South Shore & Woodlawn

South Shore and Woodlawn are South Side lakefront neighborhoods on either side of Jackson Park, and the Obama Presidential Center that opened in the park in 2026 is changing both. South Shore has the South Shore Cultural Center, a former country club on the lake with a golf course and a beach, and blocks of courtyard apartments and bungalows between 67th and 79th streets. Woodlawn, across the Midway from the University of Chicago, has 63rd Street’s rebuilt commercial strip, a rising number of new apartments and some of the city’s most contested conversations about who benefits from the Center.

Where it is

Woodlawn runs from the Midway Plaisance at 60th south to 67th and from Cottage Grove east to Stony Island; South Shore continues from 67th south to 79th and east to the lake, with Jackson Park between them and the lake. Metra Electric stops at 63rd, Stony Island, Bryn Mawr, South Shore, Windsor Park and Cheltenham, a 20-minute ride to Millennium Station. The Green Line ends at Cottage Grove and 63rd, and the 6 Jackson Park Express, 15 Jeffery Local and J14 Jeffery Jump buses run downtown. Drivers use Lake Shore Drive, which ends at 67th, or Stony Island.

What to know if you’re moving here

Prices are low for lakefront living, and the Obama Center has brought both investment and an affordable housing ordinance.

• Housing is courtyard apartments, bungalows, greystones and lakefront high-rises built from the 1900s on, with typical prices of roughly $100,000 to $500,000 as a broad editorial estimate as of September 2026.
• Street parking is easy on most blocks, with permit zones near the lakefront high-rises.
• Public schools fall under Chicago Public Schools, with Hyde Park Academy in Woodlawn and South Shore International College Prep in South Shore.
• The Woodlawn Housing Preservation Ordinance, passed in 2020, sets aside city-owned lots for affordable housing near the Center.
• Metra Electric and the Jeffery Jump bus make the downtown commute 20 to 30 minutes.
• The drawback is that commercial streets like 71st and 63rd still have long vacant stretches, and violence on some blocks remains a concern residents talk about openly.

What to do if you’re visiting

Jackson Park and the lakefront are the draw, Metra Electric gets you to both, and the food is at 63rd Street and inside the Cultural Center.

• A museum, a library branch and public gardens make up the Obama Presidential Center, which opened in Jackson Park in 2026.
• Breakfast skillets at Daley’s Restaurant at 63rd and Cottage Grove come from a kitchen that opened in 1892, the oldest in the city.
• Coffee before the Center means Robust Coffee Lounge at 63rd and Woodlawn, six blocks west of the park, or Build Coffee & Books on Blackstone inside the Experimental Station.
• A $75 Korean-inspired high tea at Han Cha and walk-in cocktails at Yunomi opened in June 2026 inside the Stony Island Arts Bank, Theaster Gates’s restored 1923 bank at 68th and Stony Island.
• Books by Black authors and signed copies fill Da Book Joint inside Pen and Paper at 69th and Stony Island, a block south of the Arts Bank.
• Shrimp and grits with a lake view and live jazz at Sunday brunch are the order at Nafsi, the restaurant inside the South Shore Cultural Center at 71st and South Shore Drive, where the free beach, nine-hole golf course and landmark ballroom are steps away.
• Imported dresses, Fulani hats and whipped shea butter stock Thiocary Fashion on Cottage Grove at 65th, a Woodlawn fixture for more than 20 years.
• Jackson Park’s Garden of the Phoenix, the Japanese garden on Wooded Island, dates to the 1893 fair, and Rainbow Beach at 79th is one of the widest beaches on the South Side.