How to Plan a Girls’ Weekend in Chicago

Chicago is a popular destination for a “girls’ weekend” or bachelorette-party weekend, both for visitors from the Midwest and around the country. The city’s mix of cultural activities, famed shopping, and dining options at affordable prices make it an attractive destination. It’s big enough that you’ll find plenty to do over a long weekend, but not so overwhelming that you’ll feel as if you can’t possibly make a dent in your sightseeing list in just a few days. Here are some ideas for things to do based on your group’s interests.

The Culture Vultures

Chicago, like most large cosmopolitan cities in the US, has several fantastic museums. You could easily spend every waking minute of your trip exploring just the largest ones – the Shedd Aquarium, Adler Planetarium, Museum of Science and Industry, Field Museum, and Art Institute – without even beginning to uncover the delights of some of the smaller, lesser known museums, like the Museum of Contemporary Art and the Chicago History Museum.

If you do plan on visiting several museums, check out a discount pass – there are a few options to choose from so compare carefully to find the best deal. Many museums also offer several free days throughout the year.

Chicago has a lively theatre scene – from Shakespearean plays to avant garde dance to Broadway musicals, there’s a show for everyone. We’re also home to several comedy clubs where you can take in stand-up and improv comedy shows, often for a very low price.

If your group is interested in the history of Chicago, there are a few fantastic tours that are both informative and entertaining. One of the best is the Chicago Architecture Foundation River Cruise. The Foundation also offers walking tours of several neighborhoods and historic buildings. For history of another sort, take the Chicago Film Tour, a bus tour that visits many of Chicago’s film sites and traces the history of the industry in Chicago.

The Pampered Princesses

Chicago has hundreds of spas, from the spendy and chic like the spa at the Peninsula to the low-cost and fun like Nail Bar (where you can bring in your own wine or beer to really get the party started), there are spas for all price ranges. Stop in for a few treatments of plan on spending the whole day indulging in a schedule of relaxing treatments.

Complete your new looks with duds from the designer shops of Michigan Avenue or the indie boutiques of Bucktown. For the scoop on where to find the best stores according to your shopping style, click here.

The Foodies

Chicago is a great destination for foodies. Boasting some of the best restaurants in the country, celeb and up-and-coming chefs cranking out some of the most inventive food in the world, and of course, some Midwest stick-to-your-ribs favorites, Chicago dining is an adventure.

It’s relatively easy to walk into a restaurant for breakfast or lunch without a reservation, but for dinner – especially if you are traveling with a larger group or want to get into the more popular restaurants – reservations are must. The most popular, hard to get into places can fill up months in advance, so if there is a place you are dying to try, call at least 6-8 week before your trip.

For some of Chicago’s best prix-fixe multi-course tasting menus, check out these eight restaurants worth a splurge. If your tastes run across the globe, try one of Chicago’s best restaurants for foreign cuisines. And don’t forget Sunday brunch; here it’s an institution.

Get hands on at cooking classes at the Chopping Block, which range from $35-80 per person, or take a wine-appreciation lesson at The Poison Cup (starting at $25 per person). Many wine shops, like Lush, also offer free wine tastings throughout the week. To see some chefs in action, head to the Green City Market, which hosts cooking demos from local chefs like Rick Bayless all summer long.

>> more on food and drink in Chicago

The Hot Mamas

Bring the kids along on your girls weekend – there’s plenty of kid-friendly fun to be had in Chicago. Aside from the museums, which each offer exhibits that will appeal to kids of all ages, check out the Lincoln Park Zoo, and plan on spending an afternoon at Navy Pier, where kids can visit the Children’s Museum, play putt-putt, snack on ice cream and hot dogs, and ride carnival rides like the giant Ferris Wheel. Older kids will also love the Magnificent Mile for its larger-than-life buildings and shops like the American Girl Place and Hershey Chocolate. When they get tired, let them rest while you take a carriage ride down Michigan Avenue.

Kids will also enjoy a trip up to enjoy the view from the glass-bottomed ledges at the Willis (former Sears) Tower, or even a day at the beach.  And of course, kids of all ages will love watching a Cubs game at Wrigley.

The Health Nuts

You can get day passes at most city gyms, or get free trial sessions for classes like Bikram Yoga, the Bar Method, and Pilates, but why not step it up a notch with something fun, unique and just for girls at “Flirty Girl Fitness” studio, which offers private group classes that teach sexy dance moves, including some maneuvers on a pole. For outdoor fitness, head to the Lakefront path, which consists of 18.5 miles of walking, running and biking trails dotted with beaches, volleyball, soccer, and tennis courts and soccer and baseball fields.

For an active way to see the city, sign up for a bike tour of Chicago or just rent some bikes for the day and take to the bike path. Kayak Chicago even rents kayaks (and offers tours) for use on the Chicago River. and Lake Michigan.

The Budget Travelers

Chicago, like many big cities, has the bright lights, the fancy restaurants, the glittering, expensive highrise hotels. But it also has the more lived-in neighborhoods, the local joints, and budget-friendly (and free) attractions that can make it as easy on the wallet as you want it to be. If your crew is worried about keeping costs low, there are lots of ways to trim your trip’s budget. Take public transportation rather than cabs, seek out BYOB restaurants, keep an eye out for free museum days during your trip, and choose bars based on their nightly food and drink specials.

>> more on saving money in Chicago

The Party Girls

There are hundreds of bars in Chicago, so finding one near wherever you are won’t be a problem. Finding the right one to make your night out unforgettable, well that can be a little more difficult. Nightlife in Chicago tends to be clustered in several areas, with each ‘hood having a typical type of bar (with exceptions of course). So where you go for bar and club hopping will depend on what kind of atmosphere you want – casual pub, frat boy party, upscale and trendy, or fashionable and clubby.

Chicago is home to lots of unique bars that don’t fit any mold, like the speak-easy style Violet Hour. There are cocktail bars, champagne bars, beer bars, dive bars, hotel bars, rooftop bars, and more, and many offer great specials that help keep the price low.

For wild bachelorette-party experience, check out Kit Kat and Howl at the Moon. Kit Kat, a gay bar in Boystown, is known for its extensive martini menu and weekend drag shows. You’ll need to call ahead to get a table; there are often multiple parties happening there each weekend. Howl at the Moon, downtown, offers nightly dueling piano and vaudeville shows that are also a hit with bachelorette parties.

Where to stay

To be close to the action of downtown and have easy access to public transportation, the best spots to stay will be on Michigan Avenue or close to it.

>> more on hotels on or near the Magnificent Mile

Photos by: leah the librarian, robelto, Steven Vance