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Summer is here, and it’s time to soak it all in—art fairs, music under the stars, farmers markets, lakeside escapes, and everything in between. Not sure where to begin? I’ve got you covered.
Here’s your go-to Q&A guide for making the most of summer in the city, suburbs, and beyond!
Q: What are the must-do summer experiences in Chicago?
A: The city’s summer scene is bursting with energy! Don’t miss these crowd-pleasers:
- 57th Street Art Fair
- Chicago SummerDance
- Faces of Fitness Festival – July 26–27
- Millennium Park Summer Film Series
- Millennium Park Summer Music Series
- Wicker Park Fest
- Taste of Chicago – Sept 5–7
- The World Within: Chicago’s Original & Best Architecture Interiors Tour
Q: What should North Shore locals (or visitors!) check out?
A: From gourmet food trucks to starry nights at Ravinia, the North Shore is packed with memorable moments:
- Art at the Glen – July 26–27
- Food Truck Thursdays @ Jens Jensen Park – Highland Park (June 5–Aug 28)
- Highwood’s Weekly Wednesday Gourmet Market – June 4–Aug 27
- Lake County Fair – July 23–27
- Northbrook Grand Prix – July 24
- Ravinia Festival – Highland Park
- Wilmette Art Fair – Aug 2–3
- Winnetka Music Festival – June 20–21
Q: I’m up for a drive—any hidden gems outside of the city?
A: Yes! Check out these highlights in nearby regions:
Northwest Indiana Favorites
- Pierogi Fest
- Cedar Lake Farmers Market
- Chesterton European Market
- Crown Point Car Cruise Nights
- Festival of the Lakes
- Hobart Lakefront Festival
- Indiana Dunes
- Lake County Fair
- LaPorte County Fair
- Porter County Fair
- Valparaiso Outdoor Movies
Southwest Michigan Escapes
- Berrien County Youth Fair
- Chalk the Block – St. Joseph
- Dowagiac Farmers Market
- Krasl Art Fair on the Bluff
- Love Creek County Park
- Mike Yore Memorial Car Show
- New Buffalo Farmers Market
- Silver Beach
- St. Joseph Farmers Market
- St. Joseph Light House
Wisconsin Weekend Fun
- A La Carte at the Zoo
- Barthel Fruit Farm
- Bastille Days
- Bear Den Zoo
- Big Star Drive-In
- Boundless Adventures
- Bristol Renaissance Faire
- Discovery World
- Eco-Justice Center
- Edelweiss Boat Cruises
- Festa Italiana
- For the Love of Flowers Farm
- German Fest
- Great Lakes Dragaway
- Harley Davidson Homecoming
- Irish Fest
- Kenosha History Center
- Lakefront Festival of Art
- Mequon Nature Preserve
- Mexican Fiesta
- Milwaukee Art Museum
- Milwaukee Kayak Company
- Milwaukee Zoo
- Mitchell Park Domes
- Pedal Tavern
- Polish Fest
- PrideFest Milwaukee
- Racine Art Museum
- Richard Bong Recreation Area
- River Bend Nature Center
- Riverwest 24 Hour Bike Race
- Sip & Purr Cat Cafe
- Summerfest Music Festival
- Waterstone Bank Air and Water Show
- Windpoint Lighthouse
- Wisconsin State Fair
Q: What about fun in the suburbs—any local treasures?
A: Each suburb has its own flavor and flair:
North & Northwest Suburbs
- Day Out With Thomas the Train
- Hideaway Brew Garden – Hoffman Estates
- Lake Arlington
- Pride Picnic – Buffalo Grove
- Strawberry Fest – Long Grove
- Rock ‘N’ Run the Runway – Wheeling
- Taste of Park Ridge
Western Suburbs
- Graue Mill & Museum
- Gathering on the Green – Western Springs
- La Grange Craft Fair
- Lockport’s Old Canal Days
- Morton Arboretum
- Taste of Oak Brook
- Scottish Festival & Highland Games
South Suburbs
- Crete Garden Walk
- Cruisin’ Frankfort
- Evergreen Park Concerts
- Frankfort Bluegrass Festival
- H-F Juneteenth Festival
- Martin Square Block Parties – Homewood
- Movies in the Park – Monee
- Taste of Orland Park
Ready to Make a Move This Summer?
If your summer plans include a fresh start—whether it’s buying your first home, upgrading your lifestyle, or downsizing for simplicity—I’m here to help guide you through the process…from City to Shore.
📲 Call or text me anytime: 847.275.7253
💻 Contact Me for new and private listings, up-to-date market insights, and personalized, white-glove service.
