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 clubsare all 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 two 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 both beautifully laid out and resting place to some of the 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.
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.
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.
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 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, 9301 S Stony Island Ave, ☎ +1 773 721-9301, . Tu-Sa 10AM-2PM. The First and Only African American childrens museum in the country is named after The Bronzeville neighborhood even though it is located much further south. $5. edit
Oak Woods Cemetery, 1035 E 67th St, ☎ +1 773 288-3800. M-F 8:30AM-4:15PM, Sa Su 8:30AM-sundown. Were it not for the somber atmosphere, Oak Woods would probably be one of Chicago's favorite parks as it is beautifully laid out and has four attractive elongated ponds. The cemetery is the final resting place of many of the South Side's most famous residents, including Olympian runner Jesse Owens, nuclear physicist Enrico Fermi, civil rights leader Ida B. Wells, Mayor William Hale Thompson (perhaps Chicago's most eccentric leader), and the first black mayor of Chicago, Harold Washington Jr. One of the more striking monuments is the memorial to the overwhelming 6,000 Confederate prisoners of war who died at Camp Douglas (on the site of the present day Illinois Institute of Technology in Bronzeville). The mayors' graves are located along the northwest shore of the largest lake (Symphony Lake). If Illinois' ugly political world interests you, you can find "Senator" Roland Burris' ostentatious monument/grave prepared in advance, with a list of his "achievements."edit
South Shore Cultural Center (SSCC), 7059 S Shore Dr, ☎ +1 773 256-0149, . Su-F 9AM-6PM, Sa 9AM-5PM. An enormous South Side landmark, which once served as the private golf clubhouse — closed to African-Americans. Times have changed. The country club went bankrupt, and the golf course and tremendous building were bought by the Chicago Park District, and then converted into a beautiful and extravagant community center with large chandeliers and floor to ceiling windows. The SSCC hosts plays, live music, and dance performances. It's no stranger to fame, having hosted the wedding receptions of countless South Side notables, including the Obamas; the exterior also served as the "Palace Hotel Ballroom" for the Blues Brothers' big gig.edit
Avalon Park Ice Skating, 1215 E 83rd St, ☎ +1 312 747-6015, . Outdoors 7AM-11PM daily, Indoor rink M-F 9AM-10PM, Sa Su 9AM-5PM. Free skating, 3$ skate rentals. edit
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 itself 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. edit
Muntu Dance Theatre of Chicago, 6800 S Wentworth Ave, ☎ +1 773 602-1135, . 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.edit
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. edit
The Rink, 1122 E 87th St, ☎ +1 773 221-3290, . T 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. edit
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. edit
Angborki Doe Designs, 2650 E 83rd St, ☎ +1 773 731-2650, . M-F 8AM-6PM, Sa 9AM-5PM. African imports, aimed at home decor from jewelry and artwork to sofas.edit
Premonition Fashion, 8159 S Stony Island Ave, ☎ +1 773 374-4472, . M-Sa 11AM-7PM, Su by appointment. A boutique specializing in trendy, very fashionable clothes by local designers for women of all sizes. The prices are outrageously low.All items $10-50. edit
Moo & Oink, 7158 S Stony Island Ave, ☎ +1 773 493-7100, . M-F 8AM-8PM, Sa 8AM-7PM, Su 8AM-6PM. The legendary Grocery Store/Butcher Shop made famous for its catchy jingle and dancing cow and pig duo seen in local commercials.edit
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.edit
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.edit
This section of the city is spoiled for terrific neighborhood restaurants. The majority of the city's most renowned soul food is served up here at famous locations like Army & Lou's and Izola's, both of which have served 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).
South Side BBQ
Follow these rules, and you'll get some great cue:
Get your sauce on the side! There's no reason not to, and it allows you to control just how drenched the meat gets.
Follow the guide. You can easily go astray in these parts with sub-par BBQ — you cannot with the ones listed below.
Order sparingly. One combo can easily feed two, so if you're solo, plan to either make it two meals or get one of the small dishes.
Make sure they've got your order right, as communication through bulletproof glass is difficult.
Take your cue somewhere else. Good options include the Midway in Hyde Park, or better still the 63rd St Pier east of Jackson Park.
This is the real deal, dig in with those fingers and make a mess!
Cafe Nine 17, 917 E 79th St, ☎ +1 773 723-2222. T W 11AM-9PM, Th-Sa 11AM-10PM, Su noon-9PM. A sandwich shop/eatery with open mic poetry nights T-W. The owner is openly gay and markets the cafe as a safe spot for the South Side LGBT community.$4-8. edit
Cafe Trinidad, 557 E 75th St, ☎ +1 773 846-8081. M-Th 11AM-8PM, F Sa 11AM-9PM, Su 12:30PM-7PM. This is one of the only places to get Trinidadian cuisine in Chicago, and it knows what it is doing with its long list of curries.$3-8. edit
Dat Donuts, 8249 S Cottage Grove Ave, ☎ +1 773 723-1002. 24 hours daily, except Su 10PM-4AM. 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.$0.25-2.50. edit
Harold's Chicken Shack #55, 100 W 87th St, ☎ +1 773 224-3314. Su-Th 11AM-midnight, F Sa 11AM-2AM. 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 ten point scale across twelve categories. And he found this location to be the best of them all! While the chicken should be fabulous, it's worth noting that there are more fights going on in that parking lot than is normal — usually between people who know each other, though.$2-5. edit
Give Me Some Sugah, 2234 E 71st St, ☎ +1 773 363-9330, . M 3:30PM-7:30PM, Tu-Sa 10AM-7:30PM. A wonderful South Shore bakery, where everything is made from scratch (the high prices reflect this).$1.50-6. edit
That's a Burger, 2134 E 71st St, ☎ +1 773 493-2080. M-Th 11AM-7PM, F Sa 11AM-9PM. 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.$4-6. edit
Barbara Ann's Barbecue, 7617 S Cottage Grove Ave, ☎ +1 773 651-5300. Tu-Th noon-midnight, F Sa noon-3AM. 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.$8-16. edit
BJ's Market & Bakery, 8734 S Stony Island Ave, ☎ +1 773 374-4700, . M-Th 11AM-9PM, F Sa 11AM-10PM, Su 11AM-8PM. 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.$8-15. edit
Captain's Hard Time Dining, 436 E 79th St, ☎ +1 773 487-2900. S,T-Th 8AM-11PM, F Sa 8AM-midnight. 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.$9-14. edit
Lem's Bar-B-Que House, 311 E 75th St, ☎ +1 773 994-2428. W-M 2PM-4AM. 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 a good 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.$5-13. edit
Maxine's Caribbean Spice, 1232 E 87th St, ☎ +1 773 933-0540. M-Th noon-10PM, F Sa noon-midnight, Su noon-9PM. 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.$7-15. edit
Soul Vegetarian East Restaurant, 205 E 75th St, ☎ +1 773 224-0104, . M-Th 7AM-10PM, F 7AM-11PM, Sa 8AM-11PM, Su 8AM-9PM. 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.$8-14. edit
Three J's Restaurant, 1713 E 75th St, ☎ +1 773 667-1360. M-Th 8AM-11PM, F Sa 8AM-11:45PM, Su 8AM-10PM. 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!).$6-12. edit
Uncle Joe's, 8211 S Cottage Grove Ave, ☎ +1 773 962-9935 (firstname.lastname@example.org), . Sa-Th 11AM-10PM, F 11AM-11PM. 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.$7-13. edit
Uncle John's BBQ, 339 E 69th St, ☎ +1 773 892-1233. M-Th noon-10PM, F Sa noon-midnight. 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.$3.50-14. edit
Wings around the World, 510 E 75th St, ☎ +1 773 483-9120, . M Tu 2PM-midnight, W noon-2AM, Th F noon-4:30AM, Sa noon-5AM, Su noon-7PM. Wings are the specialty, and they come in several flavors per nation: Canadian maple, Jamaican honey jerk, U.S. buffalo style, Japanese kamikaze, Greek lemon-garlic, etc. The sauces are rant & rave worthy and there's enough diversity to make a large order very worth it — if you're feeling splurgy, try an order of 1000 wings for $450 (call that one in first). All food is cooked to order, and the wings are big, juicy, & meaty. A note about that spicy kamikaze sauce is in order, though, it's aptly named.$7-20. edit
Yassa African Restaurant, 716 E 79th St, ☎ +1 773 488-9630, . Su-Th 11AM-10PM, F Sa 11AM-11PM. 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?!$9-12. edit
The Parrot Cage, 7059 S Shore Dr, ☎ +1 773 602-5333, . W-Sa reservations accepted 5:30PM-8:30PM, brunch Su 11AM-3PM. 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.$16-25. edit
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. Lee's Unleaded is probably the flagship club. 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, 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.edit
Artis's Lounge, 1249 E 87th St, ☎ +1 773 734-0491. 10AM-2AM daily. Written up in the paper as one of Chicago's coolest "dive bars," although one might wonder whether a local "dive bar" really appreciates such attention. In any rate, that review is dead on; everyone will know your name by the end of the night, and it has fantastic live blues Sunday and Monday nights from around 10PM-2AM. Drink prices are a bit steep, and there's a rule that no one may be inside without a drink—you'll be leaving drunk, so plan accordingly.No cover, accepts credit cards. edit
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.edit
My Soul Cafe, 7201 S Exchange Ave, ☎ +1 773 336-8592. 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. Much of the menu is shoddy, but the wraps are worth ordering. The free WiFi should keep you occupied while you sip.edit
Lee's Unleaded Blues, 7401 S South Chicago Ave, ☎ +1 773 493-3477, . T-F 8PM-2AM, Sa Su 8PM-3AM, M noon-2AM. Lee's is one of the best reasons to visit the Greater Grand Crossing neighborhood as it is a fabulous South Side blues club — definitely one of the best in Chicago. On top of that, this is one of the safer sections of the district and there's a Metra stop one block away. Blue Mondays feature a monster jam session from noon until 2AM. Be careful with the drink orders, as the club does serve a few very expensive brews.$5 cover, two-drink minimum. edit
New Apartment Lounge, 504 E 75th St, ☎ +1 773 483-7728. M-F 3PM-4AM, Sa 3PM-5AM, Su 3PM-4AM. 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.No cover, two-drink minimum. edit
Red Pepper's Masquerade, 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. edit
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.Rooms from $40 for 4 hr, $45 10 hr, $60 all night. edit
Camelot Motel, 9118 S Cottage Grove Ave, ☎ +1 773 488-3100. Rooms have a dresser, table, and television.$40 for 10 hr, $55 overnight. edit
Lake Motel, 9101 S Stony Island Ave, ☎ +1 773 731-6600. Not far from Chicago State University and the Chicago Skyway/I-90 to Indiana.$40 for 8 hr, $60 overnight, plus $2 key deposit. edit
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.$55 for 8 hr, $70 overnight. edit
Zanzibar Motel, 8101 S Stony Island Ave, ☎ +1 773 768-1430. Offers cable television and air conditioning.$40 for 10 hr, $55 overnight. edit
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.
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