Chicago's longest-running outdoor farmers market held in the heart of The Loop beneath the iconic Picasso sculpture, featuring fresh local produce, baked goods, and lunch food trucks.

Thu, Aug 27 · 12:00 PMDetails →

arts$32

The Art Institute of Chicago: Thursday Evening Hours

Extended evening hours to explore one of the world's most renowned collections of Impressionist, Post-Impressionist, and modern masterworks in the heart of downtown Chicago.

Thu, Aug 27 · 4:00 PMDetails →

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 · 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 · 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 · 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 · 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 · 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 · 1:30 PMDetails →

Curated Recommendations

Iconic Local Gems 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.

Freemorning

The Art Institute of Chicago

★ 4.8

World-class art museum housing masterpieces from Impressionism to contemporary art

Consistently ranked among the top museums globally, featuring nearly 300,000 works including Georges Seurat's 'A Sunday on La Grande Jatte', Grant Wood's 'American Gothic', and Edward Hopper's 'Nighthawks'.

~$32afternoon

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.

Freeevening

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.

~$20evening

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.

~$36morning

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.

~$35evening

Visitor Guide

Frequently Asked Questions About Chicago

What are the top things to do in Chicago?

Chicago offers a vibrant mix of live concerts, stand-up comedy shows, historic sights, culinary food halls, and scenic parks. Check our live guides for real-time recommendations.

How do I find free things to do in Chicago?

Browse our free guide to discover $0 admission public parks, free museum days, outdoor markets, and community events across Chicago.

Can I generate a custom itinerary for Chicago?

Yes! Use whattodowheretogo's AI Trip Planner to create a personalized, time-optimized schedule matching your budget, group size, and interests in seconds.