Summer in Chicago is a season like no other. The city comes alive with outdoor festivals, lakefront adventures, rooftop dining, and vibrant neighborhoods full of energy. Whether you’re a local, a visitor, or a new resident getting to know your surroundings, this guide will help you soak up every bit of sunshine the city has to offer. From neighborhood gems to can't-miss experiences, here's Lofty Real Estate's ultimate guide to enjoying summer in Chicago.
🍽️ Where to Eat: Summer Dining Hotspots
1. Parson’s Chicken & Fish – Logan Square & Lincoln Park
With its laid-back vibe, outdoor picnic tables, and frozen cocktails, Parson’s is a must-visit for a casual meal in the sunshine.
2. Aba – Fulton Market
This chic rooftop restaurant delivers Mediterranean small plates, a lush rooftop garden setting, and major date night vibes.
3. Big Star – Wicker Park
Tacos + tequila + sidewalk patio = summer perfection. It’s a Chicago favorite for a reason.
4. Piccolo Sogno – River West
Romantic courtyard dining with incredible Italian cuisine. Perfect for a summer night out.
5. Recess – West Loop
This shipping-container-themed restaurant has one of the largest patios in the city. Think bold cocktails and great people-watching.
🎮 Where to Play: Summer Activities & Events
1. Kayaking on the Chicago River
See the city from a whole new angle. Rent a kayak or join a guided tour for a scenic paddle through downtown.
2. Millennium Park Concerts & Movies
Pack a picnic and a blanket and enjoy free concerts or movies under the stars at the Jay Pritzker Pavilion.
3. Chicago Summer Festivals
- Taste of Chicago (July)
- Grant Park Music Festival (all summer)
- West Fest, Lollapalooza, Ribfest and more There’s something happening every weekend!
4. Beach Day on Lake Michigan
Head to North Avenue Beach, Oak Street Beach, or Montrose Beach for sand, sun, and skyline views.
5. Bike the Lakefront Trail
Stretching over 18 miles, this trail offers beautiful lakefront views, perfect for biking, walking, or rollerblading.
🌧️ Where to Cool Off: Best Spots to Beat the Heat
1. Maggie Daley Park Splash Pad
Great for families with young kids — centrally located and tons of fun.
2. Chicago Riverwalk
With shady seating, breezy bars, and misting fans, this downtown stretch is perfect for escaping the heat.
3. Neighborhood Ice Cream Gems
- Jeni’s Splendid Ice Creams – multiple locations
- Original Rainbow Cone – Beverly & Navy Pier
- Scooter’s Frozen Custard – Lakeview
4. Chicago Park District Pools
Free public pools are open all across the city. Check the Chicago Park District website for the one nearest you.
5. Rooftop Bars with Breeze & Views
Try Cindy’s at the Chicago Athletic Association Hotel or The Robey in Wicker Park for a cocktail and skyline breeze.
🌟 Insider Tip: Explore the Neighborhoods
Some of the best summer moments happen off the beaten path. Take time to explore:
- Pilsen for street art and tacos
- Andersonville for Swedish charm and indie shops
- Logan Square for patios, markets, and murals
- Hyde Park for historic architecture and lakeside serenity
🏠 Brought to You by Lofty Real Estate
We don’t just help you find a home, we help you discover your city. Whether you’re looking to rent, buy, or invest, our team is here to help you feel right at home in Chicago, all summer long.
