Gene Teigland
Looking for the best events in Chicago this summer? Whether you’re a lifelong local or a new resident, TAWANI Property Management has you covered. From rooftop happy hours and live music to cultural festivals and family-friendly activities, there’s something for everyone this summer. Explore our curated list and click through to grab tickets or learn more!
Live Music & Summer Concerts
Soak up the sounds of Chicago’s iconic music scene.
- Millennium Park Summer Music Series (Free)
Enjoy jazz, blues, and global music under the stars at the Jay Pritzker Pavilion. - Green Mill Cocktail Lounge
Step back in time for a live jazz set at this Prohibition-era venue in Uptown. - Lollapalooza 2025
This year’s four-day lineup is packed with global headliners—get your passes early! - Chicago Gospel Music Festival
- Ravinia Festival
Picnic on the lawn or reserve a seat for acts like John Legend, Sheryl Crow, and more. - Chicago Gospel Music Festival
This FREE inspirational music festival brings audiences of all ages and backgrounds together to celebrate the power of music.
Happy Hours, Breweries & Mixology
Raise a glass with these laid-back, flavor-forward experiences.
- Chicago Happy Hour Guide
Your go-to map for the best weekday drink specials across the city. - Revolution Brewery Tour
Take a behind-the-scenes look at one of Chicago’s favorite local brewers. - Cocktail Classes at The Violet Hour
Master the art of mixology in Wicker Park’s moody speakeasy-style bar.
Comedy, Theater & Nightlife
Laugh out loud and lean into Chicago’s iconic entertainment scene.
- The Second City
Catch improv where legends like Tina Fey and Steve Carell got their start. - Zanies Comedy Club
A rotating lineup of stand-up acts from national headliners to rising stars. - Chicago Shakespeare Theater on Navy Pier
Enjoy classic and contemporary productions with stunning lakefront views.
Culture, Arts & Free Attractions
Feed your mind with these artistic and educational experiences.
- Art Institute of Chicago – Free Thursdays for IL Residents
View world-famous works—from Monet to modern art—for free with proof of residency. - Museum of Contemporary Art – Tuesdays are Free
Explore cutting-edge art and rotating exhibitions. - Chicago Street Art Tours
Discover vibrant murals and the stories behind them in neighborhoods like Pilsen and Wicker Park. - Movies in the Parks (Grant Park & More)
Bring a blanket and enjoy free screenings of classics and new releases.
Can’t-Miss: July 4th in Downtown Chicago
Celebrate Independence Day in style.
- Navy Pier Fireworks & Lake Cruise Packages
Reserve early for the best view of Chicago’s famous 4th of July fireworks. - Chicago Riverwalk Festivities
Live music, family activities, and food vendors all weekend long.
Make the Most of Chicago Summer
Living or working in a TAWANI-managed property means you’re always near the action. Bookmark this guide, share it with friends, and make Summer 2025 your most memorable yet.
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