The way Chicago works is the way many big cities work – you can spend your entire life here, being born and going to school and living and working and dying, all without barely leaving your side of town. A city on a grid as unflinching as you will ever find, some of the street names may remain familiar wherever you go, but so wide is the chasm between its "sides," the traveler through town might sometimes feel as if they've stumbled upon a new city altogether.

These days, none of the Chicagos are quite so talked-about as the South Side. None are so grossly misunderstood, either. A complex place from the outset, poverty and violence have long been high on a list of pressing issues that the city never seems to have the time or will to address. Much of what you will have heard is true. Still, as is generally the case in these situations, there's more to the story. Much more. Next time you're in town, spend a day getting to know this side of Chicago – chances are, you'll come away wishing you'd gotten here sooner. Here's a rough sketch of a very good day in what is easily one of America's most underrated urban places.

Morning walk at Palmisano Park

A disused quarry tucked away near the intersection of three very different neighborhoods – Bridgeport, Pilsen and Chinatown – is now one of the most unexpectedly wonderful parks in the city. Featured are a proper fishing hole, a hilltop with great views of the city skyline (from here you can almost reach out and touch the Willis Tower) and a network of pathways on varied terrain for some proper exercise. When you're done, browse through Bridgeport, easily one of the South Side's most sought-after neighborhoods – Bridgeport Coffee (3101 S. Morgan) is a great place to get a feel for the way things are now. (2700 S. Halsted St.)

Breakfast at 5 Loaves Eatery

Hungry? Hop on the Dan Ryan and head for laid-back Chatham, where this tiny but very good breakfast and lunch spot serves up Southern specialties to a very local crowd (don't be shy, they're nice). Skip the stuff you could get anywhere – omelettes, for example – and go for the gusto with catfish, grits, fried chicken and waffles. Don't even think of sliding in here right after church on a Sunday. It's not happening. (405 E. 75th St.)

Pay a visit to the new Pullman National Monument

After years of tireless efforts put forth by residents and supporters, this living link to American industrial history that just so happens to be one of Chicago's most unique neighborhoods has now achieved federal recognition. Under the National Park Service, the way is now paved to an even brighter future for the former company town that once housed the employees of the Pullman Car Company. Not that you have to wait – drop in for a coffee at the Pullman Café, then head over to the visitors center for a crash course in local history. You might even stay for a drink at the Argus Brewery, just over the railroad tracks, if you happen to be nearby on a Saturday afternoon. The interesting characters that live and work here, coupled with the unusual (for Chicago) Victorian architecture of the neighborhood will have you seriously in like, if not something stronger. Find more information and current visitors center opening hours at

Grab an old-school lunch in Beverly

Even people who know and understand the South Side often forget to talk about Beverly, quite simply one of Chicago's greatest neighborhoods, period. With miles of residential blocks crammed with some of the most striking residential architecture you'll find in the Midwest, including styles rarely seen off of the coasts, Beverly in any normal city would boast some of the highest property values for miles. Chicago being what it is, Beverly remains magnificently affordable, attracting young, space-seeking families who otherwise might have long ago been priced into the suburbs. (It helps that it's one of the safest neighborhoods in the city, too.) The old traditions are still a big deal here – Calabria Imports on W. 103rd Street has been serving up some of Chicago's best Italian subs for decades now, if that's of interest. Like cheeseburgers, but feel like they're mostly never big enough? Go to Top Notch Beef Burgers on 95th Street, part classic coffee shop, part bustling social hall, and order the ¾ lb. Super King burger. (Don't fill up on fries – that thing is enormous.) Leave room, if you can, for sweet potato pie – just down the block, Jimmy Jamm's is a bakery and café known best for serving up one of Chicago's best sweet potato pies. You're welcome.  

Visit the Stony Island Arts Bank

Two blocks south of Jackson Park (soon to be home to the Obama Presidential Library), a grand old bank building that appears to be locked up tight actually houses one of Chicago's most fascinating (and newest) cultural institutions. Purchased from the city for $1 after years of abandonment, it is now a gallery, gathering place and incubator for art on the South Side. As the name implies, it is also the home to some unique collections, ranging from the vinyl archive of house music great Frankie Knuckles to the personal book collection of the founder of Jet Magazine. The space is beautiful, the rotating exhibits are tremendous – don't leave the South Side without stopping in, at least for a quick look. They're open most afternoons. More information at (6760 S. Stony Island Ave)

Sunset stroll through the nature preserve at South Shore

It looks like a rather grand old hotel, down the end of the manicured, tree-lined driveway leading from the busy corner of South Shore Drive and 71st Street, but it's actually a public park – head on in. What was once the South Shore Country Club – complete with golf course and a restaurant serving weekend brunch – now belongs entirely to the people. In pleasant weather, there's a beach, too, but any day you happen to be nearby is a good day to explore the magical little nature preserve, occupying the point just beyond the strand, a short walk from the clubhouse. In fall, look for monarch butterflies everywhere, amid the mix of wildflowers and prairie grasses. At any time of year, there are great views up the shoreline to the growing downtown skyline. (7059 S. South Shore Dr.)

Have dinner at Promontory

Heard the one about the Chicago dining scene? Then you know that you're in one of the most exciting places to eat in the country, hands down. Or, rather, you're close – the best restaurants on the South Side are typically something of a trip back in time. Change could be on the way – in bookish (but increasingly happening) Hyde Park, home to the University of Chicago, Promontory is a recent project from the talented team behind the nationally-known Longman & Eagle gastropub, up in cooler-than-you Logan Square. Part live venue, part rooftop drinks destination and very much a good New American restaurant, Promontory is even luring typically stand-offish North Siders, proving that when it comes to bridging a divide, there's nothing quite so effective as food. (5311 S. Lake Park Ave.)

For a look at current fares from all over the US and Canada, visit our listings for both Chicago (ORD) and Chicago (MDW).

All products and services mentioned on Airfarewatchdog are independently selected by our team of expert travelers. If you buy something through our links, we may earn an affiliate commission.

More Stories You'll Love