HIGH CITY GUIDE: Chicago For The Weed Connoisseur

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Something is blowing through the air in Chicago, and it’s not just the run-of-the-mill Windy City politics or the smells of the Blommer Chocolate factory permanently intoxicating the West Loop. It’s liberating aromatics of recreational cannabis thanks to HB 1438, an initiative that passed in June that makes Illinois the 11th state to join the weed revolution—good work!

Cannabis-obsessed tourists ages 21 and up will soon be able to walk into a dispensary and walk out with up to 15 grams of flower, up to 250mg of THC edibles, and 2.5 grams of concentrate (Illinois residents can purchase double that amount). The law goes into effect as of January 1, 2020, but will likely have a very typical, slightly wonky waiting period as licenses are put into effect.

Following in the footsteps of places like Oregon and Washington, smoking in public is restricted to private residences (as if that ever stopped anyone before). So, mind your manners and follow the lead of locals, unless you want to get slapped with a dirty look (at best) or an annoying, excessive fine at worst.

That said, here’s where to buy, chill, and satisfy the munchies for a dope weekender. It’s the Chicago High City Guide!

Logan Square/Humboldt Park

Where to buy

MOCA Modern Cannabis (2847 W. Fullerton Ave.) Make sure you double check your GPS before going to this Logan Square dispensary so that you don’t accidentally dial in the Museum of Contemporary Art Chicago (not a bad place to end up going after your visit, albeit in the complete opposite direction). In addition to its solid menu of expertly curated strains and cannabis products, this dispensary hosts a monthly patient mixer over at craft beer-arcade Emporium Logan Square where you can play video games stoned out of your gourd in a judgment-free zone.

Where to chill

Humboldt Park (1440 N. Humboldt Ave.) This 197-acre park might look familiar to those who have made the annual pilgrimage to Chicago for Riot Fest. But if you catch the perfect sunny afternoon when it’s not loaded up for its regular stream of festivals, the park is one of Chicago’s best chill zones. Stroll around its historic lagoon and boat house, an inland beach (summer swimming? OK), or see the latest exhibit at the National Puerto Rican Arts Museum, tucked away inside the park.

Palmer Square Park (2200 N. Kedzie Ave.) The strip along the Logan Square blue line stop and Milwaukee Avenue is where you can find all the boutiques, restaurants, and bars. But this mini 7.6 acre park situated a half mile south is where to go if you just want to chill in the grass and have a nice afternoon in the sun.

Where to satisfy the munchies

California Avenue (between Augusta and Division) It’s not a big strip, but that doesn’t matter: everyone knows this is where the chill people are at. Start with a sunny brunch at Spinning J or Flying Saucer, chill with an afternoon coffee at C.C. Fern’s. Hit up this small strip before the shops close to hit up cute weed witch shops like Humboldt House, Space Oddities, and Peach Fuzz. Grab dinner at Cafe Marie-Jeanne or Rootstock followed by drinks at the California Clipper. If you have the willpower to keep going, pick up a slice at Dante’s Pizza and then go make a 4 a.m. dive bar mistake at The Continental (2801 W. Chicago Ave.).

Milwaukee Avenue (Between Diversey and California) Most Chicagoans will roll their eyes and say Logan Square is long “over.” Use it to your advantage because there are still plenty of awesome restaurants for a DIY food crawl at places like Reno, Lula Cafe, Daisies, and Paulie Gee’s. And if you want a decent drink, solid mood lighting, and good tunes, check out Estereo, Cole’s Bar, Cafe Mustache, East Room or Spilt Milk.

Armitage Avenue (Between California and Central Park) Most tourists don’t veer to this section of Palmer Square simply because it’s a touch too far from the Blue Line and requires an Uber or Lyft. But if you’re a tourist (who happens to be a super smart stoner babe), that shouldn’t matter because you’ll probably end up using both services anyway. Here, you’ll find excellent restaurants like Giant, GROUND CONTROL!, Table, Donkey and Stick, Dos Urban Cantina and Osteria Langhe, along with late night haunts like Scofflaw, Parson’s Chicken and Fish, Best Intentions, and WeeGee’s Lounge. If you get there early and need a sweet treat, make sure to grab a soft serve from The Freeze or load up on gourmet truffles from Katherine Anne Confections.


Where to buy

The Herbal Care Center (1301 S. Western Ave.) This top notch, veteran-owned dispensary is technically in the Tri-Taylor neighborhood bordering Pilsen (but that’s the kind of neighborhood insider baseball talk only locals care about). More importantly is the variety, and it’s considered among the city’s best for flower, vape, extracts, pre-rolls, edibles, tinctures, and topicals—oh, my. First time patients also qualify for a generous $20 discount, plus extra discounts for veterans, seniors, and those who qualify for their Compassion Program.

Where to chill

18th Street (between S. Damen Ave. and S. Halsted Ave.) Not much of a planner or just don’t know where to start? Take the Pink Line to 18th Street CTA station, which marks the west end of PIlsen’s 1.5 mile main street. This is where you’ll find all of the restaurants, cafes, bars, cutesy boutiques, vinyl shops, bookstores, and best people watching. Even a leisurely stroll will take about 30 to 40 minutes, which could theoretically feel like a lifetime depending on the strain you choose and your tolerance. Lean into the adventure, meandering to places like Knee Deep Vintage, Pilsen Community Books, the Shudio, or dropping into an adults only art class at Color Cocktail Factory.

National Museum of Mexican Art (1852 S. 18th St.) Stimulate mind (and your third eye) by spending a few hours wandering around this incredible Mexican art and cultural museum showcasing talent from ancestral Latinx pioneers to local Mexican American makers. Its incredible art collection is the draw, but there’s a super sweet bonus: admission is free! Use your saved cash to donate generously or load up on cool swag like Yococalli temporary tattoos and buttons, locally made zines, and folk art trinkets. The museum is also located within Harrison Park, which is a chill place to get some fresh air or a straight up emergency panic hatch.

Halsted Avenue (Between 18th and W. Cermak Rd.) Plan it right and you’ll get the best bang for your buck as far as art goes on the monthly 2nd Fridays Gallery Night art walk night when Pilsen’s galleries open their studio spaces for a super easy (and happily stoned) art crawl on the cheap. Check out places like Lithium and the galleries within the Fountainhead Lofts building (1932 S Halsted S) and meander towards off-the-Halsted strip stops like Woman Made Gallery, NYCH Gallery, and the Pilsen Outpost.

Where to satisfy the munchies

18th Street (between S. Damen Ave. and S. Halsted Ave.) Most everything is along Pilsen’s main strip, including the food you most want to shove into your face: from the legendary Taqueria Los Comales, Carnitas Urupan, and Birrieria Reyes De Ocotlan Restaurant to long-standing hipster-centric spots like Honky Tonk Barbecue and Dusek’s Board & Beer (attached to Thalia Music Hall and Punch House).

Maxwell Street Market (800 S. Desplaines St.) This is a bit of a destination for the dedicated foodie (Sundays only; 9 a.m. to 3 p.m.), but this legendary Chicago flea is where you’ll find some of the best—and most affordable—bites in town. Legit Oaxacan tacos and huaraches, Brazilian-style street food, fresh produce, incense, soaps, and random t-shirts (always a good souvenir).

Marz Brewing (3630 S. Iron St.) Marz is a brewery...and not. Collaborating with local artists, designers, chefs, brewers, and activists, this quirky-cool brewhouse doubles as a community meeting space for cool events like drink ‘n draw over one of their excellent experimental beers. Make sure to check out the owners’ sister indie institution projects like Lumpen, Maria's Packaged Goods & Community Bar, and Kimski’s.

Lagunitas Brewing House (2607 W. 17th St.) Admittedly the crowd here tends to be a bit on the normie side, but you can’t beat the Willy Wonka-style surrealist approach to a gigantic beer factory (literally—there’s a whole blacklight hallway leading to the tap room).

Need more travel inspiration? Check out Miss Grass’ High City Guide for Toronto, Los Angeles, New York, San Francisco, and Las Vegas.

Carly Fisher is an award-winning journalist and digital specialist specializing in food, beverage, travel, wellness, lifestyle, business and cannabis topics.