Chicago/Far Southeast Side

Greater Pullman (Pullman, Roseland, West Pullman, Riverdale) is the one dish on the menu for 99% of the Far Southeast Side's visitors. It is home to the Historic Pullman District, important to American history for its early planned industrial/railroad community and subsequent strikes and socialist activism, as well as its attractive and unique architecture.

Southeast Shore (South Chicago, South Deering, East Side, Hegewisch) is a once prosperous industrial region around the mouth of the Calumet River ("The Port of Chicago") that imploded along with Chicago's steel industry. Today it is one of the least populous areas of Chicago and ranges from industrial to failed-post-industrial in character. The East Side is the most urban section of this vast expanse and has a nice commercial center along 106th St. Hegewisch is a particularly odd neighborhood — it is cut off from the rest of the city by Calumet Lake and huge manufacturing districts. As a result, the neighborhood feels almost like an independent, small, Midwestern industrial town (and indeed, a certain mayor not long ago forgot it was part of the city). Though the area has few urban attractions, the Southeast Shore does offer outdoor opportunities around Wolf Lake and Eggers Woods. (But if you are adverse to factory-vistas on the horizon, you may choose to overlook these attractions.)

The history of Pullman — the first modernist planned community in the United States — is a tragic one. George Pullman, the founder, was a liberal railroad tycoon with a reputation as a "welfare capitalist." He founded the Pullman company town with the intention of creating a perfect industrial community which would avoid the vice and extreme poverty found in urban industrial communities and therefore also avoid related worker unrest. To accomplish his goal, he built a very attractive landscaped town in the countryside to the south of Chicago. The company provided wages significantly higher than national averages and state-of-the-art utilities. He met widespread acclaim for his town, including an award for the "World's Most Perfect Town", and visitors came to see Pullman (and the World's Fair Columbian Exposition) from places as far away as Europe.

A lesson in paternalism and central planning, Pullman controlled nearly every aspect of his resident workers lives. A famous quote sums up this paternalism problem nicely, "We are born in a Pullman house, fed from the Pullman shop, taught in the Pullman school, catechized in the Pullman church, and when we die we shall be buried in the Pullman cemetery and go to the Pullman Hell." The failures of the Pullman company town foreshadowed later 20th-century planned communities which had similarly good intentions, but disastrous effects (e.g., the Ida B Wells housing projects of Bronzeville).

Following the severe 1893 economic downturn, Pullman company wages decreased while housing and utility costs remained the same, prompting large-scale violence and strikes known collectively as The Pullman Strike. The strike shut down the Chicago rail system, effectively cutting off all transportation in the western half of the U.S. President Grover Cleveland ended the strike by sending in 2,000 U.S. Army troops, the result of which left 13 strikers dead and many more injured.

The Pullman Strike played a significant role in U.S. labor and civil rights history, as A. Phillip Randolph would later rise to prominence in both areas of activism by organizing the largely African-American "Brotherhood of Sleeping Car Porters," a union for the employees of the Pullman Company. Having attained some prominence, Randolph went on to become one of the nation's foremost advocates of civil rights for African-Americans. His achievements and the history of African-Americans in U.S. labor are celebrated today in Pullman's A. Phillip Randolph Museum.

Since the 1970s the Pullman neighborhood, especially the historic district, has gentrified and experienced a racial shift as wealthier, white Chicagoans moved into the neighborhood, attracted by the rich architecture and history. Sites and homes of historical interest are being painstakingly (and slowly) restored. The neighborhood has a very quiet, sleepy feel, so be sure to visit either on a tour or while the museum and visitor center are open, or you might leave disappointed.

The CTA is not a great way to get to the Far Southeast, as there is only the 95th/Dan Ryan stop in the north of Roseland, far away from everything and anything of interest.

The Metra Electric Line is the best public transportation bet for traveling to the Far Southeast as it has numerous stops in convenient locations. The Pullman/111th St and Kensington/115th St stops on the main line are located right next to the Pullman Historic District. The Metra Electric also stops in South Chicago on a separate branch from Downtown with several stops at major street before ending at 93rd Street in South Chicago. The South Shore serves Hegewisch via the first and only stop in Illinois not shared with Metra on the way to South Bend, Indiana. It also stops at Kensington/115th St on inbound trips to Chicago from Indiana.

To an extent, buses can get you from point to point in the district, but there are no good routes coming here from the city center. If arriving by the CTA Red Line, you can take bus #111 from the 95th/Dan Ryan stop straight to the Pullman Historic District. On the southeast side bus #30 runs between South Chicago East Side and Hegewisch along South Chicago Ave, Ewing Ave and Avenue O serving both the end of the Metra at 93rd Street and the South Shore Line at Hegewisch. East-west transportation is difficult, owing to the industrial wasteland (and Lake Calumet) in the middle.

Since this is the least densely populated section of Chicago, a car is the most convenient method of travel. Free on-street parking is plentiful.

The most important highway for getting around is route I-94 along the Dan Ryan Expy and further south along the Bishop Ford Fwy. Exit at 111th for Historic Pullman or to get to Michigan Ave in Roseland, otherwise 95th and 103rd (to 106th) are useful to cross over to the East Side, and 130th is the exit of choice for Hegwisch.

The Chicago Skyway is the other main highway, which cuts across the East Side on its way to Indiana. Exits 108 (Anthony Ave/92nd St) and 110 (Indianapolis Blvd/US-20/US-41) will both let you off on the East Side, from which Historic Pullman and Hegwisch are both relatively easy drives. US-41, which cuts through the northeastern section of the East Side, is the old pre-Skyway route along the lake, and is way slower, but a good deal more interesting (and toll-free). It connects up with Lake Shore Drive farther north.

103rd/106th, and 130th Streets are the main roads for traversing the industrial wastelands lying between the western and eastern neighborhoods in the south of the district.

• Harold's Chicken Shack #35, 12700 S Halsted St, ☏ +1-773-785-4153. 11AM-2AM daily. This particular location of the great South Side fried chicken chain is an exceptional find for one reason — a drive thru window! As always, cheap, usually a little dirty, and always delicious. $2-5. 
• Old Fashioned Donuts, 11248 S Michigan Ave, ☏ +1-773-995-7420. M-Sa 6AM-6PM. Michigan Ave in Roseland is far out o the way, and not a pleasant place for a stroll, but this nearly 40 year old establishment is worth the trek for some of the freshest, most mouth-watering donuts you'll ever have. Old Fashioned Donuts is written up in the main Chicago papers every year as having the best donuts in the city (Dat Donuts is a mere tribute band). $0.20-2. 
• Skyway Doghouse, 9480 S Ewing Ave, ☏ +1-773-731-2000. Su noon-8PM daily. This is about as far from the city center as you can get, but this ramshackle little hot dog stand serves up some of Chicago's best hot dogs. They've got a drive thru, and there are usually a couple hungry squad cars "refueling" in the line. The picnic tables outside are a great place to soak up the local atmosphere, watching riced-out cars and other hungry patrons roll by. $2-4. 

• Calumet Fisheries, 3259 E 95th St, ☏ +1-773-933-9855. Su-W 10AM-9:45PM, Th 9AM-9:30PM, F-Sa 9AM-9:45PM. One of the last great waterside shrimp and fish shacks from the glory days of the Port of Chicago. Calumet Fisheries offers all sorts of breaded and fried seafood, but the slow-smoked offerings might be the top draw. They recognize this too — they advertise their smoked chubs as "fish crack." The atmosphere here is just right too, it's right by the 95th St bridge (which the Blues Brothers jumped in their car), and boasts some serious industrial vistas. Featured on Anthony Bourdain's show. $7-18. 
• Hienie's Shrimp House, 10359 S Torrence Ave, ☏ +1-773-734-8400. Su-Th 11AM-midnight, F-Sa 11AM-1AM. Hienie's has been around for decades (albeit not in the same spot) and proudly upholds grand tradition of roadside shacks full of fried seafood and chicken catering to industrial workers. Their shrimp and gizzards are simply outstanding, and their hot sauce is beloved enough by the East Siders that it's made its way into local grocery stores. Any way you slice it, the piping hot, cholesterol laden, made to order food here will be great, but it's best enjoyed on the hood of your car while gazing off into the nearby smokestacks. $4-17. 
• Ranch Steak House, 11147 S Michigan Ave, ☏ +1-773-264-0320. M-F 7AM-3PM, Sa-Su 7AM-7PM. This steak house, despite the inauspicious location, in which true restaurants with table service are extremely rare, is actually quite good and strikingly cheaper than what you would pay for comparable food downtown. $10-15. 
• Pudgy's Pizzeria, 13460 S Baltimore Ave, ☏ +1-773-646-4199. Su-Th 4PM-11PM, F-Sa 4PM-midnight. There are a lot of good pizzerias in Hegwisch, most of them bearing a name oddly similar to Pudgy's, but this is the great one. The Chicago-style thin crust pizzas here hold up well against the best in the city, with the famous entree being the garlic-drenched "Bob's Mistake." Downsides include high prices (for thin crust) and very limited seating — just two small tables, usually taken up by people waiting for their order. $5-30.