Being anointed the title of maid of honor is no small task, especially when it comes to planning the second-biggest event to the wedding: the girls weekend getaways. While you and your friends may travel together for a variety of reasons, a bachelorette party really puts on the pressure, and it can be tough to find activities that please your whole party. This forty-eight hour marathon can be an intimidating event to plan, especially when done in Chicago—a city with a ton of options and no easy way to narrow down your to-do list. An itinerary that covers the very best food, shopping and relaxation in the Windy the City is the only solution.
Day One: Morning
Start your day with a colazione italiana (Italian breakfast) at Caffee Lavazza at Eataly Chicago, then take a guided tour of this massive Italian market so you can get an idea of how this well-oiled machine of a retail shop operates. Learn about the offerings and ingredients at the fresh pasta counter, beverage section, butcher counter, seafood counter, fromagerie, Nutella bar, gelato station and pastry counter. Your group can even sign up for a special Italian cooking class to learn just how to concoct traditional recipes using the food you just purchased.
For lunch, head over to River Roast. The menu’s big on shareable dishes, so start by ordering a few items from the “bites and boards” menu, such as the shrimp and crab toast, fried olives or Chicago sashimi. For the main event, you’ll want to choose from the fire-roasted “big” fish, wood-smoked whole chicken, or slow-cooked roast beef, and your server will carve it tableside. Each comes with a mound of crispy potatoes.
Day One: Afternoon
Girls weekend getaways would never be complete without spa sessions, and after that full sensory morning, what better time to head somewhere quiet? A great place to gab and get pampered is Spa@theWit. Located within walking distance of River Roast, the venue is full service. Get your bodies wedding party-ready with a cranberry-pomegranate sugar scrub, or enjoy a full-body massage or organic facial. Refresh with tea and snacks in the “Whisper Lounge” while you wait for your friends to finish up.
Afterwards, make your way to nearby Millenium Park to see “Cloud Gate” (also known as “the bean”) up close and personal. It’s a great place to get a memorable pic of your whole group reflected in the shiny curved side of the sculpture.
Day One: Evening
As your group gets ready for a night on the town, start your evening at the mirrored bar at RM Champagne Salon. Sip a flute of Henri Mandois or try the Oma’s Heilung, which combines Scotch, grappa, honey, lemon, and cardamom bitters. They also have a well-curated selection of draft beers. Share a cheese plate as you relax on the patio.
For dinner itself, head to Formento’s, a swanky new Italian eatery in the West Loop that lends itself to lighter meals—which may be necessary, since you consumed such a bountiful lunch. They have a host of shareable plates, including the signature meatballs, various house-made pastas and whole-roasted fish. The wine list, which showcases varietals from the U.S., France and Italy, offers a nice selection of 50-plus wines for $50 and less.
Day Two: Morning
Your group may have stayed out on the town pretty late, so grabbing a few extra hours of beauty sleep in the morning of your second day in Chicago is a must. Lucky for your gang, Tippling Hall‘s brunch goes until 3 p.m. It’s a laid-back brunch with a DJ spinning soul and hip-hop grooves to entertain you as you chow down on some American classic dishes. Make it easy on yourself and order the brunch special for $27. It comes with a pastry, an entree, and bottomless mimosas.
Day Two: Afternoon
Spend your remaining hours with your friends exploring the city and shopping. There are plenty of local shops and retail stores to check out in Lincoln Park around Armitage and Halsted streets. Afterwards, head down the street for an early dinner at Boka, an award-winning restaurant specializing in new American fare. Toast your soon-to-be-married gal pal with the Appolonia, a sweet-tart sparkling drink made with vodka and Brut Rose. Then choose from tasty entrees such as the lightly smoked sea trout, grilled beef short ribs, and Peking duck breast.