Where to go for the perfect girls’ night out

During a Midwestern winter, it’s easy to hunker down and hibernate, but some occasions call for a good old fashioned ladies night.

Whether it is a much-needed mom’s night out, a college roommate reunion, girlfriend getaway or a big bachelorette bash, your girls night game needs to be en pointe.

We’ve scoured the city and suburbs for the very best places to gather your ladies — no snoozer small-plate restaurants or same-old canvas painting parties included.

From wild night to wine-ding down, here are our picks for your next (and best) girlfriend gathering.

Photo: Joni Kat Anderson

Sophistication? Seek out a speakeasy

Meet up with your favorite classy gals at the sort-of secret and totally swanky Violet Hour in Wicker Park.

Order up a round of artisanal cocktails concocted with house-made tinctures, like the Ding Dong Ditch blueberry and gin shaken martini, the stirred apple brandy Ted’s Talk, or the pisco-run-cinnamon-grapefruit Violet Hour classic, the Sideshow on the Mainstage.

There are bites to order, but you’ll probably wind up across the street at Big Star for a tray full of tacos (no regrets).

Home bodies? Make it a girls night in

Get cozy (or crazy) at your own home and arrange for a host of mobile services. Hire a comedian or bring in Jorianne the Coffee Psychic to read your cuppa joe.

My Mobile Nail Tech travels the southwest suburbs to set up a pop-up nail shop at your house, office or event.

To get the party started, hire a mobile mixologist rather than appoint a designated driver. Lush Mobile Bar, With a Twist and Chicago and Beverage Catering will all bring the booze to you, wherever you are.

Smarty-pants sippers? Get some education with your wine

Of course your greatest #squadgoal is to know all about the wine you’re drinking.

The Wine Goddess in Evanston is where your crew should be, especially on Thursday nights when owner Diana Hamann gives tastings and seminars in the shop.

The rotating class schedule includes Wine 101 and specialty sessions, like Wine & Cheese from Spain and How Wine is Made.

A mix between hipster and honky tonk? Hit up a (not so) hidden gem

Music, readings, live radio shows plus beer make The Hideout in Lincoln Park a great spot to meet up with friends who care not about pretension or aforementioned artisanal cocktails.

Take in the interviews, acoustic sets and science talks (yes, science talks) because you all love to take that stuff in together, or hang out in the even lower-key bar.

Easy, breezy? Charter a sailboat

Rent a boat (well, weather permitting) all for yourselves or save some spots on a semi-private group sail to watch fireworks, take in a glorious full moon, see a sunset, get a VIP view of the air and water show, or sun and swim during the day.

Chicago Sailboat Charters in Lakeview has many opportunities (and great specials, if you subscribe to the newsletter!) to get on the water with your girlfriends.

All boats leave from Belmont Harbor, where there’s plenty of parking and Uber-ability. Bring your own bottle (or two), corkscrew and cheese platter to turn your ride into a real experience.

Mix it up? Shake some fun into your fancy cocktails

The Martini Room in Elgin has a long list of martinis, Manhattans, cocktails and mocktails, but the fun doesn’t stop with the shaking and stirring. Belly Dance Wednesdays, Rockabilly Night, margarita tasting and other fun festivities fill this bar’s calendar.

Someone in the group will have to (wink, wink) be celebrating a milestone just so you can all order a round of the decadent Birthday Cake Martini.

There’s so much happening at this suburban hot spot, every single lady is sure to find something she loves to sip and an event she’s sure you must all attend.

So sweet! Take a chocolate tour of the city

Stop in the sweetest spots in downtown Chicago, where you’ll sample cupcakes, truffles and other delights. A well-researched guide on this 2.5-hour walking tour shares information on how it is all made, chocolate’s rich history and other fun facts, all along the Magnificent Mile.

If your mouth is already watering, check out these upcoming dates for the next Chocolate Tour of Chicago.

Written by Jessica Ashley
Jessica Ashley is a writer, coach and the voice of Single Mom Nation and its sister podcast. She wears inappropriately high heels to the playground, is mom to a teenager and a threenager and lives with her chef boyfriend on the north side of Chicago.