay Pritzker Pavilion

A 24.5-acre lakefront park in the Loop home to Anish Kapoor's iconic 'Bean' (Cloud Gate), Jaume Plensa's interactive Crown Fountain, Lurie Garden, and Frank Gehry's stainless steel Jay Pritzker Pavilion.

Free201 E Randolph St, Chicago, IL 60602

Chicago Riverwalk

4.8

Scenic 1.25-mile pedestrian promenade along the main branch of the Chicago River

A dynamic waterfront pedestrian walkway divided into distinct thematic coves lined with alfresco restaurants, wine bars, kayak launches, and unbeatable views of landmark skyscrapers.

FreeChicago Riverwalk, Chicago, IL 60601

Navy Pier

4.6

Historic 3,300-foot lakefront landmark with Centennial Wheel, dining, and scenic cruises

Chicago's famous lakefront pier extending into Lake Michigan, featuring the 200-foot Centennial Wheel, Chicago Shakespeare Theater, Miller Lite Beer Garden, Lake Michigan boat cruises, and fireworks.

~$20600 E Grand Ave, Chicago, IL 60611

Skydeck Chicago at Willis Tower

4.6

Breathtaking 103rd-floor views with glass-floor 'The Ledge' cantilever boxes

Situated on the 103rd floor of the iconic Willis Tower, offering panoramic views reaching four states and 'The Ledge'—all-glass observation boxes that extend 4.3 feet outside the building over Wacker Drive.

~$36233 S Wacker Dr, Chicago, IL 60606

360 CHICAGO Observation Deck

4.5

Panoramic 94th-floor vistas over Lake Michigan and the Mag Mile with TILT thrill ride

Perched 1,000 feet above the Magnificent Mile at 875 N Michigan Ave, offering 360-degree vistas across four states, the adrenaline-pumping TILT glass lookout, and CloudBar.

~$35875 N Michigan Ave 94th floor, Chicago, IL 60611
Common Questions

Frequently Asked Questions

What are the best weekend activities in Chicago?

This weekend in Chicago offers artisan craft markets, live music showcases, scenic nature day trips, and culinary food truck rallies.

More Curation in Chicago