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The Recreationalist’s Guide to Chicago
chi-town, windy city, the most loyal sports base ever. when it comes to chicago and recreation, there’s a lot more than what meets the eye.
Chicago is home to the largest network of alleyways in North America, weaving together to make up a seemingly infinite coast along Lake Michigan. Recreation in Chicago is about pounding the pavement. From one neighborhood to the next, each of Chicago’s corridors offers its own distinct architectural flavor, influencing the vibe of its nearby hotspots.
It’s also home to a not-so-underground art scene, a semi-underground skate scene, and a super-underground locals scene (some of which we’re uncovering in this guide). There’s a certain appreciation of old school charm mixed with bold experimentalism that Chicago locals boast — you can tell that this special fusion of newness and tradition resides in nearly every neighborhood.
In a conversation with our featured Recreationalist Mia Ghogho, it was noted that Chicago is one of those small-big cities that you might not have previously frequented if you didn’t have explicit reason to. But now? Chicago is quickly being added to all the must-see guides to America — but The Recreationalist already knew this. With Mia’s recommendations, help from local photographer Brendan Carroll, and our original Chicago tour guides Colin Heaberg and Will Gisel of Whim.World, we’re bringing you an updated 2020 guide to the Windy City.
Hyde Park
Hyde Park most certainly wasn’t invented by the Obama family. But ever since the 44th president started paying national homage to his humble beginnings, the historically diverse neighborhood (one of the few truly diverse centers in Chicago) has certainly gained some well-deserved notoriety. Now, Mia Ghogho says her second home is undergoing “a true renaissance” that makes it a must-see in our book.
Promontory Point
Runners: According to Mia, the best city route for getting in your steps is located along Promontory Point in Burnham Park. Run parallel to the crisp water’s edge of Lake Michigan, alongside the quads of bikers and skaters that also populate the trail.
If you’re looking for a longer workout, Mia suggests running southbound toward Jackson Park, where you’ll stumble upon free yoga and fitness classes across its vast grounds.
Hyde Park Art Center
If you’re planning ahead, slot some time to visit one of Mia’s local favorites, the Hyde Park Art Center. A non-profit community art hub that houses five galleries, ten artists in residence, and a school studio that offers membership-based and “pay what you can” classes, this center is truly the stuff of locals. Mia loves their pandemic-friendly hybrid ceramic classes, where you can work on your piece from home before booking time in-center to glaze and fire it to perfection.
53rd Street
A few blocks west of Promontory Point, the Lake Park & 53rd Street intersection marks the beginning of a long social corridor. From east to west, Mia likes to stop in Philz Coffee for something warm before taking her pick of lunches at Black-owned Virtue Restaurant, Giordano’s Pizzeria, Mesler Chicago in the Sophy Hotel, or vegan hotspot Can’t Believe It’s Not Meat. At the latter, Mia recommends the vegan cheesecake shake and pizza puffs. “That’s a Chicago thing. They’re like calzones, but wrapped differently.”
Bridgeport
Typically as a big city continues to grow and flourish, certain quirks of a neighborhood’s historical character might fade to be more subtext than spotlight. Not Bridgeport, says local photographer Brendan Carroll. “Even as everything grows around it, Bridgeport seems to be a place where people still just don’t care about other people seeing them. So you get to see more.”
Before you take on Bridgeport, you must first be briefed on the legend that is Ed Mar, the unspoken “People’s Mayor of Chicago” and owner of many neighborhood gems. Aside from his brick and mortars, Ed Mar also runs a radio station and bimonthly zine — both of which are exclusively dedicated to telling the stories of Bridgeport’s descendants. He’s so engrained in the local folklore that Brendan’s “seen this guy walk into restaurants and kiss babies like he’s a politician or something.” How’s that for local flavor?
Henry C. Palmisano Nature Park
One notable observation about Chicago: it’s very rare to find a piece of elevated land. That’s why Brendan labels the Henry C. Palmisano Nature Park as his favorite amongst many. Aside from all your “classic park things” — basketball and tennis courts, a park center, walking trails — there’s a giant hill for you to run up and sit on top of. “When you stand up there, you can see a back area filled with natural wildflowers and wheatgrass,” another anomaly in Chicago.
Just beyond the hill, in a tucked away nook, is a fishing pond that’s great for some quiet time to yourself.
When you’re ready to rejoin civilization, pay a visit to nearby neighborhood staple Maria’s Packaged Goods. Run by the aforementioned and infamous legend Ed Mar, this iconic spot looks like a plain Jane liquor store in front before you open a back door to the coziest bar.
If you ask a local what they’re having on a regular pizza night, nobody is ordering deep dish. That’s more of a treat!
Mythbusting Pizza
PSA: Deep dish pizza might be a Chicago thing, but according to both Mia and Brendan, it’s definitely not a Chicago local thing.
“If you ask a local what they’re having on a regular pizza night, nobody is ordering deep dish. That’s more of a treat!” says Mia.
Instead, try a tavern style slice at Phil’s Pizza. Open since the 1960s and located in an old bank (“the door is very secure for a pizza place”), this thin crusted wonder is more the local’s move.
31st Street Beach
One of the more lowkey beaches along Lake Michigan, 31st Street Beach is definitely the move when you’re looking to enjoy the water, minus the crowds. A breezy walk east of central Bridgeport, 31st Street Beach houses multiple eateries, a boat harbor, and unbeatable skyline views.
“It’s the perfect place for watching the sunrise,” says Mia. Be sure to go soon and rack up your Vitamin C before the notoriously unforgiving Chicago winter hits.
Chinatown
Though local photographer Brendan Carroll admits that Chicago’s Chinatown might be less esteemed than others, the Chi-Town neighborhood is still jam packed with rich, vibrant community culture (and the traditional comfort foods that make Chinatowns much adored).
Ping Tom Memorial Park
At the top end of Chinatown rests Ping Tom Memorial Park — arguably one of the best metropolitan parks in the city, according to Brendan. The park runs right along the south branch of the Chicago River, where you can catch a water taxi for just $9.
“Back in the day, the city started the taxi just as a means of getting people places faster, because downtown was so congested. But now people just take it for leisure. It’s a fun way to see the city,” says Brendan.
Once you’ve gotten your fill, walk over to Hing Kee for the “best soup dumplings in Chicago” (we know, bold statement).
Pilsen
Historically home to Chicago’s Mexican and Latinx community, Pilsen is a homey, urban neighborhood with a lot of spunk. While you’re in the “heart of Chicago,” check out Zins Flower Shop for some new potted friends and take a $5 fitness class at Healthy Hood Chicago, a non-profit community center that aims to decrease the gap in life expectancies between Chicago’s affluent and underprivileged communities.
West Town
For when you’re looking for that quaint inner city vibe, make like Mia and take a gallery walk through West Town. Two notable art galleries to check out: Monique Meloche Gallery and Rhona Hoffman Gallery.
After, refresh with drinks at speakeasy-inspired The Darling or The Hoxton Hotel in neighboring West Loop.
Around town in West Loop, Chicago. Photos by Mia Ghogho.
The Classics
We all know about the iconic Bean (if you don’t, imagine a metal sculpture of a literal legume), but according to our Chicago locals Mia and Brendan, along with Colin Heaberg and Will Gisel from Whim.World, these classic Chicagoan landmarks are actually worth your time.
Navy Pier
This former Navy training center turned miles-long boardwalk is the furthest thing from underrated. But according to Mia, there’s actually so much to do. Look out for its grand reopening in Spring 2021. Until then, you can still grab a drink and a view at Offshore Rooftop in & Bar.
In the mean time, sub in Navy Pier for Ohio Street Beach. Located right at the boardwalk’s opening, this quaint beach nook is still open and yours for enjoying.
Loyola Beach
One of the most northern entry points along Lake Michigan, Loyola Beach is definitely a bit more a trek — though well worth it, according to Brendan.
“Loyola Beach has one of my favorite basketball courts. It’s right on the water, so sometimes it’s so windy that it’s not realistic to play. You make a shot and ball is gone. But there’s this beautiful tree with big willows that lines the court. It’s really picturesque.”
Garfield Park Conservatory
Back in our 2019 installation of this City Guide, co-founders of Whim.World Colin Heaberg and Will Gisel named this two-acre glass ceiling greenhouse as one of their “personal favorite oases in the city.”
Find your way to the Fern Room to suddenly transport to a tropical climate that isn’t blisteringly cold and, well, Chicago. Until further notice, be sure to reserve your spot ahead of time online.
Concrete Beach
Yes, “Concrete Beach” works as a metaphor for the whole city. But in this case, we’re referring to the one mile stretch of curved concrete coastline along the Lakefront Trail that, when looking from north to south, sits directly below the Chicago skyline.
Make like Colin and Will and go for a jog, rent a bike, or dive into Lake Michigan —anything goes. Winter time? Bundle up and test the elements.
Bonus Round!
If you can, snag a homemade sandwich from Joe Morski’s Have A Good Sandwich. Run entirely out of his backyard and through Instagram, these no-frills, seriously good sammies always sell out within 20 minutes of posting.
Chicago boasts an infamously cool skate scene that’s both underground and accessible enough that all you really have to do is look in the right places. To start, check out POC and womxn-centered skate crew FroSkate, who we’ve featured here before. If you’re into spectator sport, “hang out on the outskirts of Grant Park and just watch the skaters skate,” says Mia.
Creatives! Get your film developed at urban legend, CSW Film Systems. Oson, the long-time proprietor, is allegedly “the only person in the entire city that can get your film developed in one day,” says Brendan. While you’re there, ask him to tell you one of the many local stories in his rolodex.
Urban farms are something of an emerging phenomenon in Chicago. “I’ve been really intrigued by the work that Urban Growers Collective is doing,” says Mia. Check out one of their cross-city locations to buy fresh produce and learn how urban-friendly agricultural practices can help underserved neighborhoods experience food equity.
WILDSAM Says
Before you head off to Chi-Town, buff up your cultural index right from the couch. Head to wildsam.com for the full Field Guides collection.
To Read
“The House on Mango Street” by Sandra Cisneros. Buy here.
To Listen
“Stone Crazy” by Buddy Guy. Play here.
To Watch
Pay homage to Jordan’s Bulls with “The Last Dance”. Stream here.
To Reminisce
The parade scene in “Ferris Bueller’s Day Off”. Watch here.
To Gaze
Virtual exhibits at the Art Institute of Chicago. View here.
Editor’s Note: Given the current state of the world, The Recreationalist does not encourage long distance travel to any particular region. Instead, these guides were crafted to pay homage to the local people, communities, and cultures that have kept these cities strong for generations, and perhaps even for learning a new thing or two about the place you call home.
This guide was written and edited by Joanne Xu, with contributions from Mia Ghogho, Brendan Carroll, Colin Heaberg and Will Gisel. And honestly, Ed Mar.
Featured photos by Mia Ghogho and Brendan Carroll.
Culture list and illustration by WILDSAM.
Did we miss anything? Comment your favorite Recreational spots around Chicago below.
