Eileen Gunn a RoamRight Blog Author

How to Enjoy a Fun Girlfriends Weekend in Chicago

With a central location and affordable flights from several airports around the country, Chicago is the ideal spot for a girlfriend getaway, especially if the friends are reuniting from different places. Whether a girl’s weekend means shopping and spa going, sipping cocktails or taking in some culture, you’ll find ample opportunities and choices in the Windy City.

Here’s an itinerary that includes a little bit of all those things and won’t break the bank. 

Friday Afternoon

Meet up at your hotel, freshen up from your flight and head out to explore the city, a nice walk might include the revitalized paths alongside the river, through Millennium Park or along Michigan Avenue. 

Plan to wind up at 108 N State St. at dinnertime. It looks like a standard office building but on the third floor and you’ll find Latinicity, a colorful Latin food hall that’s ideal for dinner and drinks with a group.

The full bar has beer and wine, fresh margaritas and other colorful cocktails.  Food options include great shrimp tacos, fresh ceviche, tasty soups, salads and Peruvian stir-fry, among other things. Daring diners can collect a bunch of different plates to share over drinks, but less adventurous souls will find something to enjoy, too. 

After dinner take a short walk over to Skydeck Chicago in what used to be the Sears Tower (now the Willis Tower), and take an elevator ride to the 103rd floor. The nighttime views of the city are fantastic and the glass box ledge makes for fun selfies and group photos. Maybe your margaritas will give you the courage to step out onto one and look straight down.


Start the day with a light bite and coffee, you have quite a bit of eating in front of you. 

Choose a food tour from Chicago Food Planet, which usually start around 11:00 or 11:30. Their Wicker Park and Bucktown tours are a good option because they walk you through evolving neighborhoods you might not visit otherwise that have a lot of interesting food and shopping tucked away. Be prepared for the food to range from Asian or Argentine to Middle Eastern and Mid-Western, depending on the time of year.

While still in the neighborhood explore funky local boutiques along Damen Avenue. Then pop into Tapster, a self-serve bar where you put money on a card, then use your credit at 60 taps that dispense beer, hard cider, wine, soft drinks and cocktails. Start with $10 and sample a number of different drinks to find your favorite. Mine, surprisingly, was a strawberry margarita spiked with smoky jalapeños. There’s a cozy table in the back if you can claim it.

Depending on the weather, how much shopping and sampling you did, and how much energy you have left, you can spend the rest of the afternoon exploring the Art Institute of Chicago or taking a Chicago Architecture Foundation tour on the river.

The Art Institute is too huge to see in one visit. Make a point of exploring the eclectic American wing, which is home to Grant Wood’s “American Gothic.”  The popular Impressionist gallery has notable pieces and will remind GenXers and Millennials of Ferris Bueller’s Day Off. The outdoor Bluhm Family Terrace has stellar views of the park.

The Architecture Tour, rated one of the best tours in the country, which involves sitting on a boat and taking in the sights, is less exerting. The tour guides are volunteer docents and some are better than others at engaging their audience. But they all have encyclopedic knowledge of the buildings that line the river and you’ll learn quite a bit about the city’s history and famous buildings.

Spend your evening in Old Town at Second City, the comedy shop that has produced a string of famous comedians and actors and still packs in crowds with its lively, topical improv. The attached 1959 Kitchen & Bar is a good gastro pub that features local beers and ciders and a menu with local and seasonal ingredients. The fried Brussels sprouts, pierogi, flatbreads and beignets are ideal for sharing. They also serve a pretty enticing burger. Grab a bite before the show so you can opt to stay for the second act if you want to. 


You need to rejuvenate and bond just a bit more before parting ways, and that means it’s spa time. Head to Aire Ancient Baths (with a bathing suit). You’ll relax by candle light in a series of pools and steam rooms and can add on massages or other treatments if you like. 

If your weekend falls between Main and October head to the Loews Hotel for its outdoor Streeterville Social lounge on the 8th floor for a farewell lunch. Choose a salad or steamed mussels if you’re feeling healthy after your spa morning. But be sure to share an order of chicken-fried mushrooms; they’re amazing. The setting is ideal for soaking up your last views of Chicago, taking one more group photo and planning your next weekend together. 

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Note: Available plans and coverages may have changed since this blog was published.

About the Author

Eileen Gunn

Eileen Gunn, a RoamRight Blog Author

Eileen is a journalist whose work has appeared in the HuffPost, U.S. News, Fortune, The Wall Street Journal, Parents.com and many other publications. She has traveled on five continents, three of them with her daughter. She calls New York City home. You can read Eileen's blog at Familiesgotravel.com or follow her on Facebook, Twitter, or Pinterest.

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