Ravenswood's the Long Room has served as a friendly neighborhood lounge and a leader in Chicago's craft beer scene since 2000. You won't have a dozen televisions numbing your senses here and ain't it nice to be screen-free and socialize again with an eclectic music collection adding just the right background to conversation? Belly up to the 60 ft bar or get cozy in a booth. There's an intimate back room with a vintage photo booth and a fully enclosed beer garden. The Long Room is open early morning until late night, for curated coffee, rotating beer list, and whatever spirits and classic cocktails that move you. When you need a bite, the Long Room's in house partner, The Biscuit Man, offers freshly prepared vittles breakfast, lunch, brunch and dinner.
Recommended for Lounges because: A comfortable lounge in a great Chicago neighborhood, the Long Room offers a spacious beer garden and bites from on-site The Biscuit Man.
Jacky's expert tip: The Long Room's proprietors recently finished a renovation of three apartments above the space and launched Bluebird Inn.
Zebra Lounge, located on the first floor of a vintage apartment building, has the third oldest existing liquor license in Chicago. Open in 1929, the intimate space operated through Prohibition as a speak easy. Count on live entertainment every night: piano music, from show tunes and torch songs to sing-a-longs. Michael Vaughn started working at the lounge as a waiter in 1998, bought it in 2006 and continues to offer locals and visitors a singular, classic Chicago experience among the zebra wallpaper and leather booths. Vaughn says, "The drinks are always stiff, the crowd always lively and the piano is always hot." If you request a song, tip the piano player!
Recommended for Lounges because: Zebra Lounge is a small, historic speakeasy with sturdy cocktails and live music every night of the week.
Jacky's expert tip: Zebra Lounge is busiest on the weekends but you're sure to snag a seat Tuesdays and Thursdays.
This beloved Champagne lounge is a city mainstay, relocated from its original Lake View neighborhood to River North. Chicago's only Champagne Bar has been delighting bubbles' fans by focusing on small grower/producer Champagnes for over 30 years. The beverage team has been behind the bar at Pops for over 20 years. In addition Champagne and sparkling wine by the galss or bottle, Pops serves sparkling cocktails, still wines and beer. Sip your flute at the lovely bar upstairs, or for a more intimate experience, head to the downstairs lounge bubbles (and live jazz on Sunday). Nibble bites that pair perfectly with bubbles: caviar; oysters; olives; deviled eggs; cheese and charcuterie' scallops; and bone marrow, bacon jam and baguette. Count on a couple of fine desserts, too.
Recommended for Lounges because: Chicago's only Champagne Bar has been delighting bubbles' fans by focusing on small grower/producer Champagnes for over 30 years.
Jacky's expert tip: Stop in any Monday when Champagne Specialists hand select a new Magnum to pour into your flute.
Chit Chat Lounge & Hideaway is tucked below The Swill Inn. The casual speakeasy has monthly House and Hip Hop music parties with some of city's best DJs. Have a "Stirred, Boozy and Confident" cocktail or if there's a mess of you, order a large format punch bowl serving four-to-eight thirsty friends. A short list of suds and Champagne by the glass or bottle round out the drink menu. If you need to nosh and gain some equilibrium after that punch bowl, an abbreviated food menu from the Swill Inn upstairs can get you a Chicago style dog, spicy chicken sandwich, beefy Swill rolls, barbecue chicken pizza, jazzed up fries and cookies. Whereas a herd of trendy speakeasies try too hard to channel a bygone era with chandeliers, marble bars and special passwords, this spot thankfully feels more like a naughty drinking party in your landlord's hidden basement.
Recommended for Lounges because: If you go for secreted bars, the cozy Chit Chat Lounge & Hideaway is a casual hideaway with DJ's, snacks and well-poured punch bowls.
Jacky's expert tip: Open Wednesday-Saturday at 5pm, Chit Chat's entrance can be tricky to find. Look for the spray painted lips mural to point you in the right direction.
Blue Violet, named after the Illinois State Flower, is a lounge on the second floor of Hubbard Inn that is a garden-inspired oasis in touristy River North. Plush velvet seating and swing chairs that overlook Hubbard Street and five original floral murals painted by Chicago artist Rodney Duran sing "spring" even on the coldest Chicago night. The cocktail menu is inspired by flora, too, with fun presentations and botanicals driving flavor profiles. Good bets include The Duchess with The Botanist Gin, ruby Port, rhubarb, lavender, and Earl Grey or the Golden Aster with Tito's vodka, suze, celery, pineapple, lemon and egg white. What a way to get to get your fruit and veg! Bring the gang for large format cocktails that serve four-to-six and to take you deeper in the Garden, add the relaxing effects of CBD to any cocktail.
Recommended for Lounges because: In the heart of River North, Blue Violet is a flower-strewn oasis of cocktails and warmth, right above the Hubbard Inn.
Jacky's expert tip: Start with shareable American fare in Hubbard Inn's newly renovated restaurant on the first floor before heading upstairs to Blue Violet.
The new Dandy Crown is neither sticky dive bar nor crowded cauldron of stillettos and overwhelming cologne. It a perfect neighborhood lounge located in a charming, two-story vintage brick building that seats around 90 in a bar and fireplace lounge. Jewel tones abound punctuated by murals and images of royalty (real and musical). The River West spot did its due diligence in filling the space with cushy chairs and sofas - even the bar stools are kind to the keister. Choose among classic and seasonally evolving craft cocktails; a smart selection six beers on tap, plus plenty in cans and bottles; and wine. A mix of 60's garage rock, Motown, blues, soul and current artists make you feel as though you've stepped off a red double-decker in London during Carnaby Street's heyday. Happy Hour ensues Monday-Thursday when you can get a warm Crock Pot Cocktails and beer and shot specials.
Recommended for Lounges because: An extremely comfortable and warm lounge, the Dandy Crown is an appealing addition to the list of Chicago lounges.
Jacky's expert tip: The Dandy Crown serves drinks only, but feel free to bring in your own snacks or order in.
Despite its old-timey sounding name, Ludlow Liquors took over the old Orbit Room space in 2018 with an aim to be an authentic neighborhood bar in Avondale. The lounge departs from other cocktail lounges by focusing on stirred cocktails served by the ounce and unexpectedly great grub. You can also count on good whiskey classics, all the standards, draft punches and daily $6 shot and beer combos. The kitchen satisfies with French onion soup; hot wings; Japanese veggie fritters; a two-fisted burger; and even a Caesar salad made to order. Sunday nights are probably the chillest of the week or play dominoes on Mondays while munching Sicilian style pizza. DJ's serenade on Tuesdays while the kitchen turns out Chicago style hot dogs. When the weather's fine, you'll want to head to spacious backyard patio.
Recommended for Lounges because: Nice people, good drinks, tasty food, games and music add up to a special neighborhood lounge.
Jacky's expert tip: This isn't River North - there's street parking all around Ludlow Liquors.
There are countless taverns, bars and lounges claiming to offer the largest whiskey collection in Chicago, but Twisted Spoke may have 'em all beat. The Near West Side spot opened in 1994, certainly making it one of the first to focus on Bourbon. Roof top decks? Yep, TS was ahead of the curve in this regard, too. Choose among 500 whiskeys and Whiskey Wednesday offers the best opportunity to taste everything at half-price. And if you're not a fan of hootch, know that there are at least 20 beers on tap, cellar aged beers and barrel aged cocktails. Vittles are made from scratch in house. Who would expects righteous bowl of gumbo or beef brisket smoked in-house slathered with homemade barbecue sauce on a brioche bun in a biker bar? Burgers are outstanding and Hangover Hospital takes place weekends from 9am to 3pm serving substantial brunch items.
Recommended for Lounges because: Twisted Spoke gets props for birthing the bourbon bar and roof top deck trend a quarter century ago.
Jacky's expert tip: Come by on Tuesday when staff picks a dozen brews and prices them so well you can get two.
The cocktail lounge that is California Clipper is as retro as a lounge can be - but it's not "faux" historic as in something formulated by a committee of marketing types to look and feel like old Chicago. This sweet stack of bricks dates back to the 1930's and inside the crimson decor is warm and bartenders are as friendly as they were when FDR was calling the shots. Outstanding old-timey cocktails include an Old Fashioned; Sazerac; Gimlet; Gin Rickey; Mai Tai; and a shot and beer but the menu of adult bevvies is endless from sparkling or stirred cocktails to ice cream drinks and shaved ice. The lounge hosts a succession of country & western, indie, world, jazz and soul performers practically every night of the week.
Recommended for Lounges because: California Clipper is an authentic Chicago lounge featuring an extensive list of cocktails, seductive lighting and decor, and live music nearly every night of the week.
Jacky's expert tip: When there's live music, expect a reasonable $5 cover charge, cash only (but there's an ATM near the door.
Open since 1964, Hala Kahiki may be the most authentic tiki bar and lounge in the Midwest, outlasting Trader Vic's and predating all of the rookie tikis in the city. Indeed, it's among the oldest tiki lounges in the country. James Oppedisano (the grandson of original owners, Rose and Stanley Sacharski) and his wife, Kerrie, have taken the helm to continue the voyage into the 21st century. But thankfully, not much has changed from the colorful main bar and 40 tables inside to the the outdoor patio and extremely kitschy Hawaiian and South Seas Gift Shop. You can also have a cold beer with rotating selections from Hawaiian breweries. Drinks are the thing here so choose from 130 tropical cocktails: powerful Zombies, tart Mai Tai's, sweet Bahama Mamas, coconut drinks, shots, hot drinks and cold ice cream beverages.
Recommended for Lounges because: Hala Kahiki is an unpretentious gem that lives up to its moniker, "We were tiki before it was cool."
Jacky's expert tip: On the last Saturday of every month, there's a live hula dinner and show.