Moonflower was founded by three industry veterans in Portage Park on the city's Northwest Side. It's a "plant-themed bar" that serves craft cocktails with unusual ingredients including Milkis, a South Korean milk-based soda, and Goldsaft, a German sugar beet syrup. There's a small pub menu with snacks and an extensive soul music soundtrack, and these drinks may be taken to go.

Zach Rivera, Christina Chae, and Marvin Boeving, the three founders, met while working at Machine Hospitality Group (Headquarters Beercade, Machine), and decided to open a bar together. Each of the three owners' marks may be found on the bar. Chae's own collection provides many of the plants used in the design. Because Boeving like sandwiches, they are on the menu. Rivera, whose father was a jazz drummer, curated the Spotify playlist that plays in the background for customers. Boeving is from Germany, Rivera is from Puerto Rico, and Chae was born in South Korea, thus the cocktail ingredients represent what they grew up eating and drinking.

Address: 4359 N Milwaukee Ave, Chicago, IL 60641
Website: https://www.moonflowerbar.com/

Osito's Tap, which opened in 2019, is a "speakeasy"-inspired bar that embraces the art of craft spirits, beer, and cocktails while adding a modern Latinx twist to a classic Chicago period. This community "speakeasy" is value-oriented in educating and creating a community environment that is inclusive, enjoyable, and historically remembering, with a fresh and health-conscious food menu.

With a tent and heaters for outdoor service, Osito's, which opened in 2019, is prepared for rain and cold. Growlers and cocktails are available to-go, and so are a variety of Mexican liquors such as mezcal and tequila, as well as a great selection of beer. Food is also available at Osito's, including tacos. In the ancient interior of the bar, sinking into high-back booths, or taking a seat on the patio and soaking up the sun is a great experience must-try.

Address: 2553 S Ridgeway Ave, Chicago, IL 60623

Website: https://www.ositostap.com/

This low-key cocktail bar gives a welcome neighborhood atmosphere to a stretch of Spring Street. It's a combination cocktail lounge and dive bar that offers something for everyone, and it's an offshoot of a well-regarded New York hotspot.

On a board behind the bar, there's a small list of specialty cocktails, including an ever-changing frozen concoction served from what seems to be a converted Icee machine. There's a fun mix of traditional drinks with modern twists on tap, as well as boozy slushies. There's also food, sandwiches, and waffle fries. Blond-wood tables, flower vases on the bar, wood-sill windows, and homey lamps sprouting from the exposed-brick wall all give the impression that you might spend some time here with Mom.

Address: 2943 N Milwaukee Ave, Chicago, IL 60618
Instagram: https://www.instagram.com/mothersruinchicago/

Soif is a wine lounge with the exclusivity and low-key features of a speakeasy, hidden down an unmarked staircase in Logan Square's prestigious Testaccio neighborhood.

Testaccio, the owner of Osteria Langhe's new basement wine bar, is a Roman-inspired Italian restaurant. Aldo Zaninotto, the bar's owner, is a wine buyer who uses Soif to show off his expertise, specializing in vintages from France. Open the door of Soif and be taken to a secret Parisian salon with its dimmed lighting, brasserie-style red velvet banquettes from La Sardine, festooned with pillows, and a combination of vintage wood and marble tables covered with candles. This dark and cozy basement wine bar is ideal for a date before or after dinner.

Address: 2456 N California Ave, Chicago, IL 60647

Website: https://www.soifchicago.com/

The Clipper, a Chicago icon since the 1930s, has reopened after a two-year. Since the pandemic began in spring 2020, the bar has been closed, but it reopened in February 2022 with live music (and a new sound system), as well as an upgraded drink menu.

The bar's iconic red lights and comfy vinyl booths, as well as its old wooden bar. The bar always has a dark red glow, no matter the time of night. The menu is simple with traditional cocktails like The Matador and The Cardinale, as well as community favorites like Medalla Light, Puerto Rico's favorite beer, Polish drinks, and the Chicago handshake, which consists of a shot of Malort and an Old Style.

Address: 1002 N California Ave, Chicago, IL 60622

Website: https://www.californiaclipper.com/

Pilot Project Brewing is a brewery incubator, tasting room, and café in Logan Square, Chicago, located on Milwaukee Avenue. Pilot Project was founded as a collaborative and artistically curious space to support talented brewers in a field with high obstacles to entry. Pilot, which is modeled after the music industry, serves as a launchpad for new brewers, helping with recipe development, production, business development, marketing, and distribution, among other things.

Pilot Project is a modern casual comfort zone, filled with natural light and decorated in earth tones such as brown, gray, black, and white, with traditional taproom features like a concrete floor, a bar, and handsome walnut tables. The bar fills a need in the industry for both bargoers and breweries. With a comfortable area to drink the fresh beer, coffee, and kombucha made on the premises, the large patio and well-lit inside room drew people.

Address: 2140 N Milwaukee Ave, Chicago, IL 60647

Website: https://www.pilotprojectbrewing.com/

Hopleaf has been a mecca for craft beer fans and a relaxing, welcoming neighborhood bar in Andersonville since 1992. Hopleaf has also offered thoughtfully sourced, in-house prepared, chef-inspired cuisine for over 15 years.

Hopleaf is a place to drink, eat, and talk with new and old friends without being distracted by screens, games, or live entertainment. They have a carefully curated, constantly changing variety of better beers (on 68 taps and in bottles), fine wines, spirits and cocktails, cider and meads that complement their seasonal food menu. Hopleaf's wine selection, selected by Roper, is mostly European, with a concentration on wines from Italy, France, and Spain. The wines included here are mostly from small, boutique producers that produce only a few thousand cases of wine each year.

GoodFunk, a natural wine bar and café on Wacker Drive in Chicago's Loop. It concentrates on wine made with minimal intervention. You'll find grape varieties you've never heard of from lesser-known corners of the world, made by daring winemakers who aren’t afraid to step back and let nature work its magic. GoodFunk proves that wine can be affordable, quirky, and most importantly, enjoyable when paired with equally funky, rustic food.

Sidle up to the shiny marble-topped bar and browse the stocked, ever-changing wine selection curated by Bonhomme Group wine director Colin Hofer to embrace the bugs within this intimate, narrow space (previously Cafe Bonhomme). Consider date night complete with some upscale shareables like housemade free-range Chicken Liver Pâté, Anchovy Butter Toast, and Steak Tartare with dry-aged Angus beef and confit egg yolk.

Address: 180 N Upper Wacker Drive, Chicago, IL 60606

Website: https://www.goodfunkchicago.com/

Dorothy is a comfortable cocktail lounge located below Split-Rail on Chicago Avenue. This queer-owned and -operated speakeasy beneath West Town fried chicken palace Split-Rail is back in action after two years of COVID-fueled hibernation, with wood-paneling, disco balls, pressed velvet wallpaper, an enticing array of plump burgundy-hued sectional couches and vintage lounge furniture.

While the club may lean LGBTQ+, "a friend of Dorothy" was a covert identifier for cloaked homosexual people in the mid-twentieth century, its underground doors are available to bar-goers of all backgrounds, proclaiming itself queer-friendly rather than exclusively gay. Check your preconceptions at the door, grab a well-crafted vintage drink, and get into the rhythm starting at 6 p.m. Thursday through Sunday.

Address: 2500 W Chicago Ave, Chicago, Illinois

Website: https://www.dorothydownstairs.com/

The Welcome Back Lounge is Logan Square's premier late 70's and 80's themed cocktails bar. It opened in the summer of 2020 in the middle of Logan Square's Hipster Highway and has everything you need for a fun night on the town.

Drinks are served from a brightly colored bus on their cozy mural-lined patio. There's enough tacky wallpaper and checkered linoleum flooring inside the bar to take you back to your primary school days, along with inner-child delights like Jell-O shots, fried bologna sandwiches, and canned wine. On weekends, order brats and tots for brunch, or come in for charity bingo on Monday nights, which supports a different charity each month.

Address: 2423 N Milwaukee Ave, Chicago, IL 60647

Website: https://www.welcomebackchicago.com/