The Far Southeast Side of Chicago is a huge section of Chicago with only one large tourist draw: the Pullman Historic District. Most travelers will literally just pass over this district on the Chicago Skyway, but look closely and something may catch your eye.

Understand

The Far Southeast side is vast, but has a much lower population density than the rest of the city and consequently less to offer a visitor in terms of amenities and attractions. As it is so big, it is easier to think of the Far Southeast Side in terms of its neighborhoods.

Neighborhoods

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.

Industrial Chicago on the Calumet River

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.)

Pullman history

The Greenstone Church in Pullman

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.

Get in

By train

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.

By bus

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.

By car

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.

See

Pullman Market Square

• A Philip Randolph/Pullman Porter Museum, 10406 S Maryland Ave, ☏ +1-773-928-3935. Open April-Dec 1, Th-Sa 11AM-4PM and in Feb for scheduled Black History events.. The museum, a tribute to A. Phillip Randolph, focuses on African-American culture and history, the Pullman Historic District, and U.S. Labor history. The interior has a big and rare manual tracker Organ. Admission $5. 
• Greenstone Church, 11211 S Saint Lawrence Ave, ☏ +1-773-785-1492. A landmark church in the heart of the historic Pullman community. It was initially intended to be a Unitarian church, where all the workers would go to service. That did not catch on and the church sat empty for years before becoming a Presbyterian and then Methodist church. 
• 1 Pullman National Monument Information Center, 11141 S Cottage Grove Ave, ☏ +1-773-785-8901, fax: +1-773-785-8182, foundation@pullmanil.org. T-Su 11AM-3PM. The first stop to any Pullman visit houses a 20 minute video about the town's history, several exhibits, and a gift shop. Offers guided walking tours every first Sunday of the month, as well as events and self-guided tour brochures. Be sure to head around to the back of the building (North side) to check out the impressive mural, "Visual Interpretations of Pullman," which depicts the former Pullman Arcade building coupled with an interpretation of the Pullman town and its laborers. 2 hour guided walking tours: 7$, 5$ (seniors), 4$ (students).  
• Hotel Florence, 11111 S Forrestville Ave, ☏ +1 773-660-2341. By appointment M-F 10AM-4PM. The Hotel Florence, named after Pullman's favorite daughter, is the most splendid building in the district. It was built in 1881 to accommodate visitors from all over the United States and Europe who came to see Pullman's "perfect town." The hotel is closed as it is going through a $1.2 million restoration and renovation program, but interior tours, focused on the restoration itself, can be arranged through the Historic Pullman Foundation.  
• 2 Illinois-Indiana State Line Boundary Marker, Avenue G, near 103rd St (located on the Illinois-Indiana State Boundary Line). An Obelisk marking the State Line between Illinois and Indiana near Lake Michigan just south of Calumet Park and beach along a small road leading to the front gate of the State Line Generating Station.  
• Market Square (Two blocks east of the Visitor Center at the intersection of E 112th St and S Champlain Ave). Market Square is just lovely. The Market Hall, which served as a grocery store, is being restored as it has suffered from several fires over the years. 
• Pullman Clock Tower and Factory, 111th St and Cottage Grove Ave (just north of the Hotel Florence), ☏ +1-773-660-2341. One of the world's most beautiful factories is undergoing a $3.4 million restoration, after it was badly damaged in 1998 by an arsonist. 90 minute guided tours, which focus on the restoration itself, are available by advance appointment. 
• Southeast Historical Museum (James P Fitzgibbons Southeast Chicago Historical Museum), 9801 S Avenue G (in the Calumet Park Fieldhouse), ☏ +1 815-464-7083. Th 1PM-4PM. A small history museum with exhibits celebrating the area's once mighty steel industry and Labor history. 

Do

• Annual Historic Pullman House Tour, ☏ +1-773-785-8901. October 11AM-5PM. Includes a tour of about eight historic Pullman district homes as well as the visitor center and Greenstone Church. Advance reservations strongly recommended, as the highly popular tour sells out quickly. $20, $17 (seniors or advance purchase). 
• Harborside International Golf Center, 11001 S Doty Ave, ☏ +1-312-782-7837. Open 1 Apr–30 Nov, sunrise-sunset. 36 holes of golf on the shores of Lake Calumet with some classic Far South views of the distant skyline and nearby decaying steel mills. Lighted driving range. 18 holes $82 weekdays, $95 weekends, $57 twilight. 
• 1 William W Powers State Recreation Area (Wolf Lake), 12949 S Avenue O (entrance at 126th St and Avenue O), ☏ +1-773-646-3270. sunrise-sunset, office: M-F 8AM-4PM. A conservation area around large Wolf Lake that is a study in contrasts between the industrial surroundings and the local cattails. It's a surprisingly good spot for fishing and even some hunting. In the winter, come here for ice skating and ice fishing. (updated Oct 2017)
• Method Soapbox factory tour, soapboxtours@peopleagainstdirty.com. Wednesdays. Group tours of a colorful soap factory. Schedule at least a week in advance. (updated Mar 2021)

Eat

Not a lot of four-star dining in these parts, but if you know what to look for, some of the best eating in the city is to be had in its far southeast reaches. The undisputed king of the donut is here, as is the long-reigning champion of shrimp shacks (Old Fashioned Donuts and Calumet Fisheries). Hand-Burgers has a good claim to the title of "best burger in the city." And if you like pupusas, or more generally Central American cuisine, it's time to make the trek.

Budget

• 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. 

Mid-range

• 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. 

Drink

If you're in Pullman and in the mood for a beer, you're in for more trouble than you would think. The famous Pullman Pub closed not too long ago under mysterious circumstances (asking a local about this is a very good way to start a conversation). If you like an early afternoon tipple, try the Frank Loyd Wright-style golf course club house off of 111th Street just before I-94 (open April through October); the Cal Harbor also has a bar, which is sometimes open, sometimes not. Otherwise head over to the better options on the East Side on 106th or in Hegewisch.

• Club 81, Too, 13157 S Avenue M, ☏ +1-773-646-4292. 11AM-2AM daily. The bar at the end of Chicago. Seriously, if you stumble out the wrong way, you'll fall into Wolf Lake. Old-timey moose-head decor might make you long for those bygone days of a fine cigar with your evening's whiskey, but even without the smoke, this is a great place for a beer with the establishment's legendary fish fry or Polish food. 
• Crow Bar Inc., 4001 E 106th St, ☏ +1 -73-768-6985. 10AM-2AM daily. Probably the nicest neighborhood bar on the East Side (although, that said, the nicest bar in East Side is called Crow Bar), with strong drinks, friendly clientele, and sports on the television. Amazingly you can smoke here, despite the ban, as the owner openly flouts it, keeping a "smoking tip jar" as a collection for paying the fines. It's also not a bad place to grab a corned beef sandwich. 
• Small World Inn, 3325 E 106th St, ☏ +1-773-721-2727. 11AM-11PM daily. This would seem to be yet another run of the Mill workingman's watering hole, except for the fact that it has served as a Yugoslav-American cultural center for decades. A drink here is a pleasant occasion, but focus on the menu — the Serbian cevapcicci (cheh-VAHP-chee-chee) will open your eyes to sausage possibilities you never knew existed. Entrees: $3-8. 
• Steve's Lounge, 13200 S Baltimore Ave, ☏ +1-773-646-1071. Tu-F 2PM-close, Sa-Su 3PM-close. One of the favorite (and most prominently-located) bars in Hegewisch, renowned not simply for being a nice laid-back bar, but also for their legendary fried chicken. Their dining area is only open on Fridays 4PM-8PM, but you can get the fried chicken to go whenever you like if you call ahead of time. 

Sleep

None of the Far Southeast Side's hotels are very nice and they are far from most of what you want to see in the city, so think carefully about whether it might make sense to stay elsewhere before you book a room.

• Skyway Motel, 9132 S Stony Island Ave, ☏ +1-773-221-6600. Offers king-size beds, televisions, clock radios, and some furniture. $50 for ten hours, $66 overnight. 
• Royal Castle Motel, 45 W 103rd St, ☏ +1-773-468-8100. Just off State Street in Roseland. $50 for ten hours, $60 overnight. 

Connect

There are four public libraries in the Far Southeast Side, all offering free public internet access:

• Hegewisch Library, 3048 E 130th St, ☏ +1-773-747-0046. M,W 10AM-6PM, Tu,Th noon-8PM, F-Sa 9AM-5PM. 
• Pullman Library, 11001 S Indiana Ave, ☏ +1-312-747-2033. M,W 10AM-6PM, Tu,Th noon-8PM, F-Sa 9AM-5PM. 
• South Chicago Library, 9055 S Houston Ave, ☏ +1-312-747-8065. M,W noon-8PM, Tu,Th 10AM-6PM, F-Sa 9AM-5PM. 
• Vodak East Side Library, 3710 E 106th St, ☏ +1-312-747-5500. M,W noon-8PM, Tu,Th 10AM-6PM, F-Sa 9AM-5PM. 

Stay safe

Avoiding high crime areas in the Far Southeast Side is very simple: basically anything west of the Bishop Ford Fwy aside from Historic Pullman is gangland territory (although, obviously, that varies widely from block to block). It is unlikely that any visitors would find themselves in the far-flung and benighted communities of Riverdale, West Pullman, and Roseland, aside from the steady stream of foodie pilgrims to Old Fashioned Donuts. But if you are there for reasons other than sightseeing, stick to main streets and avoid walking around at night and you should be fine. All areas east of the Bishop Ford, on the other hand, often look gritty, but this is because they are poor — not crime ridden. Hegewisch and East Side are some of the safest communities in the area.

Go next

• Travelers interested in the Labor history of Chicago should also mosey on over to the Back of the Yards neighborhood on the Southwest Side, former home to the sprawling Union Stockyards made infamous by Upton Sinclair's The Jungle.
• Pullman was not the only utopian planned industrial community in these parts. Just across the Indiana border is Marktown, a community modeled on an English village, but surrounded on all sides by three steel plants and the world's largest oil refinery.

Routes through Far Southeast Side

The Loop ← Chatham-South Shore ←

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