Where to stay
As you’re likely to be all over the city, a good plan of action is to consider which activities you’ll want within walking distance and choose your lodging accordingly. However, if your hotel of choice isn’t close to most of your events, don’t worry. Within the city, you’re likely to be just a short “L,” bus, Uber, Lyft, or cab ride away.
On a budget
For the cost-conscious bunch, Airbnb is probably your best bet, as hotel rooms are often pricey. There are many great Airbnbs throughout the city.
The Kimpton Hotel Palomar Chicago is a boutique hotel with stylish rooms and accommodations galore. Parties can also look into the many suites they have on offer if everyone wants to stay together. There’s free coffee in the morning, a wine happy hour in the evening, and if the party is up for a little pampering, indulge in in-room mani/pedis, facials, or massages.
Have a five-star experience at The Langham Hotel. For top-tier decadence (at an extra cost), the party can enjoy The Langham Club on the top floor, where guests get a private check-in and check-out, a decadent spread of refreshments throughout the day, bar service, and more. Those who opt for this treat will also have access to the hotel’s chauffeur—in case public transportation and walking in heels just aren’t your thing.
Brunch: the most important meal of the day
On the list of the many things Chicago does well, brunch is at the top. If your group is down to party from morning to night, the only place to start your day is at Zella, well-known for its gorgeous back patio, extremely boozy brunches, and Latin cuisine. For something more upscale, try the light-and-airy Summer House Santa Monica. The food ranges from heavy to light, and they also offer strong coffee and cocktails. For a more laid-back atmosphere and cocktails with some fun twists on the morning classics, Kanela Breakfast Club is a Chicago favorite with locations across the city.
Some of the bachelorettes are likely to have known each other forever; others are probably meeting for the first time. Chicago is a great city for activities everyone will enjoy, including tons of summer festivals and events, so be sure to check what’s on while you’re in town. Here are some fun mainstays everyone will love.
Rooftop bar crawl
After the brutal winter, locals take full advantage of the summer sun. Bars and restaurants have capitalized on this, and many offer outstanding rooftops. Although you might find a guided tour, it’s much more fun to customize the stops to your party’s preferences. Consider Cindy’s rooftop at the Chicago Athletic Association in the Loop for outstanding cocktails and incredible views (Bonus: Cindy’s is also an excellent brunch spot). Then, head north—and up 26 floors—to Apogee for some of the prettiest cocktails you’ll ever see. Be sure to stop by the J. Parker afterward for drinks above Lincoln Park.
A day on the lake
Cruising Lake Michigan is always fun. Check Boatsetter, which is like Airbnb for water lovers. Owners put their boats up for rent and are sometimes willing to captain them for you. Alternatively, check out an afternoon party cruise, or charter a yacht for a truly personalized experience.
Afternoon Tea at The Allis
For the sophisticated bride, afternoon tea at The Allis in Soho House has something for everyone; those who want to get a little boozy can opt for the champagne tea. The foodies among you will revel in the bites, and the constant Instagrammers won’t know what to snap first—the food, the china, or the space itself.
For dinner with a large group, small plates are always a good option. Some of the ladies can share, and others can get a few dishes to themselves. Girl and the Goat in West Loop and Sienna Tavern in River North are both run by award-winning chefs and offer delicious menus with something for everyone. Alternatively, book a private boozy cooking lesson at The Social Table in Lincoln Park. The “BYOB dinner-party-style cooking class” offers a great opportunity to catch up or get to know each other better over a shared activity. The BYOB aspect helps keep the budget in check and ensures that the bride won’t run out of her favorite tipple.
Drinking and/or dancing
Experience a little of everything during a night on the town in Chicago. Start at Bassment for a live band in a ’60s-themed atmosphere. Then, head to Beauty Bar in Noble Square. Those who want to have a drink and dance to live music will be more than happy, as will the bachelorette who chipped a nail and the one who just needs a breather—Beauty Bar also offers manicures and other salon services. Finish your night dancing at one of the many River North clubs, including Joy District, for yet another renowned rooftop experience, or head across the street and below ground to Untitled Supper Club. This speakeasy has a large stage that often features a burlesque dancer and live band. Later at night, patrons take over the stage and turn it into a dance floor as the DJ music starts.