If the excitement of the city makes your heart race a little faster, a Chicago bachelorette party should be high on your list. Tucked within the Midwestern heartland, this urban oasis is a bustling hub of culture, theater, cuisine, and nightlife to rival any major city you’ll find on the coast. Spend your time gallivanting through Millennium Park and sampling the best deep dish pizza, while of course, incorporating a Michigan Avenue shopping spree for good measure.
The Windy City is the ultimate backdrop to any girls trip, so get your Chicago bachelorette party itinerary in order and let an epic weekend unfold.
What to Do
Start your time in the city with a wander through the Chicago Riverwalk which includes a 1.25-mile pedestrian path along the Chicago River. You’ll pass eateries and public art, plus get to enjoy the city’s famous architecture along the way. If you’d rather kick back and enjoy for a guided experience, consider booking one of the city’s many famous boat tours down the river. Chicago’s First Lady offers a 90-minute architecture tour that will educate you on both the beauty and the history of the city’s buildings while giving you plenty of amazing photo ops along the way.
Next, head over to Millennium Park for a glimpse of Chicago’s iconic public sculpture known as Cloud Gate or “The Bean.” Make sure to grab a group picture right here, or head 10 minutes south to Grant Park for a photo opp at Buckingham Fountain. The stunning European-style fountain is most definitely worth a visit during its operating months from May to October.
If you’re up for more tourist action during your Chicago bachelorette party, the observation boxes and the ledge at Willis Tower Skydeck will get your adrenaline pumping in all the best ways. Or, make your way to the 96th floor of the John Hancock Center drinks with a killer view. Cocktails at The Signature Lounge are admittedly spendy, but if you time your visit right, you’ll enjoy a table by the window for an unbeatable experience.
When you’re ready to hit the ground running, Navy Pier is the place to be with amusements, food, and fun along Lake Michigan. Pier Park includes rides like the famous Centennial Wheel, but that’s not all this area has to offer. You and your girls can take in the beauty of Crystal Gardens, an indoor botanical garden featuring a six-story atrium and lakefront views.
No Chicago bachelorette party is complete without a little retail therapy on The Magnificent Mile. This North Michigan Avenue stretch is home to over 450 stores, from major department stores to luxe boutique brands, and everywhere in between. Don’t miss the eight-floor Macy’s at Water Tower Place or the array of shops at 900 North Michigan.
Where to Eat
Pizza, pasta, and gelato lovers will be in seventh heaven at Eataly Chicago—a multi-level food market that feels like you’ve just stepped into Italy. Eataly also offers cooking classes and wine tastings, so check their events calendar to book an activity for your Chicago bachelorette party.
During your River North tourist adventures, stop in at Beatrix for modern American eats in an ultra-trendy setting. This place serves up food any time of day but makes an especially great brunch location. Another dinner hot-spot to consider, The Purple Pig is a foodie’s dream located right on Michigan Avenue. The restaurant’s Mediterranean cuisine has received countless awards, as well as Michelin recognition for eight years in a row.
Every girls’ trip should include plenty of sweet indulgences, and a Chicago bachelorette party is no exception. Instagrammers will love the Doughnut Vault for its adorable exterior and artisanal creations. You’ll find a mix of classic standbys and inventive flavors at either one of their downtown locations. If cupcakes are more up your alley, Molly’s Cupcakes should immediately be added to the list. Chicago Magazine crowned their red velvet cupcake as best in the city, and their seasonally inspired center-filled cupcakes are not to be missed.
On Dearborn Street, you’ll find downtown Chicago’s Restoration Hardware, which also happens to house a much-talked-about eatery in the prettiest space you’ve ever seen. 3 Arts Club Cafe serves everything from coffee to light bites to cocktails, so relax and enjoy with the cafe’s glass dome and chandeliers glittering overhead.
You can’t leave Chicago without trying their famous deep dish pizza that’s every bit as decadent as it sounds. Giordano’s and Pequod's Pizza are a few deep dish favorites, but find any local spot and you can’t go wrong.
For a little nightlife fun during your Chicago bachelorette party, head to the rooftop restaurant of Hotel Lincoln, The J. Parker. You’ll sip on yummy cocktails with city skyline views for a perfect Chicago experience. Or, try RM Champagne in the West Loop where you’ll find bubbly French wines in a particular swanky setting.
Where to Stay
For a Chicago stay that won’t completely bust your budget, look to the Aloft Chicago City Center. Located in River North, you’ll stay right within a quick walking distance of the city’s major sites, without the tourist chaos that comes with other downtown options. As a bonus, you’ll also be under the same roof as the aforementioned restaurant, Beatrix, so you’re never far from a delicious meal or a coffee to go.
Set on Walker Driver, you can enjoy sophisticated accommodations at the Wyndham Grand Chicago. This riverfront hotel will make a great home-base, no matter what you’ve got planned for your Chicago bachelorette party. Another excellent choice, the Loews Hotel Chicago boasts lake views and luxury amenities, including their on-site spa offering massages, facials, and nail services for the ultimate girls’ getaway.
Treat yourselves to an unforgettable stay at The Gwen, which was recently named one of the best Chicago hotels by Travel + Leisure. Prefer to sleep under the stars? The Gwen has you covered with their terrace-set Urban Glamping experience available for bookings May through September. Or keep the accommodations indoors and splurge with a stay at theWit Hotel which includes an amazing rooftop lounge for you and your ladies to enjoy.