Party Style

• Determine what type of bachelorette party is best for the bride-to-be--not all girls are comfortable sporting hats in the shape of male genitalia. If you are not planning to keep the party plans secret, ask her what she would like to do or see during her big night out. Doing so can help you determine what activities to pursue and which to avoid. The good thing about planning a bachelorette party in Chicago is that there is a wide variety of things to do and see in the city. Whether you want to relax at the spa, go to a wine tasting, watch improv comedy, catch a game or check out a male revue, you'll find the opportunity to do so in Chicago.
  
  

Late Morning Brunch

• Start off a bachelorette-party weekend with brunch. There are a number of standout places to go for brunch in the city. A few options include m. Henry in Andersonville (be sure to try the blackberry blisscakes, as they are truly blissful), Earwax Cafe in Wicker Park (featuring vegetarian fare and awesome peanut-butter smoothies in a funky space) or Wishbone at its Northside or West Loop locations (Southern comfort food at its best). Another option would be to host a brunch at one of the city's (or near suburbs') park shelters (see Resources below).
  
  

Afternoon at the Spa

• The list of spas and nail salons in Chicago is nearly endless, with several in most every neighborhood. Choose one that is large enough to accommodate all party guests, and you will want to make reservations well in advance, especially for a large group of girls. A few places that cater to bachelorette parties include Diana's Nail and Spa (Downtown), Mojo Spa Boutique/Nail Spa (Wicker Park), and 10 x 2 Nails (Andersonville). In addition, Chicago-area companies such as Spa Where You Are will bring the spa experience to your home or other specified location.
  
  

Afternoon/Evening Wine Tasting

• Though not quite the vineyards of Napa Valley, Chicago offers a number of places that hold wine tastings either at their location or at your preferred location. Wine-tasting parties are offered by the Chopping Block, a cooking school in Lincoln Square. You can opt to attend a private party there or have one of their wine experts come to your home.
  
  

Mixing Things Up

• If you're looking for a little wilder time, consider bringing the party to Flirty Girl Fitness in the West Loop, where you can take a chair-dancing or pole-dancing class and learn a routine to bring back home with you. In addition, this fitness studio also features a fully stocked bar and nail salon, making it a suitable pre-party location to get ready for a night of bar-hopping.
  
  

Bar-Hopping

• There is a bar for just about every taste in the Windy City. Many places cater to bachelorette parties; be sure to dress the bride in a veil and/or sash for the evening. Places to consider include Kit Kat Lounge & Supper Club (featuring great drag performances), Pops for Champagne (swanky atmosphere and extensive champagne selection, though it comes at a price) and Sound-Bar (multi-level club with different music on each floor and several bars per floor). Call ahead to reserve a table; many bars waive the cover charge for bachelorette party attendees if reservations are made in advance.
  
  

Transportation

• The key to a fun (and safe) night out is to secure transportation beforehand. If you want to stay on the cheap, you can opt to take public transportation or cabs. If you want to take it up a notch, consider renting a limousine or Chicago trolley for the evening. Doing so will ensure that you don't have to worry about getting around and that all party guests have a safe ride home. There are several different companies in Chicago that offer trolley rentals for a bar crawl across the city; rental fees for a three-hour period start around $500 in 2009.