Tips + Trends

Chi-town Shenanigans: How to Do a Girls’ Getaway in the Windy City

Selfies at the Bean and shopping are must-dos on your girls’ getaway in Chicago. (Photo: Felix Choo / Alamy Stock Photo)

Getting your girlfriends together is hard enough. So when everyone’s schedule aligns and you’ve decided to meet in the Windy City, you’ll want to make sure there’s nothing same-old, same-old about your weekend together. Here are four new takes on the best ways for besties to have a great time in Chi-Town.

Trend Spotting

What’s a girls’ getaway without a little retail therapy? Intriguing wares await in Bucktown and Wicker Park, two hip neighborhoods west of downtown that are chock-full of indie boutiques. Two to try: Penelope’s, a bastion of little-known American and European labels; and Kokorokoko, an ’80s and ’90s vintage apparel spot for all your retro needs. Better yet, nab a spot on Chicago Traveler’s Chicago Shopping Tour. A personal stylist will take you on a curated tour of the neighborhoods’ chic yet hard-to-find boutiques, complete with discounts and flutes of bubbly with which to toast the fashion gods.

The details: The bad news? Chicago’s sales tax rate is 10.25 percent. The good news? That relatively high percentage makes it easy to estimate the total price of that sweet miniskirt you’re eyeing.

Food, Glorious Food!

Calories don’t count during girls’ weekends, so include one of Chicago’s ubiquitous summer food or wine festivals in your plans. The granddaddy of them all is Taste of Chicago — but with nearly 1.5 million people squeezing into Grant Park to nosh, you might want to tuck in at one of the newer kids on the block. The Chicago Food Truck Festival gathers more than 40 different gourmet trucks serving up everything from lemongrass chicken sliders to green tea brownies. Or hit Baconfest and throw down the smoky, fatty gauntlet at this two-day ode to the “candy of meat.”

The details: The ticket to Baconfest gets you tasting portions of all the chef-created bacon dishes you can eat. Maple bacon cupcake, anyone?


Chicago 365 Hospitality served up this BLT Skewer at Baconfest. ( Photo: Anne Petersen / courtesy Chicago Baconfest)

Rooftop Libations

Catching up over cocktails with the girls is always better when the right scene’s been set. Give yourselves some air — literally — by visiting one of Chicago’s many rooftop bars. In the River North neighborhood, make for one of the comfy, communal booths at I | O Urban Roofscape to quaff chef-crafted cocktails with your pals. At 10,000 square feet, this is Chicago’s roomiest rooftop bar — made even more special by breathtaking views of the southern skyline.

All dressed up? Head to Drumbar — an 18th-floor aerie in Chicago’s Gold Coast. This intimate lounge with an outdoor terrace strictly enforces its dress code after 8 p.m., so the baseball-cap-and-flip-flop crowd won’t kill your style vibe. And in the heart of the Loop, you can sip a Cosmo or three at Renaissance Downtown Chicago Hotel. Its rooftop lounge is set to open this spring.

Lake-Effect Fun

A morning jog along Chicago’s lakefront paths sounds like a really fun run — until the crowd of walkers forces you to put on the brakes. But there are refreshing alternatives. A stand-up paddleboard yoga class with Chicago SUP Yoga gets you out on Lake Michigan, the better to enjoy skyline views with your savasana. On the other end of the adrenaline spectrum, warn the gals to put their hair in ponytails for one of Seadog Cruise’s lakefront speedboat tours, which whip across the water, James Bond-style, to high-energy music.

The details: Chicago SUP Yoga yoga classes are held twice weekly, while Seadog’s speedboats run several times daily.

Where to stay in the Windy City? The Beaux-Arts luxury of the Renaissance Blackstone Chicago makes a perfect base for your girls’ getaway.

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