The Southwest Side of Chicago is far off the beaten path. Plenty of visitors know Midway Airport, but never see anything beyond. Truth be told, there isn't a lot to see. But the Southwest Side does hold some interest as the former home to the infamous Union Stock Yards as well as a pretty long list of hidden culinary gems well worth the trek.
The Southwest Side is large enough where you cannot understand it without understanding its neighborhoods — it is united only by its blue-collar character, proximity to the airport, and of course, the White Sox.
The Back of the Yards is a loose term encompassing the community areas of McKinley Park, Brighton Park, and New City, referring to the area's history as the home to the vast hordes of immigrant laborers in the Union Stock Yards of Upton Sinclair's The Jungle. Though the stock yards are long gone, the blue-collar character remains. The actual stock yards were located in the heart of New City between Ashland Ave and Halsted from Pershing Rd (39th St) to 47th St. Today the site is marked by the Union Stock Yard Gate and a large industrial park. The area surrounding the park is comprised of predominantly Mexican-American neighborhoods and has some good food on offer. Canaryville (between Halsted and Wentworth from Pershing to 49th) is an Irish-American neighborhood with a notoriously violent reputation. McKinley Park, on the other hand, is experiencing gentrification as younger Chicagoans are priced out of "hipper" neighborhoods.
The Union Stock Yards
The massive meatpacking industry of the Union Stock Yards developed alongside the technological innovation of the refrigerated railway car. Livestock of the agrarian Midwest were brought to the rail hub of Chicago and its stock yards to be processed and shipped off around the country. At its peak, the Union Stock Yards processed about 82% of the meat consumed in the United States!
The stock yards played a huge role in the development of the city. With the enormous wealth they brought in came some of the world's first global companies, capitalizing on the abundance of animal byproducts for use in commercial goods and technological innovations in transport, refrigeration, and the beginnings of the assembly line. Even more important to modern-day Chicago, the yards gave birth to the modern hedging industry needed to manage the inherent risks in agricultural commodities trade, establishing Chicago as a premiere world center for finance.
Further technological innovations, however, spelled doom for Chicago's centralized stock yards. The rise of interstate trucking and fast point to point shipping of meat allowed for livestock to be slaughtered where they were raised and then quickly delivered to consumers without the Chicago middleman.
Chicagoans don't lament the loss of the yards, regardless of the number of jobs they provided — the stench of manure and death was suffocating across the greater part of the city. And the environmental degradation cataloged by Upton Sinclair was extreme. The south fork of the Chicago River's South Branch (just west of Racine Ave) became known as Bubbly Creek for the methane and hydrogen sulfide gas, produced by entrails' decomposition, bubbling through the grease, chemicals, blood, and guts. It wasn't pretty.
Centered around one very large and fabulous park, Marquette Park is an ethnically mixed neighborhood divided between mostly African-Americans east of the park and Mexican-Americans immediately west of the park, along with some Polish and Lithuanian-Americans. Further west, the area becomes more ethnically inclusive, with median income playing a more prominent role in residency. Aside from the park (and its golf course), the neighborhood is alluring mostly for its great Mexican food, as well its rare-in-America Lithuanian dining. This neighborhood was once dominated by a big, wealthy, Lithuanian-American community, but its demographics began to shift dramatically following Martin Luther King Jr's anti-segregation marches (which at the time met with violence from residents). Accompanying desegregation in this neighborhood was characteristic "white flight," which put an end to the "Lithuanian Gold Coast" and heralded a more open neighborhood which recently has become a major destination in the United States for Mexican immigrants.
Around Midway, you'll find Chicago's second airport, surrounded by an ethnically diverse collection of neighborhoods. This section of town is home to a large, established Polish community, as well as more recently arrived Mexican communities. The neighborhoods of Archer Heights, Garfield Ridge, and Clearing are important centers of Polish culture in the United States; you are likely to hear as much Polish as English while walking around these neighborhoods. Polish Highlanders, or Górals dominate the local Polish population, with a unique cuisine and culture that is decidedly Balkan. A host of restaurants and cultural institutions visibly display the rustic touch of their Carpathian craft such as the Polish Highlanders Alliance of North America at Archer Ave just northeast of its intersection with Pulaski Rd. Points of interest are pretty spread out, but the food and nightlife sure beats the airport hotels. And you don't have to venture too far to find one-in-a-million pizza, or some Croatian baked goods.
In the southeast are a couple of far-flung African-American neighborhoods: Auburn Gresham and Washington Heights. Aside from the Obama family's now famous church, they have far less of interest to travelers, but both are nice enough neighborhoods and have some good places to eat if you find yourself in the area.
Englewood also deserves a mention, but mostly as a warning — it is a large, impoverished, and relatively violent neighborhood with just about nothing to offer a traveler. It is generally best to just roll through on one of the main roads (e.g., 55th St) or to avoid the area altogether.
Midway Airport (IATA: MDW)  plays second fiddle to the Chicago giant that is O'Hare International, but it nonetheless services a lot of domestic flights and is a more convenient point of entry. Just about everyone coming into this part of Chicago goes through this airport, which primarily serves domestic flights on low-cost carriers — it is the hub for Southwest Airlines.
Hourly Parking: $4 for the first hour and $2 for each additional hour
Daily Parking: $4 for the first hour, each day is $25.
Economy Parking: $2 for the first hour, $5 for two hours, and $12 per day (or just over 2 hours!)
Note: parking charges are incurred after 10 minutes in all lots, save the cell phone waiting area.
The CTA Orange Line runs through the district on its way from the Loop, providing quick and easy access to Midway Airport, as well as some northern areas of the Southwest Side from the Loop, but keep in mind that a bus transfer will likely be necessary to get you from the L station to anywhere other than the airport. Travel time is about 25-30 minutes from the Loop to Midway, but you may wait up to 30 minutes between trains during off peak hours.
The CTA Red Line (as does the slightly less convenient Green Line) runs along the eastern boundary of the district. While it is fairly far from anything of interest on the Southwest Side, you'll find an east-west bus route picking up right in front of each station (except 69th St!), running the length of that numbered street (e.g., #55 along 55th St, #63 along 63rd St, etc.).
Metra's Rock Island commuter rail line serves the southernmost neighborhoods of the district, and can get you to Auburn-Gresham or Washington Heights. But again, keep in mind that you will need to take a bus from the station to your destination. Trains depart from the downtown LaSalle Station. A ride to the Gresham station costs just over $2, to Longwood or Washington Heights just over $3.
The Metra Southwest Service goes straight from Union Station in the Near West Side to the Ashburn neighborhood, where it stops twice at "Wrightwood" and "Ashburn." Do not take this train unless you are going to Ashburn, as its stops are on the other end of the district from the airport.
CTA bus route #62, which travels along Archer Ave from McCormick Center in the Near South to Midway, is probably the most convenient route into the Southwest Side from downtown Chicago. Other important routes include the city-spanning north south routes along Halsted, Ashland, Western, Pulaski, and Cicero: #8, #9, #49, #54, and #53. The major east west routes are #47, #55, and #63, which as you might expect run the lengths of 47th, 55th, and 63rd streets.
#62 Archer is the one bus that runs directly from downtown to the Midway Area, but it actually doesn't stop at the airport (except during the overnight hours when the Orange Line 'L' is not running), so if you're coming from that way, the 'L' is a better option. From the West Side, there are convenient and direct routes along Cicero and Pulaski (#53 and #54). Bus route #55 is by far the best way to travel to Midway from the South Side, which leaves from the Museum of Science and Industry in Hyde Park.
The Dan Ryan Expressway runs down the eastern edge of the district, and heading west on the 55th/Garfield exit will take you directly to the airport. To get to the Union Stock Yard Gate, take the Pershing Rd exit from the Dan Ryan. The Stevenson Expressway lacks exits on the main roads leading into the eastern parts of the area, but the Damen Ave exit will get you on Archer, from which you can easily get onto Western, Ashland, or Halsted. For Midway take Cicero; Pulaski is useful for exploring the areas just east of the airport.
Pretty much the only way to get around the Southwest Side by public transport is by bus, but if this is the route you choose, make a point of it to plan your route ahead of time, as distances are fairly long and the bus routes generally only run along the main streets.
A car is a handy travel companion in the Southwest Side indeed. Attractions, activities, and restaurants are generally spread apart over long distances, and free on-street parking is available just about everywhere. Taxis are also a good option, but do not expect to be able to hail one off the street — you will need to call and arrange rides in advance.
The one big sight on the Southwest Side is the Union Stock Yard Gate, and even that is a pretty small attraction for how out of the way it is. Other sights appeal to narrow sections of society. The Chicago Blues Museum has a magnificent collection for anyone interested in blues history, but it remains to be seen whether it will ever have regular hours. The Balzekas Museum is of obvious interest to Lithuanian-Americans, the Indian Building to Wayne's World fanatics and roadside kitsch-seekers, and the Archives to, well, archivists (and to those who want to trace their roots in the Midwest).
Balzekas Museum of Lithuanian Culture, 6500 S Pulaski Rd, ☎ +1 773 582-6500, . 10AM-4PM daily. The Balzekas Museum has a fine collection of Lithuanian antiques, folk art, armor, coins, rare historical maps, amber jewelry, and other items exhibited chronologically. The center also includes a state-of-the-art audio-visual center and an impressive research facility for Lithuanian history and genealogy. And the gift shop is a great shopping spot for Lithuanian items.Adults: $9, seniors/students: $7, children: $3. edit
Capital Cigar Store Inc (The Indian Building), 6258 S Pulaski Rd. Forget the store, this place is famous for the giant stereotypical-looking Indian statue of Wayne's World fame on the roof. In the movie, his hand is raised in greeting, but he has an arrow through his back. More recently, however, the Midwest Eye Clinic has usurped the cigar sellers, and adopted the Indian as a billboard — the arrow is gone, he now wears large glasses, and bears an odd sign reading "Eye can see now."edit
Chicago Blues Museum, 3636 S Iron St, ☎ +1 773 828-8118. This museum is huge and has an excellent collection of blues paraphernalia and exhibits related to blues in Chicago today and in history. The museum also has exhibits pertaining to Chicago's African-American history in general, especially about the Bronzeville district in the 1920s and 30s. But the collection is on tour, and the museum is closed indefinitely.edit
La Lotería, (4100 S Ashland Ave). The largest mural in the city (500 ft), painted by Hector Duarte and Mariah de Forest, on the south wall of the Swap-O-Rama building. You can't really see it from the street — you'll need to wander deep into the parking lot for a good look.edit
National Archives & Records Administration, 7358 S Pulaski Rd, ☎ +1 773 948-9050 (email@example.com, fax: +1 773 948-9050), . M-F 8AM-4:15PM. The enormous Midwest branch of the National Archives is hidden away in the middle of nowhere, but its collection of records is enormous. The public has free and instant access to the census records, for those interested in their family genealogy, while historic federal documents are searchable only by researchers who have applied for a pass in advance.edit
Polish Highlanders Alliance of North America (Dom Podhalan), 4808 S Archer Ave, ☎ +1 773 523-7632 (firstname.lastname@example.org). Tu-F noon-9PM, Sa-Su 11AM-9PM. This is the seat of Chicago's Polish Highlanders, or Góral community which dominates the Southwest Side's Polish population. The building, which also hosts a restaurant, is styled as a Carpathian chalet in the traditional Zakopane style of architecture, and is currently undergoing renovation under the eye of famed artist Jerzy Kenar. edit
Trinity United Church of Christ, 400 W 95th St, ☎ +1 773 962-5650, . This large and influential church is a long-time pillar of Chicago's South Side, and the former home to one very famous congregant, Barack Obama, who here found his religion and was baptized. Trinity United, to the dismay of its congregants, rocketed to international infamy in the space of seconds during then Senator Obama's presidential campaign, when news outlets got their hands on a fiery sermon by the then pastor Jeremiah Wright. In the now famous clip, replayed endlessly for weeks across the cable news networks, Rev. Wright cried out, "God damn America!" The ensuing characterization of the church was hardly fair, with the short clip shown out of context, and the context itself being one very much alien to most Americans, who had not had any experience of the often radical social justice traditions of the African-American Church. In part because he was unhappy to see his former congregation harassed by reporters, and in part because his increasingly flamboyant pastor was continuing to embarrass and hurt his campaign, Obama left the church, allowing things to calm down over time, and for the congregation to get back to its purposes of worship and charity.edit
The Union Stock Yard Gate, 4200 S Peoria St. This limestone structure marks the entrance to the now defunct Union Stock Yards that dominated this section of Chicago (and the meatpacking industry of the country) in the late 19th-early 20th centuries. The current stone gate replaced an original wooden gate, designed by the legendary architect John Root, of Burnham and Root (who you'll know well if you read Devil in the White City). Look on the front of the gate for Sherman, a prize winning bull — the Second City's second most famous bovine, right on the heels of Mrs. O Leary's Cow.edit
Stock Yards Firefighter Memorial (right behind the Stockyard Gate). The stock yards produced an awful lot of grease, with a good amount of chemicals added to the mix. Unsurprisingly, the place caught on fire now and then. 1910 saw a particularly ferocious blaze, which took the lives of 21 firefighters on this spot, just behind the gate. The memorial is dedicated to all Chicago firefighters who have lost their lives to fires, 530 at the time of the dedication in 2004; their names are inscribed on the base.edit
Marquette Park, 6734 S Kedzie Ave, ☎ +1 312 747-6469, . 7AM-11PM daily. Marquette Park is huge and is a good place to get away from the urban commotion of the city. Ice skating (on the lagoon) and cross-country skiing are both possibilities during the winter. During the summer, it's likely the South Side's favorite place for a picnic or a pick-up game of soccer (or more accurately in these parts, futból). The park is also home to the Ashburn Prairie, a fine specimen of the native plant species of the area.edit
Marquette Park Golf Course, 6734 S Kedzie Ave, ☎ +1 312 747-2761, . Sunrise-sunset daily. The hidden gem that is Marquette's public golf course is considered one of Chicago's most beautiful. You will feel miles away from the city. Nine holes, 3,187 yards.Weekdays: $16, Weekends: $18. edit
Sherman Park, 1301 W 52nd St. Sunrise-sunset daily. Although lesser known than Marquette Park, this 60 acre park is historically and aesthetically its equal. Designed by architects Daniel Burnham & Co and landscape artists the Olmsted Brothers and located on (a rather unsafe stretch of) historic Garfield Boulevard, this park not only provides open green space and a beautiful lagoon, but also classically designed architecture, and a glimpse into the past, as well as the future, of the Back of the Yards area.edit
Stanley's, 43rd St. & Ashland Ave., . M-F 10:30AM - 8 PM. Stanley's is the last surviving tavern along Chicago's legendary Whiskey Row - the dozens of taverns that flanked Chicago's Union Stockyards. The business was established in 1924 by Stanley Kurek, and has been run by his family ever since. Homemade plate lunches are served daily. The family is proud to call thousands of the men and women who built Chicago both its friends and its customers.edit
The Southwest Side is not an enticing shopping destination, unless the endless strip malls on Cicero are your thing. Even Midway Airport lacks a duty free shop, as it only serves a few international flights to Mexico. But if you find yourself here and need something, you can almost certainly find it on Cicero.
Ford City Mall, 73rd St & Cicero Ave, ☎ +1 773 767-6400, . M-F 10AM-9PM, Sa 10AM-7PM, Su 10AM-6PM. This mall has a bit of history to its name. In its former life it produced engines for bomber planes during World War II under Ford Company management, and later car engines. If the mall fails to satisfy your needs, rest assured the Cicero Ave strip malls extending endlessly to the south will.edit
Sanchez Brothers Western Clothes, 1942 W 47th St, ☎ +1 773 254-4090. 10AM-8PM daily. Live out your mariachi fantasies here. The Sanchez Brothers carry all sorts of specialty clothing for Mexican bands, from cowboy hats to iguana skin boots!$20-5,000. edit
Video Strip, 3307 S Archer Ave, ☎ +1 773 927-4307, . 11AM-midnight daily. A McKinley Park video rentals shop with an eccentric collection of DVDs. If you are staying anywhere nearby, they will actually deliver the rentals to you.edit
The Southwest Side excels in three culinary areas: Mexican, Polish/Bohemian, and Chicago-style fast food. Avoid the airport hotel restaurants like the plague — there are far better (and more fairly priced) places to eat nearby. If you have a car, drop whatever you are doing and head down Pulaski Ave to Vito & Nick's for the "best pizza, anywhere." If stuck at the airport, Gold Coast Dogs will give you a bonafide Chicago Hot Dog.
Birriería Zaragoza, 4852 S Pulaski Ave, ☎ +1 773 523-3700. M-F 10AM-7PM, Sa 8AM-7PM, Su 8AM-4PM. This little South Side birriería has lately found itself featured in just about every major Chicago magazine and newspaper, and while this is surprising, it is not unwarranted. The birria tatemada on order is shredded goat, first steamed for hours and then oven roasted, coated with a mild mole sauce, served in tacos, or "en plato" in a tomato consommé. The owner is an artist first, business owner second, who has studied his narrow trade on a level unique in the city.$5-12. edit
Bobak's Sausage Company, 5275 S Archer Ave, ☎ +1 773 735-5334, . M-Sa 8AM-9PM, Su 8AM-7PM. It's unclear whether the restaurant will ever re-open, but there are tables inside the store for people who like to enjoy sausage at the source, along with other Polish favorites.$5/lb. of hot food. edit
Harold's Chicken Shack. The great South Side fried chicken chain is cheap, usually a little dirty, and always delicious. Crowded at meal times.$2-5. edit
La Cecina, 1934 W 47th St, ☎ +1 773 927-9444, . 8AM-10PM daily. Come to La Cecina for la cecina — a Guerrero-style salt-dried steak that is rehydrated with a marinade and then grilled. But if you are less in the mood for culinary refinement, and more in the mood for bull testicles, well, you are in the right place.$4-14. edit
Lindy's & Gertie's, 3685 S Archer Ave, ☎ +1 773 927-7807, . M-Th 10:30AM-10PM, F 10:30AM-midnight, Sa 11AM-midnight, Su noon-10PM. Who could go wrong with a South Side institution (since 1924) serving chili, ice cream, and beer? The interior is somewhat of a historic landmark itself, since it's barely been renovated since the roaring twenties.$2-7. edit
Nicky's, 5801 S Kedzie Ave, ☎ +1 773 436-6458. M-Sa 10:30AM-12:30AM, Su 11AM-10PM. Nicky's is another one of those legendary South Side fast food institutions rich with local tradition and absent quality controls — for the real deal, you'll want to come to this one, the original. You'll never be starved for Chicago fast food options in this part of the city, but it's worth seeking out a Nicky's for a reliably great gyros or the legendary Big Baby. Whether Chicago came up with this double decker hamburger as a challenge for the invading Big Mac, or for its predecessor the Big Boy is uncertain. Either way the toasted buns, condiments on the bottom, and most crucially, Maxwell Street-style greasy grilled onions all add up to a tasty treat. (Alas, Nicky's hot dogs suffer from rumored estrangement from Vienna Beef.)$1-8. edit
Paletería Flamingo, 2635 W 51st St, ☎ +1 773 434-3917. 11AM-10PM daily (in theory). Endless (Mexican) flavors of ice cream and Italian ice to choose from — try horchata or maybe cinnamon-apple pie.$1-5. edit
Pticek & Son Bakery, 5523 S Narragansett Ave, ☎ +1 773 585-5500, . Tu-F 4:30AM-6PM, Sa 4:30AM-5PM. A small Croatian bakery with a good range of unfamiliar treats (and some rather familiar, gooey chocolate chip cookies).25¢-$4. edit
Racine Bakery, 6216 W Archer Ave, ☎ +1 773 581-2258. M-F 6AM-7PM, Sa 6AM-6PM, Su 6AM-5PM. A nice big crowded Lithuanian bakery, with all sorts of pastries, meat/potato pies, jams, mushrooms, juices, and anything else you are missing from Silesia.25¢-$8. edit
Taquería Atotonilco #2, 1659 W 47th St, ☎ +1 773 247-5870. M-Th 9AM-1AM, F 9AM-3AM, Sa 8AM-4AM, Su 8AM-1AM. A mostly take-out taquería with a reasonably large seating section that cooks the real deal.$2-4. edit
Three Sons, 6200 S Archer Ave, ☎ +1 773 585-2767. 5AM-11PM daily. An affordable American diner, but since it's in the neighborhood it's in, the best options are in that little Polish section. Full bar.$3-8. edit
Windy City Hot Dogs, 4205 W 63rd St, ☎ +1 773 581-0332. M-Sa 10AM-10PM, Su 11AM-8PM. The place in the area to get your Chicago-style fast food: hot dogs and Italian Beef.$2-4. edit
Los Delfines Restaurant, 2750 W 63rd St, ☎ +1 773 737-4900. 10AM-8:30PM daily. Tasty Mexican food focusing on the seafood, with a full bar, open late.$9-14. edit
Los Gallos #2, 4252 S Archer Ave, ☎ +1 773 254-2081. M-Th 8AM-1:30AM, F-Sa 8AM-3:30AM, Su 7AM-1:30AM. Deceptively appearing to be a small nondescript Brighton Park taquería, this place is actually a culinary find of the first order. Breakfast is good, so is the menudo, but the delicious specialty is the Jaliscan-style carne en su juego (roughly: steak soup). The steak is roasted separate from the broth, the boiled meat of which is discarded, and then joins a cornucopia of limes, bacon, beans, cilantro, onions, habanero peppers, and radishes. Unless you are planning to feed a family, get the smallest available portion, and make it clear that you want to eat here, not takeout.$3-12. edit
Giordano's, 6314 S Cicero Ave, ☎ +1 773 585-6100, . Su-Th 11AM-11PM, F-Sa 11AM-midnight. Located at the southeastern corner of Midway Airport, if you have a layover and want to try real Chicago pizza, take any bus south along Cicero Ave, or you could take a good walk, to the third-best Chicago chain around for stuffed Chicago pizza.$14-25. edit
Lagniappe - A Creole Cajun Joynt, 1525 W 79th St, ☎ +1 773 994-6375, . Tu-Th 11AM-8PM, F-Sa 11AM-10PM. A small little joynt that serves incredible gumbo! The Cajun seafood entrees are also excellent, and $5 wangs 'n waffles always sounds just about right.$5-15. edit
Leon's Bar B Que The Original, 1158 W 59th St, ☎ +1 773 778-7828. 11AM-2AM daily. This is the ancestor of many a South Side barbecue joint, and has fed hungry ribs-lovers since Leon Finney opened it up in 1940. The links are incredible. Leon's also serves good deep dish pizza. Takeout only.$3-15. edit
Mabenka, 7844 South Cicero Ave (Technically in Burbank), ☎ +1 708 423-7679, . This is a good Polish/Lithuanian restaurant located across from Ford City Mall. It is always packed, in no small part owing to its tremendously popular pierogies and kugelis.$5-12. edit
El Patio, 4527 S Ashland Ave, ☎ +1 773 847-2595. 8AM-9:30PM daily. Excellent food and warm, friendly service in this Mexican restaurant. The seafood on offer is especially good.$8-14. edit
Seklycia, 2711 W 71st St, ☎ +1 773 476-1680. M-Sa 7AM-9PM, Su 8AM-8PM. One of the last handful of Lithuanian outposts in the city. A small Lithuanian diner catering to older Lithuanian-Americans in the neighborhood that serves fantastic apple pancakes and other traditional Lithuanian dishes at reasonable prices.$7-12. edit
Szalas Restaurant, 5214 S Archer Ave, ☎ +1 773 582-0300, . noon-11PM daily, bar until 2AM on F-Su. The name means "chalet" in Polish, and that's how the restaurant is designed; not a random quirk, though, because they serve food specific to the Polish highlands. To get in, you'll need to pull the rope over the door to ring the bell. The food's delicious, but plan to hibernate after wading through a hearty meal.$10-30. edit
Valentina's, 4506 W 63rd St, ☎ +1 773 284-5529. Su-Th 10AM-10PM, F-Sa 10AM-midnight. This place, just a few blocks from Midway, serves wonderful taco platters. And the margaritas are just fine too. The decor is light and cheery, on-street parking is plentiful, and service is friendly, all making this a wonderful place to hang out, relax, and have some top-notch Mexican food.$8-15. edit
Vito & Nick's, 8433 S Pulaski Rd, ☎ +1 773 735-2050, . M-Th 11AM-11PM, F-Sa 11AM-1AM, Su noon-11PM. It's a quiet, family-style eatery with a few older patrons chit-chatting at the bar. Widely regarded on the South Side as serving the best thin crust pizza in the city; it bears the slogan "the best pizza... anywhere," and that may well be true — to be clear, this may be the best pizza in the world. The South Side accents are thick, the decor with its shag carpeted walls and Christmas lights is South Side chic in its purest form — this is an experience to be had. Note that the sausage and giardinera is the classic order, it's cash only, and it sometimes closes early if things are slow.$6-15. edit
The Southwest Side does not rank prominently in the minds of Chicagoans when they think of city nightlife, but there are a handful of worthwhile spots, with good live music.
Groucho's, 8355 S Pulaski Ave, ☎ +1 773 767-4838. M-F 2PM-4AM, Sa noon-5AM, Su noon-4AM; Kitchen open until 3AM. A decent South Side rock club featuring better-known local and regional acts. As an added bonus, the kitchen serves bar food all night.Admission: $5, entrees: $5-11. edit
InnExile, 5758 W 65th St, ☎ +1 773 582-3510, . 8PM-2AM daily. Gay nightclub that attracts all sorts of people passing through next-door Midway with occasional live performances.edit
Linda's Lounge (Linda's Place), 1044 W 51st St, ☎ +1 773 373-2351. Blues: M 9PM-late. A small, cozy neighborhood dive bar offering live blues and soul on Mondays with L'Roy and Linda. The immediate area is a little rough, so make sure you have transportation lined up in advance. Trust in the address — there is no signage.edit
Natasha's Rome, 2441 W 69th St, ☎ +1 773 842-9816. M-F 5PM-2AM, Sa 5PM-3AM, Su 3PM-2AM. This is the nicest club in the Marquette Park neighborhood, with a laid-back bar on each of its two floors. Willie T performs live blues on Fridays, Sundays feature spoken word night, and the rest of the time there is a DJ spinning R&B and other pop music. Locals usually dominate the crowd, except on Fridays and Sundays.edit
Reese's Lounge (Burnside Lounge), 1827 W 87th St, ☎ +1 773 238-1993. 11AM-2AM daily. Live DJs W-Su, Sunday nights are all-jazz. Dress nicely, it's a swanky place.Dinners $5-6. edit
Tina's, 5440 S Narragansett Ave, ☎ +1 773 586-8767. M-Th 4PM-10PM, F-Sa 11AM-11PM, Su 2PM-10PM. A divey neighborhood sports bar that rises above the crowd for its thin-crust and stuffed Chicago style pizzas. Otherwise, cheap drinks and free pool are the draws.edit
Tony O's Studio 31, 5147 S Archer Ave, ☎ +1 773 585-7512. Su-F 8PM-2AM, Sa 8PM-3AM. A bar/nightclub that is plenty friendly, packed on weekends, and miles away from the too-cool-to-sweat clubs downtown.No cover. edit
Touch of Class, 6058 W 63rd St, ☎ +1 773 586-8177. Su-F 9AM-4AM. A neighborhood pub just west of Midway that takes pride in turning off the ear-splitting music that kills conversation in bars across the city. The atmosphere is extremely friendly and laid-back (although Notre Dame games can enliven the place up a bit).edit
Crossroads Hotel, 5300 S Pulaski Rd, ☎ +1 773 581-1188. Tattered but cheap. Just a couple blocks south of the Pulaski Orange Line station.Rooms from $50. edit
Mainway Midway Motel, 4849 S Cicero Ave, ☎ +1 773 735-0550. Another "tattered" budget option located about a half mile north from Midway along Cicero Ave, an easy bus ride.Rooms from $52 Su-Th, $67 F-Sa. edit
Skylark Motel, 5435 S Archer Ave, ☎ +1 773 582-2100. Slightly more expensive than the other budget motels, but the extra cost may be worth it — it really is a good deal nicer.Rooms from $75. edit
Carlton Inn Midway, 4944 S Archer Ave, ☎ +1 773 582-0900, +1 877 722-7586, . Located a short walk (1.5 blocks) from the Pulaski L stop. Free airport shuttle, free parking, free internet, and free breakfast. Clean, comfortable rooms.$92-159. edit
The Hotel Center is a hotel campus in Bedford Park, IL, of seven individual mid-range options, located two blocks south of the airport (about a half mile from baggage claim) at 65th St and Cicero Ave. Shuttles run between all the hotels and the airport, although (despite claims to the contrary) you cannot always get a shuttle to/from the L station, so expect to have a long trip if you are heading to the city center. If you're here and looking for food, it would be a travesty of taste to go to the center's chain restaurants. Walk a block north to Giordano's for some quality Chicago-style pizza or solid Italian dishes. Better yet, get a taxi to Vito and Nick's.
Chicago Marriott Midway, 6520 S Cicero Ave, ☎ +1 708 594-5500, +1 800 228-9292, . A fine business hotel, albeit a small step down from the usual Marriot standards.$140-220. edit
Courtyard Chicago Midway Airport, 6610 S Cicero Ave, ☎ +1 708 563-0200, . Recently renovated, but not quite as nice as the Marriott itself.$110-220. edit
Fairfield Inn & Suites Chicago Midway Airport, 6630 S Cicero Ave, ☎ +1 708 594-0090, . This location is notably nicer than most Fairfield Inns, probably closer to a three-star than a two-star. Free wireless.$110-210. edit
Hampton Inn Chicago Midway Airport, 6540 S Cicero Ave, ☎ +1 708 496-1900, . Recently renovated, bland three star hotel.$130-240. edit
Hilton Garden Inn Midway Airport, 6530 S Cicero Ave, ☎ +1 708 496-2700, . Three star hotel with free high speed wireless.$110-200. edit
Holiday Inn Express, 6500 S Cicero Ave, ☎ +1 708 458-0202, . Probably the best option of the seven (although the differences between them are pretty slight), and has a curious New Orleans theme.$140-210. edit
Sleep Inn, 6650 S Cicero Ave, ☎ +1 708 594-0001, . The most price competitive option in the hotel center has a few less frills, and like the others is a bit overpriced, but perfectly sufficient. And the continental breakfast is actually good (waffles!).$85-180. edit
Midway Airport offers high speed wireless in several lounges, restaurants, and Air Tran gates, but it is only available to Boingo  subscribers. All the following branches of the Chicago Public Library also offer free public internet access.
Back of the Yards Library, 1743 W 47th St, ☎ +1 312 747-8367. M,W 10AM-6PM, Tu,Th noon-8PM, F-Sa 9AM-5PM. edit
Brighton Park Library, 4314 S Archer Ave, ☎ +1 312 747-0666. M,W 10AM-6PM, Tu,Th noon-8PM, F-Sa 9AM-5PM. edit
A stark sort of beauty in Englewood, churches amid vacant lots
As you would expect in such a large district of the city, crime levels vary throughout. The northern and western neighborhoods, while sometimes looking gritty, should not worry you in the slightest. Marquette Park is quite safe as well, although it deteriorates a bit southeast of the actual park. Englewood, on the other hand, is a huge neighborhood notorious among Chicagoans for murders, random beatings, and what have you. Auburn-Gresham and Washington Heights rest somewhere in the middle, but they're fairly quiet and peaceful — violent crime is not happening on main streets during the day.
If your flight is not on the departures display, perhaps you were looking for O'Hare International Airport? If so, grab a cab and hope for the best. Most taxis have special rates for the MDW-ORD trip, which should cost about $50-60 at the cheapest and take about an hour. If time is not an issue, you can take the Orange Line to the Loop and transfer to the Blue Line to O'Hare for just $2.25, but it will take two hours or more.
If you are staying downtown and just want to get some authentic Mexican food, there are great options closer by in the West Side's Pilsen neighborhood.
While you are out this far from the city center, why not head even further south to the Far Southwest Side to dig the Irish pubs and brogues.
Hop on the CTA Orange Line and head downtown to the Loop to escape the outskirts and see the city you recognize from the postcards.