With rich culture, acclaimed dining, and fascinating history, Chicago is the perfect location for a family reunion. These multi-generational gatherings are a beloved tradition for many families, particularly within African American culture.
“It’s really based in love — love for their heritage and bringing it forward to the new generation. The older people are passing the torch,” says Crystal Dyer, owner of Gone Again Travel & Tours in Chicago’s Austin community.
Family reunion ideas
Specializing in Black heritage travel, Gone Again Travel & Tours has been a vital resource on Chicago’s West Side for more than 25 years. Dyer says she often organizes family reunions that showcase the city’s Black history landmarks and cultural institutions.
The agency also hosts the popular Chi-Town Soul Trolley Restaurant & History Tour, which takes visitors and locals to restaurants and historic sites throughout the city’s West Side.
We talked to Dyer about her tips for planning family reunions in Chicago, including popular attractions, activities, and more.
Obama-related sites
The country’s first Black president lived in Chicago for more than 20 years, and former First Lady Michelle Obama grew up on the city’s South Side. Today, visitors still flock to the many Chicago sites with an Obama connection.
The family’s former home in the Kenwood neighborhood, located at 5046 S. Greenwood, is a good starting point. It’s not open to the public, but you can admire the area’s many historic homes.
In nearby Hyde Park, the Obama Kissing Rock marks the location of the couple’s first kiss. And the expansive Obama Presidential Center in Jackson Park is set to open in 2026.
Explore more with our guide to Obama’s Chicago.
Global dining and soul food
As a foodie mecca, Chicago is home to an array of unique dining experiences. Dyer says that she often sees family reunions gravitate toward authentic soul food and diverse global cuisines.
Peach’s on 47th and Pearl’s Place in Bronzeville, MacArthur’s Restaurant in Austin, and Luella’s Southern Kitchen in Albany Park are all local favorites that serve up classic soul food dishes like shrimp and grits, fried catfish, and gumbo.
In the Austin community, The Bloohol is run by a father-daughter duo and showcases the flavors of Belize. Also in the neighborhood, JamGrill specializes in authentic Jamaican dishes.
Groups seeking international cuisine will love the Senegalese flavors at Yassa African Restaurant near Bronzeville and Jamaican-inspired dishes and cocktails at 14 Parish Restaurant & Rhum Bar in Hyde Park.
Check out more Black-owned restaurants in Chicago and top restaurants on the city’s South Side.
Chicago’s Black history
Black history runs deep in Chicago. A great place to begin is the DuSable Black History Museum and Education Center, the nation’s oldest independent African American museum.
The new African American Museum and Education Center in the Austin neighborhood presents exhibits and programs dedicated to preserving and showcasing Black American history.
Many family reunions have a strong interest in visiting the Pullman area, says Dyer. The National Historical Park commemorates the community’s connection to the railroad and celebrates the legacy of the Pullman porters and the first Black labor union in the United States.
Historic churches and religious establishments are also a popular request during family reunions. In the South Loop, Quinn Chapel AME Church is home to the city’s first Black congregation and was an important stop on the underground railroad.
Discover more Black history sites and monuments in Chicago.
Chicago’s legendary music scene
Chicago is known as the home of both iconic artists and pioneering genres like amplified blues, house music, Chicago-style jazz, modern gospel, and beyond.
Catch a show at classic spots like Buddy Guy’s Legends, Jazz Showcase, and The Bassment — all great spots to groove to the city’s rhythms.
Schedule a group tour of the historic Chess Records building. Once considered America’s greatest blues label, Chess Records produced notable acts like Muddy Waters, Howlin’ Wolf, Etta James, and more.
Public art and murals
There are so many works of public art and murals throughout the city that Chicago can be viewed as an outdoor art gallery. “Chicago is an art mecca,” says Dyer.
In the city’s downtown, check out the striking Kerry James Marshall mural “Rushmore” on the side of the Chicago Cultural Center. Just a few steps away on Randolph Street, the Richard Hunt sculpture “We Will” glistens in the sun.
Stroll the Wabash Arts Corridor to spot more than 20 large-scale murals, like the Muddy Waters mural that can be seen from State Street. In the evening, find a spot on the Chicago Riverwalk and enjoy ART on the MART, the largest video-projection art installation in the world.
Keep exploring public art in Chicago’s downtown and neighborhoods.
Voluntourism
Family reunions often look for ways to give back to the community during their visit, says Dyer. In Chicago, there are plenty of opportunities to do good while having fun.
Consider helping out at an urban farm like Urban Growers Collective, attending a river clean-up with Friends of the Chicago River, or helping to stock pantries at the Chicago Food Depository.
Check out these 10 Chicago businesses that give back.
