Chicago/Chatham-South Shore

This side of Chicago does not feature in many travel plans. If you ask a hotel concierge in the Near North to make arrangements for a trip here, the reaction — whether incredulous or simply bewildered — should be a sight to behold. Don't be fooled, though; Chatham and Greater Grand could be the highlight of your trip to Chicago. The best blues clubs, the last true juke joints, are way down here.

Greater Chatham (Chatham, Avalon Park, Calumet Heights, Burnside) is a residential stronghold of middle and upper class African-American Chicagoans. No sightseeing to be done, but Chatham boasts some of the best food on the South Side (including the ultimate Harold's), as well as one of the city's best blues clubs.

Greater Grand rivals Chatham for soul food, BBQ, and blues club supremacy. It also has the Oak Woods Cemetery, which is beautifully laid out, and a resting place to some of the most famous residents of the South Side's past.

South Shore is home to a lively arts scene, largely thanks to the ETA Creative Arts Foundation and the magnificent South Shore Cultural Center. It is also home to one of the city's best and least known beaches, Rainbow Beach. Incidentally, many of Chicago's most prominent black politicians call this community home. Its main commercial strip runs alongside Metra's Electric Line on 71st St and is literally lined with kids hanging out when school's not in session.

• 🌍 Bronzeville Children's Museum, 9301 S Stony Island Ave, ☏ +1-773-721-9301. Tu-Sa 10AM-2PM. The only African American children's museum in the country is named after the Bronzeville neighborhood even though it is much further south. $5. 
• 🌍 New Regal Theater (Old Avalon Theater), 1641 E 79th St. Built in 1927 as one of the South Side's most impressive movie palaces, done up in ornate Moorish Revival style, this theater was in operation well past the riots and up into the late 1970s. Since then, the theater has served as a church, and then a performance venue, before finally shuttering its doors in 2003. In 2008, however, the building caught a glimmer of new hope with a purchase by new owners hoping to turn the building into a new cultural venue. The idea hasn't quite taken hold yet, but there is reason to feel optimistic about this Chicago Landmark's long-term future. If you are not getting in for an event in the meantime (and believe it, the interior is in fabulous shape and incredibly beautiful), check out the cool mural on the side and ponder the building's incredible musical history; the venue's performers truly include every single world class blues, jazz, rhythm & blues, funk, and soul musician you can think of: John Coltrane, Count Basie, Nat King Cole, Sammy Davis Jr, Earth Wind & Fire, Duke Ellington, Ella Fitzgerald, the Supremes, Gladys Knight, the Isley Brothers, Billie Holiday, Isaac Hayes, B.B. King, Miles Davis, Stevie Wonder, Marvin Gaye, and so on. 
• 🌍 Oak Woods Cemetery, 1035 E 67th St, ☏ +1-773-288-3800. M-F 8:30AM-4:15PM, Sa Su 8:30AM-sundown. Were it not for the somber atmosphere, Oak Woods would probably be one of Chicago's favorite parks as it is beautifully laid out and has four attractive elongated ponds. The cemetery is the final resting place of many of the South Side's most famous residents, including Olympian runner Jesse Owens, nuclear physicist Enrico Fermi, civil rights leader Ida B. Wells, Mayor William Hale Thompson (perhaps Chicago's most eccentric leader), and the first black mayor of Chicago, Harold Washington Jr. One of the more striking monuments is the memorial to the overwhelming 6,000 Confederate prisoners of war who died at Camp Douglas (on the site of the present day Illinois Institute of Technology in Bronzeville). The mayors' graves are located along the northwest shore of the largest lake (Symphony Lake). If Illinois' ugly political world interests you, you can find "Senator" Roland Burris' ostentatious monument/grave prepared in advance, with a list of his "achievements." 
• 🌍 South Shore Cultural Center (SSCC), 7059 S Shore Dr, ☏ +1-773-256-0149. Su-F 9AM-6PM, Sa 9AM-5PM. An enormous South Side landmark, which once served as the private golf clubhouse — closed to African-Americans. Times have changed. The country club went bankrupt, and the golf course and tremendous building were bought by the Chicago Park District, and then converted into a beautiful and extravagant community center with large chandeliers and floor to ceiling windows. The SSCC hosts plays, live music, and dance performances. It's no stranger to fame, having hosted the wedding receptions of countless South Side notables, including the Obamas; the exterior also served as the "Palace Hotel Ballroom" for the Blues Brothers' big gig. 
• 🌍 St Michael the Archangel Church, 8237 South Shore Dr, ☏ +1 773-734-4921. Perhaps the grandest example of the Polish Cathedral style on the South Side is this towering neogothic church, built in 1909. Of course, economic-driven neighborhood change has meant the end of the Polish steelworker demographic in this parish, which is now heavily Latino. The interior is very impressive — look especially for the hand-sculpted statue of St Michael defeating Lucifer, the oak and marble communion rail, and the enormous, beautiful German-made stained glass windows. 
• Pilgrim Baptist Church of South Chicago, 3235 E 91st St, ☏ +1-773-374-3888. The Church from the Blues Brothers where James Brown played the lively reverend. 

• 🌍 Muntu Dance Theatre of Chicago, 1809 E 71st St #203, ☏ +1-773-241-6080. Check website for performance times. Muntu is an innovative and highly acclaimed Chicago dance company, which performs energetic interpretations of African and African-American dances and music. This location, their headquarters, is comprised of offices and a stage, although they regularly travel around Chicago's performance venues. 
• Avalon Park Ice Skating, 1215 E 83rd St, ☏ +1-312-747-6015. Outdoors 7AM-11PM daily, Indoor rink M-F 9AM-10PM, Sa Su 9AM-5PM. Free skating, $3 skate rentals. 
• 🌍 ETA Creative Arts Foundation, 7558 S South Chicago Ave, ☏ +1-773-752-3955. Box office M-W 10AM-6PM, Th-Su 10AM-10PM, ETA Gallery M-W 11AM-6PM, Th F 11AM-10PM, Sa 7AM-10PM, Su 2PM-10PM. A community center housing one top-notch African-American theater company, which puts on an extraordinary number of plays, nearly all of them world premieres. The theater is very nice and the community center includes two art galleries featuring mostly local African-American artists. Live music on Music Mondays (second Monday of the month). Main stage $25. 
• 🌍 Rainbow Beach, 7600 South Shore Dr, ☏ +1-312-747-0832. Summers (Memorial Day-Labor Day): 9AM-9:30PM. One of the best and biggest beaches in Chicago, boasting a magnificent South Side view of the Chicago skyline, and it has a free parking lot! Free outdoor movies are often held in the adjacent Rainbow Park. Free. 
• 🌍 The Rink, 1122 E 87th St, ☏ +1 773-221-2600. Tu 10AM-2PM (30+) 8PM-midnight (21+), W 5:30PM-8:30PM (families), Th 8PM-midnight (30+), F 7PM-11PM, Sa noon-3PM (pre-teen) 7PM-11PM (teen) midnight-4AM (18+), Su 5PM-9PM (30+) 9:30PM-1:30AM (18+). Ok, this place is cool. A roller rink oozing with South Side character and home to not a few serious skaters who flaunt their moves to smooth R&B and old school. It has shown up a bit in pop culture, from the movies "Soul Food" and "Roll Bounce" to several nationally-aired music videos. If you are intimidated by the pros on the rink but want to check the place out, there are also arcade games and pool/ping-pong tables. It is open to different age groups at different times, so make sure to double-check the hours before coming here. $7, but varies. 
• 🌍 South Shore Country Club, 7059 S Shore Dr, ☏ +1-312-747-6250. Sunrise-sunset. Nine holes of golf maintained (somewhat) by the Chicago Park Administration. Great skyline views over Lake Michigan from the course. Weekdays $11, Weekends $12.50. 

• 🌍 Angborki Doe Designs, 2650 E 83rd St, ☏ +1 773-492-5980. M-Sa 9AM-7PM. African imports, aimed at home decor from jewelry and artwork to sofas. 
• The Underground Afrocentric Book Store, 1727 E 87th St, ☏ +1-773-768-8869. M-Sa 11AM-7PM. Books by and about African-Americans. Prides itself on distributing new and controversial publications. Also sells recordings of speeches by African-American leaders, African clothing, and other odds and ends. 
• The Woodshop Art Gallery, 441 E 75th St, ☏ +1-773-994-6666. M W-Sa 9AM-6PM. Offers paintings and contemporary furniture by African-American artists as well as Haitian art, all at quite reasonable prices. 

This section of the city is spoiled for neighborhood restaurants. The city's most renowned soul food is served up here at famous locations, long serving just about every prominent African-American figure who has set foot in Chicago. The city's best Memphis-style BBQ is here, too. Greater Grand is home to the city's best donuts; Chatham to the city's best fried chicken.

Now, if you are looking for something that resembles healthy food, your options are limited. Soul Vegetarian is a very good option, and the various ethnic restaurants are not quite so heart attack-inducing (mostly Jamaican, but with the odd Trinidadian and Senegalese restaurant tossed in for good measure).

Don't be fooled. There are plenty of blues clubs throughout the city, but none hold a candle to the following. Blues clubs are undoubtedly a matter of taste — you could have a great or a bad experience at any one of these, but the risk is worth it.

South Side blues clubs, though, constitute a fragile ecosystem. Try not to descend en masse. The music and atmosphere will adapt to you; you won't get the real experience. Come in couples or trios instead, and immerse yourself in the culture of the real Chicago blues.

• 50 Yard Line Bar and Grille, 69 E 75th St, ☏ +1-773-846-0005. Su-F 11AM-2AM, Sa 11AM-3AM. A cool bar and a South Side steppers' lounge, where people dance like adults. Despite the name, this is about as far from being a sports bar as possible. 
• 🌍 Club Escape, 1530 E 75th St, ☏ +1-773-667-6454. Su-F 5PM-2AM, Sa 5PM-3AM. South Side gay bars are rare creatures. This is a very laid back and exceptionally welcoming bar/lounge frequented mostly by men and women in their 30s and 40s, dancing mostly to soul, house, and smooth jazz. 
• Chef Sara's Cafe, 7201 S Exchange Ave, ☏ +1-773-359-4637. M-F 6AM-8PM, Sa 8AM-8PM, Su 8AM-5PM. This airy, attractive, comfortable, stay-as-long-as-you-want cafe is impossible to miss, and you wouldn't want to. The fresh sandwiches, salads, and panini are all worth stopping in for. The free WiFi should keep you occupied while you sip. 
• Red Pepper Lounge, 428 E 87th St, ☏ +1-773-873-5700. M 3PM-2AM, T-F 10AM-2AM, Sa 10AM-3AM, Su noon-2AM. A Mardi Gras styled bar/restaurant serving Cajun cuisine. There's blues on Wednesdays and stand-up comedy Tuesdays and Thursdays. F-Sa usually see live DJs and lots of dancing. The entertainment is in the back room past the front bar. Dinners $5-8. (updated Oct 2017)

Know what you're getting into if you are thinking of staying here. The options are pay-by-the-hour flop houses and run-down motels, with all the shady characters, dubious mattresses, and loose security that entails. And, well, cabs might be reluctant to pick you up if you give them one of these addresses. If staying here, though, know that the motels on Stony Island are the most secure.

• Barbara Ann's Motel Two, 7621 S Cottage Grove Ave, ☏ +1-773-487-5800. Offers a bed, dresser, TV, and private bathroom. Attached to Barbara Ann's BBQ, which serves excellent rib tips. 
• Ppp Grove Motel, 9118 S Cottage Grove Ave, ☏ +1 773-488-3400. Rooms have a dresser, table, and television. 
• Stony Island Motel, 9201 S Stony Island Ave, ☏ +1-773-731-8817. The friendliest looking option in the area, with standard rooms, also close to the Skyway. 
• South Shore Motel & Suites, 8101 S Stony Island Ave, ☏ +1 773-221-5400. Offers cable television and air conditioning. 

There are four public libraries offering free wifi and public terminals. The Exchange Cafe above is another good option.

• Avalon Branch Library, 8148 S Stony Island Ave, ☏ +1-312-747-5234. M W noon-8PM, Tu Th 10AM-6PM, F-Sa 9AM-5PM. 
• 🌍 Greater Grand Crossing Branch Library, 1000 E 73rd St, ☏ +1-312-745-1608. M W 10AM-6PM, Tu Th Noon-8PM, F-Sa 9AM-5PM. 
• South Shore Branch Library, 2505 E 73rd St, ☏ +1-312-747-5281. M W 10AM-6PM, Tu Th noon-8PM, F-Sa 9AM-5PM. 
• Whitney Young Branch Library, 7901 S Dr Martin Luther King Jr Dr, ☏ +1-312-747-0039. M W 10AM-6PM, Tu Th noon-8PM, F-Sa 9AM-5PM. 

The South Side experiences here can potentially outshine those you could have anywhere else in Chicago. There's one hitch though, and that's violent crime. Alas, the levels of violent crime in this area, especially in the northwest neighborhood of Greater Grand Crossing, are higher than you'd find traveling in much of the world; travel here is not for everyone, and many travelers will find visiting this area of the city to be beyond their comfort level.

Nonetheless, a casual visitor is very unlikely to be the target of crime; you just are not spending enough time here, so the odds are you'll be fine. Avoid side streets, where you can run into unabashed drug trade. On main streets, you might get mildly harassed if you look lost, insecure, or unfamiliar with your surroundings — if it happens, avoid eye contact, and keep walking.

It's a hassle to deal with public transport, especially if you're not staying here, and waiting around in the wee hours of the night at a bus stop, having stumbled out of a bar, is not a great idea. If you're going to be at a club, you're going to have some booze, and you'll need a ride. Arranging a point-to-point taxi ride is a good idea if you are coming from downtown. Arrange that in advance; residents rightly complain about the difficulty of getting a cab at night.

• The South Side's Bronzeville and Hyde Park are just to the north and have a lot to offer a visitor interested in African-American history and culture. They also have far better hotel options, so if you are interested in basing yourself South Side, it may make sense to get a room near a Metra stop near Hyde Park.
• Chatham is often considered part of the Far Southeast Side, and there is ample reason to head further south. More soul food awaits, more blues brothers' filming locations, as well as a host of other South Side attractions like Historic Pullman.