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.

By car

If you are traveling by car, it is very easy to get into the district — the two major highways on the South Side cut right through it. From the Chicago Skyway (I-90), heading northbound, there are exits at 73rd, Stony Island Ave, 87th, and 95th (there are no exits heading southbound from the Dan Ryan junction to 92nd St, past the tollbooth). Off the Dan Ryan (I-94), the principal exits are at 67th, 71st, 76th, 79th, and 87th. The major relevant east-west routes within the area occur every mile, at 71st, 79th, and 87th. For north-south travel within the district, the most useful routes are Cottage Grove Ave, Stony Island Ave (by far the widest route), and to a lesser extent South Chicago Ave.

Parking is widely available in each neighborhood. It is a relatively poor section of the city, and is far enough away from the city center that on-street parking should be easy to find. The only main streets lacking on street parking are in South Shore, along 71st and Exchange.

By rail

Rail is not the best way to visit this section of the city, as you will need to take bus transfers wherever you want to go.
The one relevant CTA line, the Red Line, passes through the western side of Greater Grand and Chatham, right in the center of the Dan Ryan.
The Metra Electric Main Line runs straight from Millenium Station downtown through the heart of the district and, while the trains run less regularly, can be more convenient than the CTA.
For visiting South Shore, on the other hand, Metra is the best way to go, as the Electric South Chicago Branch runs right on top of the main strip the entire way through the neighborhood, with a very convenient stop right by the South Shore Cultural Center.

By bus

Bus, while certainly less convenient than driving, is the most widely used mode of transport throughout most of the district. Route #4 runs the length of Cottage Grove Ave from Chicago State University up King Drive all the way to Michigan Ave in the Loop. Route #4 runs the length of Cottage Grove Ave from Chicago State University through Hyde Park, and all the way to Michigan Ave in the Loop. #6 runs express from downtown to 47th Street running through Kenwood/Hyde Park south to Jackson Park South Shore ending at 79th Street and South Shore Drive. This route provides front door access to the South Shore Cultural Center. #28 runs along Stony Island Ave from eastern Hyde Park all the way to 103rd St on the Far Southeast Side. #14 runs from express Downtown to 67th Street and then South along Jeffery Boulevard to all the way to 103rd St on the Far Southeast Side. #15 runs just like #14 except it is a local route running from the CTA Red Line at 47th Street then east along 51st Street/Hyde Park Boulevard and then down Lake Park Avenue/Stony Island Avenue through the Hyde Park neighborhood to Jeffrey Boulevard all the way to 103rd Street as well.
For traveling east-west, the routes are simple, following the main roads: #67 along 67th St, #71 along 71st St, #75 along 75th, #79 along 79th St and #87 along 87th St.

• Bronzeville Childrens Museum

  phone: +1-773-721-9301
  address: 9301 S Stony Island Ave
  The only African American children's museum in the country is named after the Bronzeville neighborhood even though it is much further south.

• New Regal Theater

  address: 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

  phone: +1-773-288-3800
  address: 1035 E 67th St
  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

  phone: +1-773-256-0149
  address: 7059 S Shore Dr
  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

  phone: +1-773-221-0212
  address: 8231 South Shore Dr
  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.

• Muntu Dance Theatre of Chicago

  phone: +1-773-241-6080
  address: 1809 E 71st St #203
  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

  phone: +1-312-747-6015
  address: 1215 E 83rd St

• ETA Creative Arts Foundation

  phone: +1-773-752-3955
  address: 7558 S South Chicago Ave
  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).

• Rainbow Beach

  phone: +1-312-747-0832
  address: 7600 South Shore Dr
  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.

• The Rink

  phone: +1-773-221-3290
  address: 1122 E 87th St
  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.

• South Shore Country Club

  phone: +1-312-747-6250
  address: 7059 S Shore Dr
  Nine holes of golf maintained (somewhat) by the Chicago Park Administration. Great skyline views over Lake Michigan from the course.

• Angborki Doe Designs

  phone: +1-773-731-2650
  address: 2650 E 83rd St
  African imports, aimed at home decor from jewelry and artwork to sofas.

• The Underground Afrocentric Book Store

  phone: +1-773-768-8869
  address: 1727 E 87th St
  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

  phone: +1-773-994-6666
  address: 441 E 75th St
  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).

Budget

• Dat Donuts

  phone: +1-773-723-1002
  address: 8249 S Cottage Grove Ave
  A must for serious donut eaters as it is home to the legendary "Big Dat" — the mother of all donuts. In addition to quantity (i.e., size), the quality attracts devoted foodies from all over the Chicagoland area.

• Harold's Chicken Shack #55

  phone: +1-773-224-3314
  address: 100 W 87th St
  A restaurant reviewer for the Chicago Reader took on the immense and grave task of finding which Harold's is the best, visiting each and every one of the 50 or so odd locations, and reviewing them on a 10-point scale across 12 categories. And he found this location to be the best of them all! While the chicken should be fabulous, there are more fights going on in that parking lot than is normal — usually between people who know each other, though.

• Give Me Some Sugah

  phone: +1-773-363-9330
  address: 2234 E 71st St
  A wonderful South Shore bakery, where everything is made from scratch (the high prices reflect this).

• Maya's Pizza

  phone: +1-773-221-9313
  address: 8550 S Commercial Ave
  Serving a pretty delicious, thickish pan pizza pie or by the slice at nice South Chicago prices. The menu is, unsurprisingly, stuffed with random generic South Side fare, but the chicken broaster is also pretty great.

• That's a Burger

  phone: +1-773-493-2080
  address: 2134 E 71st St
  Big to-order burgers at a local favorite. Take-out only, and call ahead well in advance to avoid a long wait. The house specials are the Whammy Burger, which comes with a split Polish on top, and the T.a.B Special, topped with chili, cheese, bacon and egg. Beef or turkey.

Mid-range

• Barbara Ann's Barbecue

  phone: +1-773-651-5300
  address: 7617 S Cottage Grove Ave
  All Barbara Ann's offerings are great, but the links stand out — coarse, fatty, spicy — incredible. She also offers beef tips, which you would have trouble finding elsewhere in the city. Order the sauce on the side if you don't want your links to drown.

• BJ's Market & Bakery

  phone: +1-773-374-4700
  address: 8734 S Stony Island Ave
  This dining-hall like eatery offers some of the best soul food in a city full of great southern cooking. Moreover, the chef prides himself on cooking soul food for the heart, meaning that the food is actually healthy and won't sit so heavy in your stomach.

• Captain's Hard Time Dining

  phone: +1-773-487-2900
  address: 436 E 79th St
  Fine dining on the cheap, soul food, steaks, and seafood. Offers a $15 Sunday "Gospel buffet" from 11AM-6PM with Gospel singers performing after 2:30PM.

• Lem's Bar-B-Que House

  phone: +1-773-994-2428
  address: 311 E 75th St
  Lem's sets the standard against which all Chicago cue must be judged. That's not to say it is the best — Uncle John's could certainly give Lem's a run for its money on any day. But it serves the most reliably excellent tips and (charred) links you'll find in the city. Open late, and with a crowded parking lot.

• Maxine's Caribbean Spice

  phone: +1-773-933-0540
  address: 1232 E 87th St
  One of the best Jamaican restaurants in town. Features a weekend Caribbean breakfast which comes with sides of fried dumplings and boiled bananas. Note though, like all South Side Jamaican places, service is s l o w.

• Soul Vegetarian East Restaurant

  phone: +1-773-224-0104
  address: 205 E 75th St
  This is at once one of the best vegetarian and the best soul food restaurants in town. Occasional events range from spoken word to hip hop DJs.

• Three J's Restaurant

  phone: +1-773-667-1360
  address: 1713 E 75th St
  South Side is the place for Jamaican, and this local South Shore establishment gets five stars for the jerk chicken alone. Inside it's a nice, clean, diner-like eatery, with friendly service. Even if you never set foot in the neighborhood, you can indulge in this fine food by delivery as far as the Loop! Just know that it's cash-only, order minimum $15, you will have to step outside your hotel to get it, and call Joseph at +1-773-746-9615 for the delivery (tip him well for that drive!).

• Uncle Joe's

  phone: +1-773-962-9935
  address: 8211 S Cottage Grove Ave
  The South Side's legendary Jamaican restaurant serving great jerk meats. It has developed into a local chain, but this is the original, and widely considered the best.

• Uncle John's BBQ

  phone: +1-773-892-1233
  address: 339 E 69th St
  Uncle John's BBQ is simply the best. The tips and links are perfect, and the spare-ribs (unlike most Chicago ribs) are wonderful. This place will dispel any notions you previously carried about BBQ north of the Mason-Dixon.

• Yassa African Restaurant

  phone: +1-773-488-9630
  address: 716 E 79th St
  An authentic Senegalese Restaurant, which has made quite a name for itself (having been featured on the popular foodie TV show "Check Please"). But it remains a low-key, friendly hub for Chicago's Senegalese community. Don't miss the W,F dinner special: cow foot?!

Splurge

• The Parrot Cage

  phone: +1-773-602-5333
  address: 7059 S Shore Dr
  An upscale restaurant at the South Shore Cultural Center that offers fine seasonal American cuisine at impressively low prices, nice views of Lake Michigan, and is a great excuse to come admire the SSCC.

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. Jazz lovers spending much time in the city should not miss a Tuesday night Von Freeman gig at the New Apartment Lounge.
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

  phone: +1-773-846-0005
  address: 69 E 75th St
  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

  phone: +1-773-667-6454
  address: 1530 E 75th St
  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

  phone: +1-773-359-4637
  address: 7201 S Exchange Ave
  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.

• New Apartment Lounge

  phone: +1-773-483-7728
  address: 504 E 75th St
  This jazz club is simply extraordinary. It is small, has no cover, and hosts perhaps the best regular jazz show in Chicago. Not all nights see performances, but every Tuesday night Chicago jazz legend Von Freeman shows up with his quartet and enchants those who make it out to this small club from 10:30PM until a few hours before the sun comes up. His show attracts people from all walks of life from all over the city. If you want to sit at the bar, expect to pay for a few drinks. This club has been "closed for renovations" since January 2011.

• Red Pepper Lounge

  phone: +1-773-873-5700
  address: 428 E 87th St
  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.

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

  phone: +1-773-487-5800
  address: 7621 S Cottage Grove Ave
  Offers a bed, dresser, TV, and private bathroom. Attached to Barbara Ann's BBQ, which serves excellent rib tips.

• Camelot Motel

  phone: +1-773-488-3100
  address: 9118 S Cottage Grove Ave
  Rooms have a dresser, table, and television.

• Lake Motel

  phone: +1-773-731-6600
  address: 9101 S Stony Island Ave
  Not far from Chicago State University and the Chicago Skyway/I-90 to Indiana.

• Stony Island Motel

  phone: +1-773-731-8817
  address: 9201 S Stony Island Ave
  The friendliest looking option in the area, with standard rooms, also close to the Skyway.

• Zanzibar Motel

  phone: +1-773-768-1430
  address: 8101 S Stony Island Ave
  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

  phone: +1-312-747-5234
  address: 8148 S Stony Island Ave

• Greater Grand Crossing Branch Library

  phone: +1-312-745-1608
  address: 1000 E 73rd St

• South Shore Branch Library

  phone: +1-312-747-5281
  address: 2505 E 73rd St

• Whitney Young Branch Library

  phone: +1-312-747-0039
  address: 7901 S Dr Martin Luther King Jr Dr

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.