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Girlfriend Getaway of the Month: Chicago

The Girlfriends-In-Chief had a rare girlfriend getaway last month right here in our home base of Chicago. We may be biased, but we highly recommend the Windy City as a destination for girlfriends! Here’s our report and some tips for planning your own Chicago Girlfriend Getaway. Chicago is a friendly, beautiful city with sophisticated dining, world-class museums, excellent shopping, outdoor recreation opportunities and plenty of tourist attractions. You literally cannot go wrong with a girlfriend getaway here. We’d suggest you do a little planning before you arrive though, because deciding among the sheer number of options might slow you down a bit. Skyline photo via flickr

Where to Stay

Numerous hotels dot the Magnificent Mile, Gold Coast and downtown area. You’re sure to find one in your price range. We stayed at the delightful Hotel Monaco Chicago, a four-star boutique hotel located on the Chicago River. This hotel is really well-located close to shopping, dining, and nightlife, and also offers fabulous views of the river from some rooms. The hotel decor is uniquely chic, and the staff friendly and helpful. We truly appreciated all the special touches, from a free wine reception in the lobby each night to turndown service complete with gourmet chocolates on the pillow. Because we were celebrating Tina’s birthday, we found champagne on ice waiting for us in our room when we checked in. Wi-fi service was included in the room rate, a must for our working getaway. We had a blast blogging over drinks in the South Water Kitchen, the hotel’s adjacent restaurant and bar. Our room was comfy and adorable, with a fabulous river view and cozy window seats. Our package also included a heavenly in-room massage (the therapist really knew her stuff) and an in-room movie. Can you say “chick flick”? Overall, it was an indulgent little stay for these two working moms.

Enjoying the window seat
Enjoying the window seat
Highly recommended! Read on for theater, things to do, places to eat, online resources and more:

Theater Ops

Our hotel was brimming with theater-goers catching the closing weekend of Wicked, Spamalot, and more. The Chicago theater scene has blossomed over the last several years. Check BroadwayinChicago for all the theater opportunities. If your plans are flexible, be sure to check HotTix for same-day, half-price tickets. You may also want to catch a performance at the world-renowned Second City improvisational comedy show. Although prime-time shows often sell out in advance, it’s usually possible to walk in for the late show.


We didn’t do any shopping (sub-zero windchills put a damper on our shopping spirits!) but if shopping’s your thing, you’ll find the stores of your dreams in the Windy City. Michigan Avenue (the Magnificent Mile) has everything a girl needs. Water Tower Place is an urban mall, and there are boutiques galore in the Gold Coast. You can even set up a personalized shopping tour to find all those hidden gems. See this Chicago Tribune blog post for a list of shopping tour operators. Photo via flickr.


We had an absolutely delicious dinner at the award-winning, gourmet Mexican restaurant Frontera Grill. This is a destination restaurant and it’s hopping at dinner time. Expect a leisurely wait (great for people watching and sipping margaritas). The restaurant possibilities are too numerous to go into here. But PLEASE stay away from the tourist-trap chains and take advantage of Chicago’s excellent locally based eateries.  From four-star establishments to great steaks to funky vegetarian finds, you can eat up a storm. For local flavor go for a Chicago-style hot dog, deep-dish pizza, Italian beef sandwich, or visit the BillyGoat Tavern. Use our online resources, listed below, to scout out some spots you’ll enjoy. 

Museums, the Lakefront, and Festivals, Oh My!

One weekend in Chicago is simply not enough time to cover all the city has to offer, but here are some worthy suggestions for savoring the city’s unique offerings. We spent Sunday at the Museum of Contemporary Art, always a good choice, with thought-provoking (and a bit somber, the day we visited) exhibits. The Field Museum, Museum of Science and Industry, Shedd Aquarium and Art Institute of Chicago are among Chicago’s other major museums. The Chicago History Museum is fabulous as well. If you’re visiting in warmer weather, you might want to check out Navy Pier, a major tourist attraction, the stunning Millenium Park, or walk or bike along Lake Michigan. Chicago also hosts numerous neighborhood festivals in the summer months and these are great way to get a taste of the city’s ethnic neighborhoods. Visit Explore Chicago for a list of city neighborhood festivals. Photo via flickr.

More Tips

Consider the weather when packing. If you’re coming during spring break, don’t plan on warm weather. We’ve seen many, many tourists freezing in their cute capris and sandals in April. Summer can be very hot or very mild, so be prepared!

When you plan your trip, here are some great online resources for things to do and places to see and stay:

  • Girls Getaway Guide – Our contributor Casey Wohl did a girlfriend getaway to Chicago not long ago. Her blog posts will give you more great ideas for things to do.
  • TheLocalTourist – “Insider” tips and great calendar of events.
  • Metromix Chicago 


Talking about a girlfriend getaway is one thing, but actually planning it and doing it is quite another. We know, we’re busy too! We don’t always practice what we preach, but while on this trip we realized how vital it really is to STOP, get away, relax and renew. For many women, the only way to truly relax is to be away from home. So, give yourself permission and plan a girlfriend getaway in 2009. Even if it’s only across town, you’ll feel refreshed and more in touch with your true self. We’ll continue to bring you monthly getaway destinations. Feel free to write us with your favorites! And, if you plan a girlfriend getaway to Chicago, let us know. We’d love to answer any questions from our girlfriends!


  1. I would so love to have a girlfriends trip. I wish I had girlfriends who understood why it is so good to get away and husbands that would be understanding. (like mine)

    Comment by Amy — February 20, 2009 @ 1:49 pm

  2. While in Chicago, I highly recommend treating yourself to dinner at Tru. If your budget can’t swing a full meal, they also have an appetizers bar off to the side of the main dining area. Yummy!

    Comment by — February 21, 2009 @ 2:18 pm

  3. Great restaurant reco. Thanks!

    Comment by Dawn — February 22, 2009 @ 9:34 am

  4. I love weekend trips to Chicago! When going with my family, I like to use when planning a trip to Chicago.

    Comment by Lisa Whelpley — February 23, 2009 @ 11:53 am

  5. We are planning an August 2010 girlfriends weekend in Chicago and looking for great idea. We’re thinking of seeing a play, a great dinner, shopping, and then on our way back home to WI outlet shopping. :)

    Comment by Jessica — March 21, 2010 @ 5:56 pm

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