Guide
The Sonny Guide to Chicago Beaches
Where to swim, spread out, stop for lunch, and stay until the skyline begins to glow.
JUL 26, 2026 · 8 min read · By Sonny team
There are summer days when Chicago feels less like a city beside a lake and more like a city built entirely around one. The morning begins on the trail, lunch happens with sand still on your feet, and the skyline stays in view even after you have found a table and ordered the first round.
The lakefront stretches for roughly 26 miles, but each section has its own rhythm. Oak Street places you directly beneath the city. Montrose feels wider and more leisurely. From 31st Street and Promontory Point, the skyline appears across the water rather than above you. The pleasure is not in covering as much ground as possible, but in choosing the stretch that suits the day and allowing it to unfold.
These are our favorite ways to spend a day beside the lake.
Best for
- Starting early and staying out
- A swim with a skyline
- Taking the trail somewhere good
- Turning the beach into drinks
Our favorite ways to spend the day by the lake
01
The Classic City Beach
Oak Street · Ohio Street · North Avenue
For the full Chicago effect, stay close to downtown. Oak Street places the skyline almost directly above the sand, with chair rentals, volleyball, food, and one of the city’s most distinctive views. Ohio Street is smaller and pleasantly tucked beside Olive Park, while North Avenue brings the livelier beach-day energy. Start before noon, when the sand is calmer and the buildings are still catching the morning light.
02
The Longer, Slower Beach Day
Montrose · Osterman
Montrose is made for settling in. The beach is broad, the horizon feels open, and there are concessions, showers, kayak and volleyball rentals nearby. Beyond the busiest stretch, the surrounding natural area softens the city edges with dunes, grasses, and migratory birds. Farther north, Osterman — still called Hollywood Beach by plenty of Chicagoans — feels smaller and more neighborhood-minded, with native dune habitat along the sand.
03
The Skyline from the South
31st Street · Promontory Point
The city looks especially beautiful when viewed from across the water. Margaret T. Burroughs Beach — better known as 31st Street Beach — sits beside the harbor with a broad north-facing skyline view, concessions, and space for a proper picnic. Continue south to Promontory Point, where Alfred Caldwell’s naturalistic landscape and limestone edges create one of the lakefront’s most elegant places to linger. Bring lunch, choose a spot facing north, and stay for the late-afternoon light.
04
Lunch with the Lake Beside You
Caffè Oliva · Shore Club · The Lakefront
A lakefront day is considerably better when lunch does not require leaving the water behind. Caffè Oliva sits directly at Ohio Street Beach with Mediterranean-inspired food, cocktails, and a relaxed feet-in-the-sand atmosphere. Shore Club brings a more polished beach-club mood to North Avenue, with patio dining, cabanas, and uninterrupted lake views. At Fullerton, The Lakefront Restaurant offers a composed sit-down meal inside the historic Theater on the Lake, with seasonal terraces overlooking both the water and skyline.
Plan your day
Take it to the water
Trade the shoreline for the lake itself. Explore sailboat charters, afternoon cruises, and boat days chosen for the weather right now.