Where To Go Eat, Drink, & Enjoy CHICAGO

Here’s where you can go eat, drink, and enjoy Chicago.  I’m sure I left out a place or two, so just email me to remind me, and if you know of any cool places I should check out next time I’m in town, just let me  know.  Thanks – Bernie


Ace Hotel – 311 N. Morgan St. – I’ve stayed at the Ace Hotel in Los Angeles and London, and these are hipster boutique hotels that are quite fun. They always have cool bars in them where all the “cool kids” go

Aviary – 955 W. Fulton Market – The Aviary is an experience, more than a restaurant or a cocktail bar. They have a cool speakeasy downstairs with very limited seating and some great vintage spirts. Some have written and said that Aviary is one of the top restaurants in the country. Swanky cocktail lounge with intricate drinks in super creative presentations & clever small bites.

Cherry Circle Room/Milk Room – 12 S. Michigan Ave – Located in the old Chicago Athletic Club, this building used to be where gentlemen did their daily calisthenics but now it is a hotel, restaurants, and cocktail bar. But you can still play pool here, watch sports, and play bocce ball too. The Cherry Circle Room and Milk Room are award winning and Cherry Circle room has awesome food and cocktails. The Milk room is an exclusive 8 seat micro-bar led by award winning spirits guide; Paul McGee where you can try vintage spirits and creative cocktails. Because it’s only 8 seats, it’s boujee, and expensive, but it’s more than worth it. Cherry Cirlce Room is Certified Bonded Premises; C.B.P. IL – 12.

Cindy’s – 12 S. Michigan Ave – also inside the Chicago Athletic Club, this is a cool roof top restaurant with a great view of the lake and the shore front of the city. They have great cocktails and the food is pretty damn spot on.

Duck Duck Goat – 857 W. Fulton Market – Creative Chinese fare from celeb chef Stephanie Izard served in buzzy, ornately decorated surrounds; serving Dim Sum Brunch from 11-4:30 on Sat/Sun.

Lone Wolf – 806 W Randolf – Neighborhood tavern with an old-school vibe offering craft beers, classic cocktails & bar bites. I think they’re more than just bar bites, but they’re damn good. I love their slogan, “Mark your territory!”

Millie’s Supper Club – 2438 N Lincoln Ave – Old-school Wisconsin comfort-food spot modeled after a classic Wisconsin supper club & bars. They have classic Hamm’s Beer commercials playing on the screens, and there is LIVE MUSIC with  piano bar in keeping with the theme, and of course; fried cheese curds and prime rib!

Momotaro – 820 W Lake St – Large venue with a huge Japanese menu served in a main dining room and lower-level izakaya. The main floor features distinct stations for sushi and a dedicated Robata, and contemporary sections of the kitchen with Shigero Kitano guiding the Sushi Station. Voted #3 restaurant by Phil Vettel in “Top 50 Restaurants in Chicago”

Publican – 837 W Fulton – paying homage to oysters, pork and beer, The Publican’s eclectic menu is inspired by simple farmhouse fare in a space evocative of a European beer hall. Chef-Partner Paul Kahan and Chef de Cuisine Dennis Bernard have developed a network of purveyors to supply the restaurant with hand-selected and sustainably-raised fish, seafood and pork.


Bub City – 435 N Clark – Bub City is a fairly large bbq joint with a very extensive American and bourbon selection, and live country music nightly. Bub City is Certified Bonded Premises; C.B.P. IL – 435

Sable Kitchen & Bar – 505 N. State St– located inside the Kimpton Palomar Hotel, Sable has an extensive whisk(e)y selection and make damn tasty cocktails. If ya need a little swig of beer in-between to cleanse your pallet, they have Miller “hand grenades” (7 oz beers). Sable Is Certified Bonded Premises; C.B.P. IL – 505

Pacific Standard Time – 141 W Erie – a restaurant the brings the warmth and authenticity of California farms and artisans to the heart of downtown Chicago.

Three Dots and a Dash –  435 N Clark – (below Bub City) premier tropical tiki bar and craft cocktail destination hidden below the bustling streets of River North. Voted one of the World’s Best Bars by Drinks International.


Longman & Eagle – 2657 N Kedzie – This a favorite spot of mine in Chicago for brunch, and just having a drink. You can eat, sleep, and drink here as they have 6 guests rooms in their B&B, and although they don’t brag as much as they should, they have a Michelin star. They don’t take reservations, just stop on by and enjoy. L&E is is Certified Bonded Premises; C.B.P. IL – 2657

Billy Sunday – 3143 W Logan Blvd – Upscale cocktails and gourmet gastropub fare are served in this chic, antique-accented space. They have a nice spirits selection, and an extensive selection of vintage spirits which includes one of the largest collections of vintage Fernet and Amaro.

Scofflaw – 3201 W Armitage – Gin-centric cocktails, craft beers & pub grub served in a relaxed urban-rustic bar with cozy nooks.

Lonesome Rose – Golden Teardrop2101 N California Ave – Lonesome Rose is one of my all time favorite places to eat breakfast and/or lunch. They have awesome Mexican and tex-mex wraps and other creative dishes of that fare. Then downstairs is Golden Teardrop – which is a cool speakeasy type bar with spirit forward cocktails. The name comes from a 1950’s doo wop song, and the space is just as hip.

Lost Lake – 3154 W Diversity – Lost Lake evokes both the glamorous tropical escapism of 1930s Hollywood and the rugged nautical, island aesthetic of the world’s first tiki bar — the original Don’s Beachcomber Cafe. Decked out in tropical attire and well-versed in rum (and rhum, and ron), Lost Lake’s talented staff of friendly and knowledgeable beverage professionals are ready to take you on a mini-vacation, by way of a wildly garnished tiki cocktail.

Pink Squirrel – 2414 N Milwaukee Ave – cool neighborhood ice cream shop/cocktail bar – Classic cocktails are served in funky retro digs with a 2 lane old school duckpin bowling, shuffleboard, trophies & houseplants.

Ludlow Liquors – 2959 N California Ave –  is a neighborhood tavern slingin’ stirred cocktails by the ounce, killer … offers creative blue collar food inspired by the chefs’ Chicago upbringing.

Sportsman’s Lounge 948 N Western Ave – this is a cool old time dive bar cleaned up but not too much…cash-only hangout featuring a taxidermy theme, table games & a rotating list of cocktails & beer. The music is played on a reel to reel! Sportsman’s is a Certified Bonded Premises; C.B.P. IL – 948

California Clipper – 1002 N California Ave – Circa-1937 bar with a revamped yet still retro space & a LIVE MUSIC venue with a huge list of old-fashioned cocktails. You truly do feel transformed back to the 1930’s jazz clubs.

Best Intentions – 3281 W Armitage Ave – Refined watering hole that kept it’s dive bar roots, serving diverse beers & cocktails in laid-back digs with a killer patio, and have you ever heard of a place that has angostura bitters on tap?!

Delilah’s – 2771 N Lincoln Ave – a whiskey dive Bar with more than 500 varieties of whiskey plus movie nights & DJs spinning punk/rock/ska music. Mike Miller owns the joint and is considered one of the premier whiskey men in the country. Delilah’s is also a Certified Bonded Premises; C.B.P. IL – 2771



Big Star – 1531 N Damen Ave – Mexican street tacos, and other Mexican fare, plus margaritas & other drinks fuel a lively scene at this funky hangout. Ask them about Lunazul Tequila there…they’ll tell ya it’s the best and what they use for all their house teq drinks. They also have a lot of Bottled in Bond whiskeys and are indeed a Certified Bonded Premises; C.B.P. IL-1531!

Dove Luncheonette – 1545 Damen Ave – next door to Big Star is one of the best places you’ll ever eat breakfast in my opinion, but they also have Tex-Mex diner eats plus cocktails & lots of tequila in retro digs with counter seats & a jukebox.

The Robey Hotel – 2018 W North – cool hotel to stay at and reminds me of hotels in London and Europe where people take their lap tops to work and have coffee and small bites. They also have an awesome roof top bar with great cocktails and probably the best 360 panoramic view of Chicago.

Publican Anker – 1576 N Milwaukee Ave – Hip hangout with gastropub eats, craft beer & signature cocktails in an industrial-chic setting.

Violet Hour – 1520 N Damen – owned by the same folks as Big Star and Dove Luncheonette which are across the street, Voilet Hour is an upscale cocktail bar/speakeasy with some lite bites. They take the craft of creating cocktails very seriously here.


Big Star – 3640 N Clark St – the second location for Big Star in Wicker Park. Mexican street tacos and fare, and margaritas and other teq and whiskey drinks.

Dutch & Docs – 3600 N Clark St – serving American fare and classic cocktails. Exec Chef Chris Pandel and Pastry Chef Lauren Terrill take what they do seriously but also have fun with it along with their knowledgeable and fun staff who embrace the vibe of the neighborhood.

North City Area

Fountainhead – 1970 W Montrose Ave – A low-key bar featuring a long beer list & creative, organic pub eats plus a seasonal rooftop garden. Owned by Aaron and his crew, they have a great passion for Bourbon and American Whiskey and delivering good spirits and food in a comfortable atmosphere.

Bar on Buena – 920 W Buena Ave – is a cool, cozy bar featuring pub food & whisky/beer flights in a low-lit setting with a dog-friendly patio.

Montrose Saloon – 2933 W Montrose Ave – great renovated neighborhood dive bar with good prices, and LIVE MUSIC on some nights, with a nice big patio out back.

Kuma’s Corner – 2900 W Belmont Ave – probably one of the best burgers I’ve ever had in my life. This neighborhood bar churns out some of the best burgers and good in the country, and it’s been on Diner’s, Drive-In’s, and Dives. Heavy metal music fans started this place, and still bang their heads and dish out awesome bar food!


Walton Street Kitchen & Bar – 912 N State St – Walton Street Kitchen and Bar is a new concept from Ballyhoo Hospitality (Coda di Volpe and Gemini).  Located in a brand new, luxury condo building in the Gold Coast called No9 Walton Building there are two unique experiences in Walton Street Kitchen and Bar.  Upstairs, they are serving thoughtfully executed American cuisine and downstairs in the Lounge, they offer rare spirits and classic cocktails in a lounge atmosphere.  The bar in the lounge is hidden to truly make it feel like you’re in someone’s home.

The Old Fashioned is made with Elijah Craig and the Manhattan is made with Rittenhouse.




About bernie
-Whiskey Professor for Heaven Hill -2009 and 2012 Icons of Whiskey Award Winner - Whiskey Ambassador of the Year US and Global

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