top of page

Chicago girls' weekend

Sometimes, finding the time to recharge our batteries is challenging. I know that as a mom, the endless to-do list, kids’ activities, and the guilt of leaving it all behind can be overwhelming. However, remember that we are human, and everyone needs and deserves downtime. It makes us better people and moms. I love a girls’ weekend in Chicago.

Where to stay

There are so many wonderful options in Chicago. We stayed at The Gwen on Michigan Avenue on my most recent girls' weekend. The location provides easy access to everything Chicago offers; bonus, it’s attached to an indoor mall. The lobby and rooms are beautifully decorated in a glam/deco style.

The Gwen has some fun features, such as a rooftop terrace, a swanky bar, and two restaurants. They also offer a Tipsy Tea Party featuring traditional tea, cocktails, small bites, and a vibrant atmosphere perfect for girl time. You can also catch one of their themed events, such as Mean Girls or Sex in the City. With exceptional customer service and a champagne vending machine in the lobby, this Marriott property is spot-on for a girls’ trip.

Where to eat

It’s not an excellent trip for me without good food, and Chicago doesn’t disappoint. I love walking the different neighborhoods and exploring new places to eat. Recently, a girlfriend and I discovered Ella and Elli, a cute, cozy restaurant in the Lakeview area. It is small, and we didn’t have a table reservation, but we could sit on comfy couches next to a fire, sip delicious wine, and share plates of Italian-inspired food.

Another favorite is Hugo’s Frog Bar & Fish House. I like a good seafood restaurant, but my favorite dish is the giant slice of chocolate cake that the entire table can share.

Some other food/drink places to check out on your girls’ trip are Pops for Champagne, The Purple Pig, Girl & The Goat, Adobo Grill, and Yolk for an indulgent breakfast.

Where to Play

Shopping is an excellent choice for a girls’ trip, and Chicago has something for everyone. You could easily spend the entire weekend in stores. I recommend stopping by Rebellion, a female-owned shop in the 900 North Michigan Shops. This boutique features goods made by independent designers and artists. You will find unique clothing, handbags, jewelry, and more. The owner’s mission is to support women in business, and they even converted part of the store into a space to host events for women’s causes.

Chicago is a great place to see a show. There are Broadway productions, concerts, and the famous Second City comedy club where Joan Rivers, Bill Murray, Tina Fey, and more started their careers.

Spend some time wondering about the Art Institute, which has a beautiful café. If the weather is good, take a riverboat cruise or enjoy Chicago's beautiful outdoor spaces, such as Millennium Park, the lakefront, or Lincoln Park.

You can check the Choose Chicago events calendar for more ideas.


Let the posts come to you.

Thanks for submitting!

bottom of page