A Local’s Guide to the Best Bars in Chicago
It is a tough job, but Team Dobbs rolled up their collective sleeves and got to work! 44 years of drinking age (and that’s just me!), tirelessly exploring the dynamic bar scene of our vibrant city known for food and drink. We scouted the most luxurious establishments, dive bars in the darkest alleys, and everything in between – and now, we’re thrilled to share with you a curated list of our all-time favorites we discovered along the way. Dive in as we reveal our favorite best bars in Chicago, each with its unique charm and character, handpicked by us for unforgettable experiences.
Oldies But Goodies
(312) 725-0732 | www.sparrowchicago.com
Sparrow is a charming and sophisticated bar in Gold Coast, offering a unique blend of classic and modern cocktails in an elegant atmosphere. It’s a perfect destination for those who appreciate finely crafted drinks and a refined bar experience. Debra’s favorite: the Rosado cocktail. Divine!
(773) 878-5552 | www.greenmilljazz.com
For Michael, this is the best bar in the city. Green Mill is known for its Rat Pack on the jukebox, cheap drinks, and gritty bartenders. A Chicago staple with a rich history, it’s a favorite among locals and visitors alike.
(312) 733-2251 | Richard’s Bar on Yelp
A Deb favorite! Known for the best jukebox in town, hard-boiled eggs for 75 cents, and the only bar where you can chain smoke without getting the evil eye, Richard’s Bar provides a classic, old-school Chicago bar experience. Cash only and opens at 7am; go for the eggs for breakfast. Located in Fulton Market | West Loop.
(312) 666-9292 | www.matchboxbar.com
Described as Chicago’s most intimate bar at 460 sq. feet, The Matchbox offers top-shelf liquor and cocktails in a stylish setting. Debra’s brother Michael recalls it as his favorite spot for libations and conversation.
(773) 252-1500 | www.theviolethour.com
The Violet Hour, serving major speakeasy vibes, offers a sophisticated yet unpretentious experience in bustling Wicker Park. It’s the perfect place for those seeking a unique atmosphere with exceptional cocktails.
(872) 315-3050 | www.therobey.com
Another Wicker Park’s treasure, The Robey- Cabana Club, is a gorgeous rooftop bar with cabana vibes, offering guests a chance to enjoy daiquiris, stunning skyline views, and a dip in their triangle pool. Located on the 6th floor of a boutique hotel, it’s a unique spot for relaxation and enjoyment.
(312) 285-2912 | www.barkumiko.com
This hot spot in West Loop is an absolute favorite of Katharine. The waitstaff, the food, the libations are all top-notch. While the dining experience is an absolute must, they have recently started a carryout service for both their food and drinks.
Newer Kids on the Block
(312) 763-3674 | www.chiwinery.com
Chicago Winery brings a sophisticated wine experience to the heart of the city. Debra loves their curated selection of fine wines. Heaven for wine aficionados and casual enthusiasts alike!
(773) 647-1942 | www.moonflowerbar.com
Moonflower is known for its intimate setting and creative cocktails, making it a perfect destination for those seeking a relaxed yet sophisticated bar experience in Chicago.
Quality Time is a unique establishment in the Chicago bar scene. It’s a perfect place for those who appreciate a relaxed atmosphere with creative drink options.
(773) 871-3757 | www.theglobepub.com
“The Globe is the best soccer bar in city,” says Debra’s brother Steve. Known for its vibrant sports atmosphere and extensive selection of drinks, The Globe is a favorite for sports fans and bar enthusiasts alike.
There you have it – our top recommendations for the best bars in Chicago. Each of these spots has a special place in our hearts and offers a unique experience that’s quintessentially Chicago. Whether you’re a local or just visiting, be sure to check out these gems for an unforgettable night out.
Cheers from Debra Dobbs and the team!
To find more tips for local resources, reach out to us for a complimentary digital and/or printed copy of Debra’s Little Black Book.